4-(4-chloro-6-(4-methoxyphenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide | 924892-79-5

• 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-(4-methoxyphenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide
• 英文别名: 4-((4-chloro-6-((4-methoxyphenyl)amino)-1,3,5-triazin-2-yl)amino)-benzenesulfonamide
• CAS: 924892-79-5
• 化学式: C₁₆H₁₅ClN₆O₃S
• 分子量: 406.852
• InChiKey: NBAFELAWYBXXAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  132.12
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-(4-chloro-6-(4-methoxyphenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 8.0h， 生成 4-({4-[(2E)-2-[(2-chloro-6-fluorophenyl)methylidene]hydrazin-1-yl]-6-[(3-methoxyphenyl)amino]-1,3,5-triazin-2-yl}amino)benzene-1-sulfonamide
  参考文献：
  名称：

  Rationale design of novel substituted 1,3,5-triazine candidates as dual IDH1(R132H)/ IDH2(R140Q) inhibitors with high selectivity against acute myeloid leukemia: In vitro and in vivo preclinical investigations

  摘要：

  DOI：

  10.1016/j.bioorg.2024.107483
• 作为产物：
  描述：

  甲氧苯胺 在 sodium acetate 、 溶剂黄146 、 三乙胺 作用下， 以 水 为溶剂， 反应 3.0h， 生成 4-(4-chloro-6-(4-methoxyphenylamino)-1,3,5-triazin-2-ylamino)benzenesulfonamide
  参考文献：
  名称：

  Rationale design of novel substituted 1,3,5-triazine candidates as dual IDH1(R132H)/ IDH2(R140Q) inhibitors with high selectivity against acute myeloid leukemia: In vitro and in vivo preclinical investigations

  摘要：

  DOI：

  10.1016/j.bioorg.2024.107483

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.
• Sulphonamides incorporating 1,3,5-triazine structural motifs show antioxidant, acetylcholinesterase, butyrylcholinesterase, and tyrosinase inhibitory profile
  作者：Nabih Lolak、Mehmet Boga、Muhammed Tuneg、Gulcin Karakoc、Suleyman Akocak、Claudiu T. Supuran

  DOI：10.1080/14756366.2019.1707196

  日期：2020.1.1

  A series of 16 novel benzenesulfonamides incorporating 1,3,5-triazine moieties substituted with aromatic amines, dimethylamine, morpholine and piperidine were investigated. These compounds were assayed for antioxidant properties by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay, 2,2`-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS) radical decolarisation assay and metal chelating methods. They were also investigated as inhibitors of acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and tyrosinase, which are associated with several diseases such as Alzheimer, Parkinson and pigmentation disorders. These benzenesulfonamides showed moderate DPPH radical scavenging and metal chelating activity, and low ABTS cation radical scavenging activity. Compounds 2 b, 3d and 3 h showed inhibitory potency against AChE with % inhibition values of >90. BChE was also effectively inhibited by most of the synthesised compounds with >90% inhibition potency. Tyrosinase was less inhibited by these compounds.