(1R,2S,6R)-bicyclo[4.3.0]nonan-2-ol | 211872-48-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,6R)-bicyclo[4.3.0]nonan-2-ol
• 英文别名: (-)-(1R,2S,6R)-bicyclo[4.3.0]nonan-2-ol；cis-endo-Hydrindanol-4；(3aR,4S,7aR)-2,3,3a,4,5,6,7,7a-octahydro-1H-inden-4-ol
• CAS: 211872-48-9
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: RMRXFRZQQUJSED-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S,6R)-bicyclo[4.3.0]nonan-2-ol 、 对硝基苯基氯甲酸酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(3aR,4S,7aR)-octahydro-1H-inden-4-yl-(4-nitrophenyl)carbonate
  参考文献：
  名称：

  Design and Synthesis of Potent HIV-1 Protease Inhibitors Incorporating Hexahydrofuropyranol-Derived High Affinity P₂ Ligands: Structure−Activity Studies and Biological Evaluation

  摘要：

  The design, synthesis, and evaluation of a new series of hexahydrofuropyranol-derived HIV-1 protease inhibitors are described. We have designed a stereochemically defined hexahydrofuropyranol-derived urethane as the P2-ligand. The current ligand is designed based upon the X-ray structure of la-bound HIV-1 protease. The synthesis of (3aS,4S,7aR)-hexahydro-2H-furo[2,3-b]pyran-4-ol, (-)-7, was carried out in optically active form. Incorporation of this ligand provided inhibitor 35a, which has shown excellent enzyme inhibitory activity and antiviral potency. Our structure activity studies have indicated that the stereochemistry and the position of oxygens in the ligand are important to the observed potency of the inhibitor. Inhibitor 35a has maintained excellent potency against multidrug-resistant HIV-1 variants. An active site model of 35a was created based upon the X-ray structure of 1b-bound HIV-1 protease. The model offers molecular insights regarding ligand-binding site interactions of the hexahydrofuropyranol-derived novel P2-ligand.

  DOI：

  10.1021/jm1012787
• 作为产物：
  描述：

  cis-cyclononene oxide 在 异丙基锂 、 鹰爪豆碱 作用下， 以 乙醚 为溶剂， 生成 (1R,2S,6R)-bicyclo[4.3.0]nonan-2-ol 、 (+/-)-endo,cis-bicyclo[4.3.0]nonan-2-ol
  参考文献：
  名称：

  Enantioselective α-deprotonation–rearrangement of meso-epoxides

  摘要：

  Enantioselective alpha-deprotonation-rearrangement of medium-sized (8-, 9- and 10-membered) cycloalkene-derived meso-epoxides using organolithiums in the presence of (-)-sparteine gives bicyclic alcohols in good yields and ees.

  DOI：

  10.1039/cc9960001015

文献信息

• [EN] FUSED 6,5 BICYCLIC RING SYSTEM P2 LIGANDS, AND METHODS FOR TREATING HIV<br/>[FR] LIGANDS P2 À SYSTÈME CYCLIQUE 6,5 BICYCLIQUE FUSIONNÉ, ET PROCÉDÉS DE TRAITEMENT D'UNE INFECTION PAR LE VIH
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2012092168A1

  公开（公告）日：2012-07-05

  Inhibitors of HIV-1 protease and compositions containing them are described. Use of the inhibitors and compositions containing them to treat HIV, AIDS, and AIDS-related diseases is described.

  描述了HIV-1蛋白酶的抑制剂和含有它们的组合物。描述了使用这些抑制剂和含有它们的组合物来治疗HIV、艾滋病和艾滋病相关疾病。
• COMPOUNDS AND METHODS FOR TREATING HIV
  申请人：GHOSH Arun K.

  公开号：US20130289067A1

  公开（公告）日：2013-10-31

  Inhibitors of HIV-1 protease and compositions containing them are described. Use of the inhibitors and compositions containing them to treat HIV, AIDS, and AIDS-related diseases is described.

  本文描述了HIV-1蛋白酶抑制剂及其组合物。描述了使用这些抑制剂和组合物来治疗HIV、艾滋病和艾滋病相关疾病的方法。
• Compunds and methods for treating HIV
  申请人：Purdue Research Foundation

  公开号：US09024038B2

  公开（公告）日：2015-05-05

  Inhibitors of HIV-1 protease and compositions containing them are described. Use of the inhibitors and compositions containing them to treat HIV, AIDS, and AIDS-related diseases is described.

  本文描述了HIV-1蛋白酶抑制剂及其组成物。描述了使用这些抑制剂和组成物来治疗HIV、艾滋病和艾滋病相关疾病。
• Hodgson, David M.; Lee, Gary P.; Marriott, Robert E., Journal of the Chemical Society. Perkin transactions I, 1998, # 14, p. 2151 - 2161
  作者：Hodgson, David M.、Lee, Gary P.、Marriott, Robert E.、Thompson, Alison J.、Wisedale, Richard、Witherington, Jason

  DOI：——

  日期：——
• CLIVE D. L. J.; CHITTATTU G. J.; FARINA V.; KIEL W. A.; MENCHEN S. M.; RU+, J. AMER. CHEM. SOC., 1980, 102, NO 13, 4438-4447
  作者：CLIVE D. L. J.、 CHITTATTU G. J.、 FARINA V.、 KIEL W. A.、 MENCHEN S. M.、 RU+

  DOI：——

  日期：——