1-甲基-4-苯基-4H-吡啶-3-甲酸甲酯 | 219786-85-3

• 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
• 中文名称: 1-甲基-4-苯基-4H-吡啶-3-甲酸甲酯
• 英文名称: methyl 1,4-dihydro-1-methyl-4-phenylpyridine-3-carboxylate
• 英文别名: methyl 1-methyl-4-phenyl-1,4-dihydropyridine-3-carboxylate；methyl 1,4-dihydro-1-methyl-4-phenylpyridin-3-carboxylate；methyl 1-methyl-4-phenyl-4H-pyridine-3-carboxylate
• CAS: 219786-85-3
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: UKKTVQVIAVVILG-UHFFFAOYSA-N

物化性质

• 熔点：
  117-121 °C
• 沸点：
  344.6±42.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  1-甲基-4-苯基-4H-吡啶-3-甲酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1344000.0h， 生成 1,7-dihydroxymethyl-3,9-dimethyl-6,12-diphenyl-3,9-diazahexacyclo[6.4.0.0^2.7.0^4.11.0^5.10]dodecane
  参考文献：
  名称：

  Biological Evaluation of Bishydroxymethyl-Substituted Cage Dimeric 1,4-Dihydropyridines as a Novel Class of P-Glycoprotein Modulating Agents in Cancer Cells

  摘要：

  A series of N-substituted cage dimeric 1,4-dihydropyridines 3a-e was evaluated as inhibitors of membrane efflux pump P-glycoprotein (P-gp) in multidrug resistant (mdr) cancer cells. Structure-activity relationships (SAR) and cytotoxic properties are discussed. Effective concentrations for overcoming mdr have been demonstrated in competition studies with the P-gp substrate epirubicin.

  DOI：

  10.1021/jm058046w
• 作为产物：
  描述：

  苯基氯化镁 、 3-(甲氧羰基)-1-甲基吡啶碘化物 在 copper(l) iodide 、 二甲基硫 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到1-甲基-4-苯基-4H-吡啶-3-甲酸甲酯
  参考文献：
  名称：

  Biological Evaluation of Bishydroxymethyl-Substituted Cage Dimeric 1,4-Dihydropyridines as a Novel Class of P-Glycoprotein Modulating Agents in Cancer Cells

  摘要：

  A series of N-substituted cage dimeric 1,4-dihydropyridines 3a-e was evaluated as inhibitors of membrane efflux pump P-glycoprotein (P-gp) in multidrug resistant (mdr) cancer cells. Structure-activity relationships (SAR) and cytotoxic properties are discussed. Effective concentrations for overcoming mdr have been demonstrated in competition studies with the P-gp substrate epirubicin.

  DOI：

  10.1021/jm058046w

文献信息

• Synthesis of 3,5-diacyl-4-phenyl-1,4-dihydropyridines
  作者：M.-Lluïsa Bennasar、Cecília Juan、Joan Bosch

  DOI：10.1016/s0040-4039(98)02084-x

  日期：1998.12

  via a regio- and chemoselective addition of Ph2Cu(CN)Li2 to β-substituted N-alkylpyridinium salts, followed by acylation of the intermediate 1,4-dihydropyridines with trichloroacetic anhydride and subsequent haloform-type reaction. A similar sequence using an N-silylpyridinium salt and PhMgBr allows the preparation of the corresponding N-unsubstituted dihydropyridines.

  3,5-二酰基-4-苯基-1,4-二氢吡啶是通过将Ph 2 Cu（CN）Li 2的区域和化学选择性加成到β-取代的N-烷基吡啶鎓盐中，然后将中间体1酰化而合成的，4-二氢吡啶与三氯乙酸酐和随后的卤仿型反应。使用N-甲硅烷基吡啶鎓盐和PhMgBr的相似序列使得可以制备相应的N-未取代的二氢吡啶。
• Design and synthesis of methyl 2-methyl-7,7-dihalo-5-phenyl-2-azabicyclo[4.1.0]hept-3-ene-4-carboxylates with calcium channel antagonist activity
  作者：Javid S Mojarrad、Ramin Miri、Edward E Knaus

  DOI：10.1016/j.bmc.2004.03.063

  日期：2004.6

  A group of methyl 2-methyl-7,7-dihalo-5-(substituted-phenyl)-2-azabicyclo[4.1.0]hept-3-ene-4-carboxylates were prepared by reaction of dihalocarbenes (:CX2, X = Br, Cl) with methyl 1-methyl-4-(substituted-phenyl)-1,4-dihydropyridine-3-carboxylates. In vitro calcium channel antagonist activities were determined using a guinea pig ileum longitudinal smooth muscle assay. The title compounds exhibited weaker CC antagonist activity (10(-5)-10(-6) M range) than the reference drug nifedipine (1.4 x 10(-8) M). Structure-activity relationship studies showed that the position of a nitro substituent on the C-5 phenyl ring where the relative potency order was ortho > meta > para, and the size and/or electronegativity of the C-7 geminal-dihalo substituents (Br > Cl), were determinants of calcium channel antagonist activity. This class of compounds did not exhibit any inotropic effect on guinea pig left atria. A dihalocyclopropyl moiety is a potential bioisostere for the 2-methyl-3-methoxycarbonylvinyl moiety present in the calcium channel antagonist nifedipine. (C) 2004 Elsevier Ltd. All rights reserved.
• Formation of Novel Photodimers from 4-Aryl-1,4-dihydropyridines
  作者：Andreas Hilgeroth、Ute Baumeister

  DOI：10.1002/1521-3765(20011105)7:21<4599::aid-chem4599>3.0.co;2-u

  日期：2001.11.5

  N-substituted 3-alkoxycarbonyl-4-aryl-1,4-dihydropyridines have been photochemically investigated for the first time. In contrast to reports of analogous 3,5-dialkoxycarbonyl derivatives, they are unreactive in the solid state with shortest distances of potentially reacting double bonds of 6.883(3) A for one derivative examined by x-ray crystal structure analysis. Solution irradiation with unfiltered light (lambda greater than or equal to 270 nm) led to novel diazatetrakis-homocubanes in 30-50% yields. Diazatetrakishomocubanes were also obtained by irradiation with filtered light (lambda > 313 nm) besides head-to-tail connected syn-dimers. The irradiation of the syn-dimers with unfiltered light led to centrosymmetric cage dimers accompanied by some dimer fragmentation. Formation of the homocubanes via intermediate biradicals is supported by the available data.
• The First Functionalized 6,12-Diazatetrakishomocubanes
  作者：Andreas Hilgeroth、Ute Baumeister

  DOI：10.1002/(sici)1521-3773(20000204)39:3<576::aid-anie576>3.0.co;2-g

  日期：2000.2.4

  The photodimerization of asymmetric 4-aryl-1,4-dihydropyridines results, totally unexpectedly, in the new 6,12-diazatetrakishomocubanes 1. This is in contrast to the previously observed [2+2] photocycloaddition reactions of symmetrical 4-aryl-1,4-dihydropyridines
• Biological Evaluation of Bishydroxymethyl-Substituted Cage Dimeric 1,4-Dihydropyridines as a Novel Class of P-Glycoprotein Modulating Agents in Cancer Cells
  作者：Martin Richter、Jósef Molnár、Andreas Hilgeroth

  DOI：10.1021/jm058046w

  日期：2006.5.1

  A series of N-substituted cage dimeric 1,4-dihydropyridines 3a-e was evaluated as inhibitors of membrane efflux pump P-glycoprotein (P-gp) in multidrug resistant (mdr) cancer cells. Structure-activity relationships (SAR) and cytotoxic properties are discussed. Effective concentrations for overcoming mdr have been demonstrated in competition studies with the P-gp substrate epirubicin.