메뉴 건너뛰기




Volumn 40, Issue 10, 2010, Pages 1411-1417

Facile and efficient one-pot synthesis of β-carbolines

Author keywords

Carboline; One pot; Synthesis

Indexed keywords

1 (1' BUTENYL)BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' BENZOFURYL)BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' FURYL) 6 FUORO BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' INDOLY)BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' NAPHTHYL)BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' PYRIDYL)BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' QUINDYL) 6 METHOXY BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (2' THIOYL) 6 METHOXY BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (4' TRIFUOROMETHYLPHENYL) 6 METHYL BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 (5' ACEOXYLMETHYL 2' FURYL) 7 FUORO BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 CYCLOPENTYL BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 ETHYL BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 ISOPROPYL BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 METHYL BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; 1 N PROPYL BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; BETA CARBOLINE 3 CARBOXYLIC METHYL ESTER; BETA CARBOLINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77951573819     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910903097245     Document Type: Article
Times cited : (8)

References (36)
  • 2
    • 0036852069 scopus 로고    scopus 로고
    • Exudation of fluorescent b-carbolines from Oxalis tuberosa L. roots
    • (b) Bais, H. P.; Park, S. W.; Stermitz, F. R. Exudation of fluorescent b-carbolines from Oxalis tuberosa L. roots. Phytochemistry 2002, 61, 539-543.
    • (2002) Phytochemistry , vol.61 , pp. 539-543
    • Bais, H.P.1    Park, S.W.2    Stermitz, F.R.3
  • 5
    • 4344668984 scopus 로고    scopus 로고
    • Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases
    • (a) Rao, K. V.; Kasanah, N.; Wahyuono, S.; Tekwani, B. L.; Schinazi, R. F.; Hamann, M. T. Three new manzamine alkaloids from a common Indonesian sponge and their activity against infectious and tropical parasitic diseases. J. Nat. Prod. 2004, 67, 1314-1318;
    • (2004) J. Nat. Prod. , vol.67 , pp. 1314-1318
    • Rao, K.V.1    Kasanah, N.2    Wahyuono, S.3    Tekwani, B.L.4    Schinazi, R.F.5    Hamann, M.T.6
  • 6
    • 0035204029 scopus 로고    scopus 로고
    • New cytotoxic N-methylated-b-carboline alkaloids from the marine ascidian eudistoma gilboverde
    • (b) Rashid, M. A.; Gustafson, K. R.; Boyd, M. R. New cytotoxic N-methylated-b-carboline alkaloids from the marine ascidian eudistoma gilboverde. J. Nat. Prod. 2001, 64, 1454-1456.
    • (2001) J. Nat. Prod. , vol.64 , pp. 1454-1456
    • Rashid, M.A.1    Gustafson, K.R.2    Boyd, M.R.3
  • 7
    • 18844367724 scopus 로고    scopus 로고
    • Structure determination of a tetrahydro-b-carboline of arthropod origin: A novel alkaloid-toxin subclass from the web of spider Nephila clavipes
    • (a) Marques, M. R.; Mendes, M. A.; Tormena, C. F.; Souza, B. M.; Cesar, L. M.; Rittner, R.; Palma, M. S. Structure determination of a tetrahydro-b-carboline of arthropod origin: A novel alkaloid-toxin subclass from the web of spider Nephila clavipes. Chem Biodivers. 2005, 2, 525-534;
    • (2005) Chem Biodivers. , vol.2 , pp. 525-534
    • Marques, M.R.1    Mendes, M.A.2    Tormena, C.F.3    Souza, B.M.4    Cesar, L.M.5    Rittner, R.6    Palma, M.S.7
  • 9
    • 0029440852 scopus 로고
    • B-carbolinium cations, endogenous MPP\+ analogs, in the lumbar cerebro-spinal fluid of patients with Parkinson's disease
    • (c) Matsubara, K.; Kobayashi, S.; Kobayashi, Y.; Yamashita, K.; Koide, H.; Hatta, M.; Iwamoto, K.; Tanaka, O.; Kimura, K. b-Carbolinium cations, endogenous MPP\+ analogs, in the lumbar cerebro-spinal fluid of patients with Parkinson's disease. Neurology 1995, 45, 2240-2245;
    • (1995) Neurology , vol.45 , pp. 2240-2245
    • Matsubara, K.1    Kobayashi, S.2    Kobayashi, Y.3    Yamashita, K.4    Koide, H.5    Hatta, M.6    Iwamoto, K.7    Tanaka, O.8    Kimura, K.9
  • 10
    • 0024156978 scopus 로고
    • Harman in rat brain, lung and human CSF: Effect of alcohol consumption
    • (d) Bosin, T. R.; Borg, S.; Faull, K. F. Harman in rat brain, lung and human CSF: Effect of alcohol consumption. Alcohol 1988, 5, 505-511.
    • (1988) Alcohol , vol.5 , pp. 505-511
    • Bosin, T.R.1    Borg, S.2    Faull, K.F.3
  • 11
    • 33847241204 scopus 로고    scopus 로고
    • B-carboline alkaloids: Biochemical and pharmacological functions
    • (a) Cao, R.; Peng, W.; Wang, Z.; Xu, A. b-Carboline alkaloids: Biochemical and pharmacological functions. Curr. Med. Chem. 2007, 14, 479-500;
    • (2007) Curr. Med. Chem. , vol.14 , pp. 479-500
    • Cao, R.1    Peng, W.2    Wang, Z.3    Xu, A.4
  • 13
    • 45549095949 scopus 로고    scopus 로고
    • Synthesis of analogues of flazin, in particular, flazinamide, as promising anti-HIV agents
    • (a) Tang, J. G.; Wang, Y. H.; Wang, R. R.; Dong, Z. J.; Yang, L. M.; Zheng, Y. T.; Liu, J. K. Synthesis of analogues of flazin, in particular, flazinamide, as promising anti-HIV agents. Chem. Biodivers. 2008, 5(3), 447-460;
    • (2008) Chem. Biodivers. , vol.5 , Issue.3 , pp. 447-460
    • Tang, J.G.1    Wang, Y.H.2    Wang, R.R.3    Dong, Z.J.4    Yang, L.M.5    Zheng, Y.T.6    Liu, J.K.7
  • 15
    • 39049190931 scopus 로고    scopus 로고
    • Anti-prostate cancer activity of a b-carboline alkaloid enriched extract from Rauwolfia vomitoria
    • (a) Bemis, D. L.; Capodice, J. L.; Gorroochurn, P.; Katz, A. Z.; Buttyan, R. Anti-prostate cancer activity of a b-carboline alkaloid enriched extract from Rauwolfia vomitoria. Int. J. Oncol. 2006, 29, 1065-1073;
    • (2006) Int. J. Oncol. , vol.29 , pp. 1065-1073
    • Bemis, D.L.1    Capodice, J.L.2    Gorroochurn, P.3    Katz, A.Z.4    Buttyan, R.5
  • 16
    • 14844311297 scopus 로고    scopus 로고
    • Antitumor and neurotoxic effects of novel harmine derivatives and structure-activity relationship analysis
    • (b) Chen, Q.; Chao, R.; Chen, H.; Hou, X.; Yan, H.; Zhou, S.; Peng, W.; Xu, A. Antitumor and neurotoxic effects of novel harmine derivatives and structure-activity relationship analysis. Int. J. Cancer 2005, 114, 675-682.
    • (2005) Int. J. Cancer , vol.114 , pp. 675-682
    • Chen, Q.1    Chao, R.2    Chen, H.3    Hou, X.4    Yan, H.5    Zhou, S.6    Peng, W.7    Xu, A.8
  • 17
    • 0020672561 scopus 로고
    • B-Carbolines as benzo-diazepine receptor ligands 1: Synthesis and benzodiazepine receptor interaction of esters of b-carboline-3-carboxylic acid
    • (a) Lippke, K. P.; Schunack, W. G.; Wenning, W.; Mueller, W. E. b-Carbolines as benzo-diazepine receptor ligands, 1: Synthesis and benzodiazepine receptor interaction of esters of b-carboline-3-carboxylic acid. J. Med. Chem. 1983, 26, 499-503;
    • (1983) J. Med. Chem. , vol.26 , pp. 499-503
    • Lippke, K.P.1    Schunack, W.G.2    Wenning, W.3    Mueller, W.E.4
  • 18
    • 0029040312 scopus 로고
    • Synthetic routes to 4-amino-3-carboxy-b-carboline derivatives: Incidental formation of novel furo[3,4-c]-b-carbolin-2-ones displaying high affinities for the benzodiazepine receptor
    • (b) Dorey, G.; Dubois, L.; Potier, P.; Dodd, R. H. Synthetic routes to 4-amino-3-carboxy-b-carboline derivatives: Incidental formation of novel furo[3,4-c]-b-carbolin-2-ones displaying high affinities for the benzodiazepine receptor. J. Med. Chem. 1995, 38, 189-198.
    • (1995) J. Med. Chem. , vol.38 , pp. 189-198
    • Dorey, G.1    Dubois, L.2    Potier, P.3    Dodd, R.H.4
  • 20
    • 33745556152 scopus 로고    scopus 로고
    • Antimalarial activity of a new family of analogues of manzamine A
    • (b) Winkler, J. D.; Londregan, A. T.; Hamann, M. T. Antimalarial activity of a new family of analogues of manzamine A. Org. Lett. 2006, 8, 2591-2594.
    • (2006) Org. Lett. , vol.8 , pp. 2591-2594
    • Winkler, J.D.1    Londregan, A.T.2    Hamann, M.T.3
  • 21
    • 34548757909 scopus 로고    scopus 로고
    • Synthesis of carbolines possessing antitumor activity
    • Love, B. E. Synthesis of carbolines possessing antitumor activity. Topics Hetercycl. Chem. 2006, 2, 93-128.
    • (2006) Topics Hetercycl. Chem. , vol.2 , pp. 93-128
    • Love, B.E.1
  • 22
    • 0011054313 scopus 로고
    • 1-(1-Pyrrolin-2-yl)-b-carbolines: Synthesis of the eudistoma H, I, P
    • (a) Hino, T.; Lai, Z.; Seki, H. 1-(1-Pyrrolin-2-yl)-b-carbolines: Synthesis of the eudistoma H, I, P. Chem. Pharm. Bull. 1989, 37, 2596-2600;
    • (1989) Chem. Pharm. Bull. , Issue.37 , pp. 2596-2600
    • Hino, T.1    Lai, Z.2    Seki, H.3
  • 23
    • 0030757383 scopus 로고    scopus 로고
    • A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds
    • (b) Radchenko, O. S.; Novikov, V. L.; Elyakov, G. B. A simple and practical approach to the synthesis of the marine sponge pigment fascaplysin and related compounds. Tetrahedron Lett. 1997, 38, 5339-5342.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5339-5342
    • Radchenko, O.S.1    Novikov, V.L.2    Elyakov, G.B.3
  • 24
    • 4243241249 scopus 로고
    • The Pictet-Spengler condensation: A new direction for an old reaction
    • (a) Cox, E. D.; Cook, J. M. The Pictet-Spengler condensation: A new direction for an old reaction. Chem. Rev. 1995, 95, 1797-1842;
    • (1995) Chem. Rev. , vol.95 , pp. 1797-1842
    • Cox, E.D.1    Cook, J.M.2
  • 25
    • 0347089132 scopus 로고    scopus 로고
    • The Pictet-Spengler reaction in solid-phase combinatorial chemistry
    • (b) Nielsen, T. E.; Diness, T. E.; Meldal, M. The Pictet-Spengler reaction in solid-phase combinatorial chemistry. Curr. Opin. Drug Discov. Devel. 2003, 6, 801-814.
    • (2003) Curr. Opin. Drug Discov. Devel. , vol.6 , pp. 801-814
    • Nielsen, T.E.1    Diness, T.E.2    Meldal, M.3
  • 26
    • 33947298530 scopus 로고
    • Studies on the Fischer indole synthesis
    • (a) Robinson, B. Studies on the Fischer indole synthesis. Chem. Rev. 1969, 69, 227-250;
    • (1969) Chem. Rev. , vol.69 , pp. 227-250
    • Robinson, B.1
  • 27
    • 18144409437 scopus 로고    scopus 로고
    • A new synthesis of 4-oxygenated b-carboline derivatives by Fischer indolization
    • (b) Suzuki, H.; Tsukakoshi, Y.; Tachikawa, T. A new synthesis of 4-oxygenated b-carboline derivatives by Fischer indolization. Tetrahedron Lett. 2005, 46, 3831-3834.
    • (2005) Tetrahedron Lett. , vol.46 , pp. 3831-3834
    • Suzuki, H.1    Tsukakoshi, Y.2    Tachikawa, T.3
  • 28
    • 0038440661 scopus 로고    scopus 로고
    • Efficient one-pot synthesis of anti-HIV and antitumor compounds: Harman and substituted harmans
    • Kusurkar, R. S.; Goswami, S. K.; Vyas, S. M. Efficient one-pot synthesis of anti-HIV and antitumor compounds: Harman and substituted harmans. Tetrahedron Lett. 2003, 44, 4761-4763.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 4761-4763
    • Kusurkar, R.S.1    Goswami, S.K.2    Vyas, S.M.3
  • 29
    • 0035807570 scopus 로고    scopus 로고
    • Synthesis of β-and γ-carbolines by the palladium-catalyzed iminoannulation of internal alkynes
    • DOI 10.1021/ol010124w
    • (a) Zhang, H.; Larock, R. C. Synthesis of b and c carbolines by the palladium-catalyzed iminoannulation of internal alkynes. Org. Lett. 2001, 3, 3083-3086; (Pubitemid 33621118)
    • (2001) Organic Letters , vol.3 , Issue.20 , pp. 3083-3086
    • Zhang, H.1    Larock, R.C.2
  • 30
    • 0037127489 scopus 로고    scopus 로고
    • Synthesis of b and c-carbolines by the palladium=copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes
    • (b) Zhang, H.; Larock, R. C. Synthesis of b and c-carbolines by the palladium=copper-catalyzed coupling and copper-catalyzed or thermal cyclization of terminal acetylenes. Tetrahedron Lett. 2002, 43, 1359-1362.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 1359-1362
    • Zhang, H.1    Larock, R.C.2
  • 31
    • 0027996777 scopus 로고
    • Iminophosphorane-mediated syntheses of the fascaplysin alkaloid of marine origin and nitramarine
    • DOI 10.1016/S0040-4039(00)78515-7
    • (a) Molina, P.; Fresneda, P. M.; Garcia-Zafra, S.; Almendros, P. Iminophosphorane-mediated syntheses of the fascaplysin alkaloid of marine origin and nitramarine. Tetrahedron Lett. 1994, 35, 8851-8854; (Pubitemid 24347897)
    • (1994) Tetrahedron Letters , vol.35 , Issue.47 , pp. 8851-8854
    • Molina, P.1    Fresneda, P.M.2    Garcia-Zafra, S.3    Almendros, P.4
  • 32
    • 0029024645 scopus 로고
    • An iminophosphorane-mediated efficient synthesis of the alkaloid eudistomin U of marine origin
    • (b) Molina, P.; Fresneda, P. M.; Garcia-Zafra, S. An iminophosphorane- mediated efficient synthesis of the alkaloid eudistomin U of marine origin. Tetrahedron Lett. 1995, 36, 3581-3582;
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3581-3582
    • Molina, P.1    Fresneda, P.M.2    Garcia-Zafra, S.3
  • 33
    • 0030599680 scopus 로고    scopus 로고
    • Iminophosphorane-mediated synthesis of 1-acyl-b-carbolines: A new access to the alkaloids Eudistomin T, S and Xestomanzamine A of marine origin
    • (c) Molina, P.; Fresneda, P. M.; Garcia-Zafra, S. Iminophosphorane- mediated synthesis of 1-acyl-b-carbolines: A new access to the alkaloids Eudistomin T, S and Xestomanzamine A of marine origin. Tetrahedron Lett. 1996, 37, 9353-9356.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 9353-9356
    • Molina, P.1    Fresneda, P.M.2    Garcia-Zafra, S.3
  • 34
    • 2942693540 scopus 로고    scopus 로고
    • Synthesis of substituted carbazoles and b-carbolines by cyclization of diketoindole derivatives
    • Duval, E.; Cuny, G. D. Synthesis of substituted carbazoles and b-carbolines by cyclization of diketoindole derivatives. Tetrahedron Lett. 2004, 45, 5411-5413.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 5411-5413
    • Duval, E.1    Cuny, G.D.2
  • 35
    • 0035817362 scopus 로고    scopus 로고
    • A mild and efficient dehydrogenation of indolines
    • (a) Tilstam, U.; Harre, M.; Weinmann, H. A mild and efficient dehydrogenation of indolines. Tetrahedron Lett. 2001, 42, 5385-5387;
    • (2001) Tetrahedron Lett. , vol.42 , pp. 5385-5387
    • Tilstam, U.1    Harre, M.2    Weinmann, H.3
  • 36
    • 0036326850 scopus 로고    scopus 로고
    • Trichloroisocyanuric acid: A safe and efficient oxidant
    • (b) Tilstam, U.; Weinmann, H. Trichloroisocyanuric acid: A safe and efficient oxidant. Org. Process Res. Dev. 2002, 6, 384-393(b).
    • (2002) Org. Process Res. Dev. , vol.6 , pp. 384-393
    • Tilstam, U.1    Weinmann, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.