N,4-bis(4-chlorophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide | 181058-55-9

• 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,4-bis(4-chlorophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 181058-55-9
• 化学式: C₁₈H₁₅Cl₂N₃OS
• 分子量: 392.309
• InChiKey: WWGDVWZEEZEILD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,4-bis(4-chlorophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide 在 盐酸 、 sodium acetate 、 乙酸酐 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  S-取代的嘧啶硫酮的选择性环化：新型多取代的噻唑并嘧啶和噻唑并二嘧啶衍生物的合成和抗菌性评估

  摘要：

  合成策略基于4-芳基-N-（4-氯苯基）-6-甲基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酰胺衍生物IV a-g与一些烷基的烷基化卤化物和α-卤代酮，即甲基碘，氯乙腈和苯甲酰溴，得到相应的S-取代的衍生物Va-c。在氢氧化钾溶液的存在下，在回流下用乙醇中的溴乙酸乙酯处理IVa–c，导致形成N‐（4-氯苯基）‐7‐甲基‐3‐氧代‐5‐（芳基）‐2,3‐3单步合成中的二氢-5H-噻唑并[3,2-a]嘧啶-6-羧酰胺衍生物VIII a-c。另一方面，化合物IVa与α-卤代腈，即氯乙腈和一溴丙二腈反应，分别直接生成噻唑并[3,2-a]嘧啶衍生物Xa和Xb，化合物Xb也分别与甲酸，甲酰胺和硫氰酸铵反应分别形成噻唑二嘧啶衍生物XI-XIII。化合物VIIIa–c与吡啶中的壬二唑鎓盐偶联，得到相应的2-芳基azo唑衍生物XVIa–e。化合物IV a–g和VIIIa–c在微波辐射下重新合成。测试了一些新合成的化合物的抗菌活性。

  DOI：

  10.1002/jccs.201900199
• 作为产物：
  描述：

  对氯苯胺 、 ethyl 4-(4-chlorophenyl)-1,2,3,4-tetrahydro-6-methyl-2-thioxopyrimidine-5-carboxylate 反应 0.17h， 以65%的产率得到N,4-bis(4-chlorophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
  参考文献：
  名称：

  SYNTHESIS AND RADIATION STABILITY OF NOVEL THIAZOLOPYRIMIDINES WITH EXPECTED ANTIFUNGAL ACTIVITY

  摘要：

  A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4'-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and me structures are stable.

  DOI：

  10.1080/10426509608029657

文献信息

• Catalyst-Free, Rapid Synthesis of Fused Bicyclic Thiazolo-Pyrimidine and Pyrimido-Thiazine Derivatives by a Microwave-Assisted Method
  作者：Vijay R. Virsodia、Nikhil R. Vekariya、Atul T. Manvar、Rupesh C. Khunt、Bhavin R. Marvania、Bharat S. Savalia、Anamik K. Shah

  DOI：10.1080/10426500802077564

  日期：2008.12.23

  The present investigation deals with the rapid microwave-assisted synthesis of compounds containing fused bicyclic systems. Dihydropyrimidines obtained via a microwave-assisted Biginelli reaction were treated with dibromo alkanes under microwave conditions to yield thiazolo-pyrimidine and pyrimido-thiazine systems. The usefulness of this method lies in carrying out the reaction without a catalyst and solvent in a shorter time. The reaction was successfully extended to develop fused systems from benzimidazole-2-thiol.
• [EN] 2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE DERIVATIVES<br/>[FR] DERIVES DE 2-THIOXO-1,2,3,4-TETRAHYDROPYRIMIDINE
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2002066443A2

  公开（公告）日：2002-08-29

  The present invention is related to: (1) neutral sphingomyelinase inhibitors containing 2-thioxo 1,2,3,4-tetrahydropyrimidine derivatives of the formula (I): wherein all of the symbols have the same meanings as described hereinbefore, or a non-toxic salt thereof, a hydrate thereof, or a prodrug thereof as active ingredient, (2) novel 2-thioxo-1,2,3,4-tetrahydropyrimidine derivatives of the formula (I): wherein all of the symbols have the same meanings as described hereinbefore, or a non-toxic salt thereof, a hydrate thereof, or a prodrug thereof, (3) some novel specific compounds, and (4) process for the preparation of the compounds of the formula (Ia), or a prodrug thereof. The compounds of the present invention of the formulae (I) and (Ia) are neutral sphingomyelinase inhibitors and therefore are useful for the treatment and/or prevention of arteriosclerosis, cerebral ischemia, cardiac ischemia, lung injury, renal injury, GVHD (graft versus host diseases), transplant rejection, HIV, etc.
• Selective cyclization of S‐substituted pyrimidinethione: Synthesis and antimicrobial evaluation of novel polysubstituted thiazolopyrimidine and thiazolodipyrimidine derivatives
  作者：Hayat E. Alzahrani、Ahmed M. Fouda、Ayman M. S. Youssef

  DOI：10.1002/jccs.201900199

  日期：2020.5

  chloroacetonitrile, and phenacyl bromide to give the corresponding S‐substituted derivatives Va–c. Treatment of IVa–c with ethyl bromoacetate in ethanol under reflux in the presence of potassium hydroxide solution led to the formation of N‐(4‐chlorophenyl)‐7‐methyl‐3‐oxo‐5‐(aryl)‐2,3‐dihydro‐5H‐thiazolo[3,2‐a]pyrimidine‐6‐carboxamide derivative VIII a–c in a single‐step synthesis. On the other hand, compound

  合成策略基于4-芳基-N-（4-氯苯基）-6-甲基-2-硫代-1,2,3,4-四氢嘧啶-5-羧酰胺衍生物IV a-g与一些烷基的烷基化卤化物和α-卤代酮，即甲基碘，氯乙腈和苯甲酰溴，得到相应的S-取代的衍生物Va-c。在氢氧化钾溶液的存在下，在回流下用乙醇中的溴乙酸乙酯处理IVa–c，导致形成N‐（4-氯苯基）‐7‐甲基‐3‐氧代‐5‐（芳基）‐2,3‐3单步合成中的二氢-5H-噻唑并[3,2-a]嘧啶-6-羧酰胺衍生物VIII a-c。另一方面，化合物IVa与α-卤代腈，即氯乙腈和一溴丙二腈反应，分别直接生成噻唑并[3,2-a]嘧啶衍生物Xa和Xb，化合物Xb也分别与甲酸，甲酰胺和硫氰酸铵反应分别形成噻唑二嘧啶衍生物XI-XIII。化合物VIIIa–c与吡啶中的壬二唑鎓盐偶联，得到相应的2-芳基azo唑衍生物XVIa–e。化合物IV a–g和VIIIa–c在微波辐射下重新合成。测试了一些新合成的化合物的抗菌活性。
• SYNTHESIS AND RADIATION STABILITY OF NOVEL THIAZOLOPYRIMIDINES WITH EXPECTED ANTIFUNGAL ACTIVITY
  作者：M. M. Ghorab、Y. A. Mohamed、S. A. Mohamed、Y. A. Ammar

  DOI：10.1080/10426509608029657

  日期：1996.1.1

  A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4'-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and me structures are stable.