N,2,3-triphenyl-1,2,4-thiadiazol-5-imine;hydrobromide | 37937-63-6

• 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: N,2,3-triphenyl-1,2,4-thiadiazol-5-imine;hydrobromide
• CAS: 37937-63-6
• 化学式: Br*C₂₀H₁₆N₃S
• 分子量: 410.337
• InChiKey: VNOTVCHVYQVXGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,2,3-triphenyl-1,2,4-thiadiazol-5-imine;hydrobromide 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 16.0h， 以56%的产率得到N-benzothiazol-2-yl-N'-phenylbenzamidine
  参考文献：
  名称：

  The Synthesis of Aminobenzothiazoles from 2,3-Biaryl-5-anilino-Δ³-1,2,4-thiadiazolines

  摘要：

  2-Amidinobenzothiazoles 4 can be prepared in high yields by a thermally-promoted rearrangement of thiadiazolium salts I or thiadiazolines 2. Addition of base to the rearrangement of the thiadiazolium salts can improve the yields by the prior conversion of the thiadiazolium salts to the corresponding thiadiazoline free bases. The rearrangement of the thiadiazolines may go through an electrophilic aromatic substitution or free radical pathway.

  DOI：

  10.1081/scc-120021031
• 作为产物：
  描述：

  N-(N-Phenyl-benzimidoyl)-N'-phenyl-thioharnstoff 在 溴 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以3 g的产率得到N,2,3-triphenyl-1,2,4-thiadiazol-5-imine;hydrobromide
  参考文献：
  名称：

  Nair, M. D.; Desai, J. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 5, p. 335 - 337

  摘要：

  DOI：

文献信息

• SUBSTITUTED 5-IMINO-1,2,4-THIADIAZOLES THAT CAN BE USED TO TREAT NEURODEGENERATIVE DISEASES
  申请人：Martínez Gil Ana

  公开号：US20120225879A1

  公开（公告）日：2012-09-06

  The present invention is based on the use of a broad family of 5-imino-1,2,4-thiadiazoles as potential new drugs for the treatment of diseases in which PDE7 inhibition is important, specially inflammatory diseases, autoimmune and neurodegenerative disorders. On the other hand, compounds of the 5-imino-1,2,4-thiadiazole family are here described, as well as their synthetic procedures, and they may have great application as drug or drug candidates. Therefore, a first aspect of the present invention is related to a compound of formula (I):

  本发明基于使用广泛的5-亚氨基-1,2,4-噻二唑家族作为潜在的新药物，用于治疗PDE7抑制在其中重要的疾病，特别是炎症性疾病、自身免疫和神经退行性疾病。另一方面，描述了5-亚氨基-1,2,4-噻二唑家族的化合物及其合成方法，它们可能具有作为药物或药物候选物的重要应用。因此，本发明的第一个方面涉及式（I）的化合物：
• 2,3-Diaryl-5-anilino[1,2,4]thiadiazoles as melanocortin MC4 receptor agonists and their effects on feeding behavior in rats
  作者：Kevin Pan、Malcolm K Scott、Daniel H.S Lee、Louis J Fitzpatrick、Jeffery J Crooke、Ralph A Rivero、Daniel I Rosenthal、Anil H Vaidya、Boyu Zhao、Allen B Reitz

  DOI：10.1016/s0968-0896(02)00428-5

  日期：2003.1

  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.
• Nair, M. D.; Desai, J. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 5, p. 335 - 337
  作者：Nair, M. D.、Desai, J. A.

  DOI：——

  日期：——
• Synthesis and Structure of Some 6,7-Dihydro-thiazolo[4,5- d ][1,3,2]diaza-λ 5 -phosphorines
  作者：Mikhail A. Rensky、Vladimir S. Zyabrev、Alexander N. Chernega

  DOI：10.1080/713744577

  日期：2003.10.1

  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.
• The Synthesis of Aminobenzothiazoles from 2,3-Biaryl-5-anilino-Δ³-1,2,4-thiadiazolines
  作者：Kevin Pan、Allen B. Reitz

  DOI：10.1081/scc-120021031

  日期：2003.7

  2-Amidinobenzothiazoles 4 can be prepared in high yields by a thermally-promoted rearrangement of thiadiazolium salts I or thiadiazolines 2. Addition of base to the rearrangement of the thiadiazolium salts can improve the yields by the prior conversion of the thiadiazolium salts to the corresponding thiadiazoline free bases. The rearrangement of the thiadiazolines may go through an electrophilic aromatic substitution or free radical pathway.