1-(3-mercaptoprop-1-en-2-yl)-3-phenyl-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione | 1333497-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 1-(3-mercaptoprop-1-en-2-yl)-3-phenyl-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
• CAS: 1333497-74-7
• 化学式: C₁₉H₁₈N₂O₂S₂
• 分子量: 370.496
• InChiKey: WVQHXNSJOGUKFC-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  3-(Bromomethyl)-7-phenyl-5,16-dithia-7-aza-2-azoniatetracyclo[7.7.0.02,6.010,15]hexadeca-1(9),2(6),10(15)-trien-8-one;bromide 在 水 、 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以54%的产率得到1-(3-mercaptoprop-1-en-2-yl)-3-phenyl-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Quantitative structure-activity relationship study and directed synthesis of Thieno[2,3-d]pyrimidine-2,4-diones as monocarboxylate transporter 1 inhibitors

  摘要：

  The aim of any quantitative structure-activity relationship (QSAR) study is not only to reveal relationships between structure of molecules and their biological activity, but also to explain it within the bounds of theoretical conceptions and to use the obtained model for prediction of properties of new compounds. That provides possibility to execute directed synthesis of new compounds with required biological activities. Monocarboxylate transporter 1 (MCT1) is one of the targets in a search for new immune response modulating and antitumor agents. In the present study, QSAR model for MCT1 binding affinity is developed. Decisive influence of relative negative partial charge, solvation energy, and radius of gyration on MCT1 inhibition has been detected. Theoretical explanation of the obtained model is given, and biological activity prediction for a series of N-vinyl derivatives of thieno[2,3-d]pyrimidine-2,4-dione is made. Directed synthesis of three leading compounds has been executed according to prediction results.

  DOI：

  10.1007/s00044-011-9748-4