diethyl 2,6-dimethyl-1,4-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate | 53219-37-7

• 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: diethyl 2,6-dimethyl-1,4-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate
• 英文别名: diethyl 2,6-dimethyl-1,4-diphenyl-4H-pyridine-3,5-dicarboxylate
• CAS: 53219-37-7
• 化学式: C₂₅H₂₇NO₄
• 分子量: 405.494
• InChiKey: WMAHDMXTJVMTKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  diethyl 2,6-dimethyl-1,4-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate 在 氢氧化钾 作用下， 生成 1,4-二氢-2,6-二甲基-1,4-二苯基-3,5-吡啶二羧酸二乙酯
  参考文献：
  名称：

  Lachowicz, Monatshefte fur Chemie, 1896, vol. 17, p. 357

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄叉苯胺 以 乙醇 为溶剂， 反应 6.0h， 生成 diethyl 2,6-dimethyl-1,4-diphenyl-1,4-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  1-芳基和1-苄基-3,5-二乙氧基羰基-1,4-二氢吡啶

  摘要：

  DOI：

  10.1007/bf00552778

文献信息

• Synthesis of 1,4-dihydropyridine esters using low-melting sugar mixtures as green solvents
  作者：J. Ashwin Kumar、Gomathi Shridhar、Savita Ladage、Lakshmy Ravishankar

  DOI：10.1080/00397911.2016.1242750

  日期：2016.12.16

  sugar mixtures (LMMs) were synthesized and used for preparation of 1,4-dihydropyridines with aldehydes, 1,3-dicarbonyl compounds, and a nitrogen source as starting materials. Good yields, low reaction times, recyclability of LMMs, and catalyst-free methodology are some of the highlights of this new protocol. GRAPHICAL ABSTRACT

  摘要 合成了几种低熔点糖混合物 (LMM)，并将其用于以醛、1,3-二羰基化合物和氮源为原料制备 1,4-二氢吡啶。良好的产量、​​低反应时间、LMM 的可回收性和无催化剂方法是该新协议的一些亮点。图形概要
• Discovery of Novel Enhancers of Isoniazid Toxicity in Mycobacterium tuberculosis
  作者：Fabian Lentz、Norbert Reiling、Ana Martins、Joseph Molnár、Andreas Hilgeroth

  DOI：10.3390/molecules23040825

  日期：——

  The number of effective first-line antibiotics for the treatment of Mycobacterium tuberculosis infection is strongly limited to a few drugs. Due to emerging resistance against those drugs, second- and third-line antibiotics have been established in therapy with certain problems and also increasing mycobacterial resistance. An alternative to such novel drugs or combined therapeutic regimes which may reduce resistance development is finding enhancers of mycobacterial drug effectiveness, especially enhancers that counteract causative resistance mechanisms. Such enhancers may reduce the extracellular drug efflux mediated by bacterial efflux pumps and thus enhance the intracellular drug toxicity. We developed novel 1,4-dihydropyridines (DHPs) as potential efflux pump inhibitors with some determined P-gp affinities. The influence on the antituberculotic drug toxicity has been investigated for three prominent antituberculotic drugs. Exclusive and selective toxicity enhancing effects have been detected for isoniazid (INH) which could be related to certain substituent effects of the 1,4-DHPs. So, structure-dependent activities have been found. Thus, promising enhancers could be identified and a suggested efflux pump inhibition is discussed.

  有效的一线抗生素用于治疗结核分枝杆菌感染的种类非常有限，仅有少数几种。由于这些药物逐渐出现耐药性，二线和三线抗生素在治疗中得到了应用，但也伴随着一些问题以及结核分枝杆菌耐药性的增加。一种替代这些新药或联合治疗方案的方法是寻找可以增强结核分枝杆菌药物有效性的增强剂，特别是能够对抗由耐药机制引起的增强剂。这些增强剂可能减少细菌外排泵介导的细胞外药物排出，从而增强细胞内药物的毒性。我们开发了新型的1,4-二氢吡啶（DHPs），作为潜在的外排泵抑制剂，具有一定的P-gp亲和力。我们研究了三种主要抗结核药物对抗结核药物毒性的影响。我们发现异烟肼（INH）具有独特且选择性的毒性增强效应，这可能与1,4-DHPs的某些取代基效应有关。因此，发现了依赖于结构的活性。因此，我们可以识别出有前景的增强剂，并讨论了可能的外排泵抑制机制。
• Novel Syntheses of Heterocycles with N-(1-Haloalkyl)azinium Halides. Part V. Preparation of N-Substituted 1,4-Dihydropyridines
  作者：Jean-Jacques Vanden Eynde、Annie Mayence、André Maquestiau、Ernst Anders

  DOI：10.1080/00397919208021145

  日期：1992.12

  Abstract Thirty N-substituted Hantzsch 1,4-dihydropyridines were prepared under mild and neutral conditions from N-substituted enaminocarbonyl derivatives and aldehydes activated under the form of N-(1-chloroalkyl)pyridinium chlorides by means of thionyl chloride and pyridine. The scope of the method is discussed.

  摘要 在温和和中性条件下，以N-(1-氯烷基)吡啶氯化物形式活化的N-取代烯氨基羰基衍生物和醛，通过亚硫酰氯和吡啶制备了30个N-取代Hantzsch 1,4-二氢吡啶。讨论了该方法的范围。
• ZnO Nanoparticle-Catalyzed Multicomponent Reaction for the Synthesis of 1,4-Diaryl Dihydropyridines
  作者：Gagandeep Kour Reen、Monika Ahuja、Ashok Kumar、Rajesh Patidar、Pratibha Sharma

  DOI：10.1080/00304948.2017.1320927

  日期：2017.5.4

  Compounds in the 1,4-dihydropyridine (1,4-DHP) scaffold exhibit a wide range of pharmacological activities. The scaffold is the core of vasodilator, antitubercular, antiviral, antitumorous, antidia...

  1,4-二氢吡啶 (1,4-DHP) 支架中的化合物表现出广泛的药理活性。支架是血管扩张剂、抗结核、抗病毒、抗肿瘤、抗糖尿病...
• Neat reaction microwave technology for the synthesis of <i>N</i>-substituted-1,4-dihydropyridines
  作者：Mazaahir Kidwai、Richa Mohan

  DOI：10.1139/v03-191

  日期：2004.3.1

  Hantzsch synthesis of N-substituted-1,4-dihydropyridines (1,4-DHP) was carried out using an environmentally benign procedure. Neat reactants were subjected to microwave irradiation (MWI) to give the required products in excellent yield. Appreciable results were not obtained when conventional synthesis using neat reactants was carried out. The good yield and rate enhancement observed in the case of microwave irradiation is attributed to the uniform heating effect of microwaves.Key words: 1,4-dihydropyridines (1,4-DHP), microwave irradiation (MWI), neat reaction, solid support.

  使用环保的方法进行了N-取代的1,4-二氢吡啶（1,4-DHP）的Hantzsch合成。通过微波辐射（MWI）处理纯净的反应物，以优异的收率得到所需产物。当使用纯净的反应物进行传统合成时，没有得到令人满意的结果。在微波辐射下观察到的高收率和反应速率增强归因于微波的均匀加热效应。关键词：1,4-二氢吡啶（1,4-DHP），微波辐射（MWI），纯净反应，固体支撑。