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
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 24期
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
  • [41] STUDY OF LEAVING GROUPS FOR THE PREPARATION OF (OMEGA-F-18)FLUOROFATTY ACIDS VIA NUCLEOPHILIC FLUORINATION AND ITS APPLICATION TO THE SYNTHESIS OF 17-(F-18)FLUORO-3-METHYLHEPTADECANOIC ACID
    TAKAHASHI, T
    IDO, T
    IWATA, R
    APPLIED RADIATION AND ISOTOPES, 1991, 42 (09) : 801 - 809
  • [42] Synthesis, biological evaluation and molecular modelling studies of novel ACD- and ABD-ring steroidomimetics as inhibitors of CYP17
    Mendieta, Mariano A. E. Pinto-Bazurco
    Negri, Matthias
    Jagusch, Carsten
    Hille, Ulrike E.
    Mueller-Vieira, Ursula
    Schmidt, Dirk
    Hansen, Klaus
    Hartmann, Rolf W.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (01) : 267 - 273
  • [43] Total Syntheses of Thailanstatins A-C, Spliceostatin D, and Analogues Thereof. Stereodivergent Synthesis of Tetrasubstituted Dihydro- and Tetrahydropyrans and Design, Synthesis, Biological Evaluation, and Discovery of Potent Antitumor Agents
    Nicolaou, K. C.
    Rhoades, Derek
    Kumar, S. Mothish
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (26) : 8303 - 8320
  • [44] Synthesis and Biological Evaluation of 1α,25-Dihydroxyvitamin D3 Analogues with a Long Side Chain at C12 and Short C17 Side Chains
    Carballa, Diego M.
    Seoane, Samuel
    Zacconi, Flavia
    Perez, Xenxo
    Rumbo, Antonio
    Alvarez-Diaz, Silvia
    Jesus Larriba, Maria
    Perez-Fernandez, Roman
    Munoz, Alberto
    Maestro, Miguel
    Mourino, Antonio
    Torneiro, Mercedes
    JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (20) : 8642 - 8656
  • [45] Design, synthesis and biological evaluation of novel 1α,25-dihydroxyvitamin D3 analogues possessing aromatic ring on 2α-position
    Honzawa, S
    Hirasaka, K
    Yamamoto, Y
    Peleg, S
    Fujishima, T
    Kurihara, M
    Saito, N
    Kishimoto, S
    Sugiura, T
    Waku, K
    Hiroaki, TA
    Kittaka, A
    TETRAHEDRON, 2005, 61 (47) : 11253 - 11263
  • [46] BIOLOGICAL-ACTIVITY OF TRANSFORMED STEROIDS .13. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF D'-5-PENTARANO-CYCLOPENTANO [16-ALPHA, 17-ALPHA-PROGESTERONES
    KAMERNITSKY, AV
    KULIKOVA, LE
    LEVINA, IS
    KORKHOV, VV
    NIKITINA, GV
    TEREKHINA, AI
    ANTIPOVA, LA
    KHIMIKO-FARMATSEVTICHESKII ZHURNAL, 1979, 13 (12): : 40 - 44
  • [47] Synthesis and biological evaluation of 17β-aryl/heteroaryl ethers of 7β/15β-methyl-4-aza-5α-androstanes as steroidal 5α-reductase inhibitors.
    Sahoo, SP
    Bakshi, RK
    Durette, PL
    Gratale, D
    Hagmann, WK
    Kopka, IK
    Rasmusson, GH
    Yang, SS
    Baginsky, WF
    Cimis, G
    Harris, G
    Tolman, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U17 - U17
  • [48] TRANSFORMED STEROIDS .84. STEREOSPECIFIC CIS-OPENING OF AZIRIDINE RING OF 16, 17ALPHA-EPIMINOPREGNENOLONE BY THIOCYANIC ACID AND SYNTHESIS OF 2'-AMINO[16, 17ALPHA-D]THIAZOLINES OF 20-KETOSTEROIDS
    KALSINES, D
    KAMERNITSKII, AV
    TURUTA, AM
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1976, 25 (08): : 1734 - 1738
  • [49] Synthesis and Biological Evaluation of Thieno[3,2-d]-pyrimidinones, Thieno[3,2-d]pyrimidines and Quinazolinones: Conformationally Restricted 17β-Hydroxysteroid Dehydrogenase Type 2 (17β-HSD2) Inhibitors
    Perspicace, Enrico
    Marchais-Oberwinkler, Sandrine
    Hartmann, Rolf W.
    MOLECULES, 2013, 18 (04) : 4487 - 4509
  • [50] Synthesis and biological evaluation of novel steroidal[17,16-d][1,2,4]triazolo [1,5-a]pyrimidines
    Huang, Li-Hua
    Zheng, Yong-Fei
    Lu, Yong-Zheng
    Song, Chuan-Jun
    Wang, Yan-Guang
    Yu, Bin
    Liu, Hong-Min
    STEROIDS, 2012, 77 (06) : 710 - 715
12345