4-(2-(phenylsulfonamido)phenethyl)benzoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-(2-(phenylsulfonamido)phenethyl)benzoic acid
• 英文别名: 4-[2-[2-(Benzenesulfonamido)phenyl]ethyl]benzoic acid
• 化学式: C₂₁H₁₉NO₄S
• 分子量: 381.452
• InChiKey: YRJRYUFLDMNGKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 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

• 作为反应物：
  描述：

  4-(2-(phenylsulfonamido)phenethyl)benzoic acid 、 邻苯二胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到N-(2-aminophenyl)-4-(2-(phenylsulfonamido)phenethyl)benzamide
  参考文献：
  名称：

  Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

  摘要：

  Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI(50) of 22 +/- 2 and 12 +/- 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 mu M, and 1.47 mu M, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112158
• 作为产物：
  描述：

  (4-甲氧羰基苄基)三苯基溴化膦 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 sodium hydroxide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成 4-(2-(phenylsulfonamido)phenethyl)benzoic acid
  参考文献：
  名称：

  Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response

  摘要：

  Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI(50) of 22 +/- 2 and 12 +/- 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 mu M, and 1.47 mu M, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs. (c) 2020 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2020.112158

文献信息

• Phenylcarboxylic Acid Derivatives and Use Thereof for the Treatment of Diabetes
  申请人：Moinet Gerard

  公开号：US20080045483A1

  公开（公告）日：2008-02-21

  The invention relates to compounds of general formula (1): in which R1, R2, R3, R4, R5, A, B, D and E are as defined in Claim 1 , and also to the preparation process therefor and the therapeutic use thereof. These compounds can be used in the treatment of pathologies associated with hyperglycaemia.

  本发明涉及一般式（1）的化合物：其中R1、R2、R3、R4、R5、A、B、D和E如权利要求书所定义，并且涉及其制备过程和治疗用途。这些化合物可用于治疗与高血糖相关的病理状况。
• US7816397B2
  申请人：——

  公开号：US7816397B2

  公开（公告）日：2010-10-19
• Design, synthesis, and evaluation of N-phenyl-4-(2-phenylsulfonamido)-benzamides as microtubule-targeting agents in drug-resistant cancer cells, displaying HDAC inhibitory response
  作者：Wei-Cheng Wu、Yi-Min Liu、Mei-Hsiang Lin、Yu-Hsuan Liao、Mei-Jung Lai、Hsun-Yueh Chuang、To-Yu Hung、Chun-Han Chen、Jing-Ping Liou

  DOI：10.1016/j.ejmech.2020.112158

  日期：2020.4

  Microtubule-targeting agents (MTA) have enjoyed significant clinical success for decades. However, several mechanisms may cause inactivation of such drugs, leading to acquired resistance in patients treated with them. Therefore, drugs containing a stilbene-like skeleton and possessing dual inhibitory activity may provide a new and differentiated treatment for patients to overcome challenging acquired resistance. A new compound (16c) displays promising anticancer activity with GI(50) of 22 +/- 2 and 12 +/- 0.1 nM in vincristine-resistant nasopharyngeal (KB-Vin) cancer cells and etoposide-resistant nasopharyngeal (KB-7D) cancer cells and is better than vincristine, etoposide, ABT-751, and MS-275. A mechanistic study revealed that 16c interferes with the cell cycle distribution and induces cell cycle arrest at the G2/M phase and severe mitotic spindle defects followed by apoptosis. In addition, it produces much more significant cytotoxicity than vincristine and etoposide in the corresponding resistant cells, indicating that it may be a promising candidate to overcome drug resistance in cancer cells. Compound 16c also displays inhibitory activity against HDAC 1 and HDAC 2 with IC50 values of 1.07 mu M, and 1.47 mu M, respectively. These findings may lead to a new type of structural motif for future development of drugs that could overcome acquired resistance to MTAs. (c) 2020 Published by Elsevier Masson SAS.