1-benzyl-3-(phenyl-phenyliminomethyl)thiourea | 65739-30-2

• 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: 1-benzyl-3-(phenyl-phenyliminomethyl)thiourea
• 英文别名: N-(benzyl-thiocarbamoyl)-N'-phenyl-benzamidine；(1E)-1-[anilino(phenyl)methylidene]-3-benzylthiourea
• CAS: 65739-30-2
• 化学式: C₂₁H₁₉N₃S
• 分子量: 345.468
• InChiKey: DOOAKQCIBLSVRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-(phenyl-phenyliminomethyl)thiourea 在 吡啶 、 五氯化磷 、 溴 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 氯苯 、 苯 为溶剂， 反应 17.0h， 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：

  苯胺 在 三乙胺 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 1-benzyl-3-(phenyl-phenyliminomethyl)thiourea
  参考文献：
  名称：

  Innovative Strategy toward Mutant CFTR Rescue in Cystic Fibrosis: Design and Synthesis of Thiadiazole Inhibitors of the E3 Ligase RNF5

  摘要：

  DOI：

  10.1021/acs.jmedchem.3c00608

文献信息

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

  DOI：——

  日期：——
• Ried,W.; Moesinger,O., Chemische Berichte, 1978, vol. 111, p. 143 - 154
  作者：Ried,W.、Moesinger,O.

  DOI：——

  日期：——
• Synthesis and Biological Evaluation of a New Series of 2,3,5-Substituted [1,2,4]-Thiadiazoles as Modulators of Adenosine A₁ Receptors and Their Molecular Mechanism of Action
  作者：Anikó Göblyös、Henk de Vries、Johannes Brussee、Adriaan P. IJzerman

  DOI：10.1021/jm049337s

  日期：2005.2.1

  We synthesized two series (7a-i and 8a-i) of 2,3,5-substituted [1,2,4]-thiadiazole analogues of SCH-202676 (7a, 2,3-diphenyl-5-N-methylimino-2H-[1,2,4]-thiadiazole) with emphasis on the N-imino substituent. Compounds 7a-g,i and 8a-g at a final concentration of 1 muM significantly inhibited [H-3]CCPA (2-chloro-N-6-cyclopentyladenosine) agonist binding to human A, adenosine receptors. At the same concentration, all compounds appeared to increase [3H]DPCPX (1,3-dipropyl-8-cyclopentylxanthine) antagonist binding. Compound 7a and LUF5855 (7g) were selected for further characterization and studied in both equilibrium and kinetic radioligand binding experiments. The results suggest a nonstoichiometric interaction with the receptor. Further bioanalytical procedures (HPLC and MS) provided proof for an unusual receptor interaction in which 7a and 7g upon incubation were transformed into their corresponding thioureas 5a and 5g. We suggest that the thiadiazoles are sulfhydryl modifying agents rather than allosteric modulators, as they appear to reversibly modify the sulfhydryl groups of cysteine residues in cell membrane preparations.
• GOERDELER J.; HAAG J.; LOEBACH W., CHEM. BER., 1979, 112, NO 4, 1288-1296
  作者：GOERDELER J.、 HAAG J.、 LOEBACH W.

  DOI：——

  日期：——