메뉴 건너뛰기




Volumn 41, Issue 22, 2011, Pages 3351-3366

Elegant one-pot synthesis of quinolino[2′,3′:7,6]-cyclohept[1, 2-b]indole through friedländer and pfitzinger annulation reaction

Author keywords

Friedl nder synthesis; p TsOH; Pfitzinger synthesis; quinolino 2 , 3 :7,6 cyclohept 1,2 b indoles

Indexed keywords

11 CHLORO 6 PHENYL 7,8,9,14 TETRAHYDROQUINOLINO[2',3':7,6]CYCLOHEPT[1,2 B]INDOLE; 11 METHYL 6 PHENYL 7,8,9,14 TETRAHYDROQUINOLINO[2',3':7,6]CYCLOHEPT[1,2 B]INDOLE; 12 METHYL 6 PHENYL 7,8,9,14 TETRAHYDROQUINOLINO[2',3':7,6]CYCLOHEPT[1,2 B]INDOLE; 13 METHYL 6 PHENYL 7,8,9,14 TETRAHYDROQUINOLINO[2',3':7,6]CYCLOHEPT[1,2 B]INDOLE; 6 PHENYL 7,8,9,14 TETRAHYDROQUINOLINO [2?'3':7,6]CYCLOHEPT[1,2 B]INDOLE; 6 PHENYL 7,8,9,14 TETRAHYDROQUINOLINO[2',3':7,6]CYCLOHEPT[1,2 B]INDOLE; BENZOPHENONE; INDOLE DERIVATIVE; ISATIN; QUINOLINO[2',3':7,6]CYCLOHEPT[1,2 B]INDOLE; UNCLASSIFIED DRUG;

EID: 79960923115     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2010.518048     Document Type: Article
Times cited : (12)

References (33)
  • 1
    • 0003979828 scopus 로고    scopus 로고
    • Academic Press: San Diego
    • Sundberg, R. J. Indoles; Academic Press: San Diego, 1996; p. 175.
    • (1996) Indoles , pp. 175
    • Sundberg, R.J.1
  • 2
    • 0035137292 scopus 로고    scopus 로고
    • Marine natural products
    • DOI 10.1039/b006897g
    • Faulkner, D. J. Marine natural products. Nat. Prod. Rep. 2001, 18, 1-49. (Pubitemid 32160982)
    • (2001) Natural Product Reports , vol.18 , Issue.1 , pp. 1-49
    • Faulkner, D.J.1
  • 4
    • 34047258307 scopus 로고    scopus 로고
    • Ruthenium half-sandwich complexes as protein kinase inhibitors: Derivatization of the pyridocarbazole pharmacophore ligand
    • DOI 10.1039/b700433h
    • Pagano, N.; Maksimoska, J.; Bregman, H.; Williams, D. S.; Webster, R. D.; Xuec, F.; Meggers, E. Ruthenium half-sandwich complexes as protein kinase inhibitors: Derivatization of the pyridocarbazole pharmacophore ligand. Org. Biomol. Chem. 2007, 5, 1218-1227. (Pubitemid 46546376)
    • (2007) Organic and Biomolecular Chemistry , vol.5 , Issue.8 , pp. 1218-1227
    • Pagano, N.1    Maksimoska, J.2    Bregman, H.3    Williams, D.S.4    Webster, R.D.5    Xue, F.6    Meggers, E.7
  • 5
    • 0036826933 scopus 로고    scopus 로고
    • Isolation and synthesis of biologically active carbazole alkaloids
    • DOI 10.1021/cr020059j
    • Knolker, H.-J.; Reddy, K. R. Isolation and synthesis of biologically active carbazole alkaloids. Chem. Rev. 2002, 102, 4303-4427. (Pubitemid 35420910)
    • (2002) Chemical Reviews , vol.102 , Issue.11 , pp. 4303-4427
    • Knolker, H.-J.1    Reddy, K.R.2
  • 6
    • 77955637981 scopus 로고    scopus 로고
    • Indoloquinolines as scaffolds for drug discovery
    • Lavrado, J.; Moreira, R.; Paulo, A. Indoloquinolines as scaffolds for drug discovery. Curr. Med. Chem. 2010, 17, 2348-2370.
    • (2010) Curr. Med. Chem. , vol.17 , pp. 2348-2370
    • Lavrado, J.1    Moreira, R.2    Paulo, A.3
  • 8
    • 65249155938 scopus 로고    scopus 로고
    • Calothrixins a new class of human DNA topoisomerase i poisons
    • Khan, Q. A.; Lu, J.; Hecht, S. M. Calothrixins, a new class of human DNA topoisomerase I poisons. J. Nat. Prod. 2009, 72, 438-442.
    • (2009) J. Nat. Prod. , vol.72 , pp. 438-442
    • Khan, Q.A.1    Lu, J.2    Hecht, S.M.3
  • 9
    • 0033585089 scopus 로고    scopus 로고
    • Calothrixins A and B, novel pentacyclic metabolites from Calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells
    • DOI 10.1016/S0040-4020(99)00833-9, PII S0040402099008339
    • Rickards, R. W.; Rothschild, J. M.; Willis, A. C.; de Chazal, N. M.; Kirk, J.; Kirk, K.; Saliba, K. J.; Smith, G. D. Calothrixins A and B, novel pentacyclic metabolites from Calothrix cyanobacteria with potent activity against malaria parasites and human cancer cells. Tetrahedron 1999, 55, 13513-13520. (Pubitemid 29521193)
    • (1999) Tetrahedron , vol.55 , Issue.47 , pp. 13513-13520
    • Rickards, R.W.1    Rothschild, J.M.2    Willis, A.C.3    De Chazal, N.M.4    Kirk, J.5    Kirk, K.6    Saliba, K.J.7    Smith, G.D.8
  • 11
    • 54049095612 scopus 로고    scopus 로고
    • Thiazolyl=oxazolyl formazanyl indoles as potent anti-inflammatory agents
    • Singh, N.; Bhati, S. K.; Kumar, A. Thiazolyl=oxazolyl formazanyl indoles as potent anti-inflammatory agents. Eur. J. Med. Chem. 2008, 43, 2597-2609.
    • (2008) Eur. J. Med. Chem. , vol.43 , pp. 2597-2609
    • Singh, N.1    Bhati, S.K.2    Kumar, A.3
  • 13
    • 40649107590 scopus 로고    scopus 로고
    • Indole-3-carbinol as a chemopreventive and anti-cancer agent
    • Weng, J.-R.; Tsai, C.-H.; Kulp, S. K.; Chen, C.-S. Indole-3-carbinol as a chemopreventive and anti-cancer agent. Cancer Lett. 2008, 262, 153-163.
    • (2008) Cancer Lett. , vol.262 , pp. 153-163
    • Weng, J.-R.1    Tsai, C.-H.2    Kulp, S.K.3    Chen, C.-S.4
  • 14
    • 0028088840 scopus 로고
    • Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent
    • Tiwari, R. K.; Guo, L.; Bradlow, H. L.; Telang, N. T.; Osborne, M. P. Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. J. Natl. Cancer Inst. 1994, 86, 126-131.
    • (1994) J. Natl. Cancer Inst. , vol.86 , pp. 126-131
    • Tiwari, R.K.1    Guo, L.2    Bradlow, H.L.3    Telang, N.T.4    Osborne, M.P.5
  • 15
    • 0034932097 scopus 로고    scopus 로고
    • Synthesis of novel analogues of marine indole alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4- trifluoromethylpyridines as potential anticancer agents
    • DOI 10.1016/S0968-0896(01)00070-0, PII S0968089601000700
    • Xiong, W.; Yang, C.; Jiang, B. Synthesis of novel analogues of marine indole alkaloids: Mono(indolyl)-4-trifluoromethylpyridines and bis(indolyl)-4-trifluoromethyl pyridines as potential anticancer agents. Bioorg. Med. Chem. 2001, 9, 1773-1780. (Pubitemid 32651914)
    • (2001) Bioorganic and Medicinal Chemistry , vol.9 , Issue.7 , pp. 1773-1780
    • Xiong, W.-N.1    Yang, C.-G.2    Jiang, B.3
  • 16
    • 0033550319 scopus 로고    scopus 로고
    • Natural products with hypoglycemic, hypotensive, hypocholesterolemic, antiatherosclerotic, and antithrombotic activities
    • Wang, H. X.; Ng, T. B. Natural products with hypoglycemic, hypotensive, hypocholesterolemic, antiatherosclerotic, and antithrombotic activities. Life Sci. 1999, 65, 2663-2677.
    • (1999) Life Sci. , vol.65 , pp. 2663-2677
    • Wang, H.X.1    Ng, T.B.2
  • 18
    • 77953362320 scopus 로고    scopus 로고
    • Pharmacological evaluation of Alstonia scholaris: Anti-tussive, anti-asthmatic and expectorant activities
    • Shang, J.-H.; Cai, X.-H.; Zhao, Y.-L.; Feng, T.; Luo, X. D. Pharmacological evaluation of Alstonia scholaris: Anti-tussive, anti-asthmatic and expectorant activities. J. Ethnopharmacol. 2010, 129, 293-298.
    • (2010) J. Ethnopharmacol. , vol.129 , pp. 293-298
    • Shang, J.-H.1    Cai, X.-H.2    Zhao, Y.-L.3    Feng, T.4    Luo, X.D.5
  • 19
    • 0034535724 scopus 로고    scopus 로고
    • Synthesis and in vitro cytotoxic evaluation of N-substituted benzo[5,6]cyclohepta[b]indoles
    • Joseph, B.; Alagille, D.; Meour, J.-Y.; Lenceb, S. Synthesis and in vitro cytotoxic evaluation of N-substituted benzo[5,6]cyclohepta[b]indoles. Chem. Pharm. Bull. 2000, 48, 1872-1876. (Pubitemid 32011510)
    • (2000) Chemical and Pharmaceutical Bulletin , vol.48 , Issue.12 , pp. 1872-1876
    • Joseph, B.1    Alagille, D.2    Merour, J.-Y.3    Leonce, S.4
  • 20
    • 0031009384 scopus 로고    scopus 로고
    • Biomimetic total synthesis of ervitsine and indole alkaloids of the ervatamine group via 1,4-dihydropyridines
    • DOI 10.1021/jo9623301, PII S0022326396023304
    • Bennasar, M. L.; Vidal, B.; Bosch, J. Biomimetic total synthesis of ervitsine and indole alkaloids of the ervatamine group via 1,4-dihydropyridines. J. Org. Chem. 1997, 62, 3597-3609. (Pubitemid 27280601)
    • (1997) Journal of Organic Chemistry , vol.62 , Issue.11 , pp. 3597-3609
    • Bennasar, M.-L.1    Vidal, B.2    Bosch, J.3
  • 21
    • 34547137637 scopus 로고    scopus 로고
    • Synthetic applications of cyanoacetylated bisindoles: Synthesis of novel cycloheptadiindoles, indolocarbazoles, and related aza analogues
    • DOI 10.1021/jo0706729
    • Wahlstro, N.; Slatt, J.; Stensland, B.; Ertan, A.; Bergman, J.; Janosik, T. Synthetic applications of cyanoacetylated bisindoles: Synthesis of novel cycloheptadiindoles, indolocarbazoles, and related aza analogues. J. Org. Chem. 2007, 72, 5886-5889. (Pubitemid 47104707)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.15 , pp. 5886-5889
    • Wahlstrom, N.1    Slatt, J.2    Stensland, B.3    Ertan, A.4    Bergman, J.5    Janosik, T.6
  • 22
    • 0000476009 scopus 로고
    • Eine synthese des chinolins
    • Skraup, H. Eine synthese des chinolins. Chem. Ber. 1880, 13, 2086-2087.
    • (1880) Chem. Ber. , vol.13 , pp. 2086-2087
    • Skraup, H.1
  • 23
    • 84979140792 scopus 로고
    • Ueber eine dem Chinolin homologe
    • Doebner, O.; Miller, V. W. Ueber eine dem Chinolin homologe Base. Ber. 1881, 14, 2812-2817.
    • (1881) Base. Ber. , vol.14 , pp. 2812-2817
    • Doebner, O.1    Miller, V.W.2
  • 25
    • 0034619244 scopus 로고    scopus 로고
    • Synthesis of quinolines via rutheniumcatalysed amine exchange reaction between anilines and trialkylamines
    • Cho, C. S.; Oh, B. H.; Kim, T. J.; Shim, S. C. Synthesis of quinolines via rutheniumcatalysed amine exchange reaction between anilines and trialkylamines. J. Chem. Soc., Chem. Commun. 2000, 1885-1886.
    • (2000) J. Chem. Soc. Chem. Commun. , pp. 1885-1886
    • Cho, C.S.1    Oh, B.H.2    Kim, T.J.3    Shim, S.C.4
  • 26
    • 0037140878 scopus 로고    scopus 로고
    • Novel facile synthesis of 2,2,4 substituted 1,2-dihydroquinolines via a modified Skraup reaction
    • DOI 10.1016/S0040-4039(02)00614-7, PII S0040403902006147
    • Theclitou, M. E.; Robinson, L. A. Novel facile synthesis of 2,2,4 substituted 1,2-dihydroquinolines via amodified Skraup reaction. Tetrahedron Lett. 2002, 43, 3907-3910. (Pubitemid 34463060)
    • (2002) Tetrahedron Letters , vol.43 , Issue.21 , pp. 3907-3910
    • Theoclitou, M.-E.1    Robinson, L.A.2
  • 27
    • 0037184893 scopus 로고    scopus 로고
    • Zn(II)-mediated alkynylation-cyclization of o-trifluoroacetyl anilines: One-pot synthesis of 4-trifluoromethyl-substituted quinoline derivatives
    • DOI 10.1021/jo0204606
    • Jiang, B.; Si, Y. C. Zn(II)-mediated alkynylation cyclization of o-trifluoroacetyl anilines: One-pot synthesis of 4-trifluoromethyl-substituted quinoline derivatives. J. Org. Chem. 2002, 67, 9449-9451. (Pubitemid 36033931)
    • (2002) Journal of Organic Chemistry , vol.67 , Issue.26 , pp. 9449-9451
    • Jiang, B.1    Si, Y.-G.2
  • 28
    • 34249317266 scopus 로고    scopus 로고
    • Novel 13H-indolo[3,2-c]acridines and their methyl derivatives
    • Sridharan, M.; Rajendra Prasad, K. J. Novel 13H-indolo[3,2-c]acridines and their methyl derivatives. J. Chem. Res. 2007, 164-169.
    • (2007) J. Chem. Res. , pp. 164-169
    • Sridharan, M.1    Rajendra Prasad, K.J.2
  • 29
    • 78149462507 scopus 로고    scopus 로고
    • Simple and convenient methods for the synthesis of indolo[3,2-c]acridines
    • Prabakaran, K.; Rajendra Prasad, K. J. Simple and convenient methods for the synthesis of indolo[3,2-c]acridines. Synth. Commun. 2010, 40, 3528-3537.
    • (2010) Synth. Commun. , vol.40 , pp. 3528-3537
    • Prabakaran, K.1    Rajendra Prasad, K.J.2
  • 30
    • 77956034395 scopus 로고    scopus 로고
    • Synthesis of quinolino[20 30:7 6]cyclohept[b] indoles and their antimicrobial activities
    • Yamuna, E.; Rajendra Prasad, K. J. Synthesis of quinolino[20,30:7,6] cyclohept[b] indoles and their antimicrobial activities. J. Chem. Res. 2010, 385-389.
    • (2010) J. Chem. Res. , pp. 385-389
    • Yamuna, E.1    Rajendra Prasad, K.J.2
  • 31
    • 0346970906 scopus 로고    scopus 로고
    • Tetracyclic compounds from indolo[2,3-b] cycloheptan-1-ones: Synthesis of isoxazolo[40,30:6,7]cyclohepta[b]indoles
    • Kavitha, C.; Rajendra Prasad, K. J. Tetracyclic compounds from indolo[2,3-b] cycloheptan-1-ones: Synthesis of isoxazolo[40,30:6,7]cyclohepta[b] indoles. Heterocycl. Commun. 1999, 5, 481.
    • (1999) Heterocycl. Commun. , vol.5 , pp. 481
    • Kavitha, C.1    Rajendra Prasad, K.J.2
  • 32
    • 79960903820 scopus 로고    scopus 로고
    • Apex2 v2009.7-0. Bruker AXS Inc.: Madison WI
    • Bruker Advanced X-ray Solutions. Apex2 v2009.7-0. Bruker AXS Inc.: Madison, WI, 2009.
    • (2009) Bruker Advanced X-ray Solutions
  • 33
    • 35948971441 scopus 로고    scopus 로고
    • SHELXTL version 6.14. Bruker AXS Inc.: Madison WI
    • Bruker Advanced X-ray Solutions. SHELXTL, version 6.14. Bruker AXS Inc.: Madison, WI, 2000-2003.
    • (2000) Bruker Advanced X-ray Solutions


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.