N,N'-(disulfanediylbis(2,1-phenylene))bis(4-chlorobenzamide)

• 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: N,N'-(disulfanediylbis(2,1-phenylene))bis(4-chlorobenzamide)
• 英文别名: 4-chloro-N-[2-[[2-[(4-chlorobenzoyl)amino]phenyl]disulfanyl]phenyl]benzamide
• 化学式: C₂₆H₁₈Cl₂N₂O₂S₂
• 分子量: 525.479
• InChiKey: SQGWQHUUMAHHMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-(disulfanediylbis(2,1-phenylene))bis(4-chlorobenzamide) 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 以68%的产率得到4-chloro-N-(2-mercaptophenyl)benzamide
  参考文献：
  名称：

  Discovery of new low-molecular-weight p53–Mdmx disruptors and their anti-cancer activities

  摘要：

  Although several p53-Mdm2-binding disruptors have been identified to date, few studies have been published on p53-Mdmx-interaction inhibitors. In the present study, we demonstrated that o-aminothiophenol derivatives with molecular weights of 200-300 selectively inhibited the p53-Mdmx interaction. S-2-Isobutyramidophenyl 2-methylpropanethioate (K-178) (1c) activated p53, up-regulated the expression of its downstream genes such as p21 and Mdm2, and preferentially inhibited the growth of cancer cells with wild-type p53 over those with mutant p53. Furthermore, we found that the S-isobutyryl-deprotected forms 1b and 3b of 1c and S-2-benzamidophenyl 2-methylpropanethioate (K-181) (3c) preferentially inhibited the p53-Mdmx interaction over the p53-Mdm2 interaction, respectively, by using a Flag-p53 and glutathione S-transferase (GST)-fused protein complex (Mdm2, Mdmx, DAPK1, or PPID). In addition, the interaction of p53 with Mdmx was lost by replacing a sulfur atom with an oxygen atom in 1b and 1c. These results suggest that sulfides such as 1b, 3b, 4b, and 5b interfere with the binding of p53-Mdmx, resulting in the dissociation of the two proteins. Furthermore, the results of oral administration experiments using xenografts in nude mice indicated that 1c reduced the volume of tumor masses to 49.0% and 36.6% that of the control at 100 mg/kg and 150 mg/kg, respectively, in 40 days. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.021
• 作为产物：
  描述：

  4-氯苯甲酰氯 、 双(2-氨基苯基)二硫 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以74 %的产率得到N,N'-(disulfanediylbis(2,1-phenylene))bis(4-chlorobenzamide)
  参考文献：
  名称：

  Electrochemical oxidative cross coupling of NH-sulfoximines with disulfides

  摘要：

  报告中介绍了一种用于 NH-亚磺酰亚胺与二硫化物硫醚化反应的电化学方法。利用电化学促进这些反应无需外加氧化剂、碱和金属催化剂。

  DOI：

  10.1039/d3nj05205b

文献信息

• Solid phase synthesis of benzothiazolyl compounds
  作者：Spyros Mourtas、Dimitrios Gatos、Kleomenis Barlos

  DOI：10.1016/s0040-4039(01)00109-5

  日期：2001.3

  2-Aminobenzenethiol, bound through its thiol function to the 2-chlorotrityl (Clt)-, trityl (Trt)-, 4-methyltrityl (Mtt)- and 4-methoxytrityl (Mmt)-resins, was acylated at the amino-function by aliphatic and aromatic acids. The obtained 2-N-acylaminobenzenethiols were cleaved from the resin by treatment with trifluoroacetic acid solutions in dichloromethane. The 2-N-acyl-aminobenzenethiols released from the resin were cyclised to the corresponding 2-substituted benzothiazoles, by standing in a solution of dithiothreitol in DMF or methanol for 1-3 h at room temperature. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Discovery of new low-molecular-weight p53–Mdmx disruptors and their anti-cancer activities
  作者：Shinichi Uesato、Yoshihiro Matsuura、Saki Matsue、Takaaki Sumiyoshi、Yoshiyuki Hirata、Suzuho Takemoto、Yasuyuki Kawaratani、Yusuke Yamai、Kyoji Ishida、Tsutomu Sasaki、Masato Enari

  DOI：10.1016/j.bmc.2016.03.021

  日期：2016.4

  Although several p53-Mdm2-binding disruptors have been identified to date, few studies have been published on p53-Mdmx-interaction inhibitors. In the present study, we demonstrated that o-aminothiophenol derivatives with molecular weights of 200-300 selectively inhibited the p53-Mdmx interaction. S-2-Isobutyramidophenyl 2-methylpropanethioate (K-178) (1c) activated p53, up-regulated the expression of its downstream genes such as p21 and Mdm2, and preferentially inhibited the growth of cancer cells with wild-type p53 over those with mutant p53. Furthermore, we found that the S-isobutyryl-deprotected forms 1b and 3b of 1c and S-2-benzamidophenyl 2-methylpropanethioate (K-181) (3c) preferentially inhibited the p53-Mdmx interaction over the p53-Mdm2 interaction, respectively, by using a Flag-p53 and glutathione S-transferase (GST)-fused protein complex (Mdm2, Mdmx, DAPK1, or PPID). In addition, the interaction of p53 with Mdmx was lost by replacing a sulfur atom with an oxygen atom in 1b and 1c. These results suggest that sulfides such as 1b, 3b, 4b, and 5b interfere with the binding of p53-Mdmx, resulting in the dissociation of the two proteins. Furthermore, the results of oral administration experiments using xenografts in nude mice indicated that 1c reduced the volume of tumor masses to 49.0% and 36.6% that of the control at 100 mg/kg and 150 mg/kg, respectively, in 40 days. (C) 2016 Elsevier Ltd. All rights reserved.
• Electrochemical oxidative cross coupling of NH-sulfoximines with disulfides
  作者：Shuai Zhang、Meiqian Hu、Changsheng Qin、Shoucai Wang、Fanghua Ji、Guangbin Jiang

  DOI：10.1039/d3nj05205b

  日期：——

  An electrochemical method for thioetherification of NH-sulfoximines with disulfides is reported. The utilization of electrochemistry for facilitating these reactions eliminates the necessity for external oxidants, bases, and metal catalysts.

  报告中介绍了一种用于 NH-亚磺酰亚胺与二硫化物硫醚化反应的电化学方法。利用电化学促进这些反应无需外加氧化剂、碱和金属催化剂。