1,4-dihydro-2,6-dimethyl-4-(5'-methyl-furan-2'-yl)pyridine-3,5-dicarboxylic acid dimethyl ester | 296266-88-1

• 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: 1,4-dihydro-2,6-dimethyl-4-(5'-methyl-furan-2'-yl)pyridine-3,5-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 2,6-dimethyl-4-(5-methyl-2-furyl)-1,4-dihydropyridine-3,5-dicarboxylate；dimethyl 2,6-dimethyl-4-(5-methylfuran-2-yl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 296266-88-1
• 化学式: C₁₆H₁₉NO₅
• mdl: MFCD00405610
• 分子量: 305.331
• InChiKey: QFBBWNBTECTMDL-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  415.3±45.0 °C(Predicted)
• 密度：
  1.176±0.06 g/cm3(Predicted)
• 溶解度：
  13 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-甲基呋喃醛 、 乙酰乙酸甲酯 在 氨 作用下， 以 甲醇 为溶剂， 以70%的产率得到1,4-dihydro-2,6-dimethyl-4-(5'-methyl-furan-2'-yl)pyridine-3,5-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of 4-thiophen-2′-yl-1,4-dihydropyridines as potentiators of the CFTR chloride channel

  摘要：

  The gating of the CFTR chloride channel is altered by a group of mutations that cause cystic fibrosis. This gating defect may be corrected by small molecules called potentiators. Some 1,4-dihydropyridine (DHP) derivatives, bearing a thiophen-2-yl and a furanyl ring at the 4-position of the nucleus, were prepared and tested as CFTR potentiators. In particular, we evaluated the ability of novel DHPs to enhance the activity of the rescued Delta F508-CFTR as measured with a functional assay based on the halide-sensitive yellow fluorescent protein. Most DHPs showed an effect comparable to or better than that of the reference compound genistein. The potency was instead significantly improved, with some compounds, such as 3g, 3h, 3n, 4a, 4b, and 4d, having a half effective concentration in the submicromolar range. CoMFA analysis gave helpful suggestions to improve the activity of DHPs. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.028

文献信息

• Zn/MCM-41-catalyzed unsymmetrical Hantzsch reaction and the evaluation of optical properties and anti-cancer activities of the polyhydroquinoline products
  作者：Elaheh Farajzadeh Oskuie、Sajjad Azizi、Zarrin Ghasemi、Mahtab Pirouzmand、Behnaz Nikzad Kojanag、Jafar Soleymani

  DOI：10.1007/s00706-020-02549-x

  日期：2020.2

  investigated in the presence of MCM-41-supported ZnNO3. The polyhydroquinoline products which were obtained under mild conditions and very easy workup were evaluated for anti-cancer activities against MCF-7, SK-BR-3, and HT-29 of breast and colon cancer cells. The fluorescence emission of some products was also studied and their optical parameters were reported. Graphic abstract

  摘要在MCM-41负载的ZnNO 3的存在下，研究了各种芳基醛，二甲酮和3-氨基巴豆酸甲酯的三组分Hantzsch缩合反应。评价了在温和条件下和很容易处理后获得的聚氢喹啉产品对乳腺癌和结肠癌细胞的MCF-7，SK-BR-3和HT-29的抗癌活性。还研究了一些产物的荧光发射，并报道了它们的光学参数。 图形摘要
• Synthesis of 4-thiophen-2′-yl-1,4-dihydropyridines as potentiators of the CFTR chloride channel
  作者：Francesca Cateni、Marina Zacchigna、Nicoletta Pedemonte、Luis J.V. Galietta、Marco T. Mazzei、Paola Fossa、Michele Giampieri、Mauro Mazzei

  DOI：10.1016/j.bmc.2009.10.028

  日期：2009.12

  The gating of the CFTR chloride channel is altered by a group of mutations that cause cystic fibrosis. This gating defect may be corrected by small molecules called potentiators. Some 1,4-dihydropyridine (DHP) derivatives, bearing a thiophen-2-yl and a furanyl ring at the 4-position of the nucleus, were prepared and tested as CFTR potentiators. In particular, we evaluated the ability of novel DHPs to enhance the activity of the rescued Delta F508-CFTR as measured with a functional assay based on the halide-sensitive yellow fluorescent protein. Most DHPs showed an effect comparable to or better than that of the reference compound genistein. The potency was instead significantly improved, with some compounds, such as 3g, 3h, 3n, 4a, 4b, and 4d, having a half effective concentration in the submicromolar range. CoMFA analysis gave helpful suggestions to improve the activity of DHPs. (c) 2009 Elsevier Ltd. All rights reserved.