1-[1-(2-Methoxy-phenyl)-1-(2-methoxy-phenylamino)-meth-(Z)-ylidene]-3-phenyl-thiourea | 524923-94-2

• 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-[1-(2-Methoxy-phenyl)-1-(2-methoxy-phenylamino)-meth-(Z)-ylidene]-3-phenyl-thiourea
• 英文别名: 1-[(2-Methoxyanilino)-(2-methoxyphenyl)methylidene]-3-phenylthiourea；1-[(2-methoxyanilino)-(2-methoxyphenyl)methylidene]-3-phenylthiourea
• CAS: 524923-94-2
• 化学式: C₂₂H₂₁N₃O₂S
• 分子量: 391.494
• InChiKey: RIAXADSBYNOCKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[1-(2-Methoxy-phenyl)-1-(2-methoxy-phenylamino)-meth-(Z)-ylidene]-3-phenyl-thiourea 生成 2,3-双(2-甲氧基苯基)-N-苯基-1,2,4-噻二唑-5-亚胺
  参考文献：
  名称：

  1,2,4-thiadiazolium derivatives as melanocortin receptor modulators

  摘要：

  本发明涉及一种新型的1,2,4-噻二唑-2-ium衍生物，可用作黑色素皮质素受体的激动剂或拮抗剂。更具体地说，本发明的化合物可用于治疗代谢、中枢神经系统和皮肤疾病，如肥胖症、口服葡萄糖耐量受损、血糖升高、2型糖尿病、X综合症、糖尿病视网膜病变、脊髓损伤、神经损伤、急性神经退行性疾病、慢性神经退行性疾病、神经丛病、男性勃起功能障碍、干眼症、痤疮、干燥皮肤、老化皮肤、脂溢性皮炎、酒渣鼻、过度耳垢、美波腺障碍、假毛囊炎、酵母感染、头皮屑、汗腺炎、眼部酒渣鼻和汗腺障碍。

  公开号：

  US08501791B2
• 作为产物：
  描述：

  2-甲氧基苯甲腈 在 sodium amide 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 生成 1-[1-(2-Methoxy-phenyl)-1-(2-methoxy-phenylamino)-meth-(Z)-ylidene]-3-phenyl-thiourea
  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

• METHODS FOR THE TREATMENT OF DERMATOLOGICAL DISORDERS
  申请人：Eisinger Magdalena

  公开号：US20090215902A1

  公开（公告）日：2009-08-27

  The present invention is directed to the use of a compound of formula (I) or pharmaceutically acceptable salt thereof, for the treatment of disorders mediated by the melanocortin-5 receptor, particularly dermatological disorders; and further directed to pharmaceutical compositions containing the compound of formula (I) or a pharmaceutically acceptable salt thereof.

  本发明涉及使用式(I)化合物或其药学上可接受的盐，用于治疗通过黑色素皮质素-5受体介导的疾病，特别是皮肤病；还涉及含有式(I)化合物或其药学上可接受的盐的制药组合物。
• Non-enzymatic reduction of a 1,2,4-thiadiazolium derivative
  作者：Fa Zhang、Carmelita Estavillo、Margie Mohler、Jane Cai

  DOI：10.1016/j.bmcl.2008.01.029

  日期：2008.3

  It was discovered that 2,3-bis-(2-methoxy-phenyl)-5-phenylamino-[1,2,4]-thiadiazolium bromide (1), a 1,2,4-thiadiazolium derivative, could be reduced to the corresponding imidoylthiourea, 1-[(2-methoxy-phenyl)-(2-methoxy-phenylimino)-methyl]3-phenyl-thiourea (3), by some biologically interesting reducing reagents including glutathione, cysteine, and ascorbic acid. The reduction also occurred in Sprague - Dawley rat and Yorkshire swine plasma, suggesting that thiol containing biological molecules existing in the plasma are mainly responsible for this reaction. A facile method for preparation of 3 from 1 was established by using 2-thioethanol as reaction reagent as well as solvent. The structure of 3 was fully characterized using nuclear magnetic resonance (NMR) and mass spectrometry with electrospray ionization source (ESI-MS). Those new findings could shed light on the development of 1,2,4-thiadiazolium derivatives for their potential pharmaceutical applications. (C) 2008 Elsevier Ltd. All rights reserved.
• STABLE TOPICAL COMPOSITIONS FOR 1,2,4-THIADIAZOLE DERIVATIVES
  申请人：Janssen Pharmaceuticals, Inc.

  公开号：EP2421521A1

  公开（公告）日：2012-02-29
• US8247453B2
  申请人：——

  公开号：US8247453B2

  公开（公告）日：2012-08-21
• US8536226B2
  申请人：——

  公开号：US8536226B2

  公开（公告）日：2013-09-17