2,6-Dimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-4-phenyl-1,4-dihydropyridine | 39562-02-2

• 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: 2,6-Dimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-4-phenyl-1,4-dihydropyridine
• 英文别名: DHP-047；5-O-ethyl 3-O-methyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate；1,4-dihydro-2,6-dimethyl-4-phenyl-3,5-pyridinedicarboxylic acid ethyl methyl ester；Ethyl methyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 39562-02-2
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: SCHYNEBURMLCDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-Dimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-4-phenyl-1,4-dihydropyridine 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 1.0h， 以91%的产率得到3-ethoxycarbonyl-5-methoxycarbonyl-4-phenyl-2,6-dimethylpyridine
  参考文献：
  名称：

  轻度非均相条件下溴化铜对Hantzsch 1,4-二氢吡啶的氧化芳构化作用

  摘要：

  一种温和的非均相氧化剂溴化铜已被用于Hantzsch 1,4-二氢吡啶氧化芳构化成相应的吡啶衍生物，并以极高的收率通过简单的后处理程序分离出产物。

  DOI：

  10.1016/j.tetlet.2014.09.025
• 作为产物：
  描述：

  2-苯亚甲基乙酰乙酸乙酯 在 氢氧化钾 作用下， 以 1,4-二氧六环 为溶剂， 反应 25.0h， 生成 2,6-Dimethyl-3-ethoxycarbonyl-5-methoxycarbonyl-4-phenyl-1,4-dihydropyridine
  参考文献：
  名称：

  Esters of 1,4-dihydropyridine-3- and -3,5-carbothiolic acids

  摘要：

  DOI：

  10.1007/bf00512963

文献信息

• An Efficient Transition-Metal-Chloride/Sodium-Nitrite/TEMPO Catalytic System for Aerobic Oxidative Aromatisation of Hantzsch 1,4-Dihydropyridines
  作者：Bin-Hui Lou、Shu-Bin Chen、Jian Wang、Ying Chen、Jing-Hua Li

  DOI：10.3184/174751913x13701832537930

  日期：2013.7

  A facile and efficient transition-metal-chloride/sodium-nitrite/TEMPO catalytic system for aerobic oxidative aromati-sation of Hantzsch 1,4-dihydropyridines in high yields under mild conditions is described.

  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。
• Insights for diastereoselectivity in synthesis of 2,3-dihydropyrroles by photochemical ring contraction of 1,4-dihydropyridines
  作者：Shijie Wang、Huiqin Wang、Nana Tian、Hong Yan

  DOI：10.1016/j.tetlet.2020.152797

  日期：2021.2

  into the photoreactive substrate 1,4-dihydropyridines, an interesting diastereoselectivity of 2,3-dihydropyrroles in the process of photochemical ring contraction was observed. The diastereoselectivity of (2R,3R) and (2S,3S)-2,3-dihydropyrroles was related to the phenyl group and the chirality of C-4 in 1,4-dihydropyridines and similar to that of 1,4-dihydropyridines. The yields and diastereomeric excess

  通过将手性助剂引入光反应性底物1,4-二氢吡啶中的策略，观察到在光化学环收缩过程中2,3-二氢吡咯具有有趣的非对映选择性。（2 R，3 R）和（2 S，3 S）-2,3-二氢吡咯的非对映选择性与1,4-二氢吡啶中的苯基和C-4的手性有关，与1， 4-二氢吡啶。比较了所有获得的支持实验数据的产物的产率和非对映异构体，并在理论计算中进行了讨论。简洁的理论研究用于解释在1,4-二氢吡啶对2,3-二氢吡咯的光化学环收缩中观察到的非对映选择性。
• 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.
• VIGANTE, B. A.;OZOLS, YA. YA.;DUBUR, G. YA.;BEJLIS, YU. I.;BELASH, E. M.;+, XIMIYA GETEROTSIKL. SOEDIN., 1982, N 2, 219-228
  作者：VIGANTE, B. A.、OZOLS, YA. YA.、DUBUR, G. YA.、BEJLIS, YU. I.、BELASH, E. M.、+

  DOI：——

  日期：——
• TREATMENT OF CANCER WITH DIHYDROPYRIDINES
  申请人：Menri Group Ltd.

  公开号：EP3648764A2

  公开（公告）日：2020-05-13