메뉴 건너뛰기




Volumn 90, Issue , 2015, Pages 695-706

Synthesis and anticancer activity of some novel indolo[3,2-b] andrographolide derivatives as apoptosis-inducing agents

Author keywords

Anti cancer; Apoptosis; Cell cycle arrest; Fisher indole synthesis; Indolo 3,2 b andrographolide

Indexed keywords

14 ACETYL 19 BENZOYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 14 DEOXY 19 (2,4 DICHLOROBENZOYL) 14,15 DIHYDRO INDOLO [3,2 B]ANDROGRAPHOLIDE; 14 TERT BUTYLDIMETHYL SILYL INDOLO[3,2 B] ANDROGRAPHOLIDE; 14,19 DI(TERT BUTYLDIMETHYLSILYL) INDOLO[3,2 B] ANDROGRAPHOLIDE; 14,19 DIACETYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 14,19 DIBENZOYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 ACETYL 14 (2,4 DICHLOROBENZOYL) INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 ACETYL 14 DEOXY 14,15 DIHYDRO INDOLO[3,2B]ANDROGRAPHOLIDE; 19 ACETYL 14 TERT BUTYLDIMETHYLSILYL INDOLO[3,2 B] ANDROGRAPHOLIDE; 19 ACETYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 BENZOYL 14 DEOXY 14,15 DIHYDRO INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 BENZOYL 14 TERT BUTYLDIMETHYLSILYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 BENZOYL INDOLO[3,2 B]ANDROGRAPHOLIDE; ANDROGRAPHOLIDE; BENZYL 14 (2,4 DICHLOROPHENOXYACETYL) INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; BENZYL 14 ACETYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; BENZYL 14 DEOXY 14,15 DIDEHYDRO-INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; BENZYL 14 TERT BUTYLDIMETHYLSILYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; BENZYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; BENZYLL 14 (2,4 DICHLOROBENZOYL) INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; INDOLO[3,2 B]ANDROGRAPHOLIDE; METHYL 14 (2,4 DICHLOROBENZOYL) INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; METHYL 14 (2,4 DICHLOROPHENOXYACETYL) INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; METHYL 14 ACETYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; METHYL 14 BENZOYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; METHYL 14 DEOXY 14,15 DIDEHYDRO INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; METHYL 14 TERT BUTYLDIMETHYLSILYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; METHYL INDOLO[3,2 B]ANDROGRAPHOLIDE 19 OATE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DITERPENE; INDOLO(3,2-B)ANDROGRAPHOLIDE; 14 TERT BUTYLDIMETHYL SILYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 14 TERT BUTYLDIMETHYLSILYL ANDROGRAPHOLIDE; 14 TERT BUTYLDIMETHYLSILYL ANDROGRAPHOLIDE 19 AL; 14 TERT BUTYLDIMETHYLSILYL ANDROGRAPHOLIDE 19 OATE; 14 TERT BUTYLDIMETHYLSILYL ANDROGRAPHOLIDE 19 OIC ACID; 14,19 DI(TERT BUTYLDIMETHYLSILYL) 3 OXO ANDROGRAPHOLIDE; 14,19 DI(TERT BUTYLDIMETHYLSILYL) ANDROGRAPHOLIDE; 14,19 DI(TERT BUTYLDIMETHYLSILYL) INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 ACETYL 14 DEOXY 14,15 DIHYDRO INDOLO[3,2 B]ANDROGRAPHOLIDE; 19 ACETYL 14 TERT BUTYLDIMETHYLSILYL INDOLO[3,2 B]ANDROGRAPHOLIDE; 3,19 ISOPROPYLIDENE ANDROGRAPHOLIDE; BENZYL 14 TERT BUTYL DIMETHYLSILYL 3 OXO ANDROGRAPHOLIDE 19 OATE; BENZYL 14 TERT BUTYL DIMETHYLSILYL ANDROGRAPHOLIDE 19 OATE; METHYL 14 TERT BUTYLDIMETHYLSILYL 3 OXO ANDROGRAPHOLIDE 19 OATE; METHYL 14 TERT BUTYLDIMETHYLSILYL ANDROGRAPHOLIDE 19 OATE; UNINDEXED DRUG;

EID: 84918550944     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.12.017     Document Type: Article
Times cited : (55)

References (36)
  • 1
    • 7344225175 scopus 로고
    • The bitter constituent of andrographis paniculata nees
    • M.K. Gorter, The bitter constituent of andrographis paniculata nees, Rec. Trav. Chim. 30 (1911) 151-160.
    • (1911) Rec. Trav. Chim. , vol.30 , pp. 151-160
    • Gorter, M.K.1
  • 2
    • 0025221529 scopus 로고
    • Anti-diarrheal activity of diterpenes of andrographis paniculata (kalmegh) against Escherichia coli enterotoxin in in vivo models
    • S. Gupta, M.A. Choudhry, J.N.S. Yadava, V. Srivastava, J.S. Tandon, Anti-diarrheal activity of diterpenes of andrographis paniculata (kalmegh) against Escherichia coli enterotoxin in in vivo models, Int. J. Crude Drug Res. 28 (1990) 273-283.
    • (1990) Int. J. Crude Drug Res. , vol.28 , pp. 273-283
    • Gupta, S.1    Choudhry, M.A.2    Yadava, J.N.S.3    Srivastava, V.4    Tandon, J.S.5
  • 3
    • 0029832142 scopus 로고    scopus 로고
    • Anti-inflammatory activity of andrographolide
    • S. Madav, S.K. Tanda, J. Lal, H.C. Tripathi, Anti-inflammatory activity of andrographolide, Fitoterapia 67 (1996) 452-458.
    • (1996) Fitoterapia , vol.67 , pp. 452-458
    • Madav, S.1    Tanda, S.K.2    Lal, J.3    Tripathi, H.C.4
  • 4
    • 0027004527 scopus 로고
    • Anti-malarial activity of Andrographis paniculata (kalmegh) against Plasmodium berghei NK 65 in Mastomys natalensis
    • P. Misra, N.L. Pal, P.Y. Guru, J.C. Katiyar, V. Srivastava, J.S. Tandon, Anti-malarial activity of Andrographis paniculata (kalmegh) against Plasmodium berghei NK 65 in Mastomys natalensis, Int. J. Pharmacogn. 30 (1992) 263-274.
    • (1992) Int. J. Pharmacogn. , vol.30 , pp. 263-274
    • Misra, P.1    Pal, N.L.2    Guru, P.Y.3    Katiyar, J.C.4    Srivastava, V.5    Tandon, J.S.6
  • 6
    • 84884692577 scopus 로고    scopus 로고
    • Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDLoxidation and antioxidant activity
    • S. Pandeti, R. Sonkar, A. Shukla, G. Bhatia, N. Tadigoppula, Synthesis of new andrographolide derivatives and evaluation of their antidyslipidemic, LDLoxidation and antioxidant activity, Eur. J. Med. Chem. 69 (2013) 439-448.
    • (2013) Eur. J. Med. Chem. , vol.69 , pp. 439-448
    • Pandeti, S.1    Sonkar, R.2    Shukla, A.3    Bhatia, G.4    Tadigoppula, N.5
  • 7
    • 84890284225 scopus 로고    scopus 로고
    • Andrographolide exerts anti-hepatitis C virus activity by upregulating haeme oxygenase-1 via the p38 MAPK/Nrf2 pathway in human hepatoma cells
    • J.-C. Lee, C.-K. Tseng, K.-C. Young, H.-Y. Sun, S.-W. Wang, W.-C. Chen, C.- K. Lin, Y.-H. Wu, Andrographolide exerts anti-hepatitis C virus activity by upregulating haeme oxygenase-1 via the p38 MAPK/Nrf2 pathway in human hepatoma cells, Brit. J. Pharmacol. 171 (2014) 237-252
    • (2014) Brit. J. Pharmacol. , vol.171 , pp. 237-252
    • Lee, J.-C.1    Tseng, C.-K.2    Young, K.-C.3    Sun, H.-Y.4    Wang, S.-W.5    Chen, W.-C.6    Lin, C.-K.7    Wu, Y.-H.8
  • 8
    • 84899651898 scopus 로고    scopus 로고
    • Synthesis, structureeactivity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents
    • H. Chen, Y.-B. Ma, X.-Y. Huang, C.-A. Geng, Y. Zhao, L.-J. Wang, R.-H. Guo, W.-J. Liang, X.-M. Zhang, J.-J. Chen, Synthesis, structureeactivity relationships and biological evaluation of dehydroandrographolide and andrographolide derivatives as novel anti-hepatitis B virus agents, Bioorg. Med. Chem. Lett. 24 (2014) 2353-2359.
    • (2014) Bioorg. Med. Chem. Lett. , vol.24 , pp. 2353-2359
    • Chen, H.1    Ma, Y.-B.2    Huang, X.-Y.3    Geng, C.-A.4    Zhao, Y.5    Wang, L.-J.6    Guo, R.-H.7    Liang, W.-J.8    Zhang, X.-M.9    Chen, J.-J.10
  • 11
    • 33845936572 scopus 로고    scopus 로고
    • Antiangiogenic activity of Andrographis paniculata and andrographolide
    • K. Sheeja, C. Guruvayoorappan, G. Kuttan, Antiangiogenic activity of Andrographis paniculata and andrographolide, Int. Immunopharmacol. 7 (2007) 211-221.
    • (2007) Int. Immunopharmacol. , vol.7 , pp. 211-221
    • Sheeja, K.1    Guruvayoorappan, C.2    Kuttan, G.3
  • 12
    • 2342550564 scopus 로고    scopus 로고
    • Anticancer and immunostimulatory compounds from andrographis paniculata
    • R.A. Kumar, K. Sridevi, N.V. Kumar, S. Nanduri, S. Rajagopal, Anticancer and immunostimulatory compounds from andrographis paniculata, J. Ethnopharma 92 (2004) 291-295.
    • (2004) J. Ethnopharma , vol.92 , pp. 291-295
    • Kumar, R.A.1    Sridevi, K.2    Kumar, N.V.3    Nanduri, S.4    Rajagopal, S.5
  • 13
    • 55449109861 scopus 로고    scopus 로고
    • Cytotoxic constituents from Andrographis paniculata induce cell cycle arrest in jurkat cells
    • M. Geethangili, Y.K. Rao, S.-H. Fang, Y.-M. Tzeng, Cytotoxic constituents from Andrographis paniculata induce cell cycle arrest in jurkat cells, Phytother. Res. 22 (2008) 1336-1341
    • (2008) Phytother. Res. , vol.22 , pp. 1336-1341
    • Geethangili, M.1    Rao, Y.K.2    Fang, S.-H.3    Tzeng, Y.-M.4
  • 14
    • 54949147613 scopus 로고    scopus 로고
    • Benzylidene derivatives of andrographolide inhibits growth of breast and colon cancer cells in vitro by inducing G1 arrest and apoptosis
    • S.R. Jada, C. Matthews, M.S. Saad, A.S. Hamzah, N.H. Lajis, M.F.G. Stevens, J. Stanslas, Benzylidene derivatives of andrographolide inhibits growth of breast and colon cancer cells in vitro by inducing G1 arrest and apoptosis, Br. J. Pharmacol. 155 (2008) 641-654
    • (2008) Br. J. Pharmacol. , vol.155 , pp. 641-654
    • Jada, S.R.1    Matthews, C.2    Saad, M.S.3    Hamzah, A.S.4    Lajis, N.H.5    Stevens, M.F.G.6    Stanslas, J.7
  • 15
    • 30844438519 scopus 로고    scopus 로고
    • Andrographolide isolated from Andrographis paniculata induces cell cycle arrest and mitochondrial-mediated apoptosis in human leukemic HL-60 cells
    • H.-Y. Cheung, S.-H. Cheung, J.L. Li, C.-S. Cheung, W.-P. Lai, W.-F. Fong, F.- M. Leung, Andrographolide isolated from Andrographis paniculata induces cell cycle arrest and mitochondrial-mediated apoptosis in human leukemic HL-60 cells, Planta. Med. 71 (2005) 1106-1111.
    • (2005) Planta. Med. , vol.71 , pp. 1106-1111
    • Cheung, H.-Y.1    Cheung, S.-H.2    Li, J.L.3    Cheung, C.-S.4    Lai, W.-P.5    Fong, W.-F.6    Leung, F.-M.7
  • 16
    • 17644370288 scopus 로고    scopus 로고
    • Morphological and biochemical changes of andrographolide-induced cell death in human prostatic adenocarcinoma PC-3 cells
    • T.G. Kim, K.K. Hwi, C.S. Hung, Morphological and biochemical changes of andrographolide-induced cell death in human prostatic adenocarcinoma PC-3 cells, In Vivo 19 (2005) 551-557
    • (2005) Vivo , vol.19 , pp. 551-557
    • Kim, T.G.1    Hwi, K.K.2    Hung, C.S.3
  • 17
    • 84905164461 scopus 로고    scopus 로고
    • Andrographolide analogue induces apoptosis and autophasy mediated cell death in U937 cells
    • P. Das, D. Kumar, R. Roy, C. Chowdhury, M. Chatterjee, Andrographolide analogue induces apoptosis and autophasy mediated cell death in U937 cells, Eur. J. Cancer 48 (Suppl. 5) (2012) S156
    • (2012) Eur. J. Cancer , vol.48 , pp. S156
    • Das, P.1    Kumar, D.2    Roy, R.3    Chowdhury, C.4    Chatterjee, M.5
  • 18
    • 84874600657 scopus 로고    scopus 로고
    • Cytotoxic activity and apoptosis including potential of di-spiropyrrolidino and di-spiropyrrolizidino oxindole andrographolide derivatives
    • S.K. Dey, D. Bose, A. Hazra, S. Naskar, A. Nandy, R.N. Munda, S. Das, N. Chatterjee, N.B. Mondal, S. Banerjee, K.D. Saha, Cytotoxic activity and apoptosis including potential of di-spiropyrrolidino and di-spiropyrrolizidino oxindole andrographolide derivatives, PLoS One 8 (3) (2013) e58055.
    • (2013) PLoS One , vol.8 , Issue.3 , pp. e58055
    • Dey, S.K.1    Bose, D.2    Hazra, A.3    Naskar, S.4    Nandy, A.5    Munda, R.N.6    Das, S.7    Chatterjee, N.8    Mondal, N.B.9    Banerjee, S.10    Saha, K.D.11
  • 25
    • 78149280792 scopus 로고    scopus 로고
    • Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent
    • B. Das, C. Chowdhury, D. Kumar, R. Sen, R. Roy, P. Das, M. Chatterjee, Synthesis, cytotoxicity, and structure-activity relationship (SAR) studies of andrographolide analogues as anti-cancer agent, Bioorg. Med. Chem. Lett. 20 (2010) 6947-6950.
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 6947-6950
    • Das, B.1    Chowdhury, C.2    Kumar, D.3    Sen, R.4    Roy, R.5    Das, P.6    Chatterjee, M.7
  • 26
    • 84877582374 scopus 로고    scopus 로고
    • Synthesis and in vitro cytotoxicity of andrographolide-19-oic acid analogues as anti-cancer agents
    • D. Chen, Y. Song, Y. Lu, X. Xue, Synthesis and in vitro cytotoxicity of andrographolide-19-oic acid analogues as anti-cancer agents, Bioorg. Med. Chem. Lett. 23 (2013) 3166-3169.
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 3166-3169
    • Chen, D.1    Song, Y.2    Lu, Y.3    Xue, X.4
  • 27
    • 0031012054 scopus 로고    scopus 로고
    • Plant-derived anticancer agents
    • J.M. Pezzuto, Plant-derived anticancer agents, Biochem. Pharmacol. 53 (1997) 121-133
    • (1997) Biochem. Pharmacol. , vol.53 , pp. 121-133
    • Pezzuto, J.M.1
  • 28
    • 84861488421 scopus 로고    scopus 로고
    • Modifications on the basic skeletons of vinblastine and vincristine
    • P. Keglevich, L. Hazai, G. Kalaus, C. Szántay, Modifications on the basic skeletons of vinblastine and vincristine, Molecules 17 (2012) 5893-5914.
    • (2012) Molecules , vol.17 , pp. 5893-5914
    • Keglevich, P.1    Hazai, L.2    Kalaus, G.3    Szántay, C.4
  • 31
    • 0001097669 scopus 로고    scopus 로고
    • Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts
    • J. Einhorn, C. Einhorn, F. Ratajczak, J.-L. Pierre, Efficient and highly selective oxidation of primary alcohols to aldehydes by N-chlorosuccinimide mediated by oxoammonium salts, J. Org. Chem. 61 (1996) 7452-7454.
    • (1996) J. Org. Chem. , vol.61 , pp. 7452-7454
    • Einhorn, J.1    Einhorn, C.2    Ratajczak, F.3    Pierre, J.-L.4
  • 32
    • 33748664603 scopus 로고
    • Oxidation of a, b-unsaturated aldehydes
    • B.S. Bal, W.E. Childers Jr., H.W. Pinnick, Oxidation of a, b-unsaturated aldehydes, Tetrahedron 37 (1981) 2091-2096.
    • (1981) Tetrahedron , vol.37 , pp. 2091-2096
    • Bal, B.S.1    Childers, W.E.2    Pinnick, H.W.3
  • 35
    • 0016738010 scopus 로고
    • Rapid flow cytofluorometric analysis of mammalian cell cycle by propidium iodide staining
    • A. Krishan, Rapid flow cytofluorometric analysis of mammalian cell cycle by propidium iodide staining, J. Cell. Biol. 66 (1975) 188-193.
    • (1975) J. Cell. Biol. , vol.66 , pp. 188-193
    • Krishan, A.1
  • 36
    • 85043088818 scopus 로고    scopus 로고
    • Compound 17a was obtained as side product when 15a was synthesized from 12a while 17b was separated when 14b was prepared from 12b
    • Compound 17a was obtained as side product when 15a was synthesized from 12a while 17b was separated when 14b was prepared from 12b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.