4-{[2-(4-bromophenyl)hydrazinyl]sulfonyl}benzoic acid | 1620001-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{[2-(4-bromophenyl)hydrazinyl]sulfonyl}benzoic acid
• 英文别名: 4-[(4-Bromoanilino)sulfamoyl]benzoic acid；4-[(4-bromoanilino)sulfamoyl]benzoic acid
• CAS: 1620001-64-0
• 化学式: C₁₃H₁₁BrN₂O₄S
• 分子量: 371.211
• InChiKey: XHKFTHFLUUCVDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  4-(氯磺酰)苯甲酸 、 对溴苯肼 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以30%的产率得到4-{[2-(4-bromophenyl)hydrazinyl]sulfonyl}benzoic 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

• Dual-functional conjugates improving cancer immunochemotherapy by inhibiting tubulin polymerization and indoleamine-2,3-dioxygenase
  作者：Shixian Hua、Feihong Chen、Xinyi Wang、Shaohua Gou

  DOI：10.1016/j.ejmech.2020.112041

  日期：2020.3

  A series of novel conjugates comprising tublin and IDO inhibitors were designed, synthesized and evaluated for their antiproliferative activity. Among them, HI5, composed of combretastatin A-4 (CA-4) and (D)-1-methyltryptophan (D -MT) by a linker, exhibited the most potent antitumor activity, in particular with higher IC50 value (0.07 mu M) than CA-4 (0.21 mu M) against HeLa cancer cell line. Mechanism studies indicated that HIS can inhibit tubulin polymerization and cell migration, cause G2/M phase arrest, concurrent induce apoptosis via the mitochondrial dependent apoptosis pathway and cause reactive oxidative stress generation in HeLa cells. Furthermore, HIS can inhibit IDO expression and decrease kynurenine production, leading to stimulating T cells activation and proliferation to enhance antitumor immunity in vitro. Interestingly, HIS can effectively limit the tumor growth in the HeLa xenograft mice models without causing significant loss of body weight. Consequently, such a conjugation can be a potent and safe immunochemotherapeutic method for improving cancer therapy. (C) 2020 Elsevier Masson SAS. All rights reserved.