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Volumn 86, Issue , 2014, Pages 257-269

Design, synthesis, and structure-activity relationships of novel benzothiazole derivatives bearing the ortho-hydroxy N-carbamoylhydrazone moiety as potent antitumor agents

Author keywords

Antitumor; Benzothiazole; Ortho hydroxy N Carbamoylhydrazone moiety; Procaspase 3

Indexed keywords

4 (2 CHLOROBENZYLOXY) 2 HYDROXYBENZALDEHYDE; 4 (3 CHLOROBENZYLOXY) 2 HYDROXYBENZALDEHYDE; 4 (4 CHLOROBENZYLOXY) 2 HYDROXYBENZALDEHYDE; 4 (4 METHYLBENZYLOXY) 2 HYDROXYBENZALDEHYDE; 4 (4 TERT BUTYLBENZYLOXY) 2 HYDROXYBENZALDEHYDE; 4 (MORPHOLINOMETHYL)ANILINE; 4 BENZYLOXY 2 HYDROXYBENZALDEHYDE; 4 MORPHOLINOANILINE; 4 [(4 METHYLPIPERIDIN 1 YL)METHYL]ANILINE; 4 [(DIETHYLAMINO)METHYL]ANILINE; 4 [(DIMETHYLAMINO)METHYL]ANILINE; 6 (MORPHOLINOMETHYL)BENZO[D]THIAZOL 2 AMINE; 6 MORPHOLINOBENZO[D]THIAZOL 2 AMINE; 6 [(4-METHYLPIPERIDIN 1 YL)METHYL]BENZO[D]THIAZOL 2 AMINE; 6 [(DIETHYLAMINO)METHYL]BENZO[D]THIAZOL 2 AMINE; 6 [(DIMETHYLAMINO)METHYL]BENZO[D]THIAZOL 2 AMINE; ANTINEOPLASTIC AGENT; BENZOTHIAZOLE DERIVATIVE; N (6 MORPHOLINOBENZO[D]THIAZOL 2 YL) HYDRAZINECARBOXAMIDE; N [6 (MORPHOLINOMETHYL)BENZO[D]THIAZOL 2 YL] HYDRAZINECARBOXAMIDE; N [6 [(4 METHYLPIPERIDIN 1 YL)METHYL]BENZO[D]THIAZOL 2 YL] HYDRAZINECARBOXAMIDE; N [6 [(DIETHYLAMINO)METHYL]BENZO[D]THIAZOL 2 YL] HYDRAZINECARBOXAMIDE; N [6 [(DIMETHYLAMINO)METHYL]BENZO[D]THIAZOL 2 YL] HYDRAZINECARBOXAMIDE; PHENYL 6 (MORPHOLINOMETHYL)BENZO[D]THIAZOL 2 YLCARBAMATE; PHENYL 6 MORPHOLINOBENZO[D]THIAZOL 2 YLCARBAMATE; PHENYL 6 [(4 METHYLPIPERIDIN 1 YL)METHYL]BENZO[D]THIAZOL 2 YLCARBAMATE; PHENYL 6 [(DIETHYLAMINO)METHYL]BENZO[D]THIAZOL 2 YLCARBAMATE; PHENYL 6 [(DIMETHYLAMINO)METHYL]BENZO[D]THIAZOL 2 YLCARBAMATE; PROCASPASE 3; UNCLASSIFIED DRUG; UNINDEXED DRUG; BENZOTHIAZOLE; HYDRAZINE DERIVATIVE;

EID: 84907005799     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.08.058     Document Type: Article
Times cited : (37)

References (29)
  • 1
    • 57049119555 scopus 로고    scopus 로고
    • Targeting apoptosis: Selected anticancer strategies
    • 10.1038/nrd2662
    • S. Storey Targeting apoptosis: selected anticancer strategies Nat. Rev. Drug Discov. 7 2008 971 972 10.1038/nrd2662
    • (2008) Nat. Rev. Drug Discov. , vol.7 , pp. 971-972
    • Storey, S.1
  • 3
    • 84861034546 scopus 로고    scopus 로고
    • Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152)
    • 10.1021/jm300060k
    • J.A. Flygare, M. Beresini, N. Budha, H. Chan, I.T. Chan, S. Cheeti, F. Cohen, K. Deshayes, K. Doerner, and S.G. Eckhardt Discovery of a potent small-molecule antagonist of inhibitor of apoptosis (IAP) proteins and clinical candidate for the treatment of cancer (GDC-0152) J. Med. Chem. 55 2012 4101 4113 10.1021/jm300060k
    • (2012) J. Med. Chem. , vol.55 , pp. 4101-4113
    • Flygare, J.A.1    Beresini, M.2    Budha, N.3    Chan, H.4    Chan, I.T.5    Cheeti, S.6    Cohen, F.7    Deshayes, K.8    Doerner, K.9    Eckhardt, S.G.10
  • 6
    • 1842636513 scopus 로고    scopus 로고
    • Increased expression of Apaf-1 and procaspase-3 and the functionality of intrinsic apoptosis apparatus in non-small cell lung carcinoma
    • DOI 10.1515/BC.2004.034
    • J. Procházka, X. Liu, P. Fiala, and Z. Kinkor Increased expression of Apaf-1 and procaspase-3 and the functionality of intrinsic apoptosis apparatus in non-small cell lung carcinoma Biol. Chem. 385 2004 153 168 10.1515/BC.2004.034 (Pubitemid 38461336)
    • (2004) Biological Chemistry , vol.385 , Issue.2 , pp. 153-168
    • Krepela, E.1    Prochazka, J.2    Liu, X.3    Fiala, P.4    Kinkor, Z.5
  • 10
    • 0032588953 scopus 로고    scopus 로고
    • Characterization of the interleukin-1β-converting enzyme/Ced-3-family protease, caspase-3/CPP32, in Hodgkin's disease. Lack of caspase-3 expression in nodular lymphocyte predominance Hodgkin's disease
    • K.F. Izban, T. Wrone-Smith, E.D. His, B. Schnitzer, M.E. Quevedo, and S. Alkan Characterization of the interleukin-1β-converting enzyme/Ced-3-family protease, caspase-3/CPP32, in Hodgkin's disease: lack of Caspase-3 expression in nodular lymphocyte predominance Hodgkin's disease Am. J. Pathol. 154 1999 1439 1447 (Pubitemid 29226439)
    • (1999) American Journal of Pathology , vol.154 , Issue.5 , pp. 1439-1447
    • Izban, K.F.1    Wrone-Smith, T.2    Hsi, E.D.3    Schnitzer, B.4    Quevedo, M.E.5    Alkan, S.6
  • 11
    • 0030882685 scopus 로고    scopus 로고
    • High levels of expression and nuclear localization of interleukin-1 β converting enzyme (ICE) and CPP32 in favorable human neuroblastomas
    • A. Nakagawara, Y. Nakamura, H. Ikeda, T. Hiwasa, K. Kuida, M.S. Su, H. Zhao, A. Cnaan, and S. Sakiyama High levels of expression and nuclear localization of interleukin-1 β converting enzyme (ICE) and CPP32 in favorable human neuroblastomas Cancer Res. 57 1997 4578 4584 (Pubitemid 27441064)
    • (1997) Cancer Research , vol.57 , Issue.20 , pp. 4578-4584
    • Nakagawara, A.1    Nakamura, Y.2    Ikeda, H.3    Hiwasa, T.4    Kuida, K.5    Su, M.S.-S.6    Zhao, H.7    Cnaan, A.8    Sakiyama, S.9
  • 12
    • 70349433777 scopus 로고    scopus 로고
    • Procaspase-3 activation as an anti-cancer strategy: Structure-activity relationship of procaspase-activating compound 1 (PAC-1) and its cellular co-localization with caspase-3
    • 10.1021/jm900722z
    • Q.P. Peterson, D.C. Hsu, D.R. Goode, C.J. Novotny, R.K. Totten, and P.J. Hergenrother Procaspase-3 activation as an anti-cancer strategy: structure-activity relationship of procaspase-activating compound 1 (PAC-1) and its cellular co-localization with caspase-3 J. Med. Chem. 52 2009 5721 5731 10.1021/jm900722z
    • (2009) J. Med. Chem. , vol.52 , pp. 5721-5731
    • Peterson, Q.P.1    Hsu, D.C.2    Goode, D.R.3    Novotny, C.J.4    Totten, R.K.5    Hergenrother, P.J.6
  • 14
    • 84864757598 scopus 로고    scopus 로고
    • Design, synthesis and anticancer activities of diaryl urea derivatives bearing N-acylhydrazone moiety
    • 10.1248/cpb.c12-00234
    • B. Zhang, Y. Zhao, X. Zhai, L. Wang, J. Yang, Z. Tan, and P. Gong Design, synthesis and anticancer activities of diaryl urea derivatives bearing N-acylhydrazone moiety Chem. Pharm. Bull. 60 2011 1046 1054 10.1248/cpb.c12- 00234
    • (2011) Chem. Pharm. Bull. , vol.60 , pp. 1046-1054
    • Zhang, B.1    Zhao, Y.2    Zhai, X.3    Wang, L.4    Yang, J.5    Tan, Z.6    Gong, P.7
  • 15
    • 84863618767 scopus 로고    scopus 로고
    • Design, synthesis and antiproliferative activities of diaryl urea derivatives bearing N-acylhydrazone moiety
    • 10.1016/j.cclet. 2012. 06.009
    • B. Zhang, Y.F. Zhao, X. Zhai, W.J. Fan, J.L. Ren, C.F. Wu, and P. Gong Design, synthesis and antiproliferative activities of diaryl urea derivatives bearing N-acylhydrazone moiety Chin. Chem. Lett. 23 2012 915 918 10.1016/j.cclet. 2012. 06.009
    • (2012) Chin. Chem. Lett. , vol.23 , pp. 915-918
    • Zhang, B.1    Zhao, Y.F.2    Zhai, X.3    Fan, W.J.4    Ren, J.L.5    Wu, C.F.6    Gong, P.7
  • 17
    • 14844322778 scopus 로고    scopus 로고
    • Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure
    • DOI 10.1016/j.bmc.2005.01.033
    • K. Yamazaki, Y. Kaneko, K. Suwa, S. Ebara, K. Nakazawa, and K. Yasuno Synthesis of potent and selective inhibitors of Candida albicans N-myristoyltransferase based on the benzothiazole structure Bioorg. Med. Chem. 13 2005 2509 2522 10.1016/j.bmc.2005.01.033 (Pubitemid 40341655)
    • (2005) Bioorganic and Medicinal Chemistry , vol.13 , Issue.7 , pp. 2509-2522
    • Yamazaki, K.1    Kaneko, Y.2    Suwa, K.3    Ebara, S.4    Nakazawa, K.5    Yasuno, K.6
  • 18
    • 0035953321 scopus 로고    scopus 로고
    • Antitumor benzothiazoles. 14. Synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl)benzothiazoles
    • DOI 10.1021/jm001104n
    • I. Hutchinson, M.S. Chua, H.L. Browne, V. Trapani, T.D. Bradshaw, A.D. Westwell, and M.F. Stevens Antitumor benzothiazoles. 14.1 synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl) benzothiazoles J. Med. Chem. 44 2001 1446 1455 10.1021/jm001104n (Pubitemid 32852121)
    • (2001) Journal of Medicinal Chemistry , vol.44 , Issue.9 , pp. 1446-1455
    • Hutchinson, I.1    Chua, M.-S.2    Browne, H.L.3    Trapani, V.4    Bradshaw, T.D.5    Westwell, A.D.6    Stevens, M.F.G.7
  • 19
    • 77349118931 scopus 로고    scopus 로고
    • Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents
    • 10.1016/j.ejmech.2009.12.016
    • S. Saeed, N. Rashid, P.G. Jones, M. Ali, and R. Hussain Synthesis, characterization and biological evaluation of some thiourea derivatives bearing benzothiazole moiety as potential antimicrobial and anticancer agents Eur. J. Med. Chem. 45 2010 1323 1331 10.1016/j.ejmech.2009.12.016
    • (2010) Eur. J. Med. Chem. , vol.45 , pp. 1323-1331
    • Saeed, S.1    Rashid, N.2    Jones, P.G.3    Ali, M.4    Hussain, R.5
  • 24
    • 84877581238 scopus 로고    scopus 로고
    • Synthesis of pyrazolo [1,5-a] pyrimidine linked aminobenzothiazole conjugates as potential anticancer agents
    • 10.1016/j.bmcl.2013.03.129
    • A. Kamal, J.R. Tamboli, V.L. Nayak, S. Adil, M. Vishnuvardhan, and S. Ramakrishna Synthesis of pyrazolo [1,5-a] pyrimidine linked aminobenzothiazole conjugates as potential anticancer agents Bioorg. Med. Chem. Lett. 23 2013 3208 3215 10.1016/j.bmcl.2013.03.129
    • (2013) Bioorg. Med. Chem. Lett. , vol.23 , pp. 3208-3215
    • Kamal, A.1    Tamboli, J.R.2    Nayak, V.L.3    Adil, S.4    Vishnuvardhan, M.5    Ramakrishna, S.6
  • 26
    • 84861641797 scopus 로고    scopus 로고
    • Synthesis of 2-(5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazol-2- ylthio)-N-phenyl(benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents
    • 10.1016/j.ejmech.2012.03.033
    • R.V. Patel, P.K. Patel, P. Kumari, D.P. Rajani, and K.H. Chikhalia Synthesis of 2-(5-((1H-benzo[d]imidazol-1-yl)methyl)-1,3,4-oxadiazol-2-ylthio)- N-phenyl(benzothiazolyl) acetamides as antibacterial, antifungal and antituberculosis agents Eur. J. Med. Chem. 53 2012 41 51 10.1016/j.ejmech.2012. 03.033
    • (2012) Eur. J. Med. Chem. , vol.53 , pp. 41-51
    • Patel, R.V.1    Patel, P.K.2    Kumari, P.3    Rajani, D.P.4    Chikhalia, K.H.5
  • 27
    • 77958039797 scopus 로고    scopus 로고
    • Novel thiazolidinedione derivatives with anti-obesity effects: Dual action as PTP1B inhibitors and PPAR-γ activators
    • 10.1016/j.bmcl.2010.08.130
    • B.R. Bhattarai, B. Kafle, J.-S. Hwang, S.W. Ham, K.-H. Lee, H. Park, I.-O. Han, and H. Cho Novel thiazolidinedione derivatives with anti-obesity effects: dual action as PTP1B inhibitors and PPAR-γ activators Bioorg. Med. Chem. Lett. 20 2010 6758 6763 10.1016/j.bmcl.2010.08.130
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 6758-6763
    • Bhattarai, B.R.1    Kafle, B.2    Hwang, J.-S.3    Ham, S.W.4    Lee, K.-H.5    Park, H.6    Han, I.-O.7    Cho, H.8
  • 28
    • 80052561064 scopus 로고    scopus 로고
    • Synthesis and in-vitro anticancer activity of 3,5-bis (indolyl)-1,2,4-thiadiazoles
    • 10.1016/j.bmcl.2011.07.089
    • D. Kumar, N.M. Kumar, K.H. Chang, R. Gupta, and K. Shah Synthesis and in-vitro anticancer activity of 3,5-bis (indolyl)-1,2,4-thiadiazoles Bioorg. Med. Chem. Lett. 21 2011 5897 5900 10.1016/j.bmcl.2011.07.089
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 5897-5900
    • Kumar, D.1    Kumar, N.M.2    Chang, K.H.3    Gupta, R.4    Shah, K.5
  • 29
    • 33644982586 scopus 로고    scopus 로고
    • 2,4-Dimethoxyphenyl semicarbazones with anticonvulsant activity against three animal models of seizures: Synthesis and pharmacological evaluation
    • 10.1016/j.bmc.2005.12.041
    • R. Thirumurugan, D. Sriram, A. Saxena, J. Stables, and P. Yogeeswari 2,4-Dimethoxyphenyl semicarbazones with anticonvulsant activity against three animal models of seizures: synthesis and pharmacological evaluation Bioorg. Med. Chem. 14 2006 3106 3112 10.1016/j.bmc.2005.12.041
    • (2006) Bioorg. Med. Chem. , vol.14 , pp. 3106-3112
    • Thirumurugan, R.1    Sriram, D.2    Saxena, A.3    Stables, J.4    Yogeeswari, P.5


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