(1S,3R)-3-[(2R,5S)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]cyclopentan-1-ol | 219560-85-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R)-3-[(2R,5S)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]cyclopentan-1-ol
• CAS: 219560-85-7
• 化学式: C₁₄H₂₄N₂O₃
• 分子量: 268.356
• InChiKey: QKIVQZPVMVTMTB-NOOOWODRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3R)-3-[(2R,5S)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]cyclopentan-1-ol 在 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 氢溴酸 、 sodium methylate 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (4-Iodo-phenyl)-carbamic acid (1R,3R)-3-((S)-1-amino-2-oxo-2-pyrrolidin-1-yl-ethyl)-cyclopentyl ester
  参考文献：
  名称：

  Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl)glycine pyrrolidides and thiazolidides as dipeptidyl peptidase IV inhibitors

  摘要：

  A diastereoselective synthesis was used to prepare a series of (3-substituted-cyclopentyl and -cyclohexyl)glycine pyrrolidides and thiazolidides. The three chiral centers were generated in an unambiguous, stereochemically defined manner. Inhibitory activity was dependent on the configuration at each stereocenter and on the nature of the 3-substituent. In the cyclopentylglycine pyrrolidide series, high potency against dipeptidyl peptidase IV and good selectivity could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.013
• 作为产物：
  描述：

  (S)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1S,3R)-3-[(2R,5S)-3,6-dimethoxy-5-propan-2-yl-2,5-dihydropyrazin-2-yl]cyclopentan-1-ol
  参考文献：
  名称：

  Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl)glycine pyrrolidides and thiazolidides as dipeptidyl peptidase IV inhibitors

  摘要：

  A diastereoselective synthesis was used to prepare a series of (3-substituted-cyclopentyl and -cyclohexyl)glycine pyrrolidides and thiazolidides. The three chiral centers were generated in an unambiguous, stereochemically defined manner. Inhibitory activity was dependent on the configuration at each stereocenter and on the nature of the 3-substituent. In the cyclopentylglycine pyrrolidide series, high potency against dipeptidyl peptidase IV and good selectivity could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.013

文献信息

• Diastereoselective synthesis and configuration-dependent activity of (3-substituted-cycloalkyl)glycine pyrrolidides and thiazolidides as dipeptidyl peptidase IV inhibitors
  作者：Wallace T. Ashton、Hong Dong、Rosemary M. Sisco、George A. Doss、Barbara Leiting、Reshma A. Patel、Joseph K. Wu、Frank Marsilio、Nancy A. Thornberry、Ann E. Weber

  DOI：10.1016/j.bmcl.2003.12.013

  日期：2004.2

  A diastereoselective synthesis was used to prepare a series of (3-substituted-cyclopentyl and -cyclohexyl)glycine pyrrolidides and thiazolidides. The three chiral centers were generated in an unambiguous, stereochemically defined manner. Inhibitory activity was dependent on the configuration at each stereocenter and on the nature of the 3-substituent. In the cyclopentylglycine pyrrolidide series, high potency against dipeptidyl peptidase IV and good selectivity could be achieved. (C) 2003 Elsevier Ltd. All rights reserved.