An efficient synthesis of benzodiazepinyl phosphonates as clostripain inhibitors via FeCl 3 catalyzed four-component reaction

Organic and Biomolecular Chemistry

Volumn 9, Issue 15, 2011, Pages 5407-5413

  Bhattacharya, Asish K ^a   Rana, Kalpeshkumar C ^a   Raut, Dnyaneshwar S ^a   Mhaindarkar, Vaibhav P ^a   Khan, Mohamad I ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ENTITY; CYSTEINE PROTEASE INHIBITORS; DISEASE MODELS; EFFICIENT SYNTHESIS; GAS GANGRENE; GOOD YIELD; ONE POT; PHOSPHONATES; PROTEASE INHIBITION;

ACETONE; AMINO ACIDS; CATALYSIS; ENZYME INHIBITION; MOLECULAR SIEVES; SIEVES;

SYNTHESIS (CHEMICAL);

CHLORIDE; CLOSTRIPAIN; CYSTEINE PROTEINASE; CYSTEINE PROTEINASE INHIBITOR; FERRIC CHLORIDE; FERRIC ION; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

CATALYSIS; CHLORIDES; CYSTEINE ENDOPEPTIDASES; CYSTEINE PROTEINASE INHIBITORS; FERRIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHOSPHONIC ACIDS;

EID: 79960347743     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob01102a     Document Type: Article

References (65)

1. G. H. Posner Chem. Rev. 1986 86 831
2. A. Dömling I. Ugi Angew. Chem., Int. Ed. 2000 39 3168
3. A. Dömling Chem. Rev. 2006 106 17
4. J. P. Zhu Eur. J. Org. Chem. 2003 7 1133
5. R. V. A. Orru M. De Greef Synthesis 2003 1471
6. L. Banfi R. Riva Org. React. 2005 65 1
7. A. Strecker Ann. Chem. Pharm. 1850 91 349
8. A. Hantzsch Justus Liebigs Ann. Chem. 1882 215 1
9. P. Biginelli Ber. Dtsch. Chem. Ges. 1891 24 2962
10. C. Mannich W. Krosche Arch. Pharm. 1912 250 647
11. M. Passerini Gazz. Chim. Ital. 1922 52 126
12. H. Zhou H. Jin S. Ye X. He J. Wu Tetrahedron Lett. 2009 50 4616
13. Z. Miao B. Wang G. Zhang R. Chen Bioorg. Chem. 2006 34 167
14. Q. Ding B. Wang J. Wu Tetrahedron 2007 63 12166
15. A. Alizadeh N. Zohreh L. Zhu Tetrahedron 2009 65 2684
16. D. L. Fox N. R. Whitely R. J. Cohen R. N. Salvatore Synlett 2003 2037
17. H. Schutz, in Benzodiazepines, Springer: Heidelberg, 1982; Vol. 2, pp. 240
18. R. K. Smalley, in Comprehensive Organic Chemistry, ed., D. H. R. Barton, and, W. E. Ollis,, Pergamon, Oxford, 1979; Vol. 4, pp. 600
19. J. K. Landquist, in Comprehensive Heterocyclic Chemistry, ed., A. R. Katritzky, and, C. N. Russ,, Pergamon, Oxford, 1984; Vol. 1, pp. 166
20. A. Chimirri S. Grasso R. Ortana G. Romeo M. Zappala J. Heterocycl. Chem. 1990 27 371
21. M. C. Aversa A. Ferlazzo P. Giannetto F. I. Kohnke Synthesis 1986 3 230
22. K. V. V. Reddy P. S. Rao D. Ashok Synth. Commun. 2000 30 1825
23. R. A. Mane D. B. Ingle Indian J. Chem. Sect. B 1982 21B 973
24. K. P. Jadhav D. B. Ingle Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1983 22B 180
25. R. J. Reddy D. Ashok P. N. Sarma Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1993 32B 404
26. K. Satyanarayana M. N. A. Rao Indian J. Pharm. Sci. 1993 55 230
27. G. DeSarro A. Chimirri A. DeSarro R. Gitto M. Zappala Eur. J. Med. Chem. 1995 30 925
28. K. Vandyck M. D. Cummings O. E. Nyanguile C. W. Boutton S. Vendeville D. McGowan B. Devogelaere K. Amssoms S. Last K. Rombauts A. Tahri P. Lory L. Hu D. A. Beauchamp K. Simmen P. Raboisson J. Med. Chem. 2009 52 4099
29. D. J. Lauffer M. D. Mullican Bioorg. Med. Chem. Lett. 2002 12 1225
30. P. Kafarski B. Leczak Phosphorus, Sulfur Silicon Relat. Elem. 1991 63 193
31. R. Hirschmann A. B. Smith C. M. Taylor P. A. Benkovic S. D. Taylor K. M. Yager P. A. Sprengler S. J. Benkovic Science 1994 265 23
32. A. B. Smith C. M. Taylor S. J. Benkovic R. Hirschmann Tetrahedron Lett. 1994 35 6853
33. F. R. Atherton C. H. Hassall R. W. Lambert J. Med. Chem. 1986 29 29
34. J. G. Allen F. R. Atherton M. J. Hall C. H. Hassal S. W. Holmes R. W. Lambert L. J. Nisbet P. S. Ringrose Nature 1978 272 56
35. J. G. Allen F. R. Atherton M. J. Hall C. H. Hassall R. W. Lambert L. J. Nisbet P. S. Ringrose Antimicrob. Agents Chemother. 1979 15 684
36. F. R. Atherton M. J. Hall C. H. Hassall R. W. Lambert P. S. Ringrose Antimicrob. Agents Chemother. 1979 15 677
37. F. R. Atherton M. J. Hall C. H. Hassall R. W. Lambert W. J. Lloyd P. S. Ringrose Antimicrom. Agents Chemother. 1979 15 696
38. D. Skropeta R. Schwoerer R. R. Schmidt Bioorg. Med. Chem. Lett. 2003 13 3351
39. C. H. Hassall, in Antibiotics, ed., E. F. Hahn,, Springer Verlag: Berlin 1983, Vol VI, 1
40. D. Leung G. Abbenante D. P. Fairlie J. Med. Chem. 2000 43 305
41. H. H. Otto T. Schirmeister Chem. Rev. 1997 97 133
42. S. Hawthorne R. Hamilton B. J. Walker B. Walker Anal. Biochem. 2004 326 273
43. B. Walker S. Wharry R. J. Hamilton S. L. Martin A. Healy B. J. Walker Biochem. Biophys. Res. Commun. 2000 276 1235
44. J. Oleksyszyn J. C. Powers Biochemistry 1991 30 485
45. C. Bergin R. Hamilton B. Walker B. J. Walker Chem. Commun. 1996 1155
46. J. Jozwiak A. Komar E. Jankowska G. Martirosian Enzyme Microb. Technol. 2006 39 28
47. A. M. Gilles B. Keil FEBS Lett. 1984 173 58
48. W. H. Poryper L. W. Cunniivgham W. M. Mitchell J. Biol. Chem. 1971 246 7675
49. C. T. Supuran A. Scozzafava B. W. Clare Med. Res. Rev. 2002 22 329
50. I. R. Lepow; S. Katz J. Pensky L. Pillemer J. Immunol. 1952 69 435
51. J. D. MacLennan I. Mandl E. L. Howes J. Gen. Microbiol. 1958 18 1
52. A. K. Bhattacharya K. C. Rana Tetrahedron Lett. 2008 49 2598
53. A. K. Bhattacharya T. Kaur Synlett 2007 745
54. R. Fazaeli H. Aliyan Appl. Catal., A 2007 331 78
55. M. A. Alibeik I. M. Baltork Z. Zaghaghi B. H. Yousefi Catal. Commun. 2008 9 2496
56. A. Hegedues Z. Hell A. Potor Catal. Lett. 2005 105 3
57. B. V. S. Reddy S. Praveenkumar K. Nagaiah Synthesis 2005 480
58. S.K. De R. A. Gibbs Tetrahedron Lett. 2005 46 1811
59. W. Chen J. Lu Synlett 2005 1337
60. J. Wu F. Xu Z. Zhou Q. Shen Synth. Commun. 2006 36 457
61. R. Hekmatshoar S. Sadjadi S. Shiri M. M. Heravi M. S. Beheshtiha Synth. Commun. 2009 39 2549
62. S. T. Gao W. H. Liu J. J. Ma C. Wang Q. Liang Synth. Commun. 2009 39 3278
63. A. K. Chakraborti R. Gulhane Chem. Commun. 2003 1896
64. S. Chandrasekhar S. J. Prakash V. Jagadeshwar C. Narsihmulu Tetrahedron Lett. 2001 42 5561
65. H. Gusman J. Grogan H. M. Kagan R. F. Troxler F. G. Oppenheim FEBS Lett. 2001 489 97