메뉴 건너뛰기




Volumn 66, Issue , 2013, Pages 171-179

Efficient construction of novel D-ring modified steroidal dienamides and their cytotoxic activities

Author keywords

Apoptosis; Cell cycle arrest; Cytotoxicity; Dehydroepiandrosterone; Dienamides

Indexed keywords

AMIDE; ANTINEOPLASTIC AGENT; STEROID; 3BETA ACETOXYL 5 EN 16 (2 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (2 CYANOBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (2 FLUOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (2,4 DICHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXO ETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (3 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE; 3BETA ACETOXYL 5 EN 16 (3 METHOXYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (3,4 DICHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (3,4 DIFLUOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXO ETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (3,4,5 TRIMETHOXYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OOXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (4 BROMOBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (4 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (4 FLUOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (4 ISOPROPYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 (4 METHYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 BENZYLIDENE ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 FURYLMETHYLENE ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA ACETOXYL 5 EN 16 THIENYLMETHYLENE ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BETA HYDROXYL 5 EN 16 (2 FLUOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXO ETHYLIDENE); 3BETA HYDROXYL 5 EN 16 (3 METHOXYLBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXO ETHYLIDENE); 3BETA HYDROXYL 5 EN 16 (3,4 DICHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXO ETHYLIDENE); 3BETA HYDROXYL 5 EN 16 (3,4,5 TRIMETHOXYL BENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHULIDENE); 3BETA HYDROXYL 5 EN 16 (4 FLUOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXOETHYLIDENE); 3BTEA HYDROXYL 5 EN 16 (2 CHLOROBENZYLIDENE)ANDROSTANO 17 (2 AMINO 1 CYANO 2 OXO ETHYLIDENE); UNCLASSIFIED DRUG;

EID: 84879209332     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.05.035     Document Type: Article
Times cited : (35)

References (32)
  • 1
    • 84874656763 scopus 로고    scopus 로고
    • An overview of synthetic approaches for heterocyclic steroids
    • R. Singh, G. Panda, An overview of synthetic approaches for heterocyclic steroids, Tetrahedron 69 (2013) 2853-2884.
    • (2013) Tetrahedron , vol.69 , pp. 2853-2884
    • Singh, R.1    Panda, G.2
  • 2
    • 84872528200 scopus 로고    scopus 로고
    • Rapid microwave assisted synthesis and antimicrobial bioevaluation of novel steroidal chalcones
    • D. Kakati, R.K. Sarma, R. Saikia, N.C. Barua, J.C. Sarma, Rapid microwave assisted synthesis and antimicrobial bioevaluation of novel steroidal chalcones, Steroids 78 (2013) 321-326.
    • (2013) Steroids , vol.78 , pp. 321-326
    • Kakati, D.1    Sarma, R.K.2    Saikia, R.3    Barua, N.C.4    Sarma, J.C.5
  • 3
    • 0034811303 scopus 로고    scopus 로고
    • A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids
    • DOI 10.1016/S0149-2918(01)80114-4
    • N.T. Shahidi, A review of the chemistry, biological action, and clinical applications of anabolic-androgenic steroids, Clin. Ther. 23 (2001) 1355-1390. (Pubitemid 32912788)
    • (2001) Clinical Therapeutics , vol.23 , Issue.9 , pp. 1355-1390
    • Shahidi, N.T.1
  • 4
    • 0028354085 scopus 로고
    • A new straightforward and general approach to dienamide natural products
    • DOI 10.1016/S0040-4039(00)73051-6
    • F. Babudri, V. Fiandanese, F. Naso, A. Punzi, A new straightforward and general approach to dienamide natural products, TetrahedronLett. 35 (1994) 2067-2070. (Pubitemid 24118836)
    • (1994) Tetrahedron Letters , vol.35 , Issue.13 , pp. 2067-2070
    • Babudri, F.1    Fiandanese, V.2    Naso, F.3    Punzi, A.4
  • 5
    • 11144342196 scopus 로고    scopus 로고
    • Iron-catalyzed 1,6-addition of aryl Grignard reagents to 2,4-dienoates and -dienamides
    • DOI 10.1016/j.tetlet.2004.11.131, PII S0040403904026334
    • K. Fukuhara, H. Urabe, Iron-catalyzed 1, 6-addition of aryl Grignard reagents to 2, 4-dienoates and -dienamides, Tetrahedron Lett. 46 (2005) 603-606. (Pubitemid 40037913)
    • (2005) Tetrahedron Letters , vol.46 , Issue.4 , pp. 603-606
    • Fukuhara, K.1    Urabe, H.2
  • 6
    • 84855825345 scopus 로고    scopus 로고
    • New type of azacyclization: Thermal preparation of 4, 6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect
    • Y. Maekawa, T. Sakaguchi, H. Tsuchikawa, S. Katsumura, New type of azacyclization: thermal preparation of 4, 6-disubstituted 2-piperidinone from N-sulfonyldienamide and its substituent effect, Tetrahedron Lett. 53 (2012) 837-841.
    • (2012) Tetrahedron Lett. , vol.53 , pp. 837-841
    • Maekawa, Y.1    Sakaguchi, T.2    Tsuchikawa, H.3    Katsumura, S.4
  • 7
    • 0035847541 scopus 로고    scopus 로고
    • Total synthesis and biological evaluation of apicularen A and synthetic analogs
    • DOI 10.1016/S0040-4039(00)02245-0, PII S0040403900022450
    • A. Bhattacharjee, O.R. Seguil, J.K. De Brabander, Total synthesis and biological evaluation of Apicularen A and synthetic analogs, Tetrahedron Lett. 42 (2001) 1217-1220. (Pubitemid 32149777)
    • (2001) Tetrahedron Letters , vol.42 , Issue.7 , pp. 1217-1220
    • Bhattacharjee, A.1    Seguil, O.R.2    De Brabander, J.K.3
  • 9
    • 0030711108 scopus 로고    scopus 로고
    • Salicylihalamides A and B, novel cytotoxic macrolides from the marine Sponge Haliclona sp
    • K.L. Erickson, J.A. Beutler, J.H. Cardellina II, M.R. Boyd, Salicylihalamides A and B, novel cytotoxic macrolides from the marine Sponge Haliclona sp, J. Org. Chem. 62 (1997) 8188-8192.
    • (1997) J. Org. Chem. , vol.62 , pp. 8188-8192
    • Erickson, K.L.1    Beutler, J.A.2    Cardellina II, J.H.3    Boyd, M.R.4
  • 10
  • 12
    • 34447320366 scopus 로고
    • An efficient approach to the basic skeleton of the cis-trikentrins
    • T. Yasukouchi, K. Kanematsu, An efficient approach to the basic skeleton of the cis-trikentrins, J. Chem. Soc. Chem. Commun. 14 (1989) 953-954.
    • (1989) J. Chem. Soc. Chem. Commun. , vol.14 , pp. 953-954
    • Yasukouchi, T.1    Kanematsu, K.2
  • 14
    • 84860605049 scopus 로고    scopus 로고
    • Palladium-catalyzed asymmetric 6-endo cyclization of dienamides with substituent-driven activation
    • H. Tsuchikawa, Y. Maekawa, S. Katsumura, Palladium-catalyzed asymmetric 6-endo cyclization of dienamides with substituent-driven activation, Org. Lett. 12 (2012) 2326-2329.
    • (2012) Org. Lett. , vol.12 , pp. 2326-2329
    • Tsuchikawa, H.1    Maekawa, Y.2    Katsumura, S.3
  • 15
    • 84875935145 scopus 로고    scopus 로고
    • Hydrogen bond-assisted 6pi-azaelectrocyclization of penta-2,4-dienamides: Synthesis of dihydropyridin-2(3H)-ones
    • X. Liu, N. Zhang, J. Yang, Y. Liang, R. Zhang, D. Dong, Hydrogen bond-assisted 6pi-azaelectrocyclization of penta-2,4-dienamides: synthesis of dihydropyridin-2(3H)-ones, J. Org. Chem. 78 (2013) 3323-3328.
    • (2013) J. Org. Chem. , vol.78 , pp. 3323-3328
    • Liu, X.1    Zhang, N.2    Yang, J.3    Liang, Y.4    Zhang, R.5    Dong, D.6
  • 17
    • 84860246405 scopus 로고    scopus 로고
    • (-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of beilschmiedia kunstleri gamble
    • A. Mollataghi, A.H.A. Hadi, S.-C. Cheah, (-)-Kunstleramide, a new antioxidant and cytotoxic dienamide from the bark of beilschmiedia kunstleri gamble, Molecules 17 (2012) 4197-4208.
    • (2012) Molecules , vol.17 , pp. 4197-4208
    • Mollataghi, A.1    Hadi, A.H.A.2    Cheah, S.-C.3
  • 18
    • 0031932932 scopus 로고    scopus 로고
    • A synthetic approach to natural dienamides of insecticidal interest
    • M. Abarbri, J.-L. Parrain, A. Duchěne, A synthetic approach to natural dienamides of insecticidal interest, Synth. Commun. 28 (1998) 239-249. (Pubitemid 28089866)
    • (1998) Synthetic Communications , vol.28 , Issue.2 , pp. 239-249
    • Abarbri, M.1    Parrain, J.-L.2    Duchene, A.3
  • 19
    • 84859805419 scopus 로고    scopus 로고
    • Discovery of novel 5,5-diarylpentadienamides as orally available transient receptor potential vanilloid 1 (TRPV1) antagonists
    • O. Saku, H. Ishida, E. Atsumi, Y. Sugimoto, H. Kodaira, Y. Kato, S. Shirakura, Y. Nakasato, Discovery of novel 5,5-diarylpentadienamides as orally available transient receptor potential vanilloid 1 (TRPV1) antagonists, J. Med. Chem. 55 (2012) 3436-3451.
    • (2012) J. Med. Chem. , vol.55 , pp. 3436-3451
    • Saku, O.1    Ishida, H.2    Atsumi, E.3    Sugimoto, Y.4    Kodaira, H.5    Kato, Y.6    Shirakura, S.7    Nakasato, Y.8
  • 20
    • 84870342233 scopus 로고    scopus 로고
    • Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzyla-minocarbonyl)-3-styrylacrylo-, nitrile (4g) developed using a fragment-based approach
    • Z. Zhang, T. Song, X. Li, Z. Wu, Y. Feng, F. Xie, C. Liu, J. Qin, H. Chen, Novel soluble myeloid cell leukemia sequence 1 (Mcl-1) inhibitor (E,E)-2-(benzyla-minocarbonyl)-3-styrylacrylo-, nitrile (4g) developed using a fragment-based approach, Eur. J. Med. Chem. 59 (2013) 141-149.
    • (2013) Eur. J. Med. Chem. , vol.59 , pp. 141-149
    • Zhang, Z.1    Song, T.2    Li, X.3    Wu, Z.4    Feng, Y.5    Xie, F.6    Liu, C.7    Qin, J.8    Chen, H.9
  • 21
    • 84875191834 scopus 로고    scopus 로고
    • Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans
    • B. Yu, E. Zhang, X.N. Sun, J.L. Ren, Y. Fang, B.L. Zhang, D.Q. Yu, H.M. Liu, Facile synthesis of novel D-ring modified steroidal dienamides via rearrangement of 2H-pyrans, Steroids 78 (2013) 494-499.
    • (2013) Steroids , vol.78 , pp. 494-499
    • Yu, B.1    Zhang, E.2    Sun, X.N.3    Ren, J.L.4    Fang, Y.5    Zhang, B.L.6    Yu, D.Q.7    Liu, H.M.8
  • 22
    • 80052959265 scopus 로고    scopus 로고
    • Novel 4-azasteroidal N-glycoside analogues bearing sugar-like D ring: Synthesis and anticancer activities
    • L.H. Huang, Y.G. Wang, G. Xu, X.H. Zhang, Y.F. Zheng, H.L. He, W.Z. Fu, H.M. Liu, Novel 4-azasteroidal N-glycoside analogues bearing sugar-like D ring: synthesis and anticancer activities, Bioorg. Med. Chem. Lett. 21 (2011) 6203-6205.
    • (2011) Bioorg. Med. Chem. Lett. , vol.21 , pp. 6203-6205
    • Huang, L.H.1    Wang, Y.G.2    Xu, G.3    Zhang, X.H.4    Zheng, Y.F.5    He, H.L.6    Fu, W.Z.7    Liu, H.M.8
  • 23
    • 84859848338 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines
    • L.H. Huang, Y.F. Zheng, Y.Z. Lu, C.J. Song, Y.G. Wang, B. Yu, H.M. Liu, Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4] triazolo[1,5-a]pyrimidines, Steroids 77 (2012) 710-715.
    • (2012) Steroids , vol.77 , pp. 710-715
    • Huang, L.H.1    Zheng, Y.F.2    Lu, Y.Z.3    Song, C.J.4    Wang, Y.G.5    Yu, B.6    Liu, H.M.7
  • 24
    • 84862777530 scopus 로고    scopus 로고
    • Synthesis of novel D-ring fused 7′-aryl-androstano[17,16-d][1,2,4] triazolo [1,5-a]pyrimidines
    • L.H. Huang, Y.F. Zheng, C.J. Song, Y.G. Wang, Z.Y. Xie, Y.W. Lai, Y.Z. Lu, H.M. Liu, Synthesis of novel D-ring fused 7′-aryl-androstano[17,16-d] [1,2,4] triazolo [1,5-a]pyrimidines, Steroids 77 (2012) 367-374.
    • (2012) Steroids , vol.77 , pp. 367-374
    • Huang, L.H.1    Zheng, Y.F.2    Song, C.J.3    Wang, Y.G.4    Xie, Z.Y.5    Lai, Y.W.6    Lu, Y.Z.7    Liu, H.M.8
  • 25
    • 27844487927 scopus 로고    scopus 로고
    • Synthesis of 7α-hydroxydehydro-, epiandrosterone and 7β-hydroxy-dehydroepiandrosterone
    • H.P. Li, H.M. Liu, W.Z. Ge, L.H. Huang, L.H. Shan, Synthesis of 7α-hydroxydehydro-, epiandrosterone and 7β-hydroxy- dehydroepiandrosterone, Steroids 70 (2005) 970-973.
    • (2005) Steroids , vol.70 , pp. 970-973
    • Li, H.P.1    Liu, H.M.2    Ge, W.Z.3    Huang, L.H.4    Shan, L.H.5
  • 26
    • 71749089264 scopus 로고    scopus 로고
    • Synthesis of 3β,7α, 11α-trihydroxy-pregn-21-benzylidene- 5-en-20-one derivatives and their cytotoxic activities
    • L.H. Shan, H.M. Liu, K.X. Huang, G.F. Dai, C. Cao, R.J. Dong, Synthesis of 3β,7α, 11α-trihydroxy-pregn-21-benzylidene-5-en-20-one derivatives and their cytotoxic activities, Bioorg. Med. Chem. Lett. 19 (2009) 6637-6639.
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 6637-6639
    • Shan, L.H.1    Liu, H.M.2    Huang, K.X.3    Dai, G.F.4    Cao, C.5    Dong, R.J.6
  • 27
    • 33845943238 scopus 로고    scopus 로고
    • Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide
    • S.M. Wang, Y.B. Zhang, H.M. Liu, G.B. Yu, K.R. Wang, Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide, Steroids 72 (2007) 26-30.
    • (2007) Steroids , vol.72 , pp. 26-30
    • Wang, S.M.1    Zhang, Y.B.2    Liu, H.M.3    Yu, G.B.4    Wang, K.R.5
  • 28
    • 77950518735 scopus 로고    scopus 로고
    • Digoxin derivatives substituted by alkylidene at the butenolide part
    • H.W. Xu, G.Z. Liu, S.L. Zhu, G.F. Hong, H.M. Liu, Q. Wu, Digoxin derivatives substituted by alkylidene at the butenolide part, Steroids 75 (2010) 419-423.
    • (2010) Steroids , vol.75 , pp. 419-423
    • Xu, H.W.1    Liu, G.Z.2    Zhu, S.L.3    Hong, G.F.4    Liu, H.M.5    Wu, Q.6
  • 31
    • 67651165035 scopus 로고    scopus 로고
    • Novel modified steroid derivatives of androstanolone as chemotherapeutic anticancer agents
    • M. El-Far, G.A. Elmegeed, E.F. Eskander, H.M. Rady, M.A. Tantawy, Novel modified steroid derivatives of androstanolone as chemotherapeutic anticancer agents, Eur. J. Med. Chem. 44 (2009) 3936-3946.
    • (2009) Eur. J. Med. Chem. , vol.44 , pp. 3936-3946
    • El-Far, M.1    Elmegeed, G.A.2    Eskander, E.F.3    Rady, H.M.4    Tantawy, M.A.5
  • 32
    • 84872676363 scopus 로고    scopus 로고
    • (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconearoylacrylic acid chimeras: Design, antiproliferative activity and inhibition of tubulin polymerization
    • M.D. Vitorovic-Todorovic, A. Eric-Nikolic, B. Kolundzija, E. Hamel, S. Ristic, I.O. Juranic, B.J. Drakulic, (E)-4-Aryl-4-oxo-2-butenoic acid amides, chalconearoylacrylic acid chimeras: design, antiproliferative activity and inhibition of tubulin polymerization, Eur. J. Med. Chem. 62 (2013) 40-50.
    • (2013) Eur. J. Med. Chem. , vol.62 , pp. 40-50
    • Vitorovic-Todorovic, M.D.1    Eric-Nikolic, A.2    Kolundzija, B.3    Hamel, E.4    Ristic, S.5    Juranic, I.O.6    Drakulic, B.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.