ethyl 2-(2-ethoxy-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate | 105219-74-7

• 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: ethyl 2-(2-ethoxy-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate
• 英文别名: Ethyl 6-(ethoxycarbonyl)-1,4-dihydro-5-methyl-4-oxothieno[2,3-d]pyrimidine-2-acetate；ethyl 2-(2-ethoxy-2-oxoethyl)-5-methyl-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxylate
• CAS: 105219-74-7
• 化学式: C₁₄H₁₆N₂O₅S
• 分子量: 324.357
• InChiKey: FEGFCDAVQBEXEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-(2-ethoxy-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 ethyl 2-{2-[2-(anilinocarbonothioyl)hydrazino]-2-oxoethyl}-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety

  摘要：

  Some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety were synthesized using thieno[2,3-d]pyrimidin-3(4H)-yl)pacetohydrazides as precursors in order to determine their cytotoxicity. Compounds 5, 7-8 and 10-18 were evaluated for their cytotoxical effect on four cancer cell lines: human colorectal cancer cell line HT-29, breast cancer cells MDA-MB-231, cervical cancer cells HeLa, human liver carcinoma HepG2 and human normal diploid cell line Lep3. Exclusively high cytotoxic activity of compounds 8, 16 and 17 against MDA-MB-231 cells was ascertained and the calculated IC50 values were 3.91.10(-2), 1.2.10(-3) and 3.74.10(-2) mu M respectively. Thienopyrimidinones 10, 15 and 17 exhibited high cytotoxicity against HT-29 cell and the IC50 values were in the range 1.56.10(-3) mu M-0.13 mu M. To HeLa cell lines cytotoxicity demonstrated compounds 8, 10, 11, 13 and 15-18 but the substance 13 was the most toxic with IC50 -9.5.10(-4) mu M. Distinctly high antiproliferative activity of derivatives 10,14-15 and 17-18 was estimated against Hep G2, compound 15 showed IC50 -0.21 mu M. Proliferative effects to Lep 3 demonstrated compounds 5, 7-8, 11-14, 16, 18 whose EC50 values were from 0.12 to 2.21 mu M. The biological data highlighted that the nature and the position of the substituents influence both the cytotoxicity to the cancer cells and the proliferation properties to Lep3 of the tested compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.09.032
• 作为产物：
  描述：

  2-氨-4-甲基噻吩-3,5-二羧酸二乙酯 、 氰乙酸乙酯 在 盐酸 作用下， 以59%的产率得到ethyl 2-(2-ethoxy-2-oxoethyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Pech; Bohm, Pharmazie, 1989, vol. 44, # 11, p. 790 - 791

  摘要：

  DOI：

文献信息

• Pech; Bohm, Pharmazie, 1989, vol. 44, # 11, p. 790 - 791
  作者：Pech、Bohm

  DOI：——

  日期：——
• Synthesis and antiproliferative activity of some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety
  作者：Anelia Ts. Mavrova、Diana Wesselinova、Jordan A. Tsenov、Lubomir A. Lubenov

  DOI：10.1016/j.ejmech.2014.09.032

  日期：2014.10

  Some new thieno[2,3-d]pyrimidin-4(3H)-ones containing 1,2,4-triazole and 1,3,4-thiadiazole moiety were synthesized using thieno[2,3-d]pyrimidin-3(4H)-yl)pacetohydrazides as precursors in order to determine their cytotoxicity. Compounds 5, 7-8 and 10-18 were evaluated for their cytotoxical effect on four cancer cell lines: human colorectal cancer cell line HT-29, breast cancer cells MDA-MB-231, cervical cancer cells HeLa, human liver carcinoma HepG2 and human normal diploid cell line Lep3. Exclusively high cytotoxic activity of compounds 8, 16 and 17 against MDA-MB-231 cells was ascertained and the calculated IC50 values were 3.91.10(-2), 1.2.10(-3) and 3.74.10(-2) mu M respectively. Thienopyrimidinones 10, 15 and 17 exhibited high cytotoxicity against HT-29 cell and the IC50 values were in the range 1.56.10(-3) mu M-0.13 mu M. To HeLa cell lines cytotoxicity demonstrated compounds 8, 10, 11, 13 and 15-18 but the substance 13 was the most toxic with IC50 -9.5.10(-4) mu M. Distinctly high antiproliferative activity of derivatives 10,14-15 and 17-18 was estimated against Hep G2, compound 15 showed IC50 -0.21 mu M. Proliferative effects to Lep 3 demonstrated compounds 5, 7-8, 11-14, 16, 18 whose EC50 values were from 0.12 to 2.21 mu M. The biological data highlighted that the nature and the position of the substituents influence both the cytotoxicity to the cancer cells and the proliferation properties to Lep3 of the tested compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.