4-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydroindeno[1,2-d]pyrimidine-5-one | 896848-92-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 4-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydroindeno[1,2-d]pyrimidine-5-one
• 英文别名: 4-(4-methoxyphenyl)-2-sulfanylidene-3,4-dihydro-1H-indeno[1,2-d]pyrimidin-5-one
• CAS: 896848-92-3
• 化学式: C₁₈H₁₄N₂O₂S
• 分子量: 322.387
• InChiKey: NFNBZWYHKFLQAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3-茚满二酮 、 4-甲氧基苯甲醛 、 硫脲 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以87%的产率得到4-(4-methoxyphenyl)-2-thioxo-1,2,3,4-tetrahydroindeno[1,2-d]pyrimidine-5-one
  参考文献：
  名称：

  茚满二酮Biginelli产品的设计，合成，表征和抗菌活性

  摘要：

  已开发出一种简单有效的方法来合成4-（取代的苯基）-3,4-二氢-1H-茚并[1,2-d]嘧啶-2,5-二酮（5）和4-（取代的）（1），3-二羰基化合物（茚满二酮）的一锅三组分环缩合反应生成苯基）-2-硫代-2-2,3,4-四氢茚并[1,2-d]嘧啶-5- （6）（1），芳香醛（2）和尿素/硫脲（3/4），使用催化量的浓 在回流乙醇中的HCl。筛选代表性样品对革兰氏阴性菌，大肠杆菌和铜绿假单胞菌以及革兰氏阳性菌，金黄色葡萄球菌和白喉C杆菌的抗菌活性使用圆盘扩散法。产物的结构通过IR，1 H，13 C NMR和元素分析确认。

  DOI：

  10.1002/jhet.860

文献信息

• COMPOUNDS USEFUL FOR TREATING INJURIES FROM WARFARE AGENTS
  申请人：Wu Xinyuan

  公开号：US20150352115A1

  公开（公告）日：2015-12-10

  Compounds and compositions for treating disorders related to TRPA1 are described herein.

  本文描述了用于治疗与TRPA1相关的疾病的化合物和组合物。
• Tricyclic 3,4-dihydropyrimidine-2-thione derivatives as potent TRPA1 antagonists
  作者：Harrie J.M. Gijsen、Didier Berthelot、Michel A.J. De Cleyn、Ivo Geuens、Bert Brône、Marc Mercken

  DOI：10.1016/j.bmcl.2011.12.068

  日期：2012.1

  The transient receptor potential A1 (TRPA1) channel has been implicated in a number of inflammatory and nociceptive processes, and antagonists of the TRPA1 receptor could offer a potential treatment for conditions such as inflammatory or neuropathic pain, airway disorders, and itch. In a high throughput screen aimed at the identification of TRPA1 antagonists, 4-phenyl-2-thioxo-1,2,3,4-tetrahydroindeno[1,2-d]pyrimidin-5-one (1) was identified as a potent TRPA1 receptor antagonist. A series of analogous tricyclic 3,4-dihydropyrimidine-2-thiones has been prepared via the multi-component Biginelli reaction and subsequent derivatization. This has led to TRPA1 antagonists with potencies around 10 nM for both rat and human derived TRPA1 receptors. The activity was shown to reside exclusively in the 4R-enantiomers. (C) 2011 Elsevier Ltd. All rights reserved.
• An Efficient and Modified Biginelli-Type Synthesis of 3,4-Dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione Using Phosphorous Pentoxide
  作者：Poojali P. Warekar、Govind B. Kolekar、Madhukar B. Deshmukh、Prashant V. Anbhule

  DOI：10.1080/00397911.2014.947652

  日期：2014.12.17

  A simple, clean and convenient one-pot method has been developed for the synthesis of 4-phenyl-3,4-dihydro-1H-indeno[1,2-d]pyrimidine-2,5-dione and 4-phenyl-2-thioxo-1,2,3,4-tetrahydro-5H-indeno[1,2-d]pyrimidine-5-one by multicomponent condensation of 1,3-indanedione, aromatic aldehydes and urea/thiourea using phosphorus pentoxide in ethanol under reflux conditions. The simple workup procedure and moderate to good yields within short time are some important features of this protocol. The synthesized compounds have been interpreted on the basis of their spectroscopic data.
• COMPOUNDS USEFUL FOR TREATING DISORDERS RELATED TO TRPA1
  申请人：Wu Xinyuan

  公开号：US20160009708A1

  公开（公告）日：2016-01-14

  Compounds and compositions for treating disorders related to TRPA1 are described herein.
• US8530487B1
  申请人：——

  公开号：US8530487B1

  公开（公告）日：2013-09-10