(2R)-2-{[4-(4-chlorophenyl)benzene]sulfonamido}-3-phenylpropanoic acid | 1149369-97-0

• 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: (2R)-2-{[4-(4-chlorophenyl)benzene]sulfonamido}-3-phenylpropanoic acid
• 英文别名: (2R)-2-[[4-(4-chlorophenyl)phenyl]sulfonylamino]-3-phenylpropanoic acid
• CAS: 1149369-97-0
• 化学式: C₂₁H₁₈ClNO₄S
• 分子量: 415.897
• InChiKey: TXFOUFDGVNFIGH-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl ((4'-chloro-[1,1'-biphenyl]-4-yl)sulfonyl)-D-phenylalaninate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2R)-2-{[4-(4-chlorophenyl)benzene]sulfonamido}-3-phenylpropanoic acid
  参考文献：
  名称：

  Novel N-substituted 2-phenyl-1-sulfonylamino-cyclopropane carboxylates as selective ADAMTS-5 (Aggrecanase-2) inhibitors

  摘要：

  A series of N-substituted sulfonylamino-alkanecarboxylate ADAMTS-5 (Aggrecanase-2) inhibitors has been synthesized and the in vitro enzyme SAR is discussed. This report is the first example of carboxylate-based ADAMTS-5 inhibitors which show strong potency of IC50 < 0.1 mu M with excellent selectivity over MMP-1 and TACE. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.02.024

文献信息

• Novel N-substituted 2-phenyl-1-sulfonylamino-cyclopropane carboxylates as selective ADAMTS-5 (Aggrecanase-2) inhibitors
  作者：Makoto Shiozaki、Katsuya Maeda、Tomoya Miura、Yosuke Ogoshi、Julia Haas、Andrew M. Fryer、Ellen R. Laird、Nicole M. Littmann、Steven W. Andrews、John A. Josey、Takayuki Mimura、Yuichi Shinozaki、Hiromi Yoshiuchi、Takashi Inaba

  DOI：10.1016/j.bmcl.2009.02.024

  日期：2009.3

  A series of N-substituted sulfonylamino-alkanecarboxylate ADAMTS-5 (Aggrecanase-2) inhibitors has been synthesized and the in vitro enzyme SAR is discussed. This report is the first example of carboxylate-based ADAMTS-5 inhibitors which show strong potency of IC50 < 0.1 mu M with excellent selectivity over MMP-1 and TACE. (C) 2009 Elsevier Ltd. All rights reserved.