(±)-2,2'-((1S,2S)-cyclohexan-1,2-diyl)diacetonitrile | 3205-37-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (±)-2,2'-((1S,2S)-cyclohexan-1,2-diyl)diacetonitrile
• 英文别名: (+/-)-(trans-cyclohexane-1,2-diyl)-di-acetonitrile；(+/-)-(trans-Cyclohexan-1,2-diyl)-di-acetonitril；(+/-)-2,2'-((1S,2S)-cyclohexan-1,2-diyl)diacetonitrile；trans-2,2'-Cyclohexane-1,2-diyldiacetonitrile；2-[(1S,2S)-2-(cyanomethyl)cyclohexyl]acetonitrile
• CAS: 3205-37-6；90872-58-5；97920-04-2
• 化学式: C₁₀H₁₄N₂
• 分子量: 162.235
• InChiKey: FGLZWKOCMIRVFJ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (±)-2,2'-((1S,2S)-cyclohexan-1,2-diyl)diacetonitrile 在 sodium hydride 、 盐酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 以87%的产率得到(±)-(1S,3aR,7aS)-2-oxooctahydro-1H-indene-1-carbonitrile
  参考文献：
  名称：

  Discovery of Octahydroindenes as PAR1 Antagonists

  摘要：

  Octahydroindene was identified as a novel scaffold for protease activated receptor 1 (PAR1) antagonists. Herein, the 2-position (C2) was explored for structure activity relationship (SAR) studies. Compounds 14, 19, and 23b showed IC50 values of 1.3, 8.6, and 2.7 nM in a PAR1 radioligand binding assay, respectively, and their inhibitory activities on platelet activation were comparable to that of vorapaxar in a platelet rich plasma (PRP) aggregation assay. This series of compounds showed high potency and no significant cytotoxicity; however, the compounds were metabolically unstable in both human and rat liver microsomes. Current research efforts are focused on optimizing the compounds to improve metabolic stability and physicochemical properties as well as potency.

  DOI：

  10.1021/ml400235c
• 作为产物：
  描述：

  trans-1,2-bis(hydroxymethyl)cyclohexane di-p-toluene-sulfonate 在 potassium cyanide 、 乙醇 作用下， 生成 (±)-2,2'-((1S,2S)-cyclohexan-1,2-diyl)diacetonitrile
  参考文献：
  名称：

  435.脂环族二醇。第十七部分。十氢化萘-2：3-二醇

  摘要：

  DOI：

  10.1039/jr9580002119

文献信息

• Struktur eines<i>O, N</i>-Ketenacetals: (1<i>RS</i>, 8<i>SR</i>, 10<i>SR</i>, 4(15)<i>Z</i>)-4-äthyliden-5-oxa-3-azatricyclo [8.4.0.0^3,8]tetradecan
  作者：Albin Kümin、Emily Maverick、Paul Seiler、Noel Vanier、Lorenz Damm、Reinhard Hobi、Jack D. Dunitz、Albert Eschenmoser

  DOI：10.1002/hlca.19800630507

  日期：1980.7.9

  Structure of a O,N-Keteneacetal: (1RS, 8SR, 10SR, 4(15)Z)-4-Ethylidene-5-oxa-3-azatricyclo [8.4.0.03,8]tetradecane1

  O，N-乙缩醛的结构：（1RS，8SR，10SR，4（15）Z）-4-亚乙基-5-氧杂-3-氮杂三环[8.4.0.0 3,8 ]十四烷1
• [EN] [6+5] FUSED BICYCLES AS A THROMBIN ANTAGONIST, PROCESS FOR PREPARATION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE BICYCLES<br/>[FR] BICYCLES FUSIONNÉS [6+5] EN TANT QU'ANTAGONISTES DE LA THROMBINE, PROCÉDÉ DE PRÉPARATION DE CEUX-CI ET COMPOSITIONS PHARMACEUTIQUES CONTENANT LES BICYCLES
  申请人：KOREA RES INST CHEM TECH

  公开号：WO2011162562A2

  公开（公告）日：2011-12-29

  The present invention relates to the new [6+5] fused bicycle derivatives, pharmaceutically acceptable salts or isomers thereof, processes for preparing the same, and pharmaceutical compositions comprising the same. The [6+5] fused bicycle derivatives can antagonize the thrombin receptor and thus may be effectively used for the treatment and prevention of thrombus, platelet aggregation, atherosclerosis, restenosis, blood coagulation, hypertension, arrhythmia, angina pectoris, heart failure, inflammation and cancer when used alone or with other cardiovascular agents.
• Discovery of Octahydroindenes as PAR1 Antagonists
  作者：Sunkyung Lee、Jong-Hwan Song、Chul Min Park、Jin-Seok Kim、Ji-Hye Jeong、Woo-Young Cho、Dong-Chul Lim

  DOI：10.1021/ml400235c

  日期：2013.11.14

  Octahydroindene was identified as a novel scaffold for protease activated receptor 1 (PAR1) antagonists. Herein, the 2-position (C2) was explored for structure activity relationship (SAR) studies. Compounds 14, 19, and 23b showed IC50 values of 1.3, 8.6, and 2.7 nM in a PAR1 radioligand binding assay, respectively, and their inhibitory activities on platelet activation were comparable to that of vorapaxar in a platelet rich plasma (PRP) aggregation assay. This series of compounds showed high potency and no significant cytotoxicity; however, the compounds were metabolically unstable in both human and rat liver microsomes. Current research efforts are focused on optimizing the compounds to improve metabolic stability and physicochemical properties as well as potency.
• 435. Alicyclic glycols. Part XVII. The decalin-2 : 3-diols
  作者：Md. Erfan Ali、L. N. Owen

  DOI：10.1039/jr9580002119

  日期：——