(R)-3-(3,3-Dimethyl-butyrylamino)-pyrrolidine-1-carboxylic acid adamantan-2-yl ester | 1258074-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (R)-3-(3,3-Dimethyl-butyrylamino)-pyrrolidine-1-carboxylic acid adamantan-2-yl ester
• 英文别名: 2-adamantyl (3R)-3-(3,3-dimethylbutanoylamino)pyrrolidine-1-carboxylate
• CAS: 1258074-79-1
• 化学式: C₂₁H₃₄N₂O₃
• 分子量: 362.513
• InChiKey: ZQUIRXSOJSCSSN-CMPFZWEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,3-二甲基丁酰氯 、 2-adamantyl (3R)-3-aminopyrrolidine-1-carboxylate 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-(3,3-Dimethyl-butyrylamino)-pyrrolidine-1-carboxylic acid adamantan-2-yl ester
  参考文献：
  名称：

  Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1

  摘要：

  Synthesis of 2-adamantyl carbamate derivatives of piperidines and pyrrolidines led to the discovery of 9a with an IC50 of 15.2 nM against human 11 beta-HSD1 in adipocytes. Optimization for increased adipocyte potency, metabolic stability and selectivity afforded 11k and 11l, both of which were >25% orally bioavailable in rat. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.142

文献信息

• Discovery and optimization of adamantyl carbamate inhibitors of 11β-HSD1
  作者：Colin M. Tice、Wei Zhao、Paula M. Krosky、Barbara A. Kruk、Jennifer Berbaum、Judith A. Johnson、Yuri Bukhtiyarov、Reshma Panemangalore、Boyd B. Scott、Yi Zhao、Joseph G. Bruno、Lamont Howard、Jennifer Togias、Yuan-Jie Ye、Suresh B. Singh、Brian M. McKeever、Peter R. Lindblom、Joan Guo、Rong Guo、Herbert Nar、Annette Schuler-Metz、Richard E. Gregg、Katerina Leftheris、Richard K. Harrison、Gerard M. McGeehan、Linghang Zhuang、David A. Claremon

  DOI：10.1016/j.bmcl.2010.08.142

  日期：2010.11

  Synthesis of 2-adamantyl carbamate derivatives of piperidines and pyrrolidines led to the discovery of 9a with an IC50 of 15.2 nM against human 11 beta-HSD1 in adipocytes. Optimization for increased adipocyte potency, metabolic stability and selectivity afforded 11k and 11l, both of which were >25% orally bioavailable in rat. (C) 2010 Elsevier Ltd. All rights reserved.