메뉴 건너뛰기




Volumn 54, Issue 9, 2011, Pages 3298-3305

Synthesis and biological activity of 22-deoxo-23-oxa analogues of saponin OSW-1

Author keywords

[No Author keywords available]

Indexed keywords

21 BENZYLOXY 20 METHYLPREGN 5 ENE 3BETA,16BETA,17ALPHA TRIOL 6 O [2 O (4 METHOXYBENZOYL) BETA DEXTRO XYLOPYRANOSYL (1 3) 2' O ACETYLARABINOPYRANOSIDE]; 21 O (4 METHOXYBENZOYL) 20 METHYLPREGN 5 ENE 3BETA,16BETA,17ALPHA,21 TETRAOL 16 O [2 O (4 METHOXYBENZOYL) BETA DEXTRO XYLOPYRANOSYL (1-3) 2' ACETYL ALPHA LEVO ARABINOPYRANOSIDE]; 21 O (BUT 2 ENOYL) 20 METHYLPREGN 5 ENE 3BETA,16BETA,17ALPHA,21 TETRAOL 16 O [2 O (4 METHOXYBENZOYL) BETA DEXTRO XYLOPYRANOSYL (1-3) 2' ACETYL ALPHA LEVO ARABINOPYRANOSIDE]; 21 O (UNDEC 10 ENOYL) 20 METHYLPREGN 5 ENE 3BETA,16BETA,17ALPHA,21 TETRAOL 16 O [2 O (4 METHOXYBENZOYL) BETA DEXTRO XYLOPYRANOSYL (1-3) 2' ACETYL ALPHA LEVO ARABINOPYRANOSIDE]; AGLYCONE; ANTINEOPLASTIC AGENT; CASPASE 3; CASPASE 7; OSW 1; SAPONIN; SAPONIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79955833912     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm101648h     Document Type: Article
Times cited : (26)

References (32)
  • 1
    • 67650675111 scopus 로고    scopus 로고
    • Impact of natural products on developing new anticancer agents
    • Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Impact of natural products on developing new anticancer agents Chem. Rev. 2009, 109, 3012-3043
    • (2009) Chem. Rev. , vol.109 , pp. 3012-3043
    • Cragg, G.M.1    Grothaus, P.G.2    Newman, D.J.3
  • 2
    • 0001678648 scopus 로고
    • Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae
    • Kubo, S.; Mimaki, Y.; Terao, M.; Sashida, Y.; Nikaido, T.; Ohmoto, T. Acylated cholestane glycosides from the bulbs of Ornithogalum saundersiae Phytochemistry 1992, 31, 3969-3973
    • (1992) Phytochemistry , vol.31 , pp. 3969-3973
    • Kubo, S.1    Mimaki, Y.2    Terao, M.3    Sashida, Y.4    Nikaido, T.5    Ohmoto, T.6
  • 5
    • 27844584355 scopus 로고    scopus 로고
    • Apoptosis induced by a new member of saponin family is mediated through caspase-8-dependent cleavage of Bcl-2
    • DOI 10.1124/mol.105.015826
    • Zhu, J.; Xiong, L.; Wu, J. Apoptosis induced by a new member of saponin family is mediated through caspase-8-dependent cleavage of Bcl-2 Mol. Pharmacol. 2005, 68, 1831-1838 (Pubitemid 41656029)
    • (2005) Molecular Pharmacology , vol.68 , Issue.6 , pp. 1831-1838
    • Zhu, J.1    Xiong, L.2    Yu, B.3    Wu, J.4
  • 6
    • 0033534604 scopus 로고    scopus 로고
    • First total synthesis of an exceptionally potent antitumor saponin, OSW- 1
    • DOI 10.1021/jo981685c
    • Deng, S.; Yu, B.; Lou, Y.; Hui, Y. First total synthesis of an exceptionally potent antitumor saponin, OSW-1 J. Org. Chem. 1999, 64, 202-208 (Pubitemid 29037327)
    • (1999) Journal of Organic Chemistry , vol.64 , Issue.1 , pp. 202-208
    • Deng, S.1    Yu, B.2    Lou, Y.3    Hui, Y.4
  • 7
    • 0032485307 scopus 로고    scopus 로고
    • The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1
    • DOI 10.1016/S0040-4039(97)10814-0, PII S0040403997108140
    • Guo, C.; Fuchs, P. L. The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1 Tetrahedron Lett. 1998, 39, 1099-1102 (Pubitemid 28076179)
    • (1998) Tetrahedron Letters , vol.39 , Issue.10 , pp. 1099-1102
    • Guo, C.1    Fuchs, P.L.2
  • 8
    • 0034829735 scopus 로고    scopus 로고
    • A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1 [2]
    • DOI 10.1021/ja004098t
    • Yu, W.; Jin, Z. A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: total synthesis of a highly potent antitumor natural product OSW-1 J. Am. Chem. Soc. 2001, 123, 3369-3370 (Pubitemid 32884627)
    • (2001) Journal of the American Chemical Society , vol.123 , Issue.14 , pp. 3369-3370
    • Yu, W.1    Jin, Z.2
  • 9
    • 0037067056 scopus 로고    scopus 로고
    • Total synthesis of an antitumor natural product OSW-1
    • Yu, W.; Jin, Z. Total synthesis of an antitumor natural product OSW-1 J. Am. Chem. Soc. 2001, 124, 6576-6583
    • (2001) J. Am. Chem. Soc. , vol.124 , pp. 6576-6583
    • Yu, W.1    Jin, Z.2
  • 10
    • 0037118924 scopus 로고    scopus 로고
    • Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity
    • DOI 10.1016/S0008-6215(02)00126-X, PII S000862150200126X
    • Morzycki, J. W.; Wojtkielewicz, A. Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity Carbohydr. Res. 2002, 337, 1269-1274 (Pubitemid 34874756)
    • (2002) Carbohydrate Research , vol.337 , Issue.14 , pp. 1269-1274
    • Morzycki, J.W.1    Wojtkielewicz, A.2
  • 11
    • 0345304271 scopus 로고    scopus 로고
    • A new strategy for synthesizing the steroids with side chains from steroidal sapogenins: Synthesis of the aglycone of OSW-1 by using the intact skeleton of diosgenin
    • DOI 10.1016/j.tetlet.2003.09.227
    • Xu, Q.; Peg, X.; Tian, W. A new strategy for synthesizing the steroids with side chains from steroidal sapogenins: synthesis of the aglycone of OSW-1 by using the intact skeleton of diosgenin Tetrahedron Lett. 2003, 44, 9375-9377 (Pubitemid 37485836)
    • (2003) Tetrahedron Letters , vol.44 , Issue.52 , pp. 9375-9377
    • Xu, Q.-H.1    Peng, X.-W.2    Tian, W.-S.3
  • 12
    • 37549028745 scopus 로고    scopus 로고
    • A total synthesis of OSW-1
    • Liu, J. X. P.; Pan, Y.; Guo, Z. A total synthesis of OSW-1 J. Org. Chem. 2008, 73, 157-161
    • (2008) J. Org. Chem. , vol.73 , pp. 157-161
    • Liu, J.X.P.1    Pan, Y.2    Guo, Z.3
  • 13
    • 36849020952 scopus 로고    scopus 로고
    • A new synthesis of potent antitumor saponin OSW-1 via Wittig rearrangement
    • DOI 10.1016/j.tetlet.2007.11.087, PII S004040390702285X
    • Tsubuki, M.; Matsuo, S.; Honda, T. A new synthesis of potent antitumor saponin OSW-1 via Wittig rearrangement Tetrahedron Lett. 2008, 49, 229-232 (Pubitemid 50008663)
    • (2008) Tetrahedron Letters , vol.49 , Issue.2 , pp. 229-232
    • Tsubuki, M.1    Matsuo, S.2    Honda, T.3
  • 14
    • 28644433853 scopus 로고    scopus 로고
    • Synthesis of a highly potent antitumor saponin OSW-1 and its analogues
    • DOI 10.1007/s11101-005-1233-6
    • Morzycki, J. W.; Wojtkielewicz, A. Synthesis of highly potent antitumor saponin OSW-1 and its analogues Phytochem. Rev. 2005, 4, 259-277 (Pubitemid 41752180)
    • (2005) Phytochemistry Reviews , vol.4 , Issue.2-3 , pp. 259-277
    • Morzycki, J.W.1    Wojtkielewicz, A.2
  • 16
    • 28744456358 scopus 로고    scopus 로고
    • OSW Saponins: Facile synthesis toward a new type of structures with potent antitumor activities
    • DOI 10.1021/jo051536b
    • Shi, B.; Tang, P.; Hu, X.; Liu, J. O.; Yu, B. OSW saponins: facile synthesis toward a new type of structures with potent antitumor activities J. Org. Chem. 2005, 70, 10354-10367 (Pubitemid 41759905)
    • (2005) Journal of Organic Chemistry , vol.70 , Issue.25 , pp. 10354-10367
    • Shi, B.1    Tang, P.2    Hu, X.3    Liu, J.O.4    Yu, B.5
  • 17
    • 33846640843 scopus 로고    scopus 로고
    • Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities
    • DOI 10.1016/j.bmcl.2006.11.032, PII S0960894X06013254
    • Tang, P.; Mamdani, F.; Hu, X.; Liu, J. O.; Yu, B. Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities Bioorg. Med. Chem. Lett. 2007, 17, 1003-1007 (Pubitemid 46178544)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.4 , pp. 1003-1007
    • Tang, P.1    Mamdani, F.2    Hu, X.3    Liu, J.O.4    Yu, B.5
  • 18
    • 34548574624 scopus 로고    scopus 로고
    • Synthesis of the A,B-ring-truncated OSW saponin analogs and their antitumor activities
    • DOI 10.1016/j.bmcl.2007.08.060, PII S0960894X07010177
    • Peng, W.; Tang, P.; Hu, X.; Liu, J. O.; Yu, B. Synthesis of the A,B-ring-truncated OSW saponin analogs and their antitumor activities Bioorg. Med. Chem. Lett. 2007, 17, 5506-5509 (Pubitemid 47391333)
    • (2007) Bioorganic and Medicinal Chemistry Letters , vol.17 , Issue.20 , pp. 5506-5509
    • Peng, W.1    Tang, P.2    Hu, X.3    Liu, J.O.4    Yu, B.5
  • 23
    • 2342507229 scopus 로고    scopus 로고
    • Synthesis of OSW-1 analogs with modified side chains and their antitumor activities
    • DOI 10.1016/j.bmcl.2004.03.081, PII S0960894X04004548
    • Deng, L.; Wu, H.; Yu, B.; Jiang, M.; Wu, J. Synthesis of OSW-1 analogs with modified side chains and their antitumor activities Bioorg. Med. Chem. Lett. 2004, 14, 2781-2785 (Pubitemid 38569736)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.11 , pp. 2781-2785
    • Deng, L.1    Wu, H.2    Yu, B.3    Jiang, M.4    Wu, J.5
  • 25
    • 0035835960 scopus 로고    scopus 로고
    • Neighboring group participation in epoxide ring cleavage in reactions of some 16α,17α-oxidosteroids with lithium hydroperoxide
    • DOI 10.1016/S0040-4020(01)00051-5, PII S0040402001000515
    • Morzycki, J. W.; Gryszkiewicz, A.; Jastrze?bska, I. Neighboring group participation in the oxirane ring cleavage in some 16α,17α- oxidosteroids reactions with lithium peroxide Tetrahedron 2001, 57, 2185-2193 (Pubitemid 32200538)
    • (2001) Tetrahedron , vol.57 , Issue.11 , pp. 2185-2193
    • Morzycki, J.W.1    Gryszkiewicz, A.2    Jastrz, I.3
  • 28
    • 0035921118 scopus 로고    scopus 로고
    • Synthesis of OSW-1 analogues and a dimer and their antitumor activities
    • DOI 10.1016/S0960-894X(01)00389-4, PII S0960894X01003894
    • Ma, X.; Yu, B.; Hui, Y.; Miao, Z.; Ding, J. Synthesis of OSW-1 analogues and a dimer and their antitumor activities Bioorg. Med. Chem. Lett. 2001, 11, 2153-2156 (Pubitemid 32763020)
    • (2001) Bioorganic and Medicinal Chemistry Letters , vol.11 , Issue.16 , pp. 2153-2156
    • Ma, X.1    Yu, B.2    Hui, Y.3    Miao, Z.4    Ding, J.5
  • 29
    • 77956173116 scopus 로고    scopus 로고
    • Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1?4-linked analogue and their antitumor activities
    • Zheng, D.; Zhou, L.; Guan, Y.; Chen, X.; Zhou, W.; Chen, X.; Lei, P. Synthesis of cholestane glycosides bearing OSW-1 disaccharide or its 1?4-linked analogue and their antitumor activities Bioorg. Med. Chem. Lett. 2010, 20, 5439-5442
    • (2010) Bioorg. Med. Chem. Lett. , vol.20 , pp. 5439-5442
    • Zheng, D.1    Zhou, L.2    Guan, Y.3    Chen, X.4    Zhou, W.5    Chen, X.6    Lei, P.7
  • 31
    • 0031809920 scopus 로고    scopus 로고
    • Mechanisms controlling cellular suicide: Role of Bcl-2 and caspases
    • DOI 10.1007/s000180050171
    • Allen, R. T.; Cluck, M. W.; Agrawal, D. K. Mechanisms controlling cellular suicide: role of Bcl-2 and caspases Cell. Mol. Life Sci. 1998, 54, 427-445 (Pubitemid 28260595)
    • (1998) Cellular and Molecular Life Sciences , vol.54 , Issue.5 , pp. 427-445
    • Allen, R.T.1    Cluck, M.W.2    Agrawal, D.K.3
  • 32
    • 0036478928 scopus 로고    scopus 로고
    • The Apaf-1 apoptosome: A large caspase-activating complex
    • DOI 10.1016/S0300-9084(02)01376-7, PII S0300908402013767
    • Cain, K.; Bratton, S. B.; Cohen, G. M. The Apaf-1 apoptosome: a large caspase-activating complex Biochimie 2002, 84, 203-214 (Pubitemid 34946950)
    • (2002) Biochimie , vol.84 , Issue.2-3 , pp. 203-214
    • Cain, K.1    Bratton, S.B.2    Cohen, G.M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.