Bes(3,5-diCl)-Pro-Tyr-OtBu | 217453-67-3

• 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: Bes(3,5-diCl)-Pro-Tyr-OtBu
• 英文别名: tert-butyl (2S)-2-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-(4-hydroxyphenyl)propanoate
• CAS: 217453-67-3
• 化学式: C₂₄H₂₈Cl₂N₂O₆S
• 分子量: 543.468
• InChiKey: MXUFMXUAVZSMSD-SFTDATJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  环戊酸 、 Bes(3,5-diCl)-Pro-Tyr-OtBu 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  tert-butyl (2S)-2-[[(2S)-1-(3,5-dichlorophenyl)sulfonylpyrrolidine-2-carbonyl]amino]-3-[4-[(2-methylpropan-2-yl)oxy]phenyl]propanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Bes(3,5-diCl)-Pro-Tyr-OtBu
  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

• US6903075B1
  申请人：——

  公开号：US6903075B1

  公开（公告）日：2005-06-07
• 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.