tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate | 226066-04-2

• 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: tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate
• CAS: 226066-04-2
• 化学式: C₁₅H₁₉Cl₂NO₄S
• 分子量: 380.292
• InChiKey: FIQKRNPPGQDMPS-ZDUSSCGKSA-N

物化性质

• 沸点：
  480.4±55.0 °C(Predicted)
• 密度：
  1.367±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate 在 N-甲基吗啉 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl (S)-2-(1-((3,5-dichlorophenyl)sulfonyl)pyrrolidine-2-carboxamido)benzoate
  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 、 L-脯氨酸叔丁酯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到tert-butyl (2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  The discovery of small molecule carbamates as potent dual α4β1/α4β7 integrin antagonists

  摘要：

  The alpha(4)beta(1) and alpha(4)beta(7) integrins are implicated in several inflammatory disease states. Systematic SAR studies of an alpha(4)beta(1)-specific arylsulfonyl-Pro-Tyr lead led to the identification of a new alpha(4)beta(7) binding site, best captured by O-carbamates of Tyr for this structural class. Several compounds showed a 200- to 400-fold improvement in alpha(4)beta(7) binding affinity while maintaining subnanomolar alpha(4)beta(1) activity, for example 21, VCAM-Ig alpha(4)beta(1) IC50 = 0.13 nM. VCAM-Ig alpha(4)beta(7) IC50 = 1.92 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00710-7

文献信息

• The discovery of small molecule carbamates as potent dual α4β1/α4β7 integrin antagonists
  作者：Linda L. Chang、Quang Truong、Richard A. Mumford、Linda A. Egger、Usha Kidambi、Kathryn Lyons、Ermengilda McCauley、Gail Van Riper、Stella Vincent、John A. Schmidt、Malcolm MacCoss、William K. Hagmann

  DOI：10.1016/s0960-894x(01)00710-7

  日期：2002.1

  The alpha(4)beta(1) and alpha(4)beta(7) integrins are implicated in several inflammatory disease states. Systematic SAR studies of an alpha(4)beta(1)-specific arylsulfonyl-Pro-Tyr lead led to the identification of a new alpha(4)beta(7) binding site, best captured by O-carbamates of Tyr for this structural class. Several compounds showed a 200- to 400-fold improvement in alpha(4)beta(7) binding affinity while maintaining subnanomolar alpha(4)beta(1) activity, for example 21, VCAM-Ig alpha(4)beta(1) IC50 = 0.13 nM. VCAM-Ig alpha(4)beta(7) IC50 = 1.92 nM. (C) 2002 Elsevier Science Ltd. All rights reserved.
• 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.