2-苯基硫基乙基甲基2,4,6-三甲基-1,4-二氢吡啶-3,5-二羧酸酯 | 123875-01-4

• 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
• 中文名称: 2-苯基硫基乙基甲基2,4,6-三甲基-1,4-二氢吡啶-3,5-二羧酸酯
• 英文名称: PCA 4248
• 英文别名: PCA-4248；PCA4248；2-(phenylthio)ethyl-2,6-dimethyl-4-methyl-5-methoxycarbonyl-1,4-dihydropyridin-3-carboxylate；Ptemc；3-O-methyl 5-O-(2-phenylsulfanylethyl) 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 123875-01-4；142592-28-7；142592-29-8
• 化学式: C₁₉H₂₃NO₄S
• 分子量: 361.462
• InChiKey: DHCNAWNKZMNTIS-UHFFFAOYSA-N

物化性质

• 溶解度：
  在 DMSO 中溶解度为 100 mM，在乙醇中溶解度为 100 mM

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylic acid pivaloyloxymethyl ester 在 氢氧化钾 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 、 异丙醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 2-苯基硫基乙基甲基2,4,6-三甲基-1,4-二氢吡啶-3,5-二羧酸酯
  参考文献：
  名称：

  脂肪酶催化的4-烷基-1,4-二氢吡啶衍生物的对映选择性水解：合成（+）-和（-）-甲基2-（苯硫基）乙基1,4-二氢-2,4,6-三甲基-3 1,5-吡啶二甲酸（PCA 4248）。

  摘要：

  （+）-和（-）-PCA 4248（PAF拮抗剂）的不对称合成是使用脂肪酶催化的酰氧基甲基酯的对映选择性水解实现的。酶促反应在温和的条件下在有机溶剂中进行。

  DOI：

  10.1248/cpb.40.1083

文献信息

• 4-alkyl-1,4-dihydropyridines with PAF-antagonist activity
  申请人：Alter, S.A.

  公开号：US05177211A1

  公开（公告）日：1993-01-05

  4-alkyl-1,4-dihyropyridines, with PAF-antagonist activity, of formula (I) wherein R is saturated C.sub.1 -C.sub.4, R' is saturated C.sub.1 -C.sub.6 alkyl which may be interrupted by an oxygen atom, or 2-tetrahydrofurfuryl and R.sup.2 is saturated C.sub.1 -C.sub.4 or phenyl, the compound wherein R is methyl, R' is ethyl and R.sup.2 is phenyl remain excluded, are described. The compounds (I) are prepared by: (a) reaction of (II) with (III); (b) reaction of (IV) with (V); (c) reaction of (VI) with (III) and with (VII); (d) reaction of (VIII) with (V) and with (VII); or (e) reaction of (VIII) with (VI) and with (VII) in the presence of ammonia. The compounds (I) are useful due to their antagonist activity of the platelet activating factor. ##STR1##

  4-烷基-1,4-二氢吡啶，具有PAF拮抗活性，其化学式为（I），其中R为饱和的C.sub.1-C.sub.4，R'为饱和的C.sub.1-C.sub.6烷基，可以被氧原子中断，或2-四氢呋喃基，R.sup.2为饱和的C.sub.1-C.sub.4或苯基，其中化合物中R为甲基，R'为乙基，R.sup.2为苯基除外。化合物（I）通过以下方法制备：（a）将（II）与（III）反应；（b）将（IV）与（V）反应；（c）将（VI）与（III）和（VII）反应；（d）将（VIII）与（V）和（VII）反应；或（e）将（VIII）与（VI）和（VII）在氨的存在下反应。由于其拮抗血小板活化因子的活性，化合物（I）具有实用价值。
• Lipase-catalyzed enantioselective hydrolysis of 4-alkyl-1,4-dihydropyridine derivatives: synthesis of (+)- and (-)-methyl 2-(phenylthio)ethyl 1,4-dihydro-2,4,6-trimethyl-3,5-pyridinedicarboxylate(PCA 4248).
  作者：Hirosato EBIIKE、Kaori MARUYAMA、Kazuo ACHIWA

  DOI：10.1248/cpb.40.1083

  日期：——

  Asymmetric synthesis of (+)- and (-)-PCA 4248 (PAF antagonist) was achieved using lipase-catalyzed enantioselective hydrolysis of the acyloxymethyl esters. The enzymatic reaction proceeded under the mild conditions in an organic solvent.

  （+）-和（-）-PCA 4248（PAF拮抗剂）的不对称合成是使用脂肪酶催化的酰氧基甲基酯的对映选择性水解实现的。酶促反应在温和的条件下在有机溶剂中进行。
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Köster Hubert

  公开号：US20110118136A1

  公开（公告）日：2011-05-19

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Each compound has the formula: wherein: Z is a trityl derivative; X, the reactivity function, covalently binds to amino acid side chains of proteins; Y, the selectivity function, modulates binding of X to the amino acid side chains in proteins such that X binds to fewer proteins when Y is present than in its absence; and Q permits separation or immobilization of the capture compound. Automated systems for performing the methods also are provided.

  本文提供了捕获化合物和化合物集合以及使用这些化合物进行生物分子分析的方法。特别地，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂蛋白质混合物。每个化合物的公式为：其中：Z是三苯甲基衍生物；X是反应性功能，共价结合到蛋白质的氨基酸侧链上；Y是选择性功能，调节X与蛋白质中氨基酸侧链的结合，使得在Y存在时，X与较少的蛋白质结合，而在Y不存在时，X与更多的蛋白质结合；Q允许分离或固定捕获化合物。本文还提供了用于执行这些方法的自动化系统。
• 4-alkyl-1, 4-dihydropyridines with PAF-antagonist activity
  申请人：ALTER, S.A.

  公开号：EP0325187A1

  公开（公告）日：1989-07-26

  4-alkyl-1,4-dihyropyridines, with PAF-antagonist activity, of formula (I) wherein R is saturated C₁-C₄, R′ is saturated C₁-C₆ alkyl which may be interrupted by an oxygen atom, or 2-tetrahydrofurfuryl and R² is saturated C₁-C₄ or phenyl, the compound wherein R is methyl, R′ is ethyl and R² is phenyl remain excluded, are described. The compounds (I) are prepared by: (a) reaction of (II) with (III); (b) reaction of (IV) with (V); (c) reaction of (VI) with (III) and with (VII); (d) reaction of (VIII) with (V) and with (VII); or (e) reaction of (VIII) with (VI) and with (VII) in the presence of ammonia. The compounds (I) are useful due to their antagonist activity of the platelet activating factor.

  具有 PAF-拮抗剂活性的式 (I) 的 4-烷基-1,4-二氢吡啶类化合物 其中 R 是饱和 C₁-C₄，R′是饱和 C₁-C₆烷基，可被氧原子打断、或 2-四氢糠基且 R² 为饱和 C₁-C₄ 或苯基的化合物，不包括 R 为甲基、R′ 为乙基且 R² 为苯基的化合物。 化合物 (I) 的制备方法如下(a) (II) 与 (III) 反应；(b) (IV) 与 (V) 反应；(c) (VI) 与 (III) 和 (VII) 反应；(d) (VIII) 与 (V) 和 (VII) 反应；或 (e) (VIII) 与 (VI) 和 (VII) 在氨存在下反应。化合物(I)具有拮抗血小板活化因子的活性，因此非常有用。
• 4-Alkyl-1,4-dihydropyridine derivatives as specific PAF-acether antagonists
  作者：Carlos E. Sunkel、Miguel Fau de Casa-Juana、Luis Santos、M. Mar Gomez、Mercedes Villarroya、M. Antonia Gonzalez-Morales、Jaime G. Priego、M. Pilar Ortega

  DOI：10.1021/jm00174a017

  日期：1990.12

  A new series of 4-alkyl-1,4-dihydropyridines (1,4-DHP) were synthesized and evaluated for their ability to inhibit washed rabbit platelet aggregation induced by PAF-acether (1-O-hexadecyl/octadecyl-2-O-acetyl-sn-glycero-3-phosphorylcholine) and to reverse PAF-induced hypotension in anesthetized rats. Additionally, compounds were evaluated for their ability to inhibit the binding of radiolabeled PAF to its receptor on rabbit platelets. Among these compounds, 6I and 6L were the most potent and specific antagonists. At concentrations up to 100 microM, neither compound 6I nor compound 6L caused platelet aggregation nor did they inhibit platelet aggregation induced by collagen or adenosine diphosphate. Compound 6L did not show in vitro calcium channel blocker activity measured on vascular smooth muscle preparations of rabbit aorta and on [3H]nitrendipine binding assays. The compound did not show any cardiovascular effects in anesthetized rat at iv doses up to 1000 micrograms/kg, and the Ki value was 568.62 nmol. These results indicate that compound 6L is a potent and specific PAF antagonist with 1,4-dihydropyridine structure but devoid of a significant cardiovascular activity related to calcium-antagonist properties.