(2,6-dibromo-4-methyl-phenyl)-thiourea | 228266-56-6

• 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: (2,6-dibromo-4-methyl-phenyl)-thiourea
• 英文别名: (2,6-Dibrom-4-methyl-phenyl)-thioharnstoff；(2,6-Dibromo-4-methylphenyl)thiourea
• CAS: 228266-56-6
• 化学式: C₈H₈Br₂N₂S
• 分子量: 324.039
• InChiKey: BZQCSWUDBPFRBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2,6-dibromo-4-methyl-phenyl)-thiourea 在 硼烷四氢呋喃络合物 、 三甲基铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 47.0h， 生成 {5-[(Cyclopropylmethyl-propyl-amino)-methyl]-4-trifluoromethyl-thiazol-2-yl}-(2,6-dibromo-4-methyl-phenyl)-amine
  参考文献：
  名称：

  2-Arylaminothiazoles as high-affinity corticotropin-Releasing factor 1 receptor (CRF1R) antagonists: synthesis, binding studies and behavioral efficacy

  摘要：

  2-Arylamino-4-trifluoromethyl-5-aminomethylthiazoles represent a novel series of high-affinity corticotropin releasing factor-1 receptor (CRF1R) antagonists that are prepared in three steps in good overall yields. Herein, we report binding SAR as well as anxiolytic activity of an exemplary compound (7a, K-i = 8.6 nM) in a mouse canopy model. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.055
• 作为产物：
  描述：

  2,6-二溴-4-甲基苯胺 在 sodium hydroxide 、 丙酮 作用下， 生成 (2,6-dibromo-4-methyl-phenyl)-thiourea
  参考文献：
  名称：

  The Preparation and Hydrolysis of Mono- and Disubstituted Benzoylthioureas¹

  摘要：

  DOI：

  10.1021/ja01321a061

文献信息

• Novel matrinic acid derivatives bearing 2‐anilinothiazole structure for non‐small cell lung cancer treatment with improved Hsp90 targeting effect
  作者：Yiming Xu、Panke Zeng、Haodong Wang、Keyan Han、Gan Qiu、Yongquan Wei、Rui Chen、Lisheng Wang、Xu Liu

  DOI：10.1002/ddr.21974

  日期：2022.9

  oncoproteins, Hsp90 has emerged as a promising drug target for cancer therapy. In particular, inhibiting Hsp90 plays a vital role in the treatment of non-small cell lung cancer. Owing to undesirable outcomes of Hsp90 inhibitors in clinical trials, a series of matrinic acid compounds bearing 2-anilinothiazole moiety were designed based on the structural features allocation shared among Hsp90 inhibitors

  Hsp90 参与介导 300 多种客户蛋白（其中许多是癌蛋白）的折叠和成熟，已成为癌症治疗的有希望的药物靶点。特别是抑制Hsp90在非小细胞肺癌的治疗中起着至关重要的作用。由于 Hsp90 抑制剂在临床试验中的不良结果，基于 ATP 结合口袋内 Hsp90 抑制剂之间共享的结构特征分配，设计了一系列带有 2-苯胺噻唑部分的苦参酸化合物。大多数化合物显示出通过 MTT 测定验证的有效抗癌活性。其中，最有效的化合物C4 (IC 50 选择针对四种细胞系< 10 μM）进行进一步的机制研究。值得注意的是，C4 显示出比 17AAG 更好的安全性，具有更高的 SI 值。热迁移分析数据表明， C4与 Hsp90 (-18.85 ± 0.56°C) 表现出与根赤酚相当的强结合亲和力。机制研究证实C4显着抑制A549细胞的增殖和迁移活动。此外，C4可诱导 G1 期延长和细胞凋亡。Western印迹分析结
• The Preparation and Hydrolysis of Mono- and Disubstituted Benzoylthioureas¹
  作者：Irwin B. Douglass、F. B. Dains

  DOI：10.1021/ja01321a061

  日期：1934.6
• 2-Arylaminothiazoles as high-affinity corticotropin-Releasing factor 1 receptor (CRF1R) antagonists: synthesis, binding studies and behavioral efficacy
  作者：Gene M. Dubowchik、Jodi A. Michne、Dmitry Zuev、Wendy Schwartz、Paul M. Scola、Clint A. James、Edward H. Ruediger、Sokhom S. Pin、Kevin D. Burris、Lynn A. Balanda、Qi Gao、Dedong Wu、Lawrence Fung、Tracey Fiedler、Kaitlin E. Browman、Matthew T. Taber、Jie Zhang

  DOI：10.1016/j.bmcl.2003.08.055

  日期：2003.11

  2-Arylamino-4-trifluoromethyl-5-aminomethylthiazoles represent a novel series of high-affinity corticotropin releasing factor-1 receptor (CRF1R) antagonists that are prepared in three steps in good overall yields. Herein, we report binding SAR as well as anxiolytic activity of an exemplary compound (7a, K-i = 8.6 nM) in a mouse canopy model. (C) 2003 Elsevier Ltd. All rights reserved.