4-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide | 856219-57-3

• 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: 4-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide
• 英文别名: 4-[(4-Anilino-6-chloro-1,3,5-triazin-2-yl)amino]benzenesulfonamide
• CAS: 856219-57-3
• 化学式: C₁₅H₁₃ClN₆O₂S
• 分子量: 376.826
• InChiKey: VGEOKMJZNOMHTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 4-{[4-(phenylamino)-6-[(E)-2-(pyridin-2-ylmethylidene)hydrazin-1-yl]-1,3,5-triazin -2-yl]amino}benzene-1-sulfonamide
  参考文献：
  名称：

  通过调整活性位点的疏水和亲水边缘以遇到双尾方法，发现新的碳酸酐酶 IX 抑制剂作为抗癌剂

  摘要：

  人碳酸酐酶 IX (hCA IX) 活性位点的疏水和亲水边缘同时含有锌离子作为催化核心的一部分，同时匹配设计和合成有效和选择性抑制剂使用双尾方法. 十七种新化合物5a-q被设计为具有苯磺酰胺部分作为锌结合基团。此外，选择N-取代的腙和N-苯基片段分别作为亲水和疏水部分，以实现与活性位点的相应半部分的良好相互作用。所有合成的化合物都成功地抑制了 CA IX，IC 50值在纳摩尔范围内为 13.3 至 259 nM。化合物，5h、5c、5m、5e和5k是在低纳摩尔范围内有效抑制肿瘤相关 CA IX 同工型的前五种化合物（K I  = 13.3、22.6、25.8、26.9 和 27.2 nM，分别）。与脱靶异构体（hCA I 和 II）相比，目标化合物5a-q对肿瘤相关异构体（hCA IX 和 XII）具有显着的选择性。此外，根据 US-NCI 协议，对一组 59 种癌细胞系的抗增殖活性进行了评估。化合物5d

  DOI：

  10.1016/j.ejmech.2022.114190
• 作为产物：
  描述：

  磺胺 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 8.0h， 生成 4-(4-chloro-6-(phenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide
  参考文献：
  名称：

  Substituted benzene sulfonamides incorporating 1,3,5-triazinyl moieties potently inhibit human carbonic anhydrases II, IX and XII

  摘要：

  A series of benzene sulfonamides incorporating 1,3,5-triazinyl moieties were synthesized using cyanuric chloride as starting material. Inhibition studies against human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms were performed with the new compounds. hCA I was modestly inhibited (K(I)s in the range of 87 nM-4.35 mu M), hCA II was moderately inhibited by most of the new compounds (K(I)s in the range of 12.5-130 nM), whereas the tumor associated isoforms were potently inhibited, with K(I)s in the range of 1.2-34.1 nM against hCA IX and of 2.1-33.9 against hCA XII, respectively. Docking studies of some of the new compounds showed an effective binding mode within the enzyme active site, as demonstrated earlier by X-ray crystallography for structurally-related sulfonamides incorporating 1,3,5-triazinyl functionalities. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.048

文献信息

• Synthesis and antitumor evaluation of a novel series of triaminotriazine derivatives
  作者：Mingfang Zheng、Chenghui Xu、Jianwei Ma、Yan Sun、Feifei Du、Hong Liu、Liping Lin、Chuan Li、Jian Ding、Kaixian Chen、Hualiang Jiang

  DOI：10.1016/j.bmc.2006.11.028

  日期：2007.2

  A series of triaminotriazine derivatives (compounds 5a-f, 6a-x, and 7a-g) was designed, synthesized, and evaluated for their inhibition activities to colorectal cancer (CRC) cell lines (HCT-116 and HT-29). Most of the synthesized compounds demonstrated moderate anti-proliferatory effects on both HCT-116 and HT-29 cell lines at the concentration of 10 mu M. The inhibitory activities against HCT-116 and HT-29 cell lines were discussed to develop the structure-activity relationships of this new series. Compounds 61 and 6o exhibited prominent inhibition activities toward HCT-116, with IC50S of 0.76 and 0.92 mu M, respectively. The in vivo antitumor studies and pharmacokinctics of compound 61 showed that it might be a promising new hit for further development of antitumor agents. (c) 2006 Elsevier Ltd. All rights reserved.
• 10.1016/j.bioorg.2024.107483
  作者：Tawfik, Haytham O.、Mousa, Mai H.A.、Zaky, Mohamed Y.、El-Dessouki, Ahmed M.、Sharaky, Marwa、Abdullah, Omeima、El-Hamamsy, Mervat H.、Al-Karmalawy, Ahmed A.

  DOI：10.1016/j.bioorg.2024.107483

  日期：——
• Substituted benzene sulfonamides incorporating 1,3,5-triazinyl moieties potently inhibit human carbonic anhydrases II, IX and XII
  作者：Amrita K. Saluja、Meena Tiwari、Daniela Vullo、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2014.01.048

  日期：2014.3

  A series of benzene sulfonamides incorporating 1,3,5-triazinyl moieties were synthesized using cyanuric chloride as starting material. Inhibition studies against human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms I, II (cytosolic) and IX, XII (transmembrane, tumor-associated) isoforms were performed with the new compounds. hCA I was modestly inhibited (K(I)s in the range of 87 nM-4.35 mu M), hCA II was moderately inhibited by most of the new compounds (K(I)s in the range of 12.5-130 nM), whereas the tumor associated isoforms were potently inhibited, with K(I)s in the range of 1.2-34.1 nM against hCA IX and of 2.1-33.9 against hCA XII, respectively. Docking studies of some of the new compounds showed an effective binding mode within the enzyme active site, as demonstrated earlier by X-ray crystallography for structurally-related sulfonamides incorporating 1,3,5-triazinyl functionalities. (C) 2014 Elsevier Ltd. All rights reserved.
• Discovery of new carbonic anhydrase IX inhibitors as anticancer agents by toning the hydrophobic and hydrophilic rims of the active site to encounter the dual-tail approach
  作者：Haytham O. Tawfik、Andrea Petreni、Claudiu T. Supuran、Mervat H. El-Hamamsy

  DOI：10.1016/j.ejmech.2022.114190

  日期：2022.3

  The hydrophobic and the hydrophilic rims in the active site of human carbonic anhydrase IX (hCA IX) which as well contains a zinc ion as part of the catalytic core, were simultaneously matched to design and synthesize potent and selective inhibitors using a dual-tail approach. Seventeen new compounds, 5a-q, were designed to have the benzenesulfonamide moiety as a zinc binding group. In addition, N-substituted

  人碳酸酐酶 IX (hCA IX) 活性位点的疏水和亲水边缘同时含有锌离子作为催化核心的一部分，同时匹配设计和合成有效和选择性抑制剂使用双尾方法. 十七种新化合物5a-q被设计为具有苯磺酰胺部分作为锌结合基团。此外，选择N-取代的腙和N-苯基片段分别作为亲水和疏水部分，以实现与活性位点的相应半部分的良好相互作用。所有合成的化合物都成功地抑制了 CA IX，IC 50值在纳摩尔范围内为 13.3 至 259 nM。化合物，5h、5c、5m、5e和5k是在低纳摩尔范围内有效抑制肿瘤相关 CA IX 同工型的前五种化合物（K I  = 13.3、22.6、25.8、26.9 和 27.2 nM，分别）。与脱靶异构体（hCA I 和 II）相比，目标化合物5a-q对肿瘤相关异构体（hCA IX 和 XII）具有显着的选择性。此外，根据 US-NCI 协议，对一组 59 种癌细胞系的抗增殖活性进行了评估。化合物5d