N-(4-(2,4-dimethylphenyl)thiazol-2-yl)benzenesulfonamide | 544410-53-9

• 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-(4-(2,4-dimethylphenyl)thiazol-2-yl)benzenesulfonamide
• 英文别名: N-[4-(2,4-dimethylphenyl)-1,3-thiazol-2-yl]benzenesulfonamide
• CAS: 544410-53-9
• 化学式: C₁₇H₁₆N₂O₂S₂
• 分子量: 344.458
• InChiKey: ULLQJLDMRLWVHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-azido-2-(2-(2-(2-iodoethoxy)ethoxy)ethoxy)ethane 、 N-(4-(2,4-dimethylphenyl)thiazol-2-yl)benzenesulfonamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Series of Novel Inhibitor of Nek2/Hec1 Analogues

  摘要：

  High expression in cancer 1 (Hec1) is an oncogene overly expressed in many human cancers. Small molecule inhibitor of Nek2/Hcc1 (INH) targeting the Heel and its regulator, Nek2, in the mitotic pathway, was identified to inactivate Hec1/Nek2 function mediated by protein degradation that subsequently leads to chromosome mis-segregation and cell death. To further improve the efficacy of INH, a series of INH analogues were designed, synthesized, and evaluated. Among these 33 newly synthesized analogues, three of them, 6, 13, and 21, have 6-8 fold more potent cell killing activity than the previous lead compound INH1. Compounds 6 and 21 were chosen for analyzing the underlying action mechanism. They target directly the Hec1/Nek2 pathway and cause chromosome mis-alignment as well as cell death, a mechanism similar to that of INH1, This initial exploration of structural/functional relationship of INH may advance the progress for developing clinically applicable INH analogue.

  DOI：

  10.1021/jm8015969
• 作为产物：
  描述：

  4-(2,4-二甲基-苯基)-噻唑-2-亚胺 、 苯磺酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以55%的产率得到N-(4-(2,4-dimethylphenyl)thiazol-2-yl)benzenesulfonamide
  参考文献：
  名称：

  噻唑衍生物作为转移性癌细胞迁移和侵袭的新型抑制剂的修饰和生物学评价

  摘要：

  Fascin 最近已成为潜在的治疗靶点，因为它在癌细胞中的表达与肿瘤进展和转移密切相关。在最初发现一系列通过可能抑制肌成束蛋白功能而表现出有效抗迁移和抗侵袭活性的噻唑衍生物之后，我们在此报告了 63 种新型噻唑衍生物的设计和合成，通过进一步的结构修饰来寻找更有效的肌成束蛋白抑制剂。在噻唑氮上具有更长烷基链取代的5系列类似物比具有其他结构基序的类似物表现出更大的抗迁移活性。最强大的模拟，5p，在 24 nM 时抑制了 50% 的细胞迁移。此外，噻唑类似物显示出很强的抗血管生成活性，在鸡胚胎膜试验中阻断了新血管的形成。最后，进行了一项功能研究，以通过与 F-肌动蛋白捆绑蛋白肌成束蛋白的相互作用来研究作用机制。

  DOI：

  10.1021/jm500724x

文献信息

• ANTI-MIGRATION AND ANTI-INVASION THIAZOLE ANALOGS FOR TREATMENT OF CELLULAR PROLIFERATIVE DISEASE
  申请人：XAVIER UNIVERSITY OF LOUISIANA

  公开号：US20150274714A1

  公开（公告）日：2015-10-01

  Thiazole analog compounds and their pharmaceutically acceptable salts are disclosed, including pharmaceutical compositions comprising the thiazole analog compounds, either alone or in combination with at least one additional therapeutic agent, and/or with a pharmaceutically acceptable carrier. Methods of using the thiazole analog compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of cellular proliferative diseases, such as cancer, are also disclosed.
• US9650369B2
  申请人：——

  公开号：US9650369B2

  公开（公告）日：2017-05-16
• Synthesis and Biological Evaluation of a Series of Novel Inhibitor of Nek2/Hec1 Analogues
  作者：Xiao-Long Qiu、Guideng Li、Guikai Wu、Jiewen Zhu、Longen Zhou、Phang-Lang Chen、A. Richard Chamberlin、Wen-Hwa Lee

  DOI：10.1021/jm8015969

  日期：2009.3.26

  High expression in cancer 1 (Hec1) is an oncogene overly expressed in many human cancers. Small molecule inhibitor of Nek2/Hcc1 (INH) targeting the Heel and its regulator, Nek2, in the mitotic pathway, was identified to inactivate Hec1/Nek2 function mediated by protein degradation that subsequently leads to chromosome mis-segregation and cell death. To further improve the efficacy of INH, a series of INH analogues were designed, synthesized, and evaluated. Among these 33 newly synthesized analogues, three of them, 6, 13, and 21, have 6-8 fold more potent cell killing activity than the previous lead compound INH1. Compounds 6 and 21 were chosen for analyzing the underlying action mechanism. They target directly the Hec1/Nek2 pathway and cause chromosome mis-alignment as well as cell death, a mechanism similar to that of INH1, This initial exploration of structural/functional relationship of INH may advance the progress for developing clinically applicable INH analogue.
• Modification and Biological Evaluation of Thiazole Derivatives as Novel Inhibitors of Metastatic Cancer Cell Migration and Invasion
  作者：Shilong Zheng、Qiu Zhong、Yulan Xi、Madhusoodanan Mottamal、Qiang Zhang、Richard L. Schroeder、Jayalakshmi Sridhar、Ling He、Harris McFerrin、Guangdi Wang

  DOI：10.1021/jm500724x

  日期：2014.8.14

  emerged as a potential therapeutic target, as its expression in cancer cells is closely associated with tumor progression and metastasis. Following the initial discovery of a series of thiazole derivatives that demonstrated potent antimigration and antiinvasion activities via possible inhibition of fascin function, we report here the design and synthesis of 63 new thiazole derivatives by further structural

  Fascin 最近已成为潜在的治疗靶点，因为它在癌细胞中的表达与肿瘤进展和转移密切相关。在最初发现一系列通过可能抑制肌成束蛋白功能而表现出有效抗迁移和抗侵袭活性的噻唑衍生物之后，我们在此报告了 63 种新型噻唑衍生物的设计和合成，通过进一步的结构修饰来寻找更有效的肌成束蛋白抑制剂。在噻唑氮上具有更长烷基链取代的5系列类似物比具有其他结构基序的类似物表现出更大的抗迁移活性。最强大的模拟，5p，在 24 nM 时抑制了 50% 的细胞迁移。此外，噻唑类似物显示出很强的抗血管生成活性，在鸡胚胎膜试验中阻断了新血管的形成。最后，进行了一项功能研究，以通过与 F-肌动蛋白捆绑蛋白肌成束蛋白的相互作用来研究作用机制。