1238:
1264:
1308:
1083:
438:
287:
42:
1205:
1159:
728:
51:
723:
79:
718:
70:
1003:
94:
1649:
1577:
826:
1126:
on the reactants. These methods are commonly categorized by which and how many bonds form to make the imidazole rings. For example, the Debus method forms the (1,2), (3,4), and (1,5) bonds in imidazole, using each reactant as a fragment of the ring, and thus this method would be a three-bond-forming
2805:
Zolfigol, Mohammad A.; Khazaei, Ardeshir; Moosavi-Zare, Ahmad R.; Zare, Abdolkarim; Kruger, Hendrik G.; Asgari, Zhila; Khakyzadeh, Vahid; Kazem-Rostami, Masoud (2012-04-06). "Design of Ionic Liquid 3-Methyl-1-sulfonic Acid
Imidazolium Nitrate as Reagent for the Nitration of Aromatic Compounds by in
2337:
Van Leusen, Albert M.; Wildeman, Jurjen; Oldenziel, Otto H. (1977). "Chemistry of sulfonylmethyl isocyanides. 12. Base-induced cycloaddition of sulfonylmethyl isocyanides to carbon, nitrogen double bonds. Synthesis of 1,5-disubstituted and 1,4,5-trisubstituted imidazoles from aldimines and imidoyl
1518:. The N3 of the imidazole compound binds to the heme iron atom of ferric cytochrome P450, whereas the N4 of the triazoles bind to the heme group. The triazoles have been shown to have a higher specificity for the cytochrome P450 than imidazoles, thereby making them more potent than the imidazoles.
1352:. The Van Leusen Imidazole Synthesis allows the preparation of imidazoles from aldimines by reaction with tosylmethyl isocyanide (TosMIC). The reaction has later been expanded to a two-step synthesis in which the aldimine is generated in situ: the Van Leusen Three-Component Reaction (vL-3CR).
2323:
1632:
Imidazole is a suitable buffer for pH 6.2 to 7.8,. Pure imidazole has essentially no absorbance at protein relevant wavelengths (280 nm), however lower purities of imidazole can give notable absorbance at 280 nm. Imidazole can interfere with the
1030:
of imidazole is 14.5, making it less acidic than carboxylic acids, phenols, and imides, but slightly more acidic than alcohols. The acidic proton is the one bound to nitrogen. Deprotonation gives the imidazolide anion, which is symmetrical. As a base, the
2740:
736:
698:
2736:
2501:
Khalid, M. H.; Tokunaga, Y.; Caputy, A. J.; Walters, E. (2005). "Inhibition of tumor growth and prolonged survival of rats with intracranial gliomas following administration of clotrimazole".
794:
2590:
Sunderland, M. R.; Cruickshank, R. H.; Leighs, S. J. (2014). "The efficacy of antifungal azole and antiprotozoal compounds in protection of wool from keratin-digesting insect larvae".
1640:
Imidazole is often used in protein purification, where recombinant proteins with polyhistidine tags are immobilized onto nickel resins and eluted with a high imidazole concentration.
839:
2279:
Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. (2006). "Microwave-Mediated
Synthesis of Lophine: Developing a Mechanism To Explain a Product".
2630:
2663:
1230:= hydrogen, imidazole itself is the product. The yield of this reaction is moderate, but it seems to be the most effective method of making the 1,4 substitution.
2253:
2148:
2183:"The Microwave Spectrum of Imidazole; Complete Structure and the Electron Distribution from Nuclear Quadrupole Coupling Tensors and Dipole Moment Orientation"
484:
1073:
condense to form imidazole (glyoxaline, as it was originally named). This synthesis, while producing relatively low yields, is still used for generating
2129:
1933:
1254:
This is a general method that is able to give good yields for substituted imidazoles. In essence, it is an adaptation of the Debus method called the
1624:
column. An excess of imidazole is passed through the column, which displaces the His-tag from nickel coordination, freeing the His-tagged proteins.
2428:
1049:. The basic site is the nitrogen with the lone pair (and not bound to hydrogen). Protonation gives the imidazolium cation, which is symmetrical.
1255:
1119:
3582:
2866:
2686:
2574:
2067:
2042:
2017:
1992:
1967:
1853:
2714:
612:
1263:
2647:
1904:
1597:
2545:
2163: : 1–6. Hantzsch proposed a reform of the nomenclature of azole compounds, including a proposal to call the heterocyclic ring C
1602:
Imidazole and its derivatives have high affinity for metal cations. One of the applications of imidazole is in the purification of
452:
1237:
2236:
3636:
3349:
2762:
Molina, F; Rueda, A; Bosque-Sendra, J.M; Megias, L (1996). "Determination of proteins in the presence of imidazole buffers".
679:
1122:. Many of these syntheses can also be applied to different substituted imidazoles and imidazole derivatives by varying the
2916:
1204:
786:
1158:
846:
993:(a pair of electrons from the protonated nitrogen atom and one from each of the remaining four atoms of the ring). Some
790:
772:
385:
727:
3599:
2318:
416:
722:
2657:
1837:
1045:
to avoid confusion between the two) is approximately 7, making imidazole approximately sixty times more basic than
915:
ring but feature varied substituents. This ring system is present in important biological building blocks, such as
897:
590:
1553:
Imidazole itself has few direct applications. It is instead a precursor to a variety of agrichemicals, including
3417:
3387:
2859:
294:
3282:
1058:
1307:
1082:
2267:"Die gereinigte Substanz stellt das oxalsaure Salz einer Basis dar, die ich mit Glyoxalin bezeichenen werde."
2231:
2145:
3641:
3587:
3517:
1610:
1531:
1456:, neurodegenerative diseases and tumors of the nervous system. Other biological activities of the imidazole
1386:
Imidazole-based histidine compounds play a very important role in intracellular buffering. Histidine can be
1925:
798:
717:
282:
3554:
3201:
1426:
978:
958:
2454:"Effect of anti-fungal imidazoles on mRNA levels and enzyme activity of inducible nitric oxide synthase"
2389:
2314:
1484:
1449:
1410:
1021:
994:
951:
750:
710:
647:
2269:(The purified substance constitutes the oxalic salt of a base, which I will designate as "glyoxaline".)
1514:. The difference between the imidazoles and the triazoles involves the mechanism of inhibition of the
1286:. This reaction will give substantial yields only if the 1-vinyltetrazole is made efficiently from an
1061:, although various imidazole derivatives had been discovered as early as the 1840s. It was shown that
224:
2852:
2347:
2288:
2194:
2126:
1541:
106:
1258:. The starting materials are substituted glyoxal, aldehyde, amine, and ammonia or an ammonium salt.
3626:
3344:
3160:
1834:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1634:
1522:
1405:
Imidazole substituents are found in many pharmaceuticals. Synthetic imidazoles are present in many
1341:
1180:
1108:
1092:
782:
433:
138:
3631:
3507:
3477:
3472:
2710:
2607:
2212:
2108:
1787:
1287:
778:
184:
172:
1869:
Walba, H.; Isensee, R. W. (1961). "Acidity constants of some arylimidazoles and their cations".
1332:, and it must take place between 340 and 480 °C. This forms a very pure imidazole product.
3368:
2831:
2823:
2787:
2779:
2692:
2682:
2643:
2570:
2541:
2518:
2483:
2420:
2100:
2063:
2038:
2013:
1988:
1963:
1955:
1849:
1807:
1802:
1536:
1360:
Imidazole is incorporated into many important biological compounds. The most pervasive is the
1123:
633:
3512:
3462:
2815:
2771:
2635:
2599:
2510:
2473:
2465:
2412:
2404:
2355:
2296:
2245:
2202:
2092:
1878:
1841:
1723:
1418:
862:
579:
507:
41:
2083:
Rosemeyer, H. (2004). "The
Chemodiversity of Purine as a Constituent of Natural Products".
1896:
394:
3094:
3084:
2628:
Ebel, K., Koehler, H., Gamer, A. O., & Jäckh, R. (2002). "Imidazole and
Derivatives".
2152:
2133:
1515:
1321:
1290:, such as 2-tributylstannyltetrazole. The reaction, shown below, produces imidazole when R
1188:
924:
313:
244:
148:
2351:
2292:
2198:
437:
286:
204:
3593:
3524:
3467:
3437:
3422:
3190:
3079:
2478:
2469:
2453:
1681:
1621:
1430:
928:
817:
760:
604:
78:
1020:, which is to say that it can function both as an acid and as a base. As an acid, the
50:
3620:
3427:
3323:
3297:
3104:
3056:
3022:
2977:
2947:
2775:
2611:
1713:
1677:
1457:
1414:
568:
558:
275:
2390:"Design, synthesis, and evaluation of potential inhibitors of nitric oxide synthase"
2112:
3549:
3534:
3447:
3377:
3293:
3127:
3122:
3114:
3109:
3099:
3089:
3007:
2997:
2992:
2982:
2967:
2957:
2942:
2883:
2879:
2216:
1584:
1562:
1554:
1511:
1507:
1496:
1488:
1453:
1445:
1422:
1100:
1066:
1002:
93:
2388:
Castaño, T.; Encinas, A.; Pérez, C.; Castro, A.; Campillo, N. E.; Gil, C. (2008).
69:
2562:
2452:
Bogle, R. G.; Whitley, G. S.; Soo, S. C.; Johnstone, A. P.; Vallance, P. (1994).
1476:
The substituted imidazole derivatives are valuable in treatment of many systemic
1316:
Imidazole can also be formed in a vapor-phase reaction. The reaction occurs with
877:. It is a white or colourless solid that is soluble in water, producing a mildly
3568:
3529:
3487:
3457:
3358:
3302:
3238:
3226:
3074:
3066:
3061:
3032:
3027:
3017:
3012:
2987:
2962:
2514:
1845:
1812:
1727:
1689:
1669:
1503:
986:
932:
885:
805:
358:
1648:
3558:
3539:
3502:
3497:
3482:
3452:
3432:
3397:
3317:
3312:
3307:
3268:
3247:
3212:
3165:
3002:
2952:
2937:
2901:
2875:
2408:
1580:
1570:
1566:
1558:
1492:
1480:
1380:
1368:
1361:
1279:
1222:
with heat. The product will be a 1,4-disubstituted imidazole, but here since R
1017:
943:
639:
530:
235:
17:
2827:
2783:
2639:
2603:
2249:
3544:
3492:
3221:
3180:
3146:
2972:
2844:
2696:
1465:
1406:
1395:
1391:
1364:
1317:
1283:
1219:
936:
920:
916:
764:
405:
2835:
2522:
2424:
2104:
2096:
2791:
2487:
2207:
2182:
3442:
3185:
3137:
3047:
2375:
Biochemical
Adaptation: Mechanisms and Process in Physiological Evolution
1774:
1768:
1764:
1755:
1737:
1673:
1661:
1502:
For comparison, another group of azoles is the triazoles, which includes
1434:
1387:
1372:
1349:
1325:
1192:
1184:
1140:
1046:
974:
970:
904:
893:
882:
255:
2359:
1882:
264:
3563:
3175:
2416:
2300:
1746:
1733:
1717:
1665:
1606:
1603:
1576:
1526:
1461:
1399:
1376:
1329:
1196:
1136:
1112:
1104:
1070:
1062:
990:
889:
548:
345:
295:
2819:
1759:
1750:
1657:
1614:
1477:
1345:
1176:
1144:
1096:
969:
Imidazole is a planar 5-membered ring, that exists in two equivalent
947:
878:
659:
215:
2321:, "Process for Manufacture of Imidazoles", issued 2001-01-23
1425:
molecule, found in tea leaves and coffee beans, that stimulates the
816:
Except where otherwise noted, data are given for materials in their
756:
333:
2912:
1685:
1647:
982:
666:
369:
195:
171:
161:
1175:
The (1,2) and (2,3) bonds can be formed by treating a 1,2-diamino
1127:
synthesis. A small sampling of these methods is presented below.
2540:(6th ed.). Lippincott Williams & Wilkins. p. 930.
1740:
1521:
Some imidazole derivatives show effects on insects, for example
985:, and is highly soluble in water. The compound is classified as
977:
atom. Imidazole is a highly polar compound, as evidenced by its
324:
2848:
2136:(On compounds of thiazole (pyridines of the thiophene series),
2144: : 3118–3132, see p. 3119. See also: Hantzsch, A. (1888)
2127:"Ueber Verbindungen des Thiazols (Pyridins der Thiophenreihe)"
1617:
1438:
957:
The name "imidazole" was coined in 1887 by the German chemist
907:, contain the imidazole ring. These imidazoles share the 1,3-C
1758:, an analog with the nitrogen atom in position 1 replaced by
1749:, an analog with the nitrogen atom in position 1 replaced by
1118:
Imidazole can be synthesized by numerous methods besides the
2181:
Christen, Dines; Griffiths, John H.; Sheridan, John (1981).
1613:(IMAC). Imidazole is used to elute tagged proteins bound to
1306:
1262:
1236:
1203:
1157:
1135:
The (1,5) or (3,4) bond can be formed by the reaction of an
1081:
1001:
421:
77:
68:
49:
40:
2561:
Davis, Jennifer L.; Papich, Mark G.; Heit, Mark C. (2009).
1057:
Imidazole was first reported in 1858 by the German chemist
1660:
are known as imidazolium salts (for example, imidazolium
950:, which is the most widely occurring nitrogen-containing
563:
89 to 91 °C (192 to 196 °F; 362 to 364 K)
923:. Many drugs contain an imidazole ring, such as certain
834:
2737:"Optimizing Purification of Histidine-Tagged Proteins"
1468:
fluxes, and interference with translation initiation.
1344:
can also be employed to form imidazoles starting from
973:
forms because hydrogen can be bound to one or another
2569:(9th ed.). Wiley-Blackwell. pp. 1019–1020.
1786:
Imidazole has low acute toxicity as indicated by the
3410:
3386:
3367:
3343:
3336:
3281:
3260:
3237:
3211:
3200:
3159:
3136:
3046:
2927:
2911:
2900:
2891:
2234:[On the reaction of ammonia upon glyoxal].
1656:Salts of imidazole where the imidazole ring is the
1214:The (1,2) and (3,4) bonds can also be formed from
989:due to the presence of a planar ring containing 6
2764:Journal of Pharmaceutical and Biomedical Analysis
2232:"Ueber die Einwirkung des Ammoniaks auf Glyoxal"
357:
1452:, which makes them interesting drug targets in
1147:. The example below applies to imidazole when R
147:
2631:Ullmann's Encyclopedia of Industrial Chemistry
2565:. In Riviere, Jim E.; Papich, Mark G. (eds.).
2138:Berichte der deutschen chemischen Gesellschaft
1688:are also well known; these salts are known as
1460:relate to the downregulation of intracellular
1444:A number of substituted imidazoles, including
1379:, e.g. by binding metal cofactors, as seen in
2860:
1684:. Salts where a deprotonated imidazole is an
1525:exhibits a strong anti-feeding effect on the
1429:. It is present in the anticancer medication
8:
2662:: CS1 maint: multiple names: authors list (
2563:"Chapter 39: Antifungal and Antiviral Drugs"
1676:of imidazole. These salts have been used as
1529:-digesting Australian carpet beetle larvae
3340:
3208:
2924:
2908:
2897:
2867:
2853:
2845:
461:InChI=1S/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
436:
285:
243:
29:
2806:Situ Generation of NO2 in Acidic Media".
2477:
2206:
2171:(NH)N "imidazole" ; see pp. 2 and 4.
1611:immobilised metal affinity chromatography
997:structures of imidazole are shown below:
471:InChI=1/C3H4N2/c1-2-5-3-4-1/h1-3H,(H,4,5)
393:
2681:. Oxford: Clarendon Press. p. 325.
2567:Veterinary Pharmacology and Therapeutics
2373:Hochachka, P. W.; Somero, G. N. (2002).
1958:; Rees, C.W.R.; Scriven, E.F.V. (1984).
1726:or imidazoline, an analog where the 4,5-
1620:attached to the surface of beads in the
1575:
1356:Biological significance and applications
2623:
2621:
2033:Pozharskii, A. F.; et al. (1997).
1824:
489:
457:
432:
263:
2655:
1421:medications. Imidazole is part of the
1256:Debus-Radziszewski imidazole synthesis
1191:. A dehydrogenating catalyst, such as
810:146 °C (295 °F; 419 K)
573:256 °C (493 °F; 529 K)
276:
2155:(General observations about azoles),
2125:Hantzsch, A. and Weber, J. H. (1887)
1985:Imidazole and Benzimidazole Synthesis
1692:(for example, sodium imidazolate, NaC
1111:, forming 2,4,5-triphenylimidazole ("
464:Key: RAXXELZNTBOGNW-UHFFFAOYSA-N
223:
203:
7:
2377:. New York: Oxford University Press.
2146:"Allegemeine Bemerkungen über Azole"
1960:Comprehensive Heterocyclic Chemistry
1583:is one of several imidazole-derived
1483:. Imidazoles belong to the class of
1278:Imidazole can be synthesized by the
1777:, analogs with three nitrogen atoms
1668:). These salts are formed from the
1398:(hives) when it is produced during
348:
332:
2717:from the original on 25 April 2021
2470:10.1111/j.1476-5381.1994.tb14881.x
2010:Ring Nitrogen and Key Biomolecules
1598:Transition metal imidazole complex
903:Many natural products, especially
25:
1962:. Vol. 5. pp. 469–498.
1274:Formation from other heterocycles
1038:of the conjugate acid (cited as p
881:solution. In chemistry, it is an
2808:The Journal of Organic Chemistry
2743:from the original on 13 May 2021
2237:Annalen der Chemie und Pharmacie
2187:Zeitschrift für Naturforschung A
2035:Heterocycles in Life and Society
1936:from the original on 10 May 2023
1218:-substituted α-aminoketones and
1179:, at high temperatures, with an
1095:modification, the reactants are
824:
726:
721:
716:
92:
3350:thymidylate synthase inhibitors
2434:from the original on 2023-03-06
2256:from the original on 2020-05-30
1907:from the original on 2018-10-19
1793:of 970 mg/kg (Rat, oral).
1371:. Histidine is present in many
820:(at 25 °C , 100 kPa).
1838:The Royal Society of Chemistry
1767:, an analog with two adjacent
1448:, are selective inhibitors of
680:Occupational safety and health
1:
2679:Data for biochemical research
2538:Comprehensive Pharmacy Review
1539:with the common clothes moth
2776:10.1016/0731-7085(95)01615-5
2340:Journal of Organic Chemistry
2085:Chemistry & Biodiversity
2770:(3). Elsevier BV: 273–280.
2515:10.3171/jns.2005.103.1.0079
1846:10.1039/9781849733069-FP001
543:White or pale yellow solid
64:
36:
3658:
1983:Grimmett, M. Ross (1997).
1736:, an analog with only one
1628:Use in biological research
1595:
1472:Pharmaceutical derivatives
535:68.077 g/mol
3577:
3418:bromochlorosalicylanilide
3388:Aminoacyl tRNA synthetase
2677:Dawson, R. M. C. (1986).
2409:10.1016/j.bmc.2008.04.036
2058:Gilchrist, T. L. (1985).
2037:. John Wiley & Sons.
2012:. Kluwer Academic Press.
1716:, an analog with a fused
1652:Simple imidazolium cation
1367:, which has an imidazole
1077:-substituted imidazoles.
814:
697:
677:
672:
626:
500:
480:
448:
131:
121:
105:
100:
91:
63:
35:
2640:10.1002/14356007.a13_661
2604:10.1177/0040517513515312
2399:(Submitted manuscript).
2250:10.1002/jlac.18581070209
2230:Debus, Heinrich (1858).
1930:pubchem.ncbi.nlm.nih.gov
1241:Formation of three bonds
965:Structure and properties
919:and the related hormone
773:Precautionary statements
2634:. Weinheim: Wiley-VCH.
2315:US patent 6,177,575
1549:Industrial applications
1532:Anthrenocerus australis
1250:Formation of four bonds
892:, and has non-adjacent
653:Planar 5-membered ring
3202:Squalene monooxygenase
3039:Systemic: ketoconazole
2097:10.1002/cbdv.200490033
2060:Heterocyclic Chemistry
1653:
1592:Coordination chemistry
1588:
1516:cytochrome P450 enzyme
1427:central nervous system
1394:. Histamine can cause
1311:
1268:
1242:
1209:
1208:Formation of two bonds
1171:Formation of two bonds
1163:
1086:
1006:
979:electric dipole moment
959:Arthur Rudolf Hantzsch
82:
73:
54:
45:
3637:Simple aromatic rings
3230:Systemic: terbinafine
2536:Leon Shargel (2007).
2208:10.1515/zna-1981-1220
2008:Brown, E. G. (1998).
1840:. 2014. p. 140.
1651:
1579:
1450:nitric oxide synthase
1310:
1266:
1240:
1207:
1162:Formation of one bond
1161:
1131:Formation of one bond
1085:
1005:
648:Coordination geometry
81:
72:
53:
44:
3518:Whitfield's ointment
3345:Pyrimidine analogues
3161:Polyene antimycotics
1708:Related heterocycles
1542:Tineola bisselliella
1437:by interfering with
1324:, and hydrogen over
126:Glyoxaline (archaic)
107:Preferred IUPAC name
2360:10.1021/jo00427a012
2352:1977JOrgC..42.1153A
2293:2006JChEd..83.1658C
2199:1981ZNatA..36.1378C
1883:10.1021/jo01066a039
1672:or substitution at
1635:Lowry protein assay
1523:sulconazole nitrate
1342:Van Leusen reaction
1336:Van Leusen reaction
1267:Arduengo imidazoles
1109:glacial acetic acid
935:, and the sedative
580:Solubility in water
185:Beilstein Reference
32:
3604:Never to phase III
3508:tribromometacresol
3478:sodium thiosulfate
3473:selenium disulfide
3369:Mitotic inhibitors
2397:Bioorg. Med. Chem.
2301:10.1021/ed083p1658
2157:Annalen der Chemie
2151:2020-05-30 at the
2132:2020-05-30 at the
1987:. Academic Press.
1903:. Molekula Group.
1815:(dihydroimidazole)
1680:and precursors to
1654:
1644:Salts of imidazole
1589:
1312:
1288:organotin compound
1269:
1243:
1210:
1164:
1087:
1007:
888:, classified as a
865:with the formula C
847:Infobox references
83:
74:
55:
46:
30:
3614:
3613:
3406:
3405:
3332:
3331:
3283:β-glucan synthase
3277:
3276:
3256:
3255:
3155:
3154:
2820:10.1021/jo300137w
2688:978-0-19-855299-4
2658:cite encyclopedia
2576:978-0-8138-2061-3
2403:(11): 6193–6206.
2193:(12): 1378–1385.
2069:978-0-582-01421-3
2044:978-0-471-96033-1
2019:978-94-011-4906-8
1994:978-0-08-053445-9
1969:978-0-08-042072-1
1855:978-0-85404-182-4
1808:4-Methylimidazole
1803:1-Methylimidazole
1537:econazole nitrate
1487:, which includes
1485:azole antifungals
1124:functional groups
946:ring, it forms a
898:meta-substitution
855:Chemical compound
853:
852:
751:Hazard statements
634:Crystal structure
553:1.23 g/cm, solid
417:CompTox Dashboard
173:Interactive image
87:
86:
59:
58:
27:Chemical compound
16:(Redirected from
3649:
3513:undecylenic acid
3463:potassium iodide
3341:
3209:
2925:
2909:
2898:
2869:
2862:
2855:
2846:
2840:
2839:
2814:(7): 3640–3645.
2802:
2796:
2795:
2759:
2753:
2752:
2750:
2748:
2733:
2727:
2726:
2724:
2722:
2707:
2701:
2700:
2674:
2668:
2667:
2661:
2653:
2625:
2616:
2615:
2587:
2581:
2580:
2558:
2552:
2551:
2533:
2527:
2526:
2498:
2492:
2491:
2481:
2464:(4): 1257–1261.
2458:Br. J. Pharmacol
2449:
2443:
2442:
2440:
2439:
2433:
2394:
2385:
2379:
2378:
2370:
2364:
2363:
2346:(7): 1153–1159.
2334:
2328:
2327:
2326:
2322:
2311:
2305:
2304:
2276:
2270:
2264:
2262:
2261:
2227:
2221:
2220:
2210:
2178:
2172:
2123:
2117:
2116:
2080:
2074:
2073:
2055:
2049:
2048:
2030:
2024:
2023:
2005:
1999:
1998:
1980:
1974:
1973:
1952:
1946:
1945:
1943:
1941:
1922:
1916:
1915:
1913:
1912:
1893:
1887:
1886:
1877:(8): 2789–2791.
1866:
1860:
1859:
1832:"Front Matter".
1829:
1724:Dihydroimidazole
1433:, which combats
1419:antihypertensive
1284:1-vinyltetrazole
942:When fused to a
925:antifungal drugs
863:organic compound
837:
831:
828:
827:
800:
796:
792:
788:
784:
780:
766:
762:
758:
730:
725:
720:
508:Chemical formula
441:
440:
425:
423:
397:
361:
350:
336:
314:Gmelin Reference
297:
289:
278:
267:
247:
227:
207:
175:
151:
96:
65:
37:
33:
21:
3657:
3656:
3652:
3651:
3650:
3648:
3647:
3646:
3617:
3616:
3615:
3610:
3609:
3594:Clinical trials
3573:
3402:
3382:
3363:
3348:
3328:
3285:
3273:
3252:
3233:
3229:
3204:
3196:
3188:
3163:
3151:
3132:
3085:fosravuconazole
3042:
2918:
2917:lanosterol 14α-
2904:
2893:
2887:
2873:
2843:
2804:
2803:
2799:
2761:
2760:
2756:
2746:
2744:
2735:
2734:
2730:
2720:
2718:
2709:
2708:
2704:
2689:
2676:
2675:
2671:
2654:
2650:
2627:
2626:
2619:
2589:
2588:
2584:
2577:
2560:
2559:
2555:
2548:
2535:
2534:
2530:
2500:
2499:
2495:
2451:
2450:
2446:
2437:
2435:
2431:
2392:
2387:
2386:
2382:
2372:
2371:
2367:
2336:
2335:
2331:
2324:
2319:Arduengo, A. J.
2313:
2312:
2308:
2278:
2277:
2273:
2259:
2257:
2229:
2228:
2224:
2180:
2179:
2175:
2170:
2166:
2153:Wayback Machine
2134:Wayback Machine
2124:
2120:
2082:
2081:
2077:
2070:
2057:
2056:
2052:
2045:
2032:
2031:
2027:
2020:
2007:
2006:
2002:
1995:
1982:
1981:
1977:
1970:
1956:Karitzky, A. R.
1954:
1953:
1949:
1939:
1937:
1924:
1923:
1919:
1910:
1908:
1895:
1894:
1890:
1868:
1867:
1863:
1856:
1831:
1830:
1826:
1822:
1799:
1791:
1784:
1710:
1703:
1699:
1695:
1682:stable carbenes
1646:
1630:
1600:
1594:
1551:
1474:
1358:
1322:ethylenediamine
1301:
1297:
1293:
1276:
1252:
1229:
1225:
1199:, is required.
1189:carboxylic acid
1173:
1154:
1150:
1133:
1055:
1044:
1037:
1028:
1014:
967:
914:
910:
876:
872:
868:
856:
849:
844:
843:
842: ?)
833:
829:
825:
821:
775:
753:
739:
713:
690:
662:
650:
636:
618:
599:
582:
524:
520:
516:
510:
496:
493:
488:
487:
476:
473:
472:
466:
465:
462:
456:
455:
444:
426:
419:
400:
380:
364:
351:
339:
316:
307:
270:
250:
230:
210:
187:
178:
165:
154:
141:
127:
125:
117:
116:
28:
23:
22:
15:
12:
11:
5:
3655:
3653:
3645:
3644:
3642:Aromatic bases
3639:
3634:
3629:
3619:
3618:
3612:
3611:
3608:
3607:
3606:
3605:
3602:
3591:
3585:
3579:
3578:
3575:
3574:
3572:
3571:
3566:
3561:
3552:
3547:
3542:
3537:
3532:
3527:
3525:citronella oil
3521:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3468:salicylic acid
3465:
3460:
3455:
3450:
3445:
3440:
3438:crystal violet
3435:
3430:
3425:
3423:chlorophetanol
3420:
3414:
3412:
3408:
3407:
3404:
3403:
3401:
3400:
3393:
3391:
3384:
3383:
3381:
3380:
3373:
3371:
3365:
3364:
3362:
3361:
3354:
3352:
3338:
3334:
3333:
3330:
3329:
3327:
3326:
3321:
3315:
3310:
3305:
3300:
3289:
3287:
3279:
3278:
3275:
3274:
3272:
3271:
3264:
3262:
3258:
3257:
3254:
3253:
3251:
3250:
3243:
3241:
3235:
3234:
3232:
3231:
3224:
3217:
3215:
3206:
3198:
3197:
3195:
3194:
3191:amphotericin B
3183:
3178:
3171:
3169:
3157:
3156:
3153:
3152:
3150:
3149:
3142:
3140:
3134:
3133:
3131:
3130:
3125:
3118:
3117:
3112:
3107:
3102:
3097:
3092:
3087:
3082:
3080:fosfluconazole
3077:
3070:
3069:
3064:
3059:
3052:
3050:
3044:
3043:
3041:
3040:
3036:
3035:
3030:
3025:
3020:
3015:
3010:
3005:
3000:
2995:
2990:
2985:
2980:
2975:
2970:
2965:
2960:
2955:
2950:
2945:
2940:
2933:
2931:
2922:
2906:
2895:
2889:
2888:
2874:
2872:
2871:
2864:
2857:
2849:
2842:
2841:
2797:
2754:
2728:
2711:"1H-Imidazole"
2702:
2687:
2669:
2649:978-3527306732
2648:
2617:
2598:(9): 924–931.
2592:Textile Res. J
2582:
2575:
2553:
2546:
2528:
2493:
2444:
2380:
2365:
2329:
2306:
2271:
2244:(2): 199–208.
2222:
2173:
2168:
2164:
2118:
2091:(3): 361–401.
2075:
2068:
2062:. Bath Press.
2050:
2043:
2025:
2018:
2000:
1993:
1975:
1968:
1947:
1917:
1888:
1861:
1854:
1823:
1821:
1818:
1817:
1816:
1810:
1805:
1798:
1795:
1789:
1783:
1780:
1779:
1778:
1772:
1762:
1753:
1744:
1731:
1721:
1709:
1706:
1701:
1697:
1693:
1645:
1642:
1629:
1626:
1622:chromatography
1596:Main article:
1593:
1590:
1550:
1547:
1473:
1470:
1431:mercaptopurine
1388:decarboxylated
1357:
1354:
1338:
1337:
1314:
1313:
1299:
1295:
1291:
1275:
1272:
1271:
1270:
1251:
1248:
1247:
1246:
1245:
1244:
1227:
1223:
1212:
1211:
1172:
1169:
1168:
1167:
1152:
1148:
1139:and an α-amino
1132:
1129:
1089:
1088:
1059:Heinrich Debus
1054:
1051:
1042:
1035:
1026:
1013:
1010:
1009:
1008:
966:
963:
929:nitroimidazole
912:
908:
874:
870:
866:
854:
851:
850:
845:
823:
822:
818:standard state
815:
812:
811:
808:
802:
801:
795:P305+P351+P338
776:
771:
768:
767:
754:
749:
746:
745:
740:
735:
732:
731:
714:
709:
706:
705:
695:
694:
691:
688:
685:
684:
675:
674:
670:
669:
663:
658:
655:
654:
651:
646:
643:
642:
637:
632:
629:
628:
624:
623:
620:
616:
609:
608:
605:conjugate acid
603:6.95 (for the
601:
597:
587:
586:
583:
578:
575:
574:
571:
565:
564:
561:
555:
554:
551:
545:
544:
541:
537:
536:
533:
527:
526:
522:
518:
514:
511:
506:
503:
502:
498:
497:
495:
494:
491:
483:
482:
481:
478:
477:
475:
474:
470:
469:
467:
463:
460:
459:
451:
450:
449:
446:
445:
443:
442:
429:
427:
415:
412:
411:
408:
402:
401:
399:
398:
390:
388:
382:
381:
379:
378:
374:
372:
366:
365:
363:
362:
354:
352:
344:
341:
340:
338:
337:
329:
327:
321:
320:
317:
312:
309:
308:
306:
305:
301:
299:
291:
290:
280:
272:
271:
269:
268:
260:
258:
252:
251:
249:
248:
240:
238:
232:
231:
229:
228:
220:
218:
212:
211:
209:
208:
200:
198:
192:
191:
188:
183:
180:
179:
177:
176:
168:
166:
159:
156:
155:
153:
152:
144:
142:
137:
134:
133:
129:
128:
123:
119:
118:
110:
109:
103:
102:
98:
97:
89:
88:
85:
84:
75:
61:
60:
57:
56:
47:
26:
24:
18:Imidazole ring
14:
13:
10:
9:
6:
4:
3:
2:
3654:
3643:
3640:
3638:
3635:
3633:
3630:
3628:
3625:
3624:
3622:
3603:
3601:
3598:
3597:
3595:
3592:
3589:
3586:
3584:
3581:
3580:
3576:
3570:
3567:
3565:
3562:
3560:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3522:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3451:
3449:
3446:
3444:
3441:
3439:
3436:
3434:
3431:
3429:
3428:chlorphenesin
3426:
3424:
3421:
3419:
3416:
3415:
3413:
3409:
3399:
3395:
3394:
3392:
3389:
3385:
3379:
3375:
3374:
3372:
3370:
3366:
3360:
3356:
3355:
3353:
3351:
3346:
3342:
3339:
3337:Intracellular
3335:
3325:
3324:ibrexafungerp
3322:
3319:
3316:
3314:
3311:
3309:
3306:
3304:
3301:
3299:
3298:anidulafungin
3295:
3294:echinocandins
3291:
3290:
3288:
3284:
3280:
3270:
3266:
3265:
3263:
3259:
3249:
3245:
3244:
3242:
3240:
3236:
3228:
3225:
3223:
3219:
3218:
3216:
3214:
3210:
3207:
3203:
3199:
3192:
3187:
3184:
3182:
3179:
3177:
3173:
3172:
3170:
3167:
3162:
3158:
3148:
3144:
3143:
3141:
3139:
3135:
3129:
3126:
3124:
3120:
3119:
3116:
3113:
3111:
3108:
3106:
3105:oteseconazole
3103:
3101:
3098:
3096:
3095:isavuconazole
3093:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3072:
3071:
3068:
3065:
3063:
3060:
3058:
3057:efinaconazole
3054:
3053:
3051:
3049:
3045:
3038:
3037:
3034:
3031:
3029:
3026:
3024:
3023:sertaconazole
3021:
3019:
3016:
3014:
3011:
3009:
3006:
3004:
3001:
2999:
2996:
2994:
2991:
2989:
2986:
2984:
2981:
2979:
2978:fenticonazole
2976:
2974:
2971:
2969:
2966:
2964:
2961:
2959:
2956:
2954:
2951:
2949:
2948:chlormidazole
2946:
2944:
2941:
2939:
2935:
2934:
2932:
2930:
2926:
2923:
2920:
2914:
2910:
2907:
2903:
2899:
2896:
2890:
2885:
2881:
2877:
2870:
2865:
2863:
2858:
2856:
2851:
2850:
2847:
2837:
2833:
2829:
2825:
2821:
2817:
2813:
2809:
2801:
2798:
2793:
2789:
2785:
2781:
2777:
2773:
2769:
2765:
2758:
2755:
2742:
2738:
2732:
2729:
2716:
2712:
2706:
2703:
2698:
2694:
2690:
2684:
2680:
2673:
2670:
2665:
2659:
2651:
2645:
2641:
2637:
2633:
2632:
2624:
2622:
2618:
2613:
2609:
2605:
2601:
2597:
2593:
2586:
2583:
2578:
2572:
2568:
2564:
2557:
2554:
2549:
2547:9780781765619
2543:
2539:
2532:
2529:
2524:
2520:
2516:
2512:
2508:
2504:
2497:
2494:
2489:
2485:
2480:
2475:
2471:
2467:
2463:
2459:
2455:
2448:
2445:
2430:
2426:
2422:
2418:
2414:
2410:
2406:
2402:
2398:
2391:
2384:
2381:
2376:
2369:
2366:
2361:
2357:
2353:
2349:
2345:
2341:
2333:
2330:
2320:
2316:
2310:
2307:
2302:
2298:
2294:
2290:
2286:
2282:
2281:J. Chem. Educ
2275:
2272:
2268:
2265:From p. 205:
2255:
2251:
2247:
2243:
2239:
2238:
2233:
2226:
2223:
2218:
2214:
2209:
2204:
2200:
2196:
2192:
2188:
2184:
2177:
2174:
2162:
2158:
2154:
2150:
2147:
2143:
2139:
2135:
2131:
2128:
2122:
2119:
2114:
2110:
2106:
2102:
2098:
2094:
2090:
2086:
2079:
2076:
2071:
2065:
2061:
2054:
2051:
2046:
2040:
2036:
2029:
2026:
2021:
2015:
2011:
2004:
2001:
1996:
1990:
1986:
1979:
1976:
1971:
1965:
1961:
1957:
1951:
1948:
1935:
1931:
1927:
1921:
1918:
1906:
1902:
1898:
1892:
1889:
1884:
1880:
1876:
1872:
1865:
1862:
1857:
1851:
1847:
1843:
1839:
1836:. Cambridge:
1835:
1828:
1825:
1819:
1814:
1811:
1809:
1806:
1804:
1801:
1800:
1796:
1794:
1792:
1781:
1776:
1773:
1770:
1766:
1763:
1761:
1757:
1754:
1752:
1748:
1745:
1743:in position 1
1742:
1739:
1735:
1732:
1729:
1725:
1722:
1719:
1715:
1714:Benzimidazole
1712:
1711:
1707:
1705:
1691:
1687:
1683:
1679:
1678:ionic liquids
1675:
1671:
1667:
1663:
1659:
1650:
1643:
1641:
1638:
1636:
1627:
1625:
1623:
1619:
1616:
1612:
1608:
1605:
1599:
1591:
1586:
1585:agrichemicals
1582:
1578:
1574:
1572:
1568:
1564:
1560:
1556:
1548:
1546:
1544:
1543:
1538:
1534:
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1528:
1524:
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1500:
1498:
1494:
1490:
1486:
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1479:
1471:
1469:
1467:
1463:
1459:
1458:pharmacophore
1455:
1451:
1447:
1442:
1440:
1436:
1432:
1428:
1424:
1420:
1416:
1415:antiprotozoal
1412:
1408:
1403:
1401:
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1393:
1389:
1384:
1382:
1378:
1374:
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1327:
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1234:
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1182:
1178:
1170:
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1160:
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1121:
1116:
1114:
1110:
1106:
1102:
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1084:
1080:
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1076:
1072:
1068:
1064:
1060:
1052:
1050:
1048:
1041:
1034:
1029:
1025:
1019:
1016:Imidazole is
1011:
1004:
1000:
999:
998:
996:
992:
988:
984:
981:of 3.67
980:
976:
972:
964:
962:
961:(1857–1935).
960:
955:
953:
949:
945:
940:
938:
934:
930:
926:
922:
918:
906:
901:
899:
895:
891:
887:
884:
880:
864:
860:
848:
841:
836:
819:
813:
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807:
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803:
777:
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770:
769:
755:
752:
748:
747:
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741:
738:
734:
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729:
724:
719:
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712:
708:
707:
703:
701:
696:
692:
687:
686:
682:
681:
676:
671:
668:
664:
661:
660:Dipole moment
657:
656:
652:
649:
645:
644:
641:
638:
635:
631:
630:
625:
621:
614:
611:
610:
606:
602:
596:
592:
589:
588:
584:
581:
577:
576:
572:
570:
569:Boiling point
567:
566:
562:
560:
559:Melting point
557:
556:
552:
550:
547:
546:
542:
539:
538:
534:
532:
529:
528:
512:
509:
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434:DTXSID2029616
431:
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318:
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303:
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298:
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288:
284:
281:
279:
277:ECHA InfoCard
274:
273:
266:
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261:
259:
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254:
253:
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80:
76:
71:
67:
66:
62:
52:
48:
43:
39:
38:
34:
19:
3550:tea tree oil
3535:lemon myrtle
3448:ethylparaben
3378:griseofulvin
3239:Benzylamines
3128:ravuconazole
3123:albaconazole
3115:voriconazole
3110:posaconazole
3100:itraconazole
3090:hexaconazole
3008:neticonazole
2998:luliconazole
2993:ketoconazole
2983:flutrimazole
2968:eberconazole
2958:clotrimazole
2943:butoconazole
2928:
2811:
2807:
2800:
2767:
2763:
2757:
2745:. Retrieved
2731:
2719:. Retrieved
2705:
2678:
2672:
2629:
2595:
2591:
2585:
2566:
2556:
2537:
2531:
2509:(1): 79–86.
2506:
2503:J. Neurosurg
2502:
2496:
2461:
2457:
2447:
2436:. Retrieved
2400:
2396:
2383:
2374:
2368:
2343:
2339:
2338:chlorides".
2332:
2309:
2287:(11): 1658.
2284:
2280:
2274:
2266:
2258:. Retrieved
2241:
2235:
2225:
2190:
2186:
2176:
2160:
2156:
2141:
2137:
2121:
2088:
2084:
2078:
2059:
2053:
2034:
2028:
2009:
2003:
1984:
1978:
1959:
1950:
1938:. Retrieved
1929:
1920:
1909:. Retrieved
1901:molekula.com
1900:
1891:
1874:
1871:J. Org. Chem
1870:
1864:
1833:
1827:
1785:
1730:is saturated
1690:imidazolates
1655:
1639:
1631:
1601:
1563:clotrimazole
1555:enilconazole
1552:
1540:
1530:
1520:
1512:voriconazole
1508:itraconazole
1501:
1497:clotrimazole
1489:ketoconazole
1475:
1454:inflammation
1446:clotrimazole
1443:
1441:activities.
1423:theophylline
1404:
1385:
1359:
1339:
1315:
1302:= hydrogen.
1277:
1253:
1215:
1213:
1174:
1134:
1120:Debus method
1117:
1101:benzaldehyde
1090:
1074:
1067:formaldehyde
1056:
1039:
1032:
1023:
1015:
968:
956:
941:
902:
861:(ImH) is an
858:
857:
742:
699:
689:Main hazards
678:
594:
370:RTECS number
132:Identifiers
122:Other names
112:
3590:from market
3569:pentamidine
3530:lemon grass
3488:taurolidine
3458:polynoxylin
3359:flucytosine
3303:caspofungin
3227:terbinafine
3213:Allylamines
3075:fluconazole
3067:terconazole
3062:fluconazole
3033:tioconazole
3028:sulconazole
3018:oxiconazole
3013:omoconazole
2988:isoconazole
2963:croconazole
2921:inhibitors)
2919:demethylase
2876:Antifungals
2417:10261/87090
1940:17 February
1926:"Imidazole"
1897:"Imidazole"
1813:Imidazoline
1728:double bond
1670:protonation
1504:fluconazole
1155:= hydrogen.
1053:Preparation
1012:Amphoterism
991:π-electrons
954:in nature.
952:heterocycle
933:antibiotics
886:heterocycle
806:Flash point
737:Signal word
683:(OHS/OSH):
540:Appearance
501:Properties
283:100.005.473
205:CHEBI:16069
124:1,3-Diazole
3627:Imidazoles
3621:Categories
3559:atovaquone
3540:orange oil
3503:tolnaftate
3498:tolciclate
3483:sulbentine
3453:haloprogin
3433:ciclopirox
3398:tavaborole
3390:inhibitors
3376:Systemic:
3357:Systemic:
3318:rezafungin
3313:micafungin
3308:cilofungin
3292:Systemic:
3286:inhibitors
3269:amorolfine
3248:butenafine
3205:inhibitors
3189:Systemic:
3166:ergosterol
3073:Systemic:
3003:miconazole
2953:climbazole
2938:bifonazole
2929:Imidazoles
2905:inhibitors
2902:Ergosterol
2438:2018-07-24
2260:2016-10-01
1911:2018-10-19
1820:References
1604:His-tagged
1581:Prochloraz
1571:bifonazole
1567:prochloraz
1559:climbazole
1535:, as does
1493:miconazole
1481:infections
1411:antifungal
1407:fungicides
1402:reaction.
1381:hemoglobin
1369:side-chain
1362:amino acid
1280:photolysis
1143:or α-amino
1018:amphoteric
971:tautomeric
944:pyrimidine
931:series of
711:Pictograms
693:Corrosive
640:Monoclinic
627:Structure
531:Molar mass
395:7GBN705NH1
236:ChemSpider
160:3D model (
139:CAS Number
115:-Imidazole
31:Imidazole
3632:Alkaloids
3600:Phase III
3588:Withdrawn
3545:patchouli
3493:ticlatone
3396:Topical:
3267:Topical:
3246:Topical:
3222:naftifine
3220:Topical:
3193:, hamycin
3181:natamycin
3174:Topical:
3147:abafungin
3145:Topical:
3138:Thiazoles
3121:Unknown:
3055:Topical:
3048:Triazoles
2973:econazole
2936:Topical:
2828:0022-3263
2784:0731-7085
2612:135799368
1775:Triazoles
1396:urticaria
1392:histamine
1365:histidine
1318:formamide
1220:formamide
1093:microwave
995:resonance
937:midazolam
921:histamine
917:histidine
905:alkaloids
896:atoms in
859:Imidazole
799:P308+P313
791:P301+P310
702:labelling
406:UN number
377:NI3325000
304:206-019-2
296:EC Number
225:ChEMBL540
3443:dimazole
3186:nystatin
3168:binding)
2894:membrane
2836:22409592
2741:Archived
2715:Archived
2697:11865673
2523:16121977
2429:Archived
2425:18477512
2254:Archived
2149:Archived
2130:Archived
2113:12416667
2105:17191854
1934:Archived
1905:Archived
1797:See also
1769:nitrogen
1765:Pyrazole
1756:Thiazole
1738:nitrogen
1674:nitrogen
1662:chloride
1607:proteins
1435:leukemia
1400:allergic
1373:proteins
1350:aldimine
1326:platinum
1193:platinum
1185:aldehyde
1141:aldehyde
1047:pyridine
987:aromatic
975:nitrogen
894:nitrogen
883:aromatic
879:alkaline
673:Hazards
585:633 g/L
256:DrugBank
149:288-32-4
3564:dapsone
3176:hamycin
2792:8851751
2488:7518297
2479:1910171
2348:Bibcode
2289:Bibcode
2217:3522351
2195:Bibcode
1747:Oxazole
1734:Pyrrole
1718:benzene
1666:nitrate
1527:keratin
1377:enzymes
1348:and an
1330:alumina
1197:alumina
1181:alcohol
1137:imidate
1113:lophine
1105:ammonia
1091:In one
1071:ammonia
1063:glyoxal
890:diazole
840:what is
838: (
622:206 nm
591:Acidity
549:Density
525:
346:PubChem
265:DB03366
190:103853
3583:WHO-EM
3411:Others
3261:Others
2913:Azoles
2834:
2826:
2790:
2782:
2747:13 May
2721:13 May
2695:
2685:
2646:
2610:
2573:
2544:
2521:
2486:
2476:
2423:
2325:
2317:,
2215:
2111:
2103:
2066:
2041:
2016:
1991:
1966:
1852:
1782:Safety
1760:sulfur
1751:oxygen
1658:cation
1615:nickel
1569:, and
1510:, and
1495:, and
1478:fungal
1417:, and
1346:TosMIC
1177:alkane
1145:acetal
1097:benzil
1069:, and
948:purine
927:, the
835:verify
832:
743:Danger
613:UV-vis
492:c1cnc1
485:SMILES
334:C01589
216:ChEMBL
101:Names
2892:Wall/
2608:S2CID
2432:(PDF)
2393:(PDF)
2213:S2CID
2109:S2CID
1771:atoms
1686:anion
1187:, or
765:H360D
665:3.61
453:InChI
410:3263
319:1417
196:ChEBI
162:JSmol
2882:and
2832:PMID
2824:ISSN
2788:PMID
2780:ISSN
2749:2021
2723:2021
2693:OCLC
2683:ISBN
2664:link
2644:ISBN
2571:ISBN
2542:ISBN
2519:PMID
2484:PMID
2421:PMID
2101:PMID
2064:ISBN
2039:ISBN
2014:ISBN
1989:ISBN
1964:ISBN
1942:2024
1850:ISBN
1741:atom
1720:ring
1618:ions
1464:and
1409:and
1375:and
1340:The
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1103:and
787:P280
783:P270
779:P263
761:H314
757:H302
386:UNII
325:KEGG
3555:PCP
2884:J02
2880:D01
2816:doi
2772:doi
2636:doi
2600:doi
2511:doi
2507:103
2474:PMC
2466:doi
2462:111
2413:hdl
2405:doi
2356:doi
2297:doi
2246:doi
2242:107
2203:doi
2161:249
2093:doi
1879:doi
1842:doi
1704:).
1664:or
1609:in
1439:DNA
1390:to
1328:on
1298:= R
1294:= R
1282:of
1226:= R
1195:on
1151:= R
1107:in
700:GHS
617:max
607:)
422:EPA
359:795
349:CID
245:773
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1027:a
1024:K
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