Stereodivergent Synthesis of 17-α and 17-β-Aryl Steroids: Application and Biological Evaluation of D-Ring Cortistatin Analogues

被引:52
|
作者
Shi, Jun [1 ]
Shigehisa, Hiroki [1 ]
Guerrero, Carlos A. [1 ]
Shenvi, Ryan A. [1 ]
Li, Chuang-Chuang [1 ]
Baran, Phil S. [1 ]
机构
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
关键词
angiogenesis; asymmetric synthesis; natural products; CATALYTIC HYDROGENOLYSIS; CONCISE SYNTHESIS; ALKALOIDS; STEREOCHEMISTRY; HYDROGENATION; ALCOHOLS;
D O I
10.1002/anie.200901116
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
One stereocenter makes all the difference: The synthesis and biological evaluation of 17-epi-cortistatin A is reported from a common intermediate used to procure natural cortistatin A. The synthesis features a unique stereocontrolled Raney-Ni reduction process that can be employed to reliably produce both α- and β-configured Dring aryl steroids. Biological evaluations of these "cortalogs" are reported for the first time. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:4328 / 4331
页数:4
相关论文
共 50 条
  • [21] ON THE CONSTRUCTION OF THE C/D-RING SYSTEMS OF APHIDICOLIN AND STEMODIN - A REGIOSPECIFIC AND STEREOSPECIFIC SYNTHESIS OF 17-NORAPHIDICOLAN-16-ONE AND 17-NORSTEMODAN-16-ONE
    BRAVETTI, D
    BETTOLO, RM
    LUPI, A
    HELVETICA CHIMICA ACTA, 1982, 65 (01) : 371 - 376
  • [22] Design, synthesis and biological evaluation of D-ring opened galantamine analogs as multifunctional anti-Alzheimer agents
    Fang, Lei
    Fang, Xubin
    Gou, Shaohua
    Lupp, Amelie
    Lenhardt, Isabel
    Sun, Yanyan
    Huang, Zhangjian
    Chen, Yao
    Zhang, Yihua
    Fleck, Christian
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 76 : 376 - 386
  • [23] Transport of bile acids, sulfated steroids, estradiol 17-β-D-glucuronide, and leukotriene C4 by human multidrug resistance protein 8 (ABCC11)
    Chen, ZS
    Guo, YP
    Belinsky, MG
    Kotova, E
    Kruh, GD
    MOLECULAR PHARMACOLOGY, 2005, 67 (02) : 545 - 557
  • [24] Design, synthesis and biological evaluation of paclitaxel-mimics possessing only the oxetane D-ring and side chain structures
    Chen, Xing-Xiu
    Gao, Feng
    Wang, Qi
    Huang, Xing
    Wang, Dan
    FITOTERAPIA, 2014, 92 : 111 - 115
  • [25] Synthesis and biological evaluation of D-ring fused 1,2,3-thiadiazole dehydroepiandrosterone derivatives as antitumor agents
    Cui, Hai-Wei
    Peng, Shihong
    Gu, Xiang-Zhong
    Chen, Huang
    He, Yuan
    Gao, Wei
    Lv, Fang
    Wang, Jin-Hua
    Wang, Yan
    Xie, Jia
    Liu, Ming-Yao
    Yi, Zhengfang
    Qiu, Wen-Wei
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 111 : 126 - 137
  • [26] Synthesis of cis and trans isomers of D-ring linked bis-steroid pyrazines from 16α-bromo-17-oxosteroids
    Lotowski, Z
    Morzycki, JW
    Niewczas, IS
    Zdanowicz, M
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 2002, 67 (01) : 47 - 54
  • [27] BIOLOGICAL-ACTIVITY OF TRANSFORMED STEROIDS .14. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF ISOXAZOLINO-[16-ALPHA,17-ALPHA-D] AND ISOXAZOLIDINO[16-ALPHA,17-ALPHA-D] STEROIDS
    KAMERNITSKY, AV
    LEVINA, IS
    TEREKHINA, AI
    GRITSINA, GI
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1980, 14 (01): : 37 - 40
  • [28] Pd(PPh3)4/AgOAc-catalyzed coupling of 17-steroidal triflates and alkynes: Highly efficient synthesis of D-ring unsaturated 17-alkynylsteroids
    Sun, Qian
    Jiang, Chenggang
    Xu, Hangxian
    Zhang, Zonglei
    Liu, Lanhai
    Wang, Cunde
    STEROIDS, 2010, 75 (12) : 936 - 943
  • [29] TRANSFORMATION STEROIDS .97. SYNTHESIS OF D'5-PENTARANES-PENTACYCLIC STEROIDS WITH A SUPPLEMENTARY 5-MEMBERED RING D' AT POSITIONS 16, 17
    KAMERNITSKII, AV
    KULIKOVA, LE
    LEVINA, IS
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1978, 27 (06): : 1214 - 1216
  • [30] Synthesis and biological evaluation of 1α,25-dihydroxyvitamin D3 analogues with aromatic side chains attached at C-17
    Liu, Chao
    Zhao, Guo-Dong
    Mao, Xinliang
    Suenaga, Tsutomu
    Fujishima, Toshie
    Zhang, Cheng-Mei
    Liu, Zhao-Peng
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 : 569 - 575