1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide

• 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: 1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide
• 英文别名: 4-(4-methoxyphenyl)-6-methyl-N-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxamide；4-(4-methoxyphenyl)-6-methyl-N-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxamide
• 化学式: C₁₉H₁₉N₃O₂S
• 分子量: 353.445
• InChiKey: FJEYALULZAPMIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  94.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯苯甲醛 、 氯乙酸 、 1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide 在 sodium acetate 、 乙酸酐 、 溶剂黄146 作用下， 以78.63%的产率得到5-(4-methoxyphenyl)-N-phenyl-2-(4-chlorobenzylidene)-7-methyl-3-oxo-2,3-dihydro-5H-(1,3)-thiazolo-(3,2-a)-pyrimidine-6-carboxamide
  参考文献：
  名称：

  In vitro anti-inflammatory potential and QSAR analysis of oxazolo/thiazolo pyrimidine derivatives

  摘要：

  Twenty-six different benzylidene oxazolo/thiazolo (3,2-a)-pyrimidine-6-carboxamide derivatives were synthesized and evaluated for their anti-inflammatory potential by protein denaturation method. The structures of title compounds were characterized by IR and NMR spectral data. The SAR studies reveal that compounds containing electron withdrawing polar group at para position of 5-phenyl ring and electron withdrawing non-polar group at para position of 2-benzylidene moiety of thiazolo pyrimidine nucleus have better anti-inflammatory potential. The 2D-QSAR studies were performed on VLife MDS software which reveals that anti-inflammatory potential of benzylidene-3-oxo-5H-oxazolo/thiazolo (3,2-a)-pyrimidine-6-carboxamides is dependent on estate contribution, alignment independent, individual and path count descriptors.

  DOI：

  10.1007/s00044-012-0189-5
• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 N-乙酰乙酰苯胺 、 硫脲 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以100%的产率得到1,2,3,4-tetrahydro-6-methyl-4-(4-methoxyphenyl)-2-thioxo-N-phenylpyrimidine-5-carboxamide
  参考文献：
  名称：

  噻唑并[3,2-a]嘧啶酮衍生物作为Bcl-2家族蛋白的一般抑制剂的发现和开发

  摘要：

  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。

  DOI：

  10.1002/cmdc.201000484

文献信息

• 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。
• Sharaf, M. A. F.; Aal, F. A. Abdel; Fattah, A. M. Abdel, Journal of Chemical Research, Miniprint, 1996, # 8, p. 1956 - 1969
  作者：Sharaf, M. A. F.、Aal, F. A. Abdel、Fattah, A. M. Abdel、Khalik, A. M. R. Abdel

  DOI：——

  日期：——
• In vitro anti-inflammatory potential and QSAR analysis of oxazolo/thiazolo pyrimidine derivatives
  作者：Ramesh L. Sawant、Charusheela A. Bansode、Jyoti B. Wadekar

  DOI：10.1007/s00044-012-0189-5

  日期：2013.4

  Twenty-six different benzylidene oxazolo/thiazolo (3,2-a)-pyrimidine-6-carboxamide derivatives were synthesized and evaluated for their anti-inflammatory potential by protein denaturation method. The structures of title compounds were characterized by IR and NMR spectral data. The SAR studies reveal that compounds containing electron withdrawing polar group at para position of 5-phenyl ring and electron withdrawing non-polar group at para position of 2-benzylidene moiety of thiazolo pyrimidine nucleus have better anti-inflammatory potential. The 2D-QSAR studies were performed on VLife MDS software which reveals that anti-inflammatory potential of benzylidene-3-oxo-5H-oxazolo/thiazolo (3,2-a)-pyrimidine-6-carboxamides is dependent on estate contribution, alignment independent, individual and path count descriptors.
• Efficient Synthesis of 5-Carboxanilide-Dihydropyrimidinones Using Cobalt(II) Nitrate Hexahydrate
  作者：Mehrnoush Kangan、Nourallah Hazeri、Afshin Yazdani-Elah-Abadi、Malek-Taher Maghsoodlou

  DOI：10.1002/jccs.201600841

  日期：2017.5

  5‐Carboxanilide‐dihydropyrimidinone derivatives were synthesized in good yield in a three‐component and efficient process by the condensation reaction of acetoacetanilide, aldehyde and urea/thiourea in the presence of cobalt(II) nitrate hexahydrate as catalyst in ethanol at ambient condition.

  在六水合硝酸钴（II）在乙醇中的存在下，在环境条件下，通过乙酰乙酰苯胺，醛和脲/硫脲的缩合反应，可以在三组分且高效的过程中以高收率合成5-羧基苯胺基-二氢嘧啶酮衍生物。