2-[(2-azabicyclo[2.2.2]octane-3-carbonyl)amino]-3-(4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl)propionic acid methyl ester | 872168-11-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[(2-azabicyclo[2.2.2]octane-3-carbonyl)amino]-3-(4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl)propionic acid methyl ester
• 英文别名: 2-[(2-aza-bicyclo[2.2.2]octane-3-carbonyl)-amino]-3-{4-[(3,5-dichloro-pyridine-4-carbonyl)-amino]-phenyl}-propionic acid methyl ester；methyl (2S)-2-[[(3S)-2-azabicyclo[2.2.2]octane-3-carbonyl]amino]-3-[4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl]propanoate
• CAS: 872168-11-1
• 化学式: C₂₄H₂₆Cl₂N₄O₄
• 分子量: 505.401
• InChiKey: KQADYLFPSAQKCF-PGRUHTEZSA-N

物化性质

• 沸点：
  645.6±55.0 °C(Predicted)
• 密度：
  1.369±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[(2-azabicyclo[2.2.2]octane-3-carbonyl)amino]-3-(4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl)propionic acid methyl ester 、 3,3-二甲基丁醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.08h， 生成 methyl (2S)-3-[4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl]-2-[[(3S)-2-(3,3-dimethylbutyl)-2-azabicyclo[2.2.2]octane-3-carbonyl]amino]propanoate
  参考文献：
  名称：

  WO2006/96807

  摘要：

  公开号：
• 作为产物：
  描述：

  甲基(3S)-2-氮杂双环[2.2.2]辛烷-3-羧酸酯 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 2-[(2-azabicyclo[2.2.2]octane-3-carbonyl)amino]-3-(4-[(3,5-dichloropyridine-4-carbonyl)amino]phenyl)propionic acid methyl ester
  参考文献：
  名称：

  Aza-bicyclic amino acid carboxamides as α4β1/α4β7 integrin receptor antagonists

  摘要：

  A series of N-carboxy, N-alkyl, and N-carboxamido azabicyclo[2.2.2]octane carboxamides were prepared and assayed for inhibition Of alpha(4)beta(1)-VCAM-1 and alpha(4)beta(7)-MAdCAM-1 interactions. Potency and alpha(4)beta(1)/alpha(4)beta(7) selectivity were sensitive to the substituent R-1-R-3 in the structures 6, 7, and 8. Several compounds demonstrated low nanomolar balanced alpha(4)beta(1)/alpha(4)beta(7) in vitro activity. Two compounds were selected for in vivo leukocytosis studies and demonstrated increases in circulating lymphocytes up to 250% over control. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.022

文献信息

• Aza-bicyclic amino acid carboxamides as α4β1/α4β7 integrin receptor antagonists
  作者：Alexey B. Dyatkin、Yong Gong、Tamara A. Miskowski、Edward S. Kimball、Stephen M. Prouty、M. Carolyn Fisher、Rosemary J. Santulli、Craig R. Schneider、Nathaniel H. Wallace、Pamela J. Hornby、Craig Diamond、William A. Kinney、Bruce E. Maryanoff、Bruce P. Damiano、Wei He

  DOI：10.1016/j.bmc.2005.07.022

  日期：2005.12

  A series of N-carboxy, N-alkyl, and N-carboxamido azabicyclo[2.2.2]octane carboxamides were prepared and assayed for inhibition Of alpha(4)beta(1)-VCAM-1 and alpha(4)beta(7)-MAdCAM-1 interactions. Potency and alpha(4)beta(1)/alpha(4)beta(7) selectivity were sensitive to the substituent R-1-R-3 in the structures 6, 7, and 8. Several compounds demonstrated low nanomolar balanced alpha(4)beta(1)/alpha(4)beta(7) in vitro activity. Two compounds were selected for in vivo leukocytosis studies and demonstrated increases in circulating lymphocytes up to 250% over control. (c) 2005 Elsevier Ltd. All rights reserved.
• WO2006/96807
  申请人：——

  公开号：——

  公开（公告）日：——