3-benzyl-5-methyl-4-oxo-2-sulfanyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide | 1400635-07-5

• 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: 3-benzyl-5-methyl-4-oxo-2-sulfanyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide
• 英文别名: 3-benzyl-5-methyl-4-oxo-2-sulfanylidene-1H-thieno[2,3-d]pyrimidine-6-carboxamide
• CAS: 1400635-07-5
• 化学式: C₁₅H₁₃N₃O₂S₂
• 分子量: 331.419
• InChiKey: UXQJQCWVFKADFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-methyl-4-oxo-2-sulfanyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 3-benzyl-2-hydrazino-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of some novel thienopyrimidines and fused thienopyrimidines as anti-inflammatory agents

  摘要：

  Some new substituted thienopyrimidine derivatives comprising thioxo, thioalkyl and pyrazolyl derivatives as well as fused thienotriazolopyrimidine and thienopyrimidinotriazine ring systems were prepared from 3-benzyl-2-hydrazino-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide 4. The designed compounds were evaluated for their anti-inflammatory activity. Compounds 4, 9, 10 and 13 showed the highest anti-inflammatory effect compared with the reference drug diclofenac sodium. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.007
• 作为产物：
  描述：

  异硫氰酸苯甲酯 、 2-氨在-5-氨基羰基-4-甲基-3-噻吩羧酸乙酯 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 以78%的产率得到3-benzyl-5-methyl-4-oxo-2-sulfanyl-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of some novel thienopyrimidines and fused thienopyrimidines as anti-inflammatory agents

  摘要：

  Some new substituted thienopyrimidine derivatives comprising thioxo, thioalkyl and pyrazolyl derivatives as well as fused thienotriazolopyrimidine and thienopyrimidinotriazine ring systems were prepared from 3-benzyl-2-hydrazino-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxamide 4. The designed compounds were evaluated for their anti-inflammatory activity. Compounds 4, 9, 10 and 13 showed the highest anti-inflammatory effect compared with the reference drug diclofenac sodium. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.007

文献信息

• Synthesis and molecular docking study of some 3,4-dihydrothieno[2,3-d]pyrimidine derivatives as potential antimicrobial agents
  作者：Omaima G. Shaaban、Doaa A.E. Issa、Alaa A. El-Tombary、Shrouk M. Abd El Wahab、Abeer E. Abdel Wahab、Ibrahim A. Abdelwahab

  DOI：10.1016/j.bioorg.2019.102934

  日期：2019.7

  In continuation of our research program aiming at developing new potent antimicrobial agents, new series of substituted 3,4-dihydrothieno[2,3-d]pyrimidines was synthesized. The newly synthesized compounds were preliminary tested for their in vitro activity against six bacterial and three fungal strains using the agar diffusion technique. The results revealed that compounds 7, 8a, 10b, 10d and 11b exhibited

  在继续致力于开发新型有效抗菌剂的研究计划的过程中，合成了一系列新的取代的3,4-二氢噻吩并[2,3-d]嘧啶类化合物。使用琼脂扩散技术，初步测试了新合成的化合物对六种细菌和三种真菌菌株的体外活性。结果表明，化合物7、8a，10b，10d和11b表现出左氧氟沙星对革兰氏阴性细菌铜绿假单胞菌的效力的一半，而化合物5a，8b，10c和12表现出左氧氟沙星对变形杆菌的效力的一半。而化合物7、10b，10d和11b则显示出氨苄西林对革兰氏阳性细菌枯草芽孢杆菌的一半活性。大多数化合物显示出很高的抗真菌效力。化合物3、6、7、9b，10a，11a，11b，图15和16显示出克霉唑对烟曲霉的效力是其两倍。化合物3、4、5a，5b，9b，10a，10b，10c，13、15、16和18显示出克霉唑对米根霉的活性翻倍。活性化合物与炭疽杆菌DHPS活性位点的分子对接研究显示，与共结晶的配体相比，与酶活性位点的各种相互作用均获得了良好的评分。