([4-(氯磺酰基)苯甲酰基]氨基)乙酸 | 155493-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: ([4-(氯磺酰基)苯甲酰基]氨基)乙酸
• 英文名称: 2-{[4-(chlorosulfonyl)phenyl]formamido}acetic acid
• 英文别名: N-[4-(chlorosulfonyl)benzoyl]glycine；{[4-(Chlorosulfonyl)benzoyl]amino}acetic acid；2-[(4-chlorosulfonylbenzoyl)amino]acetic acid
• CAS: 155493-93-9
• 化学式: C₉H₈ClNO₅S
• mdl: MFCD06340099
• 分子量: 277.685
• InChiKey: CBDGPFVSWUUXJX-UHFFFAOYSA-N

物化性质

• 沸点：
  538.4±35.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  ([4-(氯磺酰基)苯甲酰基]氨基)乙酸 、 3-甲苯肼 以 二氯甲烷 为溶剂， 反应 3.0h， 以58%的产率得到N-(4-{[2-(3-methylphenyl)hydrazinyl]sulfonyl}benzoyl)glycine
  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

• Structure–Activity Relationship of USP5 Inhibitors
  作者：Mandeep K. Mann、Carlos A. Zepeda-Velázquez、Héctor González-Álvarez、Aiping Dong、Taira Kiyota、Ahmed M. Aman、Peter Loppnau、Yanjun Li、Brian Wilson、Cheryl H. Arrowsmith、Rima Al-Awar、Rachel J. Harding、Matthieu Schapira

  DOI：10.1021/acs.jmedchem.1c00889

  日期：2021.10.28

  competitively inhibits the catalytic activity of the enzyme. Exploration of the structure–activity relationship, complemented with crystallographic characterization of the ZnF-UBD bound to multiple ligands, led to the identification of 64, which binds to the USP5 ZnF-UBD with a KD of 2.8 μM and is selective over nine proteins containing structurally similar ZnF-UBD domains. 64 inhibits the USP5 catalytic

  USP5 是一种去泛素化酶，与包括癌症在内的一系列疾病有关，但迄今为止尚未报道过靶向 USP5 的化学探针。在这里，我们展示了一个化学系列的进展，该系列占据 USP5 的一个特征不佳的锌指泛素结合域 (ZnF-UBD) 的 C 端泛素结合位点，并竞争性地抑制酶的催化活性。探索结构-活性关系，辅以结合多个配体的 ZnF-UBD 的晶体学表征，鉴定出64 种，其与 USP5 ZnF-UBD 结合，K D为 2.8 μM，对九种蛋白质具有选择性包含结构相似的 ZnF-UBD 结构域。64在体外试验中抑制双泛素底物的 USP5 催化裂解。这项研究为发现描述细胞中 USP5 功能的化学探针提供了化学和结构框架。
• 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.