methyl 3-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]bicyclo[2.2.2]octane-2-carboxylate | 226066-23-5

• 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: methyl 3-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]bicyclo[2.2.2]octane-2-carboxylate
• CAS: 226066-23-5
• 化学式: C₂₁H₂₆Cl₂N₂O₅S
• 分子量: 489.42
• InChiKey: PHFAWIBXBBEOFH-GSXKWFGOSA-N

物化性质

• 密度：
  1.453±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]bicyclo[2.2.2]octane-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 3-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]bicyclo[2.2.2]octane-2-carboxylic acid
  参考文献：
  名称：

  Highly constrained bicyclic VLA-4 antagonists

  摘要：

  VLA-4 is implicated in several inflammatory and autoimmune disease states. A series of cyclic P-amino acids (beta-aa) was studied as VLA-4 antagonists. Binding affinity was highly dependent on the dihedral angle (phi) between the amino and the carboxyl termini of the beta-aa. Compound 5m where the beta-aa is embedded in a bicycle possesses the most preferred phi (120 degrees). It is a potent and bioavailable VLA-4 antagonist (VCAM-Ig alpha 4 beta 1 IC50 = 54 nM, rat po F = 49%). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.011
• 作为产物：
  描述：

  3,5-二氯苯磺酰氯 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]bicyclo[2.2.2]octane-2-carboxylate
  参考文献：
  名称：

  Highly constrained bicyclic VLA-4 antagonists

  摘要：

  VLA-4 is implicated in several inflammatory and autoimmune disease states. A series of cyclic P-amino acids (beta-aa) was studied as VLA-4 antagonists. Binding affinity was highly dependent on the dihedral angle (phi) between the amino and the carboxyl termini of the beta-aa. Compound 5m where the beta-aa is embedded in a bicycle possesses the most preferred phi (120 degrees). It is a potent and bioavailable VLA-4 antagonist (VCAM-Ig alpha 4 beta 1 IC50 = 54 nM, rat po F = 49%). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.011

文献信息

• US6271252B1
  申请人：——

  公开号：US6271252B1

  公开（公告）日：2001-08-07
• Highly constrained bicyclic VLA-4 antagonists
  作者：Linda L. Chang、Quang Truong、George A. Doss、Malcolm MacCoss、Kathryn Lyons、Ermengilda McCauley、Richard Mumford、Gail Forrest、Stella Vincent、John A. Schmidt、William K. Hagmann

  DOI：10.1016/j.bmcl.2006.11.011

  日期：2007.2

  VLA-4 is implicated in several inflammatory and autoimmune disease states. A series of cyclic P-amino acids (beta-aa) was studied as VLA-4 antagonists. Binding affinity was highly dependent on the dihedral angle (phi) between the amino and the carboxyl termini of the beta-aa. Compound 5m where the beta-aa is embedded in a bicycle possesses the most preferred phi (120 degrees). It is a potent and bioavailable VLA-4 antagonist (VCAM-Ig alpha 4 beta 1 IC50 = 54 nM, rat po F = 49%). (c) 2006 Elsevier Ltd. All rights reserved.