Prakash Om, Hussain Khalid, Kumar Ravi, Wadhwa Deepak, Sharma Chetan, Aneja Kamal R
Department of Chemistry, Dyal Singh College, Karnal 132 001, India.
Org Med Chem Lett. 2011 Aug 3;1(1):5. doi: 10.1186/2191-2858-1-5.
Dialkyl 1,4-dihydro-2,6-dimethylpyridine-3,5-dicarboxylates (1,4-DHP) have now been recognized as vital drugs. Some of these derivatives such as amlodipine, felodipine, isradipine, etc. have been commercialized. In view of wide range of biological properties associated with 1,4-DHP and owing to the biological importance of the oxidation step of 1,4-DHP, we carried out the synthesis and antimicrobial evaluation of new diethyl 1,4-dihydro-2,6-dimethyl-4-(3-aryl-1-phenyl-4-pyrazolyl)pyridine-3,5-dicarboxylates (2a-g) and diethyl 2,6-dimethyl-4-(3-aryl-1-phenyl-4-pyrazolyl)pyridine-3,5-dicarboxylates (3a-g).
Synthesis of a series of new diethyl 1,4-dihydro-2,6-dimethyl-4-(3-aryl-1-phenyl-4-pyrazolyl)pyridine-3,5-dicarboxylates (2a-g) has been accomplished by multicomponent cyclocondensation reaction of ethyl acetoacetate, 3-aryl-1-phenyl pyrazole-4-carboxaldehyde (1a-g) and ammonium acetate. The dihydropyridines 2a-g were smoothly converted to new diethyl 2,6-dimethyl-4-(3-aryl-1-phenyl-4-pyrazolyl)pyridine-3,5-dicarboxylates (3a-g) using HTIB ([Hydroxy (tosyloxy)iodo]benzene, Koser's reagent) as the oxidizing agent. The antimicrobial studies of the title compounds, 2a-g &3a-g, are also described.
二烷基1,4 - 二氢 - 2,6 - 二甲基吡啶 - 3,5 - 二羧酸酯（1,4 - DHP）现已被公认为重要药物。其中一些衍生物如氨氯地平、非洛地平、伊拉地平等等已实现商业化。鉴于1,4 - DHP具有广泛的生物学特性，且由于1,4 - DHP氧化步骤的生物学重要性，我们开展了新型二乙基1,4 - 二氢 - 2,6 - 二甲基 - 4 -（3 - 芳基 - 1 - 苯基 - 4 - 吡唑基）吡啶 - 3,5 - 二羧酸酯（2a - g）和二乙基2,6 - 二甲基 - 4 -（3 - 芳基 - 1 - 苯基 - 4 - 吡唑基）吡啶 - 3,5 - 二羧酸酯（3a - g）的合成及抗菌活性评价。
通过乙酰乙酸乙酯、3 - 芳基 - 1 - 苯基吡唑 - 4 - 甲醛（1a - g）和乙酸铵的多组分环缩合反应，完成了一系列新型二乙基1,4 - 二氢 - 2,6 - 二甲基 - 4 -（3 - 芳基 - 1 - 苯基 - 4 - 吡唑基）吡啶 - 3,5 - 二羧酸酯（2a - g）的合成。使用HTIB（[羟基（对甲苯磺酰氧基）碘]苯，科泽试剂）作为氧化剂，二氢吡啶2a - g顺利转化为新型二乙基2,6 - 二甲基 - 4 -（3 - 芳基 - 1 - 苯基 - 4 - 吡唑基）吡啶 - 3,5 - 二羧酸酯（3a - g）。还描述了标题化合物2a - g和3a - g的抗菌研究。
