ethyl methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate | 39562-29-3

• 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: ethyl methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: 2,6-dimethyl-4-(4'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester；1,4-dihydro-2,6-dimethyl-4-(4-nitrophenyl)pyridine-3,5-dicarboxylic acid ethyl methyl ester；5-O-ethyl 3-O-methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 39562-29-3
• 化学式: C₁₈H₂₀N₂O₆
• 分子量: 360.367
• InChiKey: OUYHHVXCWZAPMH-UHFFFAOYSA-N

物化性质

• 熔点：
  151-153 °C(Solv: ethanol (64-17-5))
• 沸点：
  503.3±50.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate 在 2,2,6,6-四甲基哌啶氧化物 、 iron(III) chloride hexahydrate 、 氧气 、 sodium nitrite 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 0.83h， 以96%的产率得到3-ethyl 5-methyl 4-(4-nitrophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  An Efficient Transition-Metal-Chloride/Sodium-Nitrite/TEMPO Catalytic System for Aerobic Oxidative Aromatisation of Hantzsch 1,4-Dihydropyridines

  摘要：

  本文介绍了一种简便高效的过渡金属氯化物/亚硝酸钠/TEMPO 催化系统，该系统可在温和的条件下有氧氧化芳香化汉茨奇 1,4-二氢吡啶并获得高产率。

  DOI：

  10.3184/174751913x13701832537930
• 作为产物：
  描述：

  ethyl 5-(4-nitrophenyl)-3-oxopent-4-enoate 、 β-氨基巴豆酸甲酯 以 乙醇 为溶剂， 以85%的产率得到ethyl methyl 2,6-dimethyl-4-(4-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Pharmaceutical compositions containing unsymmetrical esters of

  摘要：

  含有不对称酯化的1,4-二氢吡啶-3,5-二羧酸的药物组合物作为活性成分，并使用方法。所述成分是在二氢吡啶核的4位被苯基取代的不对称1,4-二氢吡啶-3,5-二羧酸酯，该苯基含有至少一个硝基、氰基、叠氮基、烷基硫醚或烷基磺酰基取代基。这些组合物具有心血管活性，可用于促进冠状血管扩张，并且在治疗高血压方面具有用途。

  公开号：

  US03932645A1

文献信息

• Chemical compounds having ion channel blocking activity for the treatment of immune dysfunction
  申请人：——

  公开号：US20020119989A1

  公开（公告）日：2002-08-29

  The present invention relates to chemical compounds having inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca), and the use of such compounds for the treatment or alleviation of diseases or conditions relating to immune dysfunction. Moreover, the invention relates to a method of screening a chemical compound for inhibitory activity on an intermediate conductance Ca 2+ activated potassium channel (IK Ca).

  本发明涉及具有对中间电导性Ca2+激活钾通道（IK Ca）具有抑制活性的化合物，以及利用这种化合物治疗或缓解与免疫功能紊乱相关的疾病或症状。此外，本发明涉及一种筛选化合物对中间电导性Ca2+激活钾通道（IK Ca）具有抑制活性的方法。
• Three-Component One-Pot Synthesis of Unsymmetrical 1,4-dihydropyridine Derivatives in Aqueous Media
  作者：Da-Qing Shi、Chen-Xia Yu、Qi-Ya Zhuang

  DOI：10.3184/030823408x339791

  日期：2008.8

  A series of methyl ethyl 2,6-dimethyl-4-substituted-1,4-dihydropyridine-3,5-dicarboxylates were synthesised by the three-component reaction of aldehydes, ethyl acetoacetate and methyl β-aminocrotonate in the presence of triethylbenzylammonium chloride (TEBAC) in aqueous medium. This method has the advantage of good yields.

  在三乙基苄基氯化铵存在下，通过醛、乙酰乙酸乙酯和β-氨基巴豆酸甲酯的三组分反应合成了一系列2,6-二甲基-4-取代-1,4-二氢吡啶-3,5-二甲酸乙酯。 (TEBAC) 在水性介质中。这种方法的优点是收率好。
• Interaction of 1,4-Dihydropyridine and Pyridine Derivatives with Adenosine Receptors:  Selectivity for A₃ Receptors
  作者：A. Michiel van Rhee、Ji-long Jiang、Neli Melman、Mark E. Olah、Gary L. Stiles、Kenneth A. Jacobson

  DOI：10.1021/jm9600205

  日期：1996.1.1

  1,4-Dihydropyridine and pyridine derivatives bound to three subtypes of adenosine receptors in the micromolar range. Affinity was determined in radioligand binding assays at rat brain A(1) and A(2A) receptors using [H-3]-(R)-PIA [[H-3]-(R)-N-6-(phenylisopropyl)adenosine] and [H-3]CGS 21680 [[H-3]-2-[[4-(2-carboxyethyl)phenyl]ethylamino]-5'-(N-ethylcarbamoyl)adenosine], respectively. Affinity was determined at cloned human and rat A(3) receptors using [I-125]AB-MECA [N-6-(4-amino-3-iodobenzyl)-5'-(N-methylcarbamoyl)adenosine]. Structure-activity analysis at adenosine receptors indicated that sterically bulky groups at the 4-, 5-, and 6-positions are tolerated. (R,S)-Nicardipine, 12, displayed K-i values of 19.6 and 63.8 mu M at rat A(1) and A(2A) receptors, respectively, and 3.25 mu M at human A(3) receptors. Similarly, (R)-niguldipine, 14, displayed K-i values of 41.3 and 1.90 mu M at A(1) and A(3) receptors, respectively, and was inactive at A(2A) receptors. A preference for the R- vs the S-enantiomer was observed for several dihydropyridines at adenosine receptors, in contrast with the selectivity at L-type Ca2+ channels. A 4-trans-beta-styryl derivative, 24, with a K-i value of 0.670 mu M at A(3) receptors, was 24-fold selective vs A(1) receptors (K-i = 16.1 mu M) and 74-fold vs A(2A) receptors (K-i = 49.3 mu M). The affinity of 24 at L-type Ca2+ channels, measured in rat brain membranes using [H-3]isradipine, indicated a K-i value of 0.694 mu M, and the compound is thus nonselective between A(3) receptors and L-type Ca2+ channels. Inclusion of a 6-phenyl group enhanced A(3) receptor selectivity: Compound 28 (MRS1097; 3,5-diethyl 2-methyl-6-phenyl-4-(trans-2-phenylvinyl)-1,4(R,S)-dihydro-pyridine-3,5-dicarboxylate) was 55-fold selective vs A(1) receptors, 44-fold selective vs A(2A) receptors, and over 1000-fold selective vs L-type Ca2+ channels. In addition, compound 28 attenuated the A(3) agonist-elicited inhibitory effect on adenylylcyclase. Furthermore, whereas nicardipine, 12, displaced radioligand from the Na+-independent adenosine transporter with an apparent affinity of 5.36 +/- 1.51 mu M, compound 28 displaced less than 10% of total binding at a concentration of 100 mu M. Pyridine derivatives, when bearing a 4-alkyl but not a 4-phenyl group, maintained affinity for adenosine receptors. These findings indicate that the dihydropyridines may provide leads for the development of novel, selective A(3) adenosine antagonists.
• US3932645A
  申请人：——

  公开号：US3932645A

  公开（公告）日：1976-01-13
• US6545028B2
  申请人：——

  公开号：US6545028B2

  公开（公告）日：2003-04-08