(S)-1-cyclohexylpropan-2-yl carbonochloridate | 851317-54-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (S)-1-cyclohexylpropan-2-yl carbonochloridate
• CAS: 851317-54-9
• 化学式: C₁₀H₁₇ClO₂
• 分子量: 204.697
• InChiKey: ZNDUGXMUFHLFHB-QMMMGPOBSA-N

物化性质

• 沸点：
  255.9±9.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-1-cyclohexylpropan-2-yl carbonochloridate 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 (1-Cyano-pyrrolidin-3-yl)-carbamic acid (S)-2-cyclohexyl-1-methyl-ethyl ester
  参考文献：
  名称：

  Novel and potent cyclic cyanamide-based cathepsin K inhibitors

  摘要：

  Starting from a PDE IV inhibitor hit derived from high throughput screening of the compound collection, a key pyrrolidine cyanamide pharmacophore was identified. Modifications of the pyrrolidine ring produced enhancements in cathepsin K inhibition. An X-ray co-crystal structure of a cyanamide with cathepsin K confirmed the mode of inhibition.

  DOI：

  10.1016/j.bmcl.2005.02.033
• 作为产物：
  描述：

  (S)-(+)-1-苯基-2-丙醇 在 rhodium(III) chloride 氢气 、 甲基三辛基氯化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (S)-1-cyclohexylpropan-2-yl carbonochloridate
  参考文献：
  名称：

  Ketoheterocycle-based inhibitors of cathepsin K: A novel entry into the synthesis of peptidic ketoheterocycles

  摘要：

  Ketoheterocyclic inhibitors of cathepsin K have been disclosed. SAR of potency enhancing P-2-P-3 groups coupled with ketoheterocyclic warheads to provide cathepsin K inhibitors have been described. In addition, a novel route to access alpha-ketothiazoles using a key thioamide functionality has been disclosed. The mild method employed allows for the presence of diverse functional groups, such as amide and carbamate functionalities, commonly found in protease inhibitors that have peptidomimetic scaffolds. This new method should provide a quick entry into functionally diverse protease inhibitors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.091

文献信息

• Acyclic cyanamide-based inhibitors of cathepsin K
  作者：David G. Barrett、David N. Deaton、Anne M. Hassell、Robert B. McFadyen、Aaron B. Miller、Larry R. Miller、J. Alan Payne、Lisa M. Shewchuk、Derril H. Willard、Lois L. Wright

  DOI：10.1016/j.bmcl.2005.04.032

  日期：2005.6

  Conversion of the proline-derived cyanamide lead to an acyclic cyanamide capable of forming an additional hydrogen bond with cathepsin K resulted in a large increase in inhibitory activity. An X-ray structure of a co-crystal of a cyanamide with cathepsin K confirmed the enzyme interaction. Furthermore, a representative acyclic cyanamide inhibitor 6r was able to attenuate bone resorption in the rat calvarial model.