Convenient synthesis of a library of lactam-fused β-carbolines via the Ugi reaction

Synthesis

Volumn , Issue 3, 2011, Pages 419-430

  Hutait, Samiran ^a   Nayak, Maloy ^a   Penta, Ashok ^a   Batra, Sanjay ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

carbolines; multicomponent reactions; Ugi reaction

Indexed keywords

CARBOLINES; CHEMICAL LIBRARIES; ISONITRILES; MULTI-COMPONENT REACTIONS; THREE COMPONENT REACTIONS; UGI REACTION;

ACETIC ACID; PH; PYRIDINE;

SYNTHESIS (CHEMICAL);

BETA CARBOLINE DERIVATIVE; LACTAM; METHYL 4 [(2 CYANO 3 PHENYLALLYL)CARBAMOYL] 5 (4 METHOXYPHENYL) 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(2 CYANO 3 PHENYLALLYL)CARBAMOYL] 6 OXO 5 (2 PHENYLETHYL) 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 5 (4 METHOXYPHENYL) 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 5 (FURAN 2 YLMETHYL) 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 5 (METHOXYCARBONYLMETHYL) 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 5 (2 PHENYLETHYL) 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 5 PHENYL 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 5 PROPYL 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 (3 HYDROXYPROPYL) 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 (4 CHLOROPHENYL) 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 (4 CHLOROPHENYL) 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 (4 METHOXYPHENYL) 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 (FURAN 2 YLMETHYL) 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 (METHOXYCARBONYLMETHYL) 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 ALLYL 4 [(2 CYANO 3 PHENYLALLYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 ALLYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 ALLYL 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 BENZYL 4 [(2 CYANO 3 PHENYLALLYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 BENZYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 BENZYL 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 CYCLOHEXYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 CYCLOHEXYL 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 CYCLOPROPYL 4 [(ETHOXYCARBONYLMETHYL)CARBAMOYL] 6 OXO 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 5 CYCLOPROPYL 6 OXO 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 6 OXO 5 (2 PHENYLETHYL) 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 6 OXO 5 PHENYL 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; METHYL 6 OXO 5 PROPYL 4 [(4 TOLYLSULFONYLMETHYL)CARBAMOYL] 4,5,6,7 TETRAHYDRO 3,5,7A TRIAZACYCLOHEPTA[JK]FLUORENE 2 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; DRUG SYNTHESIS;

EID: 79151486106     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258374     Document Type: Article

References (31)

1. Selected references only:, Cao R, Peng W, Wang Z, Xu A, Curr. Med. Chem. 2007 14 479; and references cited therein
2. Cao R, Guan X, Shi B, Chen Z, Ren Z, Peng W, Song H, Eur. J. Med. Chem. 2010 45 2503
3. Ma C, Cao R, Shi B, Li S, Chen Z, Yi W, Peng W, Ren Z, Song H, Eur. J. Med. Chem. 2010 45 1515
4. Chen Z, Cao R, Shi B, Yi W, Yu L, Song H, Ren Z, Peng W, Bioorg. Med. Chem. Lett. 2010 20 3876
5. Wu Q, Cao R, Feng M, Guan X, Ma C, Liu J, Song H, Peng W, Eur. J. Med. Chem. 2009 44 533
6. Kumar R, Gupta L, Pal P, Khan S, Singh N, Katiyar S B., Meena S, Sarkar J, Sinha S, Kanaujiya J K., Lochab S, Trivedi A K., Chauhan P M. S., Eur. J. Med. Chem. 2010 45 2265
7. Wu J, Zhao M, Qian K, Lee K H., Morris-Natschke S, Peng S, Eur. J. Med. Chem. 2009 44 4153
8. Rook Y, Schmidtke K U., Gaube F, Schepmann D, Wunsch B, Heilmann J, Lehmann J, Winckler T, J. Med. Chem. 2010 53 3611
9. Jiao W H., Gao H, Li C Y., Zhao F, Jiang R W., Wang Y, Zhou G X., Yao X S., J. Nat. Prod. 2010 73 167
10. Inman W D., Bray W M., Gassner N C., Lokey R S., Tenney K, Shen Y Y., TenDyke K, Suh T, Crews P, J. Nat. Prod. 2010 73 255
11. Soriano-Agaton F, Lagoutte D, Poupon E, Roblot F, Fournet A, Gantier J C., Hocquemiller R, J. Nat. Prod. 2005 68 1581
12. Kuo P C., Shi L S., Damu A G., Su C R., Huang C H., Ke C H., Wu J B., Lin A J., Bastow K F., Lee K H., Wu T S., J. Nat. Prod. 2003 66 1324
13. Anderson L A., Harris A, Phillipson J D., J. Nat. Prod. 1983 46 374
14. Rowinsky E K., Donehower R C., In Cancer Chemotherapy and Biotherapy Chabner B A. Longo D L. Lippincott-Raven Publishers Philadelphia 1996 263
15. Singh V, Hutait S, Batra S, Eur. J. Org. Chem. 2009 6211
16. Singh V, Hutait S, Biswas S, Batra S, Eur. J. Org. Chem. 2010 531
17. Singh V, Hutait S, Batra S, Eur. J. Org. Chem. 2010 3684
18. Hutait S, Singh V, Batra S, Eur. J. Org. Chem. 2010 6269
19. Hutait S, Batra S, Tetrahedron Lett. 2010 51 5781
20. Dmling A, Ugi I, Angew. Chem. Int. Ed. 2000 39 3168
21. Nair V, Rajesh C, Vinod A U., Bindu S, Sreekanth A R., Mathen J S., Balagopal L, Acc. Chem. Res. 2003 36 899
22. Dmling A, Chem. Rev. 2006 106 17
23. Multicomponent Reactions Zhu J Bienaym H Wiley-VCH Weinheim 2005
24. Lamberth C, Jeanguenat A, Cederbaum F, De Mesmaeker A, Zeller M, Kempf H.-J, Zeun R, Bioorg. Med. Chem. 2008 16 1531
25. Toure B B., Hall D G., Chem. Rev. 2009 109 4439
26. Zhang J, Jacobson A, Rusche J R., Herlihy W, J. Org. Chem. 1999 64 1074
27. Potapov V V., Fetisova N A., Nikitin A V., Ivachtchenko A V., Tetrahedron Lett. 2009 50 2790; and references cited therein
28. Ilyn A P., Trifilenkov A S., Kuzovkova J A., Kutepov S A., Nikitin A V., Ivachtchenko A V., J. Org. Chem. 2005 70 1478
29. Ghandi M, Zarezadeh N, Taheri A, Tetrahedron 2010 66 8231
30. Nayak M, Kanojiya S, Batra S, Synthesis 2009 431
31. Nayak M, Batra S, Tetrahedron Lett. 2010 51 510