263:
57:
48:
608:
419:
414:
35:
539:
619:
613:
Vince lactam is also an intermediate in the synthesis of various nucleoside analogs such as difluoro guanosine derivatives (V), carbocyclic oxanosine and related derivatives (VI), and precursors for azidocarbonucleosides (VII). The lactam has found several applications in targeting an array of
618:
602:
Vince lactam has been extensively used for the preparation of various carbocyclic nucleosides with medicinal applications in mind, including carbocyclic puromycin (I), carbocyclic Ara-A (II), carbovir (III) and guanine as well as azaguanine carbocyclic derivatives (IV)
582:
2-azabicyclohept-5-en-3-one. This lactam is a versatile chemical intermediate used in organic and medicinal chemistry. It is used as a synthetic precursor for three drugs (approved or in clinical trials). It is named after
614:
different diseased conditions by providing various non-nucleoside therapeutic molecules as well. Some well known examples include scaffolds for the preparation of glycosidase inhibitors (VIII) and GABA-AT inhibitors (IX).
427:
394:
607:
497:
552:
1000:
320:
647:(8), pp 4642–4686."2-Azabicyclohept-5-en-3-one: Chemical Profile of a Versatile Synthetic Building Block and its Impact on the Development of Therapeutics"
285:
137:
489:
995:
145:
485:
559:
463:
513:
481:
241:
418:
185:
584:
706:
413:
911:
Saito, Y.; Nakamura, M.; Ohno, T.; Chaicharoenpong, C.; Ichikawa, E.; Yamamura, S.; Kato, K.; Umezawa, K.
588:
441:
406:
501:
258:
75:
271:
658:
477:
93:
469:
56:
47:
743:
575:
174:
166:
990:
751:
348:
104:
505:
112:
493:
262:
517:
530:
984:
304:(1R,4S): InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1
294:(1S,4R): InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
221:
521:
229:
473:
451:
755:
702:
376:
156:
587:
who has used the structural features of this molecule for the preparation of
596:
17:
34:
592:
455:
663:
207:
186:
579:
529:
Except where otherwise noted, data are given for materials in their
447:
591:. Vince's work with this lactam eventually led to his synthesis of
144:
136:
125:
741:"Synthesis of carbovir and abacavir from a carbocyclic precursor"
891:
Toyota, A.; Aizawa, M.; Habutani, C.; Katagiri, N.; Kaneko, C.
599:
synthesis is also dependent on Vince lactam starting material.
509:
246:
55:
46:
547:
871:Toyota, A.; Habutani, C.; Katagiri, N.; Kaneko, C.
228:
220:
111:
103:
931:Kiss, L.; Forro, E.; Sillanpaa, R.; Fulop, F.
769:"A brief history of the development of Ziagen"
746:in nucleic acid chemistry Ed. Beaucage, S. L.
8:
659:"Simplifying Syntheses Is Always A Key Goal"
261:
173:
165:
26:
630:
325:
290:
270:
257:
307:Key: DDUFYKNOXPZZIW-UHNVWZDZSA-N
297:Key: DDUFYKNOXPZZIW-CRCLSJGQSA-N
7:
790:Vince, R.; Daluge, S.; Brownell, J.
574:is the commercial name given to the
1001:Heterocyclic compounds with 2 rings
210:
25:
947:Rommel, M.; Ernst, A.; Koert, U.
617:
606:
537:
417:
412:
366:
360:
33:
533:(at 25 °C , 100 kPa).
657:Rouhi, A. M. (July 14, 2003).
369:
354:
1:
756:10.1002/0471142700.nc1404s25
328:(1S,4R): O=C1N2\C=C/1C2
963:Mineno, T.; Miller, M,. J.
851:Peterson, M. L.; Vince, R.
80:2-Azabicyclohept-5-en-3-one
42:
1017:
333:(1R,4S): C12C=C1NC2=O
750:, Chapter 14 Unit 14.4.
527:
393:
388:
341:
316:
281:
86:
74:
69:
41:
32:
705:Center for Drug Design,
464:Precautionary statements
707:University of Minnesota
589:carbocyclic nucleosides
198:(1R,4S): 418-530-1
195:(1S,4R): 627-840-6
810:Daluge, S.; Vince, R.
719:Daluge, S.; Vince, R.
60:
51:
996:Nitrogen heterocycles
703:"Robert Vince, Ph.D."
637:Singh, R.; Vince, R.
59:
50:
831:Vince, R.; Hua, M.
76:Preferred IUPAC name
739:Vince, R.; Hua, M.
681:Holt-Tiffin, K. E.
384: g·mol
29:
949:Eur. J. Org. Chem.
560:Infobox references
61:
52:
27:
873:Tetrahedron Lett.
744:Current Protocols
576:bicyclic molecule
568:Chemical compound
566:
565:
442:Hazard statements
242:CompTox Dashboard
146:Interactive image
138:Interactive image
65:
64:
16:(Redirected from
1008:
975:
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349:Chemical formula
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555: ?)
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259:DTXSID401336090
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129:
118:
96:
82:
81:
23:
22:
15:
12:
11:
5:
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1004:
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993:
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913:J. Antibiotics
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531:standard state
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498:P305+P351+P338
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272:DTXSID10369337
269:(1R,4S):
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24:
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10:
9:
6:
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3:
2:
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1002:
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994:
992:
989:
988:
986:
973:
969:
966:
965:J. Org. Chem.
960:
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944:
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868:
865:
861:
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853:J. Med. Chem.
848:
845:
841:
837:
834:
833:J. Med. Chem.
828:
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821:
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813:
812:J. Org. Chem.
807:
804:
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792:J. Med. Chem.
787:
784:
780:
776:
773:
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764:
761:
757:
753:
749:
745:
742:
736:
733:
730:, 2311-2320.
729:
725:
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721:J. Org. Chem.
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28:Vince lactam
19:
974:, 6591-6596.
971:
967:
964:
959:
954:, 4408-4430.
951:
948:
943:
935:
932:
927:
919:
915:
912:
907:
902:, 8783-8798.
899:
895:
892:
887:
882:, 5665-5668.
879:
875:
872:
867:
862:, 1214-1219.
859:
855:
852:
847:
839:
835:
832:
827:
822:, 2311-2320.
819:
815:
811:
806:
798:
794:
791:
786:
778:
774:
771:
768:
763:
747:
740:
735:
727:
723:
720:
715:
697:
689:
685:
683:Chimica Oggi
682:
677:
668:
662:
652:
644:
641:
638:
633:
616:
612:
605:
601:
585:Robert Vince
572:Vince lactam
571:
570:
433:
395:
87:Identifiers
18:Vince Lactam
893:Tetrahedron
428:Signal word
342:Properties
105:130931-83-8
985:Categories
938:, 153-160.
922:, 309-313.
781:, 127-134.
772:Chemtracts
767:Vince, R.
639:Chem. Rev.
625:References
407:Pictograms
377:Molar mass
157:ChemSpider
124:3D model (
113:79200-56-9
94:CAS Number
933:Synthesis
671:(28): 40.
597:Peramivir
514:P333+P313
494:P302+P352
490:P301+P312
398:labelling
187:EC Number
692:, 23-25.
664:C&EN
593:abacavir
389:Hazards
222:11789150
991:Lactams
801:, 2400.
553:what is
551: (
382:109.128
230:2725037
208:PubChem
175:9963824
167:2007146
580:lactam
548:verify
545:
434:Danger
321:SMILES
70:Names
842:, 17.
642:2012,
286:InChI
126:JSmol
968:2003
952:2007
936:2010
916:2000
896:1995
876:1994
856:1990
836:1990
816:1978
795:1986
775:2008
748:2006
724:1978
686:2009
522:P501
518:P363
510:P330
506:P321
502:P310
486:P280
482:P272
478:P270
474:P264
470:P261
456:H318
452:H317
448:H302
752:doi
645:112
396:GHS
247:EPA
211:CID
987::
972:68
970:,
920:53
918:,
900:36
898:,
880:35
878:,
860:33
858:,
840:33
838:,
820:43
818:,
814:,
799:29
797:,
779:21
777:,
728:43
726:,
690:27
688:,
669:80
667:.
661:.
595:.
578:γ-
520:,
516:,
512:,
508:,
504:,
500:,
496:,
492:,
488:,
484:,
480:,
476:,
472:,
454:,
450:,
400::
758:.
754::
709:.
543:N
370:O
367:N
364:7
361:H
358:6
355:C
249:)
245:(
128:)
20:)
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