(2S)-2-[(3,5-dichlorophenyl)sulfonyl-methylamino]-3-methylbutanoic acid | 226066-16-6

• 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: (2S)-2-[(3,5-dichlorophenyl)sulfonyl-methylamino]-3-methylbutanoic acid
• CAS: 226066-16-6
• 化学式: C₁₂H₁₅Cl₂NO₄S
• 分子量: 340.227
• InChiKey: TXDOZXQTOBNJEC-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-2-[(3,5-dichlorophenyl)sulfonyl-methylamino]-3-methylbutanoic acid 在 N-甲基吗啉 、 sodium hydroxide 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2-((S)-2-(3,5-dichloro-N-methylphenylsulfonamido)-3-methylbutanamido)cyclohexanecarboxylic 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 4-二甲氨基吡啶 、 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 (2S)-2-[(3,5-dichlorophenyl)sulfonyl-methylamino]-3-methylbutanoic 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

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.