메뉴 건너뛰기




Volumn 50, Issue 15, 2007, Pages 3667-3673

New analogues of the potent cytotoxic saponin OSW-1

Author keywords

[No Author keywords available]

Indexed keywords

3BETA,16BETA,17ALPHA TRIHYDROXYCHOLEST 5 EN 22 ONE 16 O [O [2 O (4 MTEHOXYBENZOYL) BETA DEXTRO XYLOPYRANOSYL](1-3) 2 O ACETYL ALPHA ARABINOPYRANOSIDE; OSW 1; SAPONIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34547571520     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0613572     Document Type: Article
Times cited : (45)

References (51)
  • 2
    • 0034831086 scopus 로고    scopus 로고
    • Advances in cancer therapy with plant based natural products
    • Mukherjee, A. K.; Basu, S.; Sarkar, N.; Ghosh, A. C. Advances in cancer therapy with plant based natural products. Curr. Med. Chem. 2001, 8, 1467-1486.
    • (2001) Curr. Med. Chem , vol.8 , pp. 1467-1486
    • Mukherjee, A.K.1    Basu, S.2    Sarkar, N.3    Ghosh, A.C.4
  • 4
    • 0028139458 scopus 로고    scopus 로고
    • Fukuzawa, S.; Matsunaga, S.; Fusetani, N. Ritterazine A, a highly cytotoxic dimeric steroidal alkaloid, from the tunicate Ritterella tokioka. J. Org. Chem. 1994, 59, 6164-6166.
    • Fukuzawa, S.; Matsunaga, S.; Fusetani, N. Ritterazine A, a highly cytotoxic dimeric steroidal alkaloid, from the tunicate Ritterella tokioka. J. Org. Chem. 1994, 59, 6164-6166.
  • 5
    • 0033151262 scopus 로고    scopus 로고
    • Possible mechanisms of poclitaxel-induced apoptosis
    • Fan, W. Possible mechanisms of poclitaxel-induced apoptosis. Biochem. Pharmacol. 1999, 57, 1215-1221.
    • (1999) Biochem. Pharmacol , vol.57 , pp. 1215-1221
    • Fan, W.1
  • 6
    • 0037864005 scopus 로고    scopus 로고
    • Natural products for cancer prevention: A global perspective
    • Reddy, L.; Odhav, B.; Bhoola, K. D. Natural products for cancer prevention: A global perspective. Pharmacol. Ther. 2003, 99, 1-13.
    • (2003) Pharmacol. Ther , vol.99 , pp. 1-13
    • Reddy, L.1    Odhav, B.2    Bhoola, K.D.3
  • 7
    • 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
  • 9
    • 34547611529 scopus 로고    scopus 로고
    • Structures and biological activities of plant glycosides: Cholestane glycosides from Ornithogalum saundersiae, O. thyrsoides and Galtonia candicans, and their cytotoxic and antitumor activities
    • Mimaki, Y. Structures and biological activities of plant glycosides: cholestane glycosides from Ornithogalum saundersiae, O. thyrsoides and Galtonia candicans, and their cytotoxic and antitumor activities. Nat. Prod. Commun. 2006, 1, 247-253.
    • (2006) Nat. Prod. Commun , vol.1 , pp. 247-253
    • Mimaki, Y.1
  • 10
    • 0038268820 scopus 로고    scopus 로고
    • Approaches towards the synthesis of cephalostatins, ritterazines and saponins from Ornithogalum saundersiae - New natural products with cytostatic activity
    • Gryszkiewicz-Wojtkielewicz, A.; Jastrzebska, I.; Morzycki, J. W.; Romanowska, D. B. Approaches towards the synthesis of cephalostatins, ritterazines and saponins from Ornithogalum saundersiae - New natural products with cytostatic activity. Curr. Org. Chem. 2003, 7, 1257-1277.
    • (2003) Curr. Org. Chem , vol.7 , pp. 1257-1277
    • Gryszkiewicz-Wojtkielewicz, A.1    Jastrzebska, I.2    Morzycki, J.W.3    Romanowska, D.B.4
  • 12
    • 0032485307 scopus 로고    scopus 로고
    • The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1
    • 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.
    • (1998) Tetrahedron Lett , vol.39 , pp. 1099-1102
    • Guo, C.1    Fuchs, P.L.2
  • 13
    • 0035649771 scopus 로고    scopus 로고
    • Synthesis of the potent antitumor saponin OSW-1 aglycone
    • Morzycki, J. W.; Gryszkiewicz, A. Synthesis of the potent antitumor saponin OSW-1 aglycone. Pol. J. Chem. 2001, 75, 983-989.
    • (2001) Pol. J. Chem , vol.75 , pp. 983-989
    • Morzycki, J.W.1    Gryszkiewicz, A.2
  • 14
    • 0034829735 scopus 로고    scopus 로고
    • A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of highly potent antitumor natural product OSW-1
    • Yu, W.; Jin, Z. A new strategy for the stereoselective introduction of steroid side chain via α-alkoxy vinyl cuprates: Total synthesis of highly potent antitumor natural product OSW-1. J. Am. Chem. Soc. 2001, 123, 3369-3370.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 3369-3370
    • Yu, W.1    Jin, Z.2
  • 15
    • 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
    • Xu, Q.; Peng, 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.
    • (2003) Tetrahedron Lett , vol.44 , pp. 9375-9377
    • Xu, Q.1    Peng, X.2    Tian, W.3
  • 16
    • 0033534604 scopus 로고    scopus 로고
    • First total synthesis of an exceptionally potent antitumor saponin, OSW-1
    • 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.
    • (1999) J. Org. Chem , vol.64 , pp. 202-208
    • Deng, S.1    Yu, B.2    Lou, Y.3    Hui, Y.4
  • 17
    • 0037118924 scopus 로고    scopus 로고
    • Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity
    • Morzycki, J. W.; Wojtkielewicz, A. Synthesis of a cholestane glycoside OSW-1 with potent cytostatic activity. Carbohydr. Res. 2002, 337, 1269-1274.
    • (2002) Carbohydr. Res , vol.337 , pp. 1269-1274
    • Morzycki, J.W.1    Wojtkielewicz, A.2
  • 18
    • 0037067056 scopus 로고    scopus 로고
    • The total synthesis of the natural product OSW-1
    • Yu, W.; Jin, Z. The total synthesis of the natural product OSW-1. J. Am. Chem. Soc. 2002, 124, 6576-6583.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 6576-6583
    • Yu, W.1    Jin, Z.2
  • 19
    • 4544291577 scopus 로고    scopus 로고
    • 23-Oxa-analogues of OSW-1: Efficient synthesis and extremely potent antitumor activity
    • Shi, B.; Wu, H.; Yu, B.; Wu, J. 23-Oxa-analogues of OSW-1: Efficient synthesis and extremely potent antitumor activity. Angew. Chem., Int. Ed. 2004, 43, 4324-4327.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 4324-4327
    • Shi, B.1    Wu, H.2    Yu, B.3    Wu, J.4
  • 20
    • 0035921118 scopus 로고    scopus 로고
    • Synthesis of OSW-1 analogues and a dimer and their antitumor activities
    • 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.
    • (2001) Bioorg. Med. Chem. Lett , vol.11 , pp. 2153-2156
    • Ma, X.1    Yu, B.2    Hui, Y.3    Miao, Z.4    Ding, J.5
  • 21
    • 2342507229 scopus 로고    scopus 로고
    • Synthesis of OSW-1 analogs with modified side chains and their antitumor activities
    • 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.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 2781-2785
    • Deng, L.1    Wu, H.2    Yu, B.3    Jiang, M.4    Wu, J.5
  • 22
    • 4544291577 scopus 로고    scopus 로고
    • 23-Oxa-analogues of OSW-1: Efficient synthesis and extremely potent antitumor activity
    • Shi, B.; Wu, H.; Yu, B.; Wu, J. 23-Oxa-analogues of OSW-1: Efficient synthesis and extremely potent antitumor activity. Angew. Chem., Int. Ed. 2004, 43, 4324-4327.
    • (2004) Angew. Chem., Int. Ed , vol.43 , pp. 4324-4327
    • Shi, B.1    Wu, H.2    Yu, B.3    Wu, J.4
  • 23
    • 28744456358 scopus 로고    scopus 로고
    • Shi, B.; Tang, P.; Hu, X.; Liu, X. O.; Yu, B. OSW Saponins: Facile synthesis toward a new type of structures with potent antitumor activities. J. Org. Chem. 2005, 70, 10354-10367.
    • Shi, B.; Tang, P.; Hu, X.; Liu, X. O.; Yu, B. OSW Saponins: Facile synthesis toward a new type of structures with potent antitumor activities. J. Org. Chem. 2005, 70, 10354-10367.
  • 24
    • 33645782284 scopus 로고    scopus 로고
    • A highly efficient synthesis of 22-deoxy-OSW-1 by utilizing the intact skeleton of diosgenin
    • Qin, J.; Tian, W.; Lin, W. A highly efficient synthesis of 22-deoxy-OSW-1 by utilizing the intact skeleton of diosgenin. Tetrahedron Lett. 2006, 47, 3217-3219.
    • (2006) Tetrahedron Lett , vol.47 , pp. 3217-3219
    • Qin, J.1    Tian, W.2    Lin, W.3
  • 25
    • 28644433853 scopus 로고    scopus 로고
    • Synthesis of a highly potent antitumor saponin OSW-1 and its analogues
    • Morzycki, J. W.; Wojtkielewicz, A. Synthesis of a highly potent antitumor saponin OSW-1 and its analogues. Phytochem. Rev. 2005, 4, 259-277.
    • (2005) Phytochem. Rev , vol.4 , pp. 259-277
    • Morzycki, J.W.1    Wojtkielewicz, A.2
  • 26
    • 33846640843 scopus 로고    scopus 로고
    • Synthesis of OSW saponin analogs with modified sugar residues and their antiproliferative activities
    • 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.
    • (2007) Bioorg. Med. Chem. Lett , vol.17 , pp. 1003-1007
    • Tang, P.1    Mamdani, F.2    Hu, X.3    Liu, J.O.4    Yu, B.5
  • 30
    • 0346828785 scopus 로고    scopus 로고
    • Identification and structure determination of four triterpene saponins from some middle-east plants
    • Soliman, H. S. M.; Simon, A.; Tóth, G.; Duddeck, H. Identification and structure determination of four triterpene saponins from some middle-east plants. Magn. Reson. Chem. 2001, 39, 567-576.
    • (2001) Magn. Reson. Chem , vol.39 , pp. 567-576
    • Soliman, H.S.M.1    Simon, A.2    Tóth, G.3    Duddeck, H.4
  • 31
    • 0032882506 scopus 로고    scopus 로고
    • Akihisha, T.; Kimura, Y.; Tai, T. Arai, K. Astertarone B, a hydroxytriterpenoid ketone from the roots of Aster tataricus L. Chem. Pharm. Bull. 1999, 47, 1161-1163.
    • Akihisha, T.; Kimura, Y.; Tai, T. Arai, K. Astertarone B, a hydroxytriterpenoid ketone from the roots of Aster tataricus L. Chem. Pharm. Bull. 1999, 47, 1161-1163.
  • 34
    • 0034612136 scopus 로고    scopus 로고
    • Some reactions of 16α,17α-oxido-steroids: A study related to the synthesis of the potent antitumor saponin OSW-1 aglycone
    • Morzycki, J. W.; Gryszkiewicz, A.; Jastrzȩbska, I. Some reactions of 16α,17α-oxido-steroids: A study related to the synthesis of the potent antitumor saponin OSW-1 aglycone. Tetrahedron Lett. 2000, 41, 3751-3754.
    • (2000) Tetrahedron Lett , vol.41 , pp. 3751-3754
    • Morzycki, J.W.1    Gryszkiewicz, A.2    Jastrzȩbska, I.3
  • 35
    • 0035835960 scopus 로고    scopus 로고
    • Neighboring group participation in epoxide ring cleavage in reactions of some 16α,-17α-oxidosteroids with lithium hydroperoxide
    • Morzycki, J. W.; Gryszkiewicz, A.; Jastrzȩbska, I. Neighboring group participation in epoxide ring cleavage in reactions of some 16α,-17α-oxidosteroids with lithium hydroperoxide. Tetrahedron 2001, 57, 2185-2193.
    • (2001) Tetrahedron , vol.57 , pp. 2185-2193
    • Morzycki, J.W.1    Gryszkiewicz, A.2    Jastrzȩbska, I.3
  • 36
    • 5144233105 scopus 로고
    • MLEV-17 based two-dimensional homonuclear magnetization transfer spectroscopy
    • Bax, A.; Davis, D. G. MLEV-17 based two-dimensional homonuclear magnetization transfer spectroscopy. J. Magn. Reson. 1985, 65, 355-360.
    • (1985) J. Magn. Reson , vol.65 , pp. 355-360
    • Bax, A.1    Davis, D.G.2
  • 37
    • 0005963761 scopus 로고
    • Multiple quantum filters for elucidating NMR coupling networks
    • Piantini, U.; Sørensen, O. W.; Ernst, R. R. Multiple quantum filters for elucidating NMR coupling networks. J. Am. Chem. Soc. 1982, 104, 6800-6801.
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 6800-6801
    • Piantini, U.1    Sørensen, O.W.2    Ernst, R.R.3
  • 39
    • 0011491177 scopus 로고
    • Structure determination of a tetrasaccharide: Transient nuclear Overhauser effects in the rotating frame
    • Bothner-By, A. A.; Stephens, R. L.; Lee, J.-M., Warren, C. D.; Jeanloz, R. W. Structure determination of a tetrasaccharide: Transient nuclear Overhauser effects in the rotating frame. J. Am. Chem. Soc. 1984, 106, 811-813.
    • (1984) J. Am. Chem. Soc , vol.106 , pp. 811-813
    • Bothner-By, A.A.1    Stephens, R.L.2    Lee, J.-M.3    Warren, C.D.4    Jeanloz, R.W.5
  • 40
    • 5144229966 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax, A.; Davis, D. G. Practical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Reson. 1985, 63, 207-213.
    • (1985) J. Magn. Reson , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 41
    • 44949276869 scopus 로고
    • Sensitivity improvement in proton-detected twodimensional heteronuclear correlation NMR spectroscopy
    • Palmer, A. G., III; Cavanagh, J.; Wright, P. E. Sensitivity improvement in proton-detected twodimensional heteronuclear correlation NMR spectroscopy. J. Magn. Reson. 1991, 93, 151-170.
    • (1991) J. Magn. Reson , vol.93 , pp. 151-170
    • Palmer III, A.G.1    Cavanagh, J.2    Wright, P.E.3
  • 42
    • 0006925492 scopus 로고
    • Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity
    • Kay, L. E.; Keifer, P.; Saarinen, T. Pure absorption gradient enhanced heteronuclear single quantum correlation spectroscopy with improved sensitivity. J. Am. Chem. Soc. 1992, 114, 10663-10665.
    • (1992) J. Am. Chem. Soc , vol.114 , pp. 10663-10665
    • Kay, L.E.1    Keifer, P.2    Saarinen, T.3
  • 43
    • 0345311216 scopus 로고
    • 13C assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR
    • 13C assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by 2D multiple quantum NMR. J. Am. Chem. Soc. 1986, 108, 2093-2094.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 2093-2094
    • Bax, A.1    Summers, M.F.2
  • 44
    • 0037899660 scopus 로고    scopus 로고
    • Polarizable atomic multipole water model for molecular mechanics simulation
    • Ren, P.; Ponder, J. W. Polarizable atomic multipole water model for molecular mechanics simulation. J. Phys. Chem. B 2003, 107, 5933-5947.
    • (2003) J. Phys. Chem. B , vol.107 , pp. 5933-5947
    • Ren, P.1    Ponder, J.W.2
  • 45
    • 0036890275 scopus 로고    scopus 로고
    • Consistent treatment of inter- and intramolecular polarization in molecular mechanics calculations
    • Ren, P.; Ponder, J. W. Consistent treatment of inter- and intramolecular polarization in molecular mechanics calculations. J. Comput. Chem. 2002, 23, 1497-1506.
    • (2002) J. Comput. Chem , vol.23 , pp. 1497-1506
    • Ren, P.1    Ponder, J.W.2
  • 46
    • 0024821263 scopus 로고
    • Molecular mechanics. The MM3 force field for hydrocarbons
    • Allinger, N. L.; Yuh, Y. H.; Lii, J.-H. Molecular mechanics. The MM3 force field for hydrocarbons. J. Am. Chem. Soc. 1989, 111, 8551-8566.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 8551-8566
    • Allinger, N.L.1    Yuh, Y.H.2    Lii, J.-H.3
  • 47
    • 0029878720 scopus 로고    scopus 로고
    • Humphrey, W.; Dalke, A.; Schulten, K. VMD - Visual molecular dynamics. J. Mol. Graphics 1996, 14, 33-38.
    • Humphrey, W.; Dalke, A.; Schulten, K. VMD - Visual molecular dynamics. J. Mol. Graphics 1996, 14, 33-38.
  • 49
    • 0000394426 scopus 로고
    • Some multistep methods for use in molecular dynamics calculations
    • Beeman, D. Some multistep methods for use in molecular dynamics calculations. J. Comput. Phys. 1976, 20, 130-139.
    • (1976) J. Comput. Phys , vol.20 , pp. 130-139
    • Beeman, D.1
  • 51
    • 84966262179 scopus 로고
    • Updating quasi-Newton matrices with limited storage
    • Nocedal, J. Updating quasi-Newton matrices with limited storage. Math. Comp. 1980, 35, 773-782.
    • (1980) Math. Comp , vol.35 , pp. 773-782
    • Nocedal, J.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.