Methyl 4-methyl-2-sulfanylidene-6-(4-tert-butylphenyl)-3,6-dihydro-1H-pyrimidine-5-carboxylate | 6376-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Methyl 4-methyl-2-sulfanylidene-6-(4-tert-butylphenyl)-3,6-dihydro-1H-pyrimidine-5-carboxylate
• 英文别名: methyl 4-(4-tert-butylphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 6376-62-1
• 化学式: C₁₇H₂₂N₂O₂S
• 分子量: 318.44
• InChiKey: VKVARPMNHYIHFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 4-methyl-2-sulfanylidene-6-(4-tert-butylphenyl)-3,6-dihydro-1H-pyrimidine-5-carboxylate 、 copper dichloride 以 乙醇 为溶剂， 反应 48.0h， 以33%的产率得到
  参考文献：
  名称：

  Synthesis, spectral characterization and X-ray crystallographic study of new copper(I) complexes. Antitumor activity in colon cancer

  摘要：

  Three novel copper(I) complexes with three methyl 4-aryl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione-5-carboxylate ligands were synthesized and fully characterized by elemental analysis, magnetic susceptibility, molar conductivity, ESI-MS, FTIR, UV-Vis and NMR. The difference between the three ligands is located in the aryl group: 4-(tert-butyl)phenyl (HL1), 2,6-dichlorophenyl (HL2) and 2,4-dichlor-ophenyl (HL3). Two ligands and complex 2 were characterized by single-crystal X-ray diffraction. The complex [CuCI(HL2)(2)]center dot dmso exhibits an almost perfect trigonal planar coordination geometry crystallizing in a space group P2(1)/n, through the two sulfur atoms of the ligands, one chlorine atom bonded to the copper(l) and solvated with one molecule of dimethyl sulfoxide. The anticancer activity was evaluated in vitro against human colorectal cancer (CRC) cell line (Caco-2). The complexes have cytotoxic effect with IC50 values of 28.46, 25.03 and 38.83 mu M respectively. Moreover, complexes 1 and 2 are able to strongly induce apoptosis in this CRC in vitro model. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.08.023

文献信息

• Synthesis, spectral characterization and X-ray crystallographic study of new copper(I) complexes. Antitumor activity in colon cancer
  作者：Noelia González-Ballesteros、David Pérez-Álvarez、M. Carmen Rodríguez-Argüelles、Marta S.C. Henriques、José A. Paixão、Sonia Prado-López

  DOI：10.1016/j.poly.2016.08.023

  日期：2016.11

  Three novel copper(I) complexes with three methyl 4-aryl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione-5-carboxylate ligands were synthesized and fully characterized by elemental analysis, magnetic susceptibility, molar conductivity, ESI-MS, FTIR, UV-Vis and NMR. The difference between the three ligands is located in the aryl group: 4-(tert-butyl)phenyl (HL1), 2,6-dichlorophenyl (HL2) and 2,4-dichlor-ophenyl (HL3). Two ligands and complex 2 were characterized by single-crystal X-ray diffraction. The complex [CuCI(HL2)(2)]center dot dmso exhibits an almost perfect trigonal planar coordination geometry crystallizing in a space group P2(1)/n, through the two sulfur atoms of the ligands, one chlorine atom bonded to the copper(l) and solvated with one molecule of dimethyl sulfoxide. The anticancer activity was evaluated in vitro against human colorectal cancer (CRC) cell line (Caco-2). The complexes have cytotoxic effect with IC50 values of 28.46, 25.03 and 38.83 mu M respectively. Moreover, complexes 1 and 2 are able to strongly induce apoptosis in this CRC in vitro model. (C) 2016 Elsevier Ltd. All rights reserved.