Efficient synthesis of naturally occurring skeleton 5-7-6 tricyclic pyrrolo[2,1- c ][1,4]benzodiazepin-5-one and its derivatives via cationic π-cyclization

Synthesis

Volumn , Issue 23, 2010, Pages 4087-4095

  Sharma, Sudhir K ^a   Mandadapu, Anil K ^a   Kumaresan, K ^a   Arora, Ashish ^a   Gauniyal, Harsh M ^a   Kundu, Bijoy ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

cyclization; antibiotics; oxidation; pyrrole; reduction

Indexed keywords

EFFICIENT METHOD; EFFICIENT SYNTHESIS; NATURALLY OCCURRING; PYRROLE;

ANTIBIOTICS; NITROGEN COMPOUNDS; OXIDATION;

CYCLIZATION;

11 (2,3 DICHLOROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 11 (4 BROMOPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 11 (4 CHLOROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 11 (4 CHLOROPHENYL) 7 METHYL 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 11 (4 FLUOROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 4 (9 CHLORO 5 OXO 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 11 YL)BENZONITRILE; 5 7 6 TRICYCLIC PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 5 7 6 TRICYCLIC PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE DERIVATIVE; 7 CHLORO 11 (4 NITROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 7 METHYL 11 (4 NITROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 8 CHLORO 11 (4 NITROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 9 CHLORO 11 (3,4 DICHLOROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; 9 CHLORO 11 (4 NITROPHENYL) 5H PYRROLO[2,1 C][1,4]BENZODIAZEPIN 5 ONE; BENZODIAZEPINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; REACTION ANALYSIS; REDUCTION;

EID: 78650185335     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258277     Document Type: Article

References (63)

1. Jetze J T., Curr. Bioact. Compd. 2009 5 1
2. Kaiser M, Wetzel S, Kumar K, Waldmann H, Cell. Mol. Life Sci. 2008 65 1186
3. Newman D J., Cragg G M., J. Nat. Prod. 2007 70 461
4. Nren-Müller A, Reis-Corrpa I, Prinz H Jr., Rosenbaum C, Saxena K, Schwalbe H, Vestweber D, Cagna G, Schunk S, Schwarz O, Schiewe H, Waldmann H, Proc. Natl. Acad. Sci. U.S.A. 2006 103 10606
5. Koch M A., Schuffenhauer A, Scheck M, Wetzel S, Casaulta M, Odermatt A, Ertl P, Waldmann H, Proc. Natl. Acad. Sci. U.S.A. 2005 102 17272
6. Shang S, Tan D S., Curr. Opin. Chem. Biol. 2005 9 248
7. Frank R, Curr. Opin. Biotechnol. 2004 15 573
8. Schreiber S L., Science 2000 287 1964
9. Liu D R., Schultz P G., Angew. Chem., Int. Ed. Engl. 1999 38 36
10. Nicolaou K C., Pfefferkorn J A., Roecker A J., Cao G Q., Barluenga S, Mitchell H J., J. Am. Chem. Soc. 2000 122 9939
11. Hong B C., Nimje R Y., Curr. Org. Chem. 2006 10 2191
12. Brown J M., Cooley N A., Chem. Rev. 1988 88 1031
13. Agarwal P K., Sawant D, Sharma S, Kundu B, Eur. J. Org. Chem. 2009 2 292
14. Mandadapu A K., Saifuddin M, Agarwal P K., Kundu B, Org. Biomol. Chem. 2009 7 2796
15. Agarwal P K., Saifuddin M, Kundu B, Tetrahedron 2010 66 862
16. Komatsu N, Kimura K, Abe S, Kagitani Y, J. Antibiot. 1980 33 54
17. Arima K, Kosaka M, Tamura G, Imanaka H, Sakai H, J. Antibiot. 1972 25 437
18. Shimizu K, Kawamoto I, Tomita F, Morimoto M, Fujimoto K, J. Antibiot. 1982 35 972
19. Brazhnikova M G., Konstantinova N V., Mesentsev A S., J. Antibiot. 1972 25 668
20. Leber J D., Hoover J R. E., Holden K G., Johnson R K., Hecht S M., J. Am. Chem. Soc. 1988 110 2992
21. Mohr N, Budzikiewicz H, Tetrahedron 1982 38 147
22. Rahbaek L, Breinholt J, Frisvad J C., Christophersen C, J. Org. Chem. 1999 64 1689
23. Denny W A., Curr. Med. Chem. 2001 8 533
24. Hadjivassileva T, Thurston D E., Taylor P W., J. Antimicrob. Chemother. 2005 56 513
25. Thurston D E., Br. J. Cancer 1999 80 65
26. Kamal A, Rao M V., Laxman N, Ramesh G, Reddy G S., Curr. Med. Chem.: Anti-Cancer Agents 2002 2 215
27. Antonow D, Barata T, Jenkins T C., Parkinson G N., Howard P W., Thurston D E., Zloh M, Biochemistry 2008 47 11818
28. Kaneko T, Wong H, Doyle T W., J. Antibiot. 1984 37 300
29. Clark R L., Carter K C., Mullen A B., Coxon G D., Owusu-Dapaah G, McFarlane E, DuongThi M D., Grant M H., Tettey J N., Mackay S P., Bioorg. Med. Chem. Lett. 2007 17 624
30. Guaciaro M A., Harrington P M., Karp G M., US 5,438,035 1995; Chem. Abstr. 1995, 123, 191231
31. Fotso S, Zabriskie T M., Proteau P J., Flatt P M., Santosa D A., Sulastri M T., J. Nat. Prod. 2009 72 690
32. Albright J D., Reich M F., Sum F W., Delos S E. G., EP 636,625 1995; Chem. Abstr. 1995, 123, 228225
33. Albright J D., Reich M F., Sum F W., Delos S E. G., US 5,516,774 1996; Chem. Abstr. 1996, 125, 114720
34. Albright J D., Reich M F., Sum F W., Delos S E. G., US 5,733,905 1998; Chem. Abstr. 1998, 128, 2574526
35. Carey F A., Giuliano R M., J. Org. Chem. 1981 46 1366
36. Hu W P., Wang J J., Lin F L., Lin Y C., Lin S R., Hsu M H., J. Org. Chem. 2001 66 2881
37. Gil C, Brase S, Chem. Eur. J. 2005 11 2680
38. Masterson L A., Croker S J., Jenkins T C., Howarda P W., Thurstona D E., Bioorg. Med. Chem. Lett. 2004 14 901
39. Rahbk L, Breinholt J, J. Nat. Prod. 1999 62 904
40. Kitamura T, Sato Y, Mori M, Tetrahedron 2004 60 9649
41. Fabis F, Santos J S. O., Jolivet S F., Rault S, Tetrahedron Lett. 2001 42 5183
42. Gillard A C., Fabis F, Fouchet S J., Rault S, Tetrahedron Lett. 1997 38 2211
43. Kamal A, Rao M V., Reddy B S., Chem. Heterocycl. Compd. (Engl. Transl.) 1998 34 1342
44. Kamal A, Howard P W., Reddy B S. N., Reddy B S. P., Thurston D E., Tetrahedron 1997 53 3223
45. Kraus G A., Melekhov A, Tetrahedron 1998 54 11749
46. Wells G, Martin C R. H., Howard P W., Sands Z A., Laughton C A., Tiberghien A, Woo C K., Masterson L A., Stephenson M J., Hartley J A., Jenkins T C., Shnyder S D., Loadman P M., Waring M J., Thurston D E., J. Med. Chem. 2006 49 5442
47. Thurston D E., Bose D S., Chem. Rev. 1994 94 433
48. Parker K A., Fedynyshyn T H., Tetrahedron Lett. 1979 20 1657
49. Wingler F M., Houben-Weyl 4th ed., Vol. 7/2a Georg Thieme Verlag Stuttgart 1952 581
50. DSilva C, Iqbal R, Synthesis 1996 457
51. Connon S J., Angew. Chem. Int. Ed. 2008 47 1176
52. Soerens D, Sandrin J, Ungemach F, Mokry P, Wu G S., Yamanaka E, Hutchkins L, DiPierro M, Cook J M., J. Org. Chem. 1979 44 535
53. Sandrin D, Soerens J, Mokry P, Cook J M., Heterocycles 1977 6 1133
54. Dai W M., Zhu H J., Hao X J., Tetrahedron Lett. 1996 37 5971
55. Czerwinski K M., Deng L, Cook J M., Tetrahedron Lett. 1994 33 4721
56. Zhang L H., Bi Y Z., Yu F X., Menzia G, Cook J M., Heterocycles 1992 34 517
57. Ungemach F, DiPierro M, Weber R, Cook J M., J. Org. Chem. 1981 46 164
58. Jawdosiuk M, Cook J M., J. Org. Chem. 1984 49 2699
59. Bonnet D, Ganesan A, J. Comb. Chem. 2002 4 546
60. Wang H, Ganesan A, Org. Lett. 1999 1 1647
61. Zawadzka A, Leniewski A, Maurin J K., Wojtasiewicz K, Czarnocki Z, Org. Lett. 2001 3 997
62. Gremmen C, Wanner M J., Koommen G J., Tetrahedron Lett. 2001 42 8885
63. Gremmen C, Willemse B, Wanner M J., Koomen G J., Org. Lett. 2000 2 1955