Synthesis of novel steroidal D-ring substituted isoxazoline derivatives of 17-oxoandrostanes

被引：27
|
作者：
Banday, Abid H. [1 ]
Singh, Swarn [1 ]
Alam, M. Sarwar [2 ]
Reddy, Dorna M.
Gupta, B. D. [1 ]
Kumar, H. M. Sampath [1 ]
机构：
[1] Indian Inst Integrat Med, Synthet Chem Div, Jammu 180001, India
[2] Jamia Hamdard, Dept Chem, New Delhi 110062, India
来源：
STEROIDS | 2008年 / 73卷 / 03期
关键词：
isoxazolines; androstanes; nitrileoxide; cycloaddition;
D O I：
10.1016/j.steroids.2007.10.014
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A facile synthesis of isoxazoline derivatives of 17-oxoandrostane at the side chain of D-ring is reported. The scheme involves the transformation of the starting dehydroepiandrosterone acetate (ketone) to the Knoevenegel product, reduction to the nitrile, and elimination to the carboxaldehyde. Cycloaddition of nitrileoxides across olefinic aldehyde intermediate led to the synthesis of novel side chain isoxazoline derivatives. (C) 2007 Elsevier Inc. All rights reserved.
引用
收藏
页码：370 / 374
页数：5
相关论文
共 50 条
  • [41] A stereocontrolled approach to substituted piperidones and piperidines: flavopiridol D-ring analogs
    Gross, A
    Borcherding, DR
    Friedrich, D
    Sabol, JS
    TETRAHEDRON LETTERS, 2001, 42 (09) : 1631 - 1633
  • [42] D-ring substituted rhazinilam analogues:: Semisynthesis and evaluation of antitubulin activity
    Dupont, C
    Guénard, D
    Tchertanov, L
    Thoret, S
    Guéritte, F
    BIOORGANIC & MEDICINAL CHEMISTRY, 1999, 7 (12) : 2961 - 2969
  • [43] SYNTHESIS OF 6,7-DIHYDRO-9,10-DIMETHOXYDIBENZO[a,f]QUINO-LIZINIUM SALT AND ITS D-RING SUBSTITUTED DERIVATIVES
    Yamazaki, Kazuo
    Aritake, Mai
    Takamoto, Shungo
    Tabata, Midori
    Yanagihara, Sachiko
    Uji, Keisuke
    Ohyama, Kazuaki
    Ogiso, Kei
    Sugahara, Takumi
    Tatara, Ai
    Hosono, Tetsuji
    Suzuki, Keitaro
    Ohba, Masashi
    HETEROCYCLES, 2017, 94 (03) : 503 - 514
  • [44] Synthesis and anti-tumor evaluation of B-ring substituted steroidal pyrazoline derivatives
    Shamsuzzaman
    Khanam, Hena
    Mashrai, Ashraf
    Sherwani, Asif
    Owais, Mohammad
    Siddiqui, Nazish
    STEROIDS, 2013, 78 (12-13) : 1263 - 1272
  • [45] A novel D-ring modified taxoid: synthesis and biological evaluation of a γ-lactone analogue of docetaxel
    Gao, Feng
    Yang, Zhan-Kun
    Chen, Qiao-Hong
    Chen, Xiao-Guang
    Wang, Feng-Peng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (02) : 361 - 366
  • [46] Synthesis and Preliminary Screening of Novel A- and D-Ring Modified Steroids as Aromatase Inhibitors
    Yadav, Mange Ram
    Sabale, Prafulla M.
    Giridhar, Rajani
    Baria, Dharmendra
    Zimmer, Christina
    Hartmann, Rolf W.
    LETTERS IN DRUG DESIGN & DISCOVERY, 2011, 8 (10) : 943 - 950
  • [47] Stereodivergent Synthesis of 17-α and 17-β-Aryl Steroids: Application and Biological Evaluation of D-Ring Cortistatin Analogues
    Shi, Jun
    Shigehisa, Hiroki
    Guerrero, Carlos A.
    Shenvi, Ryan A.
    Li, Chuang-Chuang
    Baran, Phil S.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (24) : 4328 - 4331
  • [48] Stereoselective Synthesis of Tetrahydropyran D-Ring of Methyl Sartortuoate
    Yao Hequan
    Gao Yuan
    Liu Peng
    Xu Xingxiang
    CHINESE JOURNAL OF CHEMISTRY, 2009, 27 (10) : 2025 - 2030
  • [49] NEW STEREOCONTROLLED SYNTHESIS OF D-RING AROMATIC STEROID
    KAMETANI, T
    NEMOTO, H
    TETRAHEDRON LETTERS, 1979, (35) : 3309 - 3310
  • [50] REGIOSELECTIVE SYNTHESIS OF D-RING SUBSTITUTED BENZ(A)ANTHRACENES BY ONE-POT PHOTOCHEMICAL-REACTION
    MARUYAMA, K
    TOJO, M
    IWAMOTO, H
    OTSUKI, T
    CHEMISTRY LETTERS, 1980, (07) : 827 - 830
12345