On topography and functionality in the B-D rings of cephalostatin cytotoxins

被引:21
作者
LaCour, TG [1 ]
Guo, CX
Ma, SH
Jeong, JU
Boyd, MR
Matsunaga, S
Fusetani, N
Fuchs, PL
机构
[1] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA
[2] NCI, Frederick Canc Res & Dev Ctr, Frederick, MD 21702 USA
[3] Univ Tokyo, Marine Biochem Lab, Bunkyo Ku, Tokyo 113, Japan
关键词
D O I
10.1016/S0960-894X(99)00430-8
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Analogues 12'beta-hydroxycephalostatin 1 (9), 7'-deoxyritterazine G (10), and 14-epi-7'-deoxyritterazine B (11) were prepared via our protocol for unsymmetrical pyrazine synthesis. Cytotoxicity against human tumors was also determined for the first time for ritterazines, with femtomolar potency and a high correlation to cephalostatins observed. The SAR of these and related. compounds provide insight into the importance of topography and certain chemical functionality in the B-D and B'-D' rings of cephalostatin type antineoplastics. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2587 / 2592
页数:6
相关论文
共 24 条
  • [1] ALLEY MC, 1988, CANCER RES, V48, P589
  • [2] TRIS(TRIMETHYLSILYL)SILANE AND DIPHENYLSILANE IN THE RADICAL CHAIN DIDEOXYGENATION OF 1,6-ANHYDRO-D-GLUCOSE - A COMPARATIVE-STUDY
    BARTON, DHR
    JANG, DO
    JASZBERENYI, JC
    [J]. TETRAHEDRON LETTERS, 1992, 33 (44) : 6629 - 6632
  • [3] Cytotoxic geranyl stilbenes from Macaranga schweinfurthii
    Beutler, JA
    Shoemaker, RH
    Johnson, T
    Boyd, MR
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (12): : 1509 - 1512
  • [4] SYNTHESIS OF A C-14',C-15' DIHYDRO DERIVATIVE OF THE SOUTH HEXACYCLIC STEROID UNIT OF CEPHALOSTATIN-1 .1. REGIOSPECIFIC RH[II]-MEDIATED INTERMOLECULAR OXYGEN ALKYLATION OF A PRIMARY NEOPENTYL ALCOHOL
    BHANDARU, S
    FUCHS, PL
    [J]. TETRAHEDRON LETTERS, 1995, 36 (46) : 8347 - 8350
  • [5] Boyd M.R., 1997, ANTICANCER DRUG DEV, P23, DOI 10.1007/978-1-4615-8152-9_2
  • [6] SOME PRACTICAL CONSIDERATIONS AND APPLICATIONS OF THE NATIONAL-CANCER-INSTITUTE IN-VITRO ANTICANCER DRUG DISCOVERY SCREEN
    BOYD, MR
    PAULI, KD
    [J]. DRUG DEVELOPMENT RESEARCH, 1995, 34 (02) : 91 - 109
  • [7] Directed synthesis of nonsymmetrical bis-steroidal pyrazines and the first biologically active cephalostatin analogues
    Drogemuller, M
    Jautelat, R
    Winterfeldt, E
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14): : 1572 - 1574
  • [8] Drögemüller M, 1998, EUR J ORG CHEM, V1998, P2811
  • [9] Isolation of 13 new ritterazines from the tunicate Ritterella tokioka and chemical transformation of ritterazine B
    Fukuzawa, S
    Matsunaga, S
    Fusetani, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) : 4484 - 4491
  • [10] LANTHANOIDS IN ORGANIC-SYNTHESIS .6. THE REDUCTION OF ALPHA-ENONES BY SODIUM-BOROHYDRIDE IN THE PRESENCE OF LANTHANOID CHLORIDES - SYNTHETIC AND MECHANISTIC ASPECTS
    GEMAL, AL
    LUCHE, JL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) : 5454 - 5459