3-(4-{[2-(4-bromophenyl)hydrazinyl]sulfonyl}phenyl)propanoic acid | 1620001-62-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-(4-{[2-(4-bromophenyl)hydrazinyl]sulfonyl}phenyl)propanoic acid
• 英文别名: 3-[4-[(4-Bromoanilino)sulfamoyl]phenyl]propanoic acid；3-[4-[(4-bromoanilino)sulfamoyl]phenyl]propanoic acid
• CAS: 1620001-62-8
• 化学式: C₁₅H₁₅BrN₂O₄S
• 分子量: 399.265
• InChiKey: QPEULQGQPJSUHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-氯磺酰基)丙酸 、 对溴苯肼 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到3-(4-{[2-(4-bromophenyl)hydrazinyl]sulfonyl}phenyl)propanoic acid
  参考文献：
  名称：

  Discovery and structure–activity relationships of phenyl benzenesulfonylhydrazides as novel indoleamine 2,3-dioxygenase inhibitors

  摘要：

  A novel class of phenyl benzenesulfonylhydrazides has been identified as potent inhibitors of indoleamine 2,3-dioxygenase (IDO), and their structure-activity relationship was explored. Coupling reactions between various benzenesulfonyl chlorides and phenylhydrazides were utilized to synthesize the sulfonylhydrazides bearing various substituents. Compound 3i exhibited 61 nM of IC50 in enzymatic assay and 172 nM of EC50 in the HeLa cell. The computational study of 3i suggested that the major interactions between 3i and IDO protein are the coordination of sulfone and heme iron, the hydrogen bonding and hydrophobic interactions between 3i and IDO. This novel class of IDO inhibitor provides a new direction to discover effective anti-cancer agents. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.084

文献信息

• Discovery and structure–activity relationships of phenyl benzenesulfonylhydrazides as novel indoleamine 2,3-dioxygenase inhibitors
  作者：Ming-Fu Cheng、Ming-Shiu Hung、Jen-Shin Song、Shu-Yu Lin、Fang-Yu Liao、Mine-Hsine Wu、Wenchi Hsiao、Chia-Ling Hsieh、Jian-Sung Wu、Yu-Sheng Chao、Chuan Shih、Su-Ying Wu、Shau-Hua Ueng

  DOI：10.1016/j.bmcl.2014.05.084

  日期：2014.8

  A novel class of phenyl benzenesulfonylhydrazides has been identified as potent inhibitors of indoleamine 2,3-dioxygenase (IDO), and their structure-activity relationship was explored. Coupling reactions between various benzenesulfonyl chlorides and phenylhydrazides were utilized to synthesize the sulfonylhydrazides bearing various substituents. Compound 3i exhibited 61 nM of IC50 in enzymatic assay and 172 nM of EC50 in the HeLa cell. The computational study of 3i suggested that the major interactions between 3i and IDO protein are the coordination of sulfone and heme iron, the hydrogen bonding and hydrophobic interactions between 3i and IDO. This novel class of IDO inhibitor provides a new direction to discover effective anti-cancer agents. (C) 2014 Elsevier Ltd. All rights reserved.