N-[3-(2,5-dichlorobenzyloxy)-4-(methyl(methylsulfonyl)amino)phenyl]-4-methoxybenzamide | 1372688-37-3

• 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-[3-(2,5-dichlorobenzyloxy)-4-(methyl(methylsulfonyl)amino)phenyl]-4-methoxybenzamide
• 英文别名: N-(3-((2,5-dichlorobenzyl)oxy)-4-(N-methylmethylsulfonamido)phenyl)-4-methoxybenzamide；N-[3-(2,5-dichloro-benzyloxy)-4-(methanesulfonyl-methyl-amino)-phenyl]-4-methoxy-benzamide；N-[3-[(2,5-dichlorophenyl)methoxy]-4-[methyl(methylsulfonyl)amino]phenyl]-4-methoxybenzamide
• CAS: 1372688-37-3
• 化学式: C₂₃H₂₂Cl₂N₂O₅S
• 分子量: 509.41
• InChiKey: SHFBQYJDSBVZSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  93.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-[2-[(2,5-dichlorophenyl)methoxy]-4-nitrophenyl]methanesulfonamide 在 iron(III) chloride 、 sodium hydride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-[3-(2,5-dichlorobenzyloxy)-4-(methyl(methylsulfonyl)amino)phenyl]-4-methoxybenzamide
  参考文献：
  名称：

  开发尼美舒利类似物作为靶向微管蛋白和 HSP27 的双重抑制剂治疗女性癌症

  摘要：

  在药物再利用范式中，已经用于治疗特定疾病的药物也可以治疗替代疾病。最近，除抗炎作用外，尼美舒​​利还被报道为一种抗肿瘤剂。微管蛋白和热休克蛋白 27 (HSP27) 是发现抗癌疗法的有吸引力的靶标，因为它们在癌细胞中均上调。在这方面，本研究旨在通过抑制微管蛋白和 HSP27 功能开发尼美舒利骨架，合成、表征和生物学评估新的尼美舒利类似物作为抗癌剂。合成的试剂通过 1H NMR、13C NMR、IR、熔点以及吸热和放热 DSC 分析进行表征。使用 GC-MS 技术确认分子量。N-(3-((2, 5-二氯苄基）氧基）-4-（N-甲基甲基磺酰氨基）苯基）-4-碘代苯甲酰胺（L4剂）的结构使用X射线晶体学分析确认。配体采用三斜晶系a  = 8.194(14) Å, b  = 10.75(3) Å, c  = 14.21(2) Å 和 P-1 的空间群。使用蛋白质印迹分析在收获的 SKOV3 和 SKBR3

  DOI：

  10.1016/j.molstruc.2021.131479

文献信息

• AMIDE DERIVATIVES OF BENZENE-SULFONANILIDE, PHARMACEUTICAL COMPOSITION THEREOF AND METHOD FOR CANCER TREATMENT USING THE SAME
  申请人：Su Bin

  公开号：US20120095092A1

  公开（公告）日：2012-04-19

  The invention provides a compound of formula (I), a pharmaceutical composition thereof, a method of preparing a medicament for the treatment of a cancer, and a method of treating cancers. The invention exhibits merits against cancers such as significantly higher potency and effectiveness over a broader range of cancers. In formula (I), R a is a benzyl group with alkyl and/or alkoxy; R b is selected from H and alkyl groups; R f is an alkyl; and R 3 is selected from a substituted phenyl, a heterocyclic group, and wherein Rc is selected from a fused ring, fused rings, and any bivalent cyclic group.

  该发明提供了一种式(I)的化合物，其药物组成物，用于治疗癌症的药物制备方法，以及治疗癌症的方法。该发明展示了针对癌症的优点，如在更广泛的癌症范围内具有显着更高的效力和有效性。在式(I)中，R是含有烷基和/或烷氧基的苄基；R被选自H和烷基；Rf是烷基；而R3被选自取代苯基、杂环基，以及其中Rc被选自融合环、融合环和任何二价环状基团。
• Synthesis and Anticancer Mechanism Investigation of Dual Hsp27 and Tubulin Inhibitors
  作者：Bo Zhong、Snigdha Chennamaneni、Rati Lama、Xin Yi、Werner J. Geldenhuys、John J. Pink、Afshin Dowlati、Yan Xu、Aimin Zhou、Bin Su

  DOI：10.1021/jm4004736

  日期：2013.7.11

  Heat shock protein 27 (Hsp27) is a chaperone protein, and its expression is increased in response to various stress stimuli including anticancer chemotherapy, which allows the cells to survive and causes drug resistance. We previously identified lead compounds that bound to Hsp27 and tubulin via proteomic approaches. Systematic ligand based optimization in the current study significantly increased the cell growth inhibition and apoptosis inducing activities of the compounds. Compared to the lead compounds, one of the new derivatives exhibited much better potency to inhibit tubulin polymerization but a decreased activity to inhibit Hsp27 chaperone function, suggesting that the structural modification dissected the dual targeting effects of the compound. The most potent compounds 20 and 22 exhibited strong cell proliferation inhibitory activities at subnanomolar concentration against 60 human cancer cell lines conducted by Developmental Therapeutic Program at the National Cancer Institute and represented promising candidates for anticancer drug development.
• US8802895B2
  申请人：——

  公开号：US8802895B2

  公开（公告）日：2014-08-12
• [EN] AMIDE DERIVATIVES OF BENZENE-SULFONANILIDE, PHARMACEUTICAL COMPOSITION THEREOF AND METHOD FOR CANCER TREATMENT USING THE SAME<br/>[FR] DÉRIVÉS AMIDE DE BENZÈNE-SULFONANILIDE, COMPOSITION PHARMACEUTIQUE LES CONTENANT ET MÉTHODE DE TRAITEMENT DU CANCER LES UTILISANT
  申请人：UNIV STATE CLEVELAND

  公开号：WO2012054417A1

  公开（公告）日：2012-04-26

  The invention provides a compound of formula (I), a pharmaceutical composition thereof, a method of preparing a medicament for the treatment of a cancer, and a method of treating cancers. The invention exhibits merits against cancers such as significantly higher potency and effectiveness over a broader range of cancers. In formula (I), Ra is a benzyl group with alkyl and/or alkoxy; Rb is selected from H and alkyl groups; Rf is an alkyl; and R3 is selected from a (Formula) substituted phenyl, a heterocyclic group, and, Formula, wherein Rc is selected from a fused ring, fused rings, and any bivalent cyclic group. Formula (I)
• Development of nimesulide analogs as a dual inhibitor targeting tubulin and HSP27 for treatment of female cancers
  作者：Laila A. Jaragh-Alhadad、Gamaleldin I. Harisa、Fars K. Alanazi

  DOI：10.1016/j.molstruc.2021.131479

  日期：2022.1

  The synthesized agents were characterized by 1H NMR, 13C NMR, IR, melting point and both endothermic and exothermic DSC analysis. The molecular weight was confirmed using GC–MS technique. N-(3-((2,5-dichlorobenzyl)oxy)-4-(N-methylmethylsulfonamido)phenyl)-4-iodobenzamide (agent L4) structure was confirmed using X-ray crystallographic analysis. The ligands adopt triclinic crystal with a = 8.194(14)

  在药物再利用范式中，已经用于治疗特定疾病的药物也可以治疗替代疾病。最近，除抗炎作用外，尼美舒​​利还被报道为一种抗肿瘤剂。微管蛋白和热休克蛋白 27 (HSP27) 是发现抗癌疗法的有吸引力的靶标，因为它们在癌细胞中均上调。在这方面，本研究旨在通过抑制微管蛋白和 HSP27 功能开发尼美舒利骨架，合成、表征和生物学评估新的尼美舒利类似物作为抗癌剂。合成的试剂通过 1H NMR、13C NMR、IR、熔点以及吸热和放热 DSC 分析进行表征。使用 GC-MS 技术确认分子量。N-(3-((2, 5-二氯苄基）氧基）-4-（N-甲基甲基磺酰氨基）苯基）-4-碘代苯甲酰胺（L4剂）的结构使用X射线晶体学分析确认。配体采用三斜晶系a  = 8.194(14) Å, b  = 10.75(3) Å, c  = 14.21(2) Å 和 P-1 的空间群。使用蛋白质印迹分析在收获的 SKOV3 和 SKBR3