methyl 4-bromo-2,5-dimethyl-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate | 120935-95-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 4-bromo-2,5-dimethyl-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate
• 英文别名: Methyl 4-Bromo-2,5-dimethyl-1-((2-(trimethylsilyl) ethoxy)methyl)-1H-pyrrole-3-carboxylate；methyl 4-Bromo-2,5-dimethyl-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-pyrrole-3-carboxylate；methyl 4-bromo-2,5-dimethyl-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrole-3-carboxylate；methyl 4-bromo-2,5-dimethyl-1-(2-trimethylsilylethoxymethyl)pyrrole-3-carboxylate
• CAS: 120935-95-7
• 化学式: C₁₄H₂₄BrNO₃Si
• 分子量: 362.339
• InChiKey: ISDYLKQQYYSAFP-UHFFFAOYSA-N

物化性质

• 沸点：
  385.6±42.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-bromo-2,5-dimethyl-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate 在 正丁基锂 、 三氟化硼乙醚 、 苄基三甲基氢氧化铵 作用下， 反应 2.25h， 生成 2,5-二甲基-4-[2-(苯基甲基)苯甲酰]-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  Discovery and synthesis of methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogs: the first examples of a new class of calcium channel activator

  摘要：

  Methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate, FPL 64176 (1), is the first example of a new class of calcium channel activator (CCA) that does not act on any of the well-defined calcium channel modulator receptor sites, as typified by verapamil, diltiazem, and the dihydropyridines. The potent activity of 1, having the 2-(phenylmethyl)benzoyl substituent, was predicted using QSAR on an initial set of less potent benzoylpyrroles. When compared to the CCA Bay K 8644, 1 has simialr potency on calcium uptake into GH3 cells (both have EC50 approximately 0.015 muM) but is appreciably more potent functionally at increasing contractility in a guinea pig atria preparation (1 has EC50 = 0.049 muM vs Bay K 8644 EC50 = 1.95 muM). 1 is an achiral, pharmacologically clean agonist with no demonstrable partial agonist properties and possesses appreciably higher efficacy than Bay K 8644. It should therefore become a useful biochemical and pharmacological tool for the study of calcium channels in many cell types.

  DOI：

  10.1021/jm00071a004
• 作为产物：
  描述：

  2,5-二氯吡咯-3-羧酸甲酯 在 pyridinium hydrobromide perbromide 、 sodium hydride 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 2.75h， 生成 methyl 4-bromo-2,5-dimethyl-1-<<2-(trimethylsilyl)ethoxy>methyl>-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Discovery and synthesis of methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogs: the first examples of a new class of calcium channel activator

  摘要：

  Methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate, FPL 64176 (1), is the first example of a new class of calcium channel activator (CCA) that does not act on any of the well-defined calcium channel modulator receptor sites, as typified by verapamil, diltiazem, and the dihydropyridines. The potent activity of 1, having the 2-(phenylmethyl)benzoyl substituent, was predicted using QSAR on an initial set of less potent benzoylpyrroles. When compared to the CCA Bay K 8644, 1 has simialr potency on calcium uptake into GH3 cells (both have EC50 approximately 0.015 muM) but is appreciably more potent functionally at increasing contractility in a guinea pig atria preparation (1 has EC50 = 0.049 muM vs Bay K 8644 EC50 = 1.95 muM). 1 is an achiral, pharmacologically clean agonist with no demonstrable partial agonist properties and possesses appreciably higher efficacy than Bay K 8644. It should therefore become a useful biochemical and pharmacological tool for the study of calcium channels in many cell types.

  DOI：

  10.1021/jm00071a004

文献信息

• Fused ring compound
  申请人：Tawaraishi Taisuke

  公开号：US20080194617A1

  公开（公告）日：2008-08-14

  The present invention provides an agent for the prophylaxis or treatment of diabetes, which has a superior hypoglycemic action, and is associated with a fewer side effects such as body weight gain and the like. The present invention relates an agent for the prophylaxis or treatment of diabetes, which comprises a compound represented by wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof.

  本发明提供了一种用于预防或治疗糖尿病的药剂，具有优越的降血糖作用，并且与较少的副作用（如体重增加等）相关。本发明涉及一种用于预防或治疗糖尿病的药剂，包括由下式表示的化合物：其中每个符号如描述中所定义，或其盐或前药。
• Pyrrole derivatives, process for their preparation and pharmaceutical compositions containing them
  申请人：FISONS plc

  公开号：EP0300688A1

  公开（公告）日：1989-01-25

  Compounds of formula I, wherein R₁, R₂, R₃ and R₅ have the meanings defined in the specification, G2 represents a chain -(CH₂)z(W)y-, in which W has various meanings including C=O, and up to two of the methylene segments in the chain (CH₂)z are optionally replaced by -NH- and one segment is optionally replaced by -O- or -(C=NR₄₀)-, and the chain is optionally unsaturated and optionally substituted, and A is a 5- or 6-membered ring or a bicyclic or tricyclic fused ring system, A being optionally substituted by various substituents, possess useful pharmacological properties, in particular as cardiotonics. Also described are processes for the preparation of compounds of formula I, pharmaceutical compositions containing them and methods of treatment involving their use.

  式I的化合物，其中R₁、R₂、R₃和R₅的含义如规范中定义，G2代表一个链-(CH₂)z(W)y-，其中W具有包括C=O在内的各种含义，并且链中的(CH₂)z的最多两个亚甲基段可以选择性地被-NH-替换，一个段可以选择性地被-O-或-(C=NR₄₀)-替换，链可以是不饱和的和/或选择性地被取代的，A是一个5-或6-成员环或一个双环或三环融合环系统，A可以选择性地被各种取代基取代，具有有用的药理学性质，尤其是作为心力衰竭药。还描述了制备式I化合物的方法、含有它们的制药组合物以及涉及其使用的治疗方法。
• Discovery and synthesis of methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate (FPL 64176) and analogs: the first examples of a new class of calcium channel activator
  作者：Andrew J. G. Baxter、John Dixon、Francis Ince、Carol N. Manners、Simon J. Teague

  DOI：10.1021/jm00071a004

  日期：1993.9

  Methyl 2,5-dimethyl-4-[2-(phenylmethyl)benzoyl]-1H-pyrrole-3-carboxylate, FPL 64176 (1), is the first example of a new class of calcium channel activator (CCA) that does not act on any of the well-defined calcium channel modulator receptor sites, as typified by verapamil, diltiazem, and the dihydropyridines. The potent activity of 1, having the 2-(phenylmethyl)benzoyl substituent, was predicted using QSAR on an initial set of less potent benzoylpyrroles. When compared to the CCA Bay K 8644, 1 has simialr potency on calcium uptake into GH3 cells (both have EC50 approximately 0.015 muM) but is appreciably more potent functionally at increasing contractility in a guinea pig atria preparation (1 has EC50 = 0.049 muM vs Bay K 8644 EC50 = 1.95 muM). 1 is an achiral, pharmacologically clean agonist with no demonstrable partial agonist properties and possesses appreciably higher efficacy than Bay K 8644. It should therefore become a useful biochemical and pharmacological tool for the study of calcium channels in many cell types.