Synthesis of novel anti-inflammatory steroidal macrocycles using ring closing metathesis reaction

被引:5
作者
Biju, Purakkattle [1 ]
Bitar, Rema [1 ]
Lim, Yeon-Hee [1 ]
Wang, Ying [1 ]
Berlin, Michael [1 ]
Aslanian, Robert [1 ]
McCormick, Kevin [1 ]
机构
[1] Merck Res Labs, Dept Med Chem, Kenilworth, NJ 07033 USA
关键词
Steroids; Macrocyclic lactones; Ring closing metathesis; Prednisolone; Grubb's catalyst; INHIBITORS; DISCOVERY;
D O I
10.1016/j.tetlet.2014.12.048
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel class of 13 and 16 membered steroidal macrocycles were synthesized by using ring closing metathesis reaction from the readily available anti-inflammatory steroids such as prednisolone, 6-methyl prednisolone, and 16-methyl prednisolone. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:636 / 638
页数:3
相关论文
共 16 条
  • [1] Ali A., 2004, [No title captured], Patent No. [WO2004/066920, 2004066920]
  • [2] Potent Macrocyclic Inhibitors of Insulin-Regulated Aminopeptidase (IRAP) by Olefin Ring-Closing Metathesis
    Andersson, Hanna
    Demaegdt, Heidi
    Johnsson, Anders
    Vauquelin, Georges
    Lindeberg, Gunnar
    Hallberg, Mathias
    Erdelyi, Mate
    Karlen, Anders
    Hallberg, Anders
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (11) : 3779 - 3792
  • [3] [Anonymous], 2010, Drug Discov Today Technol, V7, pe95, DOI 10.1016/j.ddtec.2010.06.002
  • [4] Advances in the Development of Macrocyclic Inhibitors of Hepatitis C Virus NS3-4A Protease
    Avolio, Salvatore
    Summa, Vincenzo
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2010, 10 (14) : 1403 - 1422
  • [5] Steroidal C-21 heteroaryl thioethers (Part 2): Discovery of orally bioavailable selective glucocorticoid receptor modulators (dissociated steroids)
    Biju, Purakkattle
    McCormick, Kevin
    Aslanian, Robert
    Berlin, Michael
    Solomon, Daniel
    Wang, Hongwu
    Lee, Yoon Joo
    Bitar, Rema
    Prelusky, Daniel
    Mcleod, Robbie
    Jia, Yanlin
    Fernandez, Xiomora
    Eckel, Stephen
    House, Aileen
    Lieber, Gissela
    Jimenez, Johanna
    Kelly, George
    Chapman, Richard
    Phillips, Jonathan
    Anthes, John
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) : 1086 - 1090
  • [6] Steroidal C-21 mercapto derivatives as dissociated steroids: Discovery of an inhaled dissociated steroid
    Biju, Purakkattle
    McCormick, Kevin
    Aslanian, Robert
    Berlin, Michael
    Solomon, Daniel
    Chapman, Richard
    McLeod, Robbie
    Prelusky, Daniel
    Eckel, Stephen
    Kelly, George
    Natiello, Michelle
    House, Aileen
    Fernandez, Xiomara
    Bitar, Rema
    Phillips, Jonathan
    Anthes, John
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (21) : 6343 - 6347
  • [7] Blondeau JM, 2012, EXPERT REV CLIN PHAR, V5, P9, DOI [10.1586/ecp.11.71, 10.1586/ECP.11.71]
  • [8] Gradillas A., 2010, Metathesis in Natural Product Synthesis, P149
  • [9] Recent developments in the discovery of selective glucocorticoid receptor modulators (SGRMs)
    Hudson, Andrew R.
    Roach, Steven L.
    Higuchi, Robert I.
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2008, 8 (09) : 750 - 765
  • [10] Diversity-oriented synthesis of macrocyclic peptidomimetics
    Isidro-Llobet, Albert
    Murillo, Tiffanie
    Bello, Paula
    Cilibrizzi, Agostino
    Hodgkinson, James T.
    Galloway, Warren R. J. D.
    Bender, Andreas
    Welch, Martin
    Spring, David R.
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (17) : 6793 - 6798