N-benzyl-2,3-diphenyl-1,2,4-thiadiazol-2-ium-5-amine;bromide

• 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-benzyl-2,3-diphenyl-1,2,4-thiadiazol-2-ium-5-amine;bromide
• 化学式: Br*C₂₁H₁₈N₃S
• 分子量: 424.364
• InChiKey: HYPVVDDMDISSNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.28
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  53.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-2,3-diphenyl-1,2,4-thiadiazol-2-ium-5-amine;bromide 在 五氯化磷 、 三乙胺 作用下， 以 二氯甲烷 、 氯苯 、 苯 为溶剂， 反应 16.0h， 生成 7-benzyl-6,7-dihydro-2,2,4-tris(methylamino)-6-(N-phenylbenzimidoyl)imino-thiazolo[4,5-d][1,3,2]diaza-λ⁵-phosphorine
  参考文献：
  名称：

  Synthesis and Structure of Some 6,7-Dihydro-thiazolo[4,5- d ][1,3,2]diaza-λ 5 -phosphorines

  摘要：

  1,2,4-Thiadiazol-5(2H)-imines 1 react with malononitrile under ring cleavage cycloaddition and subsequent ring rearrangement. The products 2 incorporate the enaminonitrile fragment. Treatment of compounds 2 with phosphorus pentachloride results in thiazolo[4,5-d][1,3,2]diaza-lambda(5)-phosphorine derivatives 3 with a reactive chloro, substituent in position 2 and 4 which can be substituted by various nucleophiles. The structure of the trimethoxy derivative 7c was determined by an X-ray structure analysis.

  DOI：

  10.1080/713744577
• 作为产物：
  描述：

  (1E)-1-[Anilino(phenyl)methylidene]-3-benzylthiourea 在 溴 作用下， 以 氯仿 为溶剂， 生成 N-benzyl-2,3-diphenyl-1,2,4-thiadiazol-2-ium-5-amine;bromide
  参考文献：
  名称：

  2,3-Diaryl-5-anilino[1,2,4]thiadiazoles as melanocortin MC4 receptor agonists and their effects on feeding behavior in rats

  摘要：

  The melanocortin-4 receptor (MC4) modulates physiological functions such as feeding behavior, nerve regeneration, and drug addiction. Using a high throughput screen based on I-121-NDP-MSH binding to the human MC4 receptor, we discovered 2,3-diaryl-5-anilino[1,2,4]thiadiazoles 3 as potent and selective MC4 receptor agonists. Through SAR development on the three attached aryl rings, we improved the binding affinity from 174 nM to 4.4 nM IC50. When delivered intraperitoneally, compounds 3a, 3b, and 3c induced significant inhibition of food intake in a fasting-induced feeding model in rats. When delivered orally, these compounds lost activity, mainly due to rapid metabolism to inactive imidoylthiourea reduction products. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00428-5

文献信息

• Goerdeler,J. et al., Chemische Berichte, 1979, vol. 112, p. 1288 - 1296
  作者：Goerdeler,J. et al.

  DOI：——

  日期：——
• Innovative Strategy toward Mutant CFTR Rescue in Cystic Fibrosis: Design and Synthesis of Thiadiazole Inhibitors of the E3 Ligase RNF5
  作者：Irene Brusa、Elvira Sondo、Emanuela Pesce、Valeria Tomati、Dario Gioia、Federico Falchi、Beatrice Balboni、Jose Antonio Ortega Martínez、Marina Veronesi、Elisa Romeo、Natasha Margaroli、Maurizio Recanatini、Stefania Girotto、Nicoletta Pedemonte、Marinella Roberti、Andrea Cavalli

  DOI：10.1021/acs.jmedchem.3c00608

  日期：2023.7.27