cis-(+/-)-benzyl[2-(hydroxymethyl)cyclohexyl]carbamate | 213672-78-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-(+/-)-benzyl[2-(hydroxymethyl)cyclohexyl]carbamate
• 英文别名: benzyl N-[(1S,2R)-2-(hydroxymethyl)cyclohexyl]carbamate
• CAS: 213672-78-7
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: YGKOCIWFRPQJLH-KBPBESRZSA-N

物化性质

• 沸点：
  437.5±24.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-(+/-)-benzyl[2-(hydroxymethyl)cyclohexyl]carbamate 在 palladium on activated charcoal 草酰氯 、 氢气 、 三乙酰氧基硼氢化钠 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 生成 1-(((+/-)-2-cis)-2-((4-benzylpiperidin-1-yl)methyl)cyclohexyl)-3-(3-methoxyphenyl)urea
  参考文献：
  名称：

  Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency

  摘要：

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.

  DOI：

  10.1021/jm049530m
• 作为产物：
  描述：

  1-(R)-cis-2-aminocyclohexanemethanol 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 cis-(+/-)-benzyl[2-(hydroxymethyl)cyclohexyl]carbamate
  参考文献：
  名称：

  Enzymatic resolution of alicyclic 1,3-amino alcohols in organic media

  摘要：

  Racemic cis- and trans-2-aminocyclohexane-1-methanol and cis- and trans-2-amino-4-cyclohexene-1-methanol were resolved via lipase-catalysed O-acylation of their Z derivatives, using vinyl butyrate in different ether solvents. In accordance with the empirical rule, most of the screened lipases preferred the 1S enantiomer. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00236-5

文献信息

• NOVEL CARBOXYLIC ACID COMPOUNDS USEFUL FOR INHIBITING MICROSOMAL PROSTAGLANDIN E2 SYNTHASE-1
  申请人：Eli Lilly and Company

  公开号：EP3221304B1

  公开（公告）日：2019-07-24
• Novel Carboxylic Acid Compounds Useful for Inhibiting Microsomal Prostaglandin E2 Synthase-1
  申请人：Eli Lilly and Company

  公开号：US20170313679A1

  公开（公告）日：2017-11-02

  The present invention provides compounds of Formula 1, or a pharmaceutically acceptable salts, thereof, where R, X, A, E, and G are as described herein, methods of preparing the compounds, and use of the compounds to treat pain and/or inflammation.
• US9969714B2
  申请人：——

  公开号：US9969714B2

  公开（公告）日：2018-05-15