N-(4-methylthio-phenyl)benzamidine | 613663-88-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(4-methylthio-phenyl)benzamidine
• 英文别名: N'-(4-methylsulfanylphenyl)benzenecarboximidamide
• CAS: 613663-88-0
• 化学式: C₁₄H₁₄N₂S
• mdl: MFCD19457290
• 分子量: 242.345
• InChiKey: UEMCKSUWNLDKAT-UHFFFAOYSA-N

物化性质

• 沸点：
  366.2±44.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methylthio-phenyl)benzamidine 在 碳酸氢钠 、 对甲苯磺酸 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 8.5h， 生成 1-(4-Methylsulfanyl-phenyl)-2-phenyl-4-trifluoromethyl-1H-imidazole
  参考文献：
  名称：

  Selective Cyclooxygenase-2 Inhibitors:  Heteroaryl Modified 1,2-Diarylimidazoles Are Potent, Orally Active Antiinflammatory Agents

  摘要：

  A series of heteroaryl modified 1,2-diarylimidazoles has been synthesized and found to be potent and highly selective (1000-9000-fold) inhibitors of the human COX-2. 3-Pyridyl derived COX-2 selective inhibitor (25) exhibited excellent activity in acute (carrageenan induced paw edema, ED50 = 5.4 mg/kg) and chronic (adjuvant induced arthritis, ED50 = 0.25 mg/kg) models of inflammation. The relatively long half-life of 25 in rat and dog prompted investigation of the pyridyl and other heteroaromatic systems containing potential metabolic functionalities. A number of substituted pyridyl and thiazole containing compounds (e.g., 44, 46, 54, 76, and 78) demonstrated excellent oral activity in every efficacy model evaluated. Several orally active diarylimidazoles exhibited desirable pharmacokinetics profiles and showed no CI toxicity in the rat up to 100 mg/kg in both acute and chronic models. The paper describes facile and practical syntheses of the targeted diarylimidazoles. The structure-activity relationships and antiinflammatory properties of a series of diarylimidazoles are discussed.

  DOI：

  10.1021/jm0000719
• 作为产物：
  描述：

  4-甲硫基苯硼酸 、 苯甲脒 在 copper diacetate 、 potassium carbonate 作用下， 以 异丙醇 为溶剂， 反应 2.0h， 以71%的产率得到N-(4-methylthio-phenyl)benzamidine
  参考文献：
  名称：

  喷他脒的直接、后期单-N-芳基化：方法开发、机理洞察和获得针对二脒抗性寄生虫的新型抗寄生虫药的便捷途径

  摘要：

  获得抗寄生虫脒：在 Chan-Lam 条件下使用脒的选择性单N-芳基化策略获得了喷他脒的第一个单N-芳基化类似物。在喷他脒和耐二胺脒的锥虫菌株以及对墨西哥利什曼原虫没有交叉耐药性的几种类似物中观察到对动质体寄生虫的亚微摩尔活性。这项工作突出了 Chan-Lam 单N-芳基化在开发针对二脒抗性锥虫病和利什曼病的治疗线索的潜力。

  DOI：

  10.1002/cmdc.202100509

文献信息

• Novel pyrimidon derivatives
  申请人：Orchid Chemical & Pharmaceuticals Limited

  公开号：US20040259891A1

  公开（公告）日：2004-12-23

  The present invention relates to novel pyrimidones of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention more particularly novel pyrimidones of the general formula (I). 1

  本发明涉及一种新的嘧啶酮，其通式为(I)，它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、水合物、溶剂合物、药用盐及含有它们的药用成分。本发明更具体地涉及通式(I)的新嘧啶酮。
• Novel pyrimidone derivatives
  申请人：Orchid Chemicals & Pharmaceuticals Limited

  公开号：US20030225075A1

  公开（公告）日：2003-12-04

  The present invention relates to novel pyrimidone derivatives of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention more particularly provides novel pyrimidone derivatives of the general formula (I) and a method thereof. 1

  本发明涉及一般式（I）的新型嘧啶酮衍生物，它们的衍生物、类似物、互变异构体、立体异构体、多晶形态、水合物、溶剂合物、药学上可接受的盐以及含有它们的药学上可接受的组合物。本发明更具体地提供了一般式（I）的新型嘧啶酮衍生物及其制备方法。
• Copper-catalyzed annulation of amidines for quinazoline synthesis
  作者：Yunhe Lv、Yan Li、Tao Xiong、Weiya Pu、Hongwei Zhang、Kai Sun、Qun Liu、Qian Zhang

  DOI：10.1039/c3cc43129k

  日期：——

  An efficient Cu-catalyzed synthesis of quinazolines via the C–N bond formation reactions between N–H bonds of amidines and C(sp3)–H bonds adjacent to sulfur or nitrogen atoms in the commonly used solvents, such as DMSO, DMF, DMA, NMP or TMEDA, followed by intramolecular C–C bond formation reactions was developed for the first time.

  本研究首次开发了一种铜催化喹唑啉类化合物的高效合成方法，即在 DMSO、DMF、DMA、NMP 或 TMEDA 等常用溶剂中，通过脒的 N-H 键与邻近硫或氮原子的 C（sp3）-H 键之间的 C-N 键形成反应，然后进行分子内 C-C 键形成反应。
• Pyrimidone derivatives
  申请人：Bexel Pharmaceuticals Inc.

  公开号：US07365069B2

  公开（公告）日：2008-04-29

  The present invention relates to novel pyrimidones of the general formula (I), their derivatives, their analogs, their tautomeric forms, their stereoisomers, their polymorphs, their hydrates, their solvates, their pharmaceutically acceptable salts and pharmaceutically acceptable compositions containing them. The present invention more particularly novel pyrimidones of the general formula (I)

  本发明涉及一种新的嘧啶酮，其一般式为（I），其衍生物，类似物，互变异构体，立体异构体，多晶形态，水合物，溶剂化物，药学上可接受的盐以及含有它们的药学上可接受的组合物。本发明更具体地涉及一种新的嘧啶酮，其一般式为（I）。
• PYRIMIDONE DERIVATIVES USEFUL FOR THE TREATMENT OF INFLAMMATION AND IMMUNOLOGICAL DISEASES
  申请人：Orchid Chemicals and Pharmaceuticals Ltd

  公开号：EP1492774A2

  公开（公告）日：2005-01-05