dimethyl 2,6-dimethyl-4-[2-methyl-6-trifluoromethylimidazo[2,1-b][1,3]thiazol-5-yl]-1,4-dihydropyridine-3,5-dicarboxylate | 1015756-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: dimethyl 2,6-dimethyl-4-[2-methyl-6-trifluoromethylimidazo[2,1-b][1,3]thiazol-5-yl]-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: Dimethyl 2,6-dimethyl-4-[2-methyl-6-(trifluoromethyl)imidazo[2,1-b][1,3]thiazol-5-yl]-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 1015756-60-1
• 化学式: C₁₈H₁₈F₃N₃O₄S
• 分子量: 429.42
• InChiKey: XAUDUPYNNKYCBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-甲基-6-(三氟甲基)咪唑并[2,1-b]噻唑-5-甲醛 、 乙酰乙酸甲酯 在 ammonium hydroxide 作用下， 以 异丙醇 为溶剂， 以18%的产率得到dimethyl 2,6-dimethyl-4-[2-methyl-6-trifluoromethylimidazo[2,1-b][1,3]thiazol-5-yl]-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  硝苯地平和地尔硫卓类似物抑制 MDR1 活性和诱导细胞凋亡：体外分析。

  摘要：

  我们在此报告了两种硝苯地平类化合物 1 和 2 在 A2780/DX3 细胞中逆转多药耐药性 1 (MDR1)，它们是 1,4-二氢吡啶 (1,4-DHPs) 钙通道库的一部分在 C-4 中带有不同取代的咪唑并 [2,1-b] 噻唑系统的调节剂。通过甲基噻唑四唑 (MTT) 测定、细胞荧光法和荧光显微镜，我们评估了它们在我们的细胞系统中逆转 MDR 的能力。此外，连同化合物3（地尔硫卓样8-(4-氯苯基)-5-甲基-8-[(2Z)-pent-2-en-1-yloxy]-8H-[1,2,4] oxadiazolo[3,4-c][1,4]thiazin-3-one) 我们通过 4',6-二脒基-2-苯基吲哚后的核形态分析，分析了它们在暴露于多柔比星后增强触发细胞凋亡的能力(DAPI), 异硫氰酸荧光素 (FITC)-膜联蛋白-V/碘化丙啶 (PI) 染色和半胱天冬酶活性测定。我们的结果表明，化合物

  DOI：

  10.1007/s10637-009-9340-7

文献信息

• Imidazo[2,1-<i>b</i>]thiazole System: A Scaffold Endowing Dihydropyridines with Selective Cardiodepressant Activity
  作者：Roberta Budriesi、Pierfranco Ioan、Alessandra Locatelli、Sandro Cosconati、Alberto Leoni、Maria P. Ugenti、Aldo Andreani、Rosanna Di Toro、Andrea Bedini、Santi Spampinato、Luciana Marinelli、Ettore Novellino、Alberto Chiarini

  DOI：10.1021/jm070681+

  日期：2008.3.1

  The synthesis, characterization, and functional in vitro assays in cardiac tissues and smooth muscle (vascular and nonvascular) of a number of 4-imidazo[2,1-b]thiazole-1,4-dihydropyridines are reported. The binding properties for the novel compounds have been investigated and the interaction with the binding site common to other aryl-dihydropyridines has been demonstrated. Interestingly, the novel 4-aryl-dihydropyridines are L-type calcium channel blockers with a peculiar pharmacological behavior. Indeed, the imidazo[2,1-b]thiazole system is found to confer to the dihydropyridine scaffold an inotropic and/or chronotropic cardiovascular activity with a high selectivity toward the nonvascular tissue. Finally, molecular modeling studies were undertaken for the most representative compounds with the aim of describing the binding properties of the new ligands at molecular level and to rationalize the found structure-activity relationship data. Due to the observed pharmacological behavior of our compounds, they might be promising agents for the treatment of specific cardiovascular pathologies such as cardiac hypertrophy and ischemia.