6-methyl-N,4-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide | 182170-90-7

• 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: 6-methyl-N,4-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
• 英文别名: 4-methyl-N,6-diphenyl-2-sulfanyl-1,6-dihydropyrimidine-5-carboxamide；6-methyl-N,4-diphenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 182170-90-7
• 化学式: C₁₈H₁₇N₃OS
• 分子量: 323.418
• InChiKey: XHVDKHPVDSMLJL-UHFFFAOYSA-N

物化性质

• 熔点：
  216-217 °C(Solv: ethanol (64-17-5))
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 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：

  6-methyl-N,4-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide 在 氢氧化钾 、 盐酸羟胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 5-amino-10-methyl-N,12-diphenyl-7-thia-1,3,4,9-tetrazatricyclo[6.4.0.02,6]dodeca-2,5,8,10-tetraene-11-carboxamide
  参考文献：
  名称：

  Sharaf, M. A. F.; Aal, F. A. Abdel; Fattah, A. M. Abdel, Journal of Chemical Research, Miniprint, 1996, # 8, p. 1956 - 1969

  摘要：

  DOI：
• 作为产物：
  描述：

  6-methyl-N,4-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbothioamide 在 溶剂黄146 、 sodium nitrite 作用下， 反应 8.0h， 以40%的产率得到6-methyl-N,4-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide
  参考文献：
  名称：

  2-Acylthioacetamides in the Biginelli Reaction

  摘要：

  We have demonstrated for the first time a Biginelli reaction of 2-acylthioacetamides with aromatic aldehydes and ureas or thioureas, leading to N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydro-pyrimidine-5-carbothioamides. The regioselectivity of this process matched the concept of hard/soft Lewis acids and bases. It was established that nitrous acid or other oxidants converted the synthesized compounds into N-Ar-1-4-Ar-2-6-R-1-1-R-2-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine-5-carboxamides, and not the expected 4-Ar-2-6-R-1-1-R-2-5-(1,3-benzothiazol-2-yl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  DOI：

  10.1007/s10593-014-1429-z

文献信息

• Iron-catalyzed four-member multicomponent reaction for assembly of (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones
  作者：Zhiguo Zhang、Lianqiang Zhang、Xinyu Duan、Xiangqian Yan、Yan Yan、Qingfeng Liu、Tongxin Liu、Guisheng Zhang

  DOI：10.1016/j.tet.2015.07.039

  日期：2015.10

  A novel iron-catalyzed one-pot multi-component tandem reaction of acetoacetamide, urea, and two molecules of aryl aldehydes has been developed. This reaction provides a general, straightforward, practical and useful method for the preparation of potential bioactive (E)-6-arylvinyl-3,4-dihydropyrimidin-2(1H)-ones. They are also versatile precursors leading to diverse drug-like dihydropyrimidin-2(1H)-one

  已开发出一种新的铁催化的乙酰乙酰胺，尿素和两分子芳基醛的单锅多组分串联反应。该反应为制备潜在的生物活性（E）-6-芳基乙烯基-3,4-二氢嘧啶-2（1 H）-酮提供了一种通用，直接，实用和有用的方法。它们还是通用的前体，可产生多种药物样的二氢嘧啶-2（1 H）-一衍生物。避免质子酸并使用单一廉价且对环境无害的催化剂的特征使该方法更有价值。
• Discovery and Development of Thiazolo[3,2-a]pyrimidinone Derivatives as General Inhibitors of Bcl-2 Family Proteins
  作者：Bingcheng Zhou、Xun Li、Yan Li、Yaochun Xu、Zhengxi Zhang、Mi Zhou、Xinglong Zhang、Zhen Liu、Jiahai Zhou、Chunyang Cao、Biao Yu、Renxiao Wang

  DOI：10.1002/cmdc.201000484

  日期：2011.5.2

  A class of compounds with a common thiazolo[3,2‐a]pyrimidinone motif has been developed as general inhibitors of Bcl‐2 family proteins. The lead compound was originally identified in a random screening of a small compound library using a fluorescence polarization‐based competitive binding assay. Its binding to the Bcl‐xL protein was further confirmed by 15N‐HSQC NMR experiments. Structural modifications

  一类具有常见的噻唑并[3,2- a ]嘧啶酮基序的化合物已被开发为Bcl-2家族蛋白的一般抑制剂。最初使用基于荧光偏振的竞争结合测定法对小型化合物库进行随机筛选来鉴定先导化合物。15 N-HSQC NMR实验进一步证实了其与Bcl-x L蛋白的结合。分子模型研究的结果指导了对先导化合物的结构修饰。与先导化合物相比，在获得的42种化合物中，许多化合物与Bcl-2家族蛋白的结合亲和力大大提高。最有效的化合物BCL‐LZH‐ 40抑制BH3肽与Bcl‐x L的结合和Bcl-2和Mcl-1的与抑制常数（ķ我）的17，534和200N的中号，分别。
• Methods and compositions for treating pain
  申请人：Moran M. Magdalene

  公开号：US20070219222A1

  公开（公告）日：2007-09-20

  The present application relates to compounds and methods for treating pain, incontinence and other conditions.

  本申请涉及化合物和治疗疼痛、失禁和其他疾病的方法。
• Ultrasound-Assisted Synthesis of 6-Methyl-1,2,3,4-tetrahydro-<i>N</i>-aryl-2-oxo/thio-4-arylpyrimidine-5-carboxamides Catalyzed by Uranyl Nitrate Hexahydrate
  作者：K. Venkatesan、V. S. V. Satyanarayana、A. Sivakumar

  DOI：10.1002/jccs.201300380

  日期：2014.6

  An efficient and simple method developed for the synthesis of 6‐methyl‐1,2,3,4‐tetrahydro‐N‐aryl‐2‐oxo/thio‐4‐arylpyrimidine‐5‐carboxamide derivatives (4a‐o) using UO2(NO3)2.6H2O catalyst under conventional and ultrasonic conditions. The ultrasound irradiation synthesis had shown several advantages such as milder conditions, shorter reaction times and higher yields. The structures of all the newly

  使用UO 2合成6-甲基-1,2,3,4-四氢-N-芳基-2-氧代/硫代-4-芳基嘧啶-5-羧酰胺衍生物（4a-o）的有效而简单的方法（NO 3）2 .6H 2 O催化剂在常规和超声条件下。超声辐射合成显示出一些优点，例如条件温和，反应时间更短和产率更高。所有新合成的化合物的结构均已通过FT-IR，1 H NMR，13 C NMR和质谱证实。
• Synthesis of pyrimidine carboxamide derivatives catalyzed by uranyl nitrate hexa Hydrate with their antibacterial and antioxidant studies
  作者：K. Venkatesan、V. S. V. Satyanarayana、A. Sivakumar

  DOI：10.4314/bcse.v30i1.11

  日期：——

  An efficient and simple method was developed for the synthesis pyrimidine-5-carboxamides using UO 2 (NO 3 ) 2 .6H 2 O catalyst under conventional and microwave irradiation. The synthesis of dihydropyrimidine using uranyl nitrate had shown many advantages such as easy work up, shorter reaction times and higher yields using acetonitrile as a solvent. The structures of the synthesized compounds were confirmed

  开发了一种高效简单的方法，在常规和微波辐射下，使用UO 2（NO 3）2 .6H 2 O催化剂合成嘧啶-5-甲酰胺。用硝酸铀酰合成二氢嘧啶显示出许多优点，例如易于处理，较短的反应时间和使用乙腈作为溶剂的较高产率。合成的化合物的结构通过FT-IR，1 H NMR，13 C NMR和质谱数据确认。筛选了所有合成的化合物的体外抗氧化和抗菌活性，并报道了结果。关键词：微波，硝酸铀酰，抗氧化剂，抗菌公牛。化学 Soc。埃塞俄比亚。2016，30（1），119-128。DOI：http：//dx.doi.org/10.4314/bcse.v30i1.11