Stereospecific synthesis of a novel azetido[2,1-c][1,4]benzodiazepine (ABD) ring system with DNA recognition potential

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5839-5842

  Bose, D Subhas ^a   Srinivas, P ^a   Gurjar, M K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; AZETIDO[2,1 C][1,4]BENZODIAZEPINE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DNA BINDING; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0003586598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01297-5     Document Type: Article

References (20)

1. a) Hurley, L.H.; Boyd, F.L. Trends Pharmacol. Sci. 1988, 9, 402.
2. (b) Hurley, L.H. J. Med. Chem. 1989, 32, 2027.
3. (c) Thurston, D.E.; Thompson, A.S. Chem. Br. 1990, 26, 767.
4. Thurston, D.E. Advances in the study of Pyrrolo[2,1-c]]1,4]-benzodiazepine (PBD) Antitumor Antibiotics. In Molecular Aspects of Anticancer Drug-DNA Interactions; Neidle, S. Waring. M.J., Eds.; Macmillan Press Ltd: Basingstoke, Hants, U.K., 1993, vol.1, pp 54-88.
5. (a) Hurley, L.H.; Reck, T.; Thurston, D.E.; Langley, D.R.; Holden, K.G.; Hertzberg, R.P.; Hoover, J.R.E.; Gallagher, G.; Jr. Faucette, L.F.; Mong, S.-M.; Johnson, R.K. Chem. Res. Toxicol. 1988, 1, 258.
6. (b) Hertzberg, R.P.; Hecht, S.M.; Reynolds, V.L.; Molineux, I.J.; Hurley, I.H. Biochemistry 1986, 25, 1249.
7. (a) Puvvada, M.S.; Hartley, J.A.; Jenkins, T.C.; Thurston, D.E. Nucleic Acids Res. 1993, 21, 3671.
8. (b) Puvvada, M.S.; Forrow, S.A.; Hartley, J.A.; Stephenson, P.; Gibson, I.; Jenkins, T.C.; Thurston, D.E. Biochemistry, 1997, 36, 2478.
9. Thurston, D.E.; Bose, D.S. Chem. Rev. 1994, 94, 433.
10. (a) Bose, D.S.; Thompson, A.S.; Ching, J.A.; Hartley, J.A.; Berardini, M.D.; Jenkins, T.C.; Neidle, S.; Hurley, L.H.; Thurston, D.E. J. Am. Chem. Soc. 1992, 114, 4939.
11. (b) Bose, D.S.; Thompson, A.S.; Smellie, M.; Berardini, M.D.; Hartley, J.A.; Jenkins, T.C.; Neidle, S.; Thurston, D.E. J. Chem. Soc., Chem. Commun. 1992, 1518.
12. (c) Thurston, D.E.; Bose, D.S.; Thompson, A.S.; Howard, P.W.; Leoni, A.; Croker, S.J.; Jenkins, T.C.; Neidle, S.; Hartley, J.A.; Hurley, L.H. J. Org.Chem. 1996, 61, 8141.
13. (a) Thurston, D.E.; Murty, V.S.; Langley, D.R.; Jones, G.B. Synthesis 1990, 81.
14. (b) Bose, D.S.; Jones, G.B.; Thurston, D.E. Tetrahedron 1992, 48, 751.
15. Prepared according to Rama Rao, A.V.; Gurjar, M.K.; Kaiwar, V. Tet. Asymm. 1992, 3, 859.
16. (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett., 1994, 35, 8019.
17. (b) Gurjar, M.K.; Henry, Jr. J.T.; Bose, D.S.; Rama Rao, A.V. Tetrahedron Lett., 1996, 37, 6605.
18. Peterson, M.L.; Vince, R. J. Med. Chem. 1991, 34, 2787.
19. O'Neil, I.A.; Murray, C.L.; Hunter, R.C.; Kalindjian, S.B.; Jenkins, T.C. Syn. Lett., 1997, 75.
20. +, 10%), 264(100), 220(30), 174(15), 130(48), 117(74), 91(66), 43(98).