(E)-1-methyl-2-<2-(methoxycarbonyl)ethenyl>pyrrole | 69917-84-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-1-methyl-2-<2-(methoxycarbonyl)ethenyl>pyrrole
• 英文别名: Ethyl (E)-3-(1-methyl-1H-pyrrol-2-yl)propenoate；(E)-methyl 3-(1-methyl-1H-pyrrol-2-yl)acrylate；methyl (E)-3-(1-methyl-2-pyrrolyl)propenoate；E-β-(1-Methyl-2-pyrrolyl)-acrylsaeuremethylester；trans-(2-Methoxycarbonyl-vinyl)-1-methyl-pyrrol；(E)-3-(1-Methyl-1h-pyrrol-2-yl)-2-propenoic acid methyl ester；methyl (E)-3-(1-methylpyrrol-2-yl)prop-2-enoate
• CAS: 69917-84-6
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: CVSAYGHLNZROIU-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-methyl-2-<2-(methoxycarbonyl)ethenyl>pyrrole 在 palladium diacetate 甲醇 、 sodium tetrahydroborate 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 4.0h， 生成 (1S,2S)-2-(5-Hydroxymethyl-1-methyl-1H-pyrrol-2-yl)-cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors

  摘要：

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.

  DOI：

  10.1021/jm00124a027
• 作为产物：
  描述：

  N-甲基-2-吡咯甲醛 、 甲氧甲酰基甲基三苯基溴化膦 在 sodium methylate 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以97%的产率得到(E)-1-methyl-2-<2-(methoxycarbonyl)ethenyl>pyrrole
  参考文献：
  名称：

  [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors

  摘要：

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.

  DOI：

  10.1021/jm00124a027

文献信息

• Gregory, Barrie; Hinz, Werner; Jones, R. Alan, Journal of Chemical Research, Miniprint, 1984, # 10, p. 2801 - 2821
  作者：Gregory, Barrie、Hinz, Werner、Jones, R. Alan、Arques, Jose Sepulveda

  DOI：——

  日期：——
• Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries
  作者：Ping Lu、Jeffrey J. Jackson、John A. Eickhoff、Armen Zakarian

  DOI：10.1021/ja512213c

  日期：2015.1.21

  Michael addition is a premier synthetic method for carbon-carbon and carbon-heteroatom bond formation. Using chiral dilithium amides as traceless auxiliaries, we report the direct enantioselective Michael addition of carboxylic acids. A free carboxyl group in the product provides versatility for further functionalization, and the chiral reagent can be readily recovered by extraction with aqueous acid. The method has been applied in the enantioselective total synthesis of the purported structure of pulveraven B.
• Diels-Alder reactions of vinyl derivatives of five-membered monoheterocyclic compounds
  作者：Wayland E. Noland、Chang Kiu Lee、Sun Kun Bae、Bong Yul Chung、Chi Sun Hahn、Keun Jae Kim

  DOI：10.1021/jo00163a011

  日期：1983.7
• LEE, CHANG, KIU;BAE, SUN, KUN;CHUNG, BONG, YUL;HAHN, CHI, SUN;KIM, KEUN, +, J. ORG. CHEM., 1983, 48, N 15, 2488-2491
  作者：LEE, CHANG, KIU、BAE, SUN, KUN、CHUNG, BONG, YUL、HAHN, CHI, SUN、KIM, KEUN, +

  DOI：——

  日期：——
• [(1H-Imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl]pyrroles as thromboxane synthetase inhibitors
  作者：Gregory R. Martinez、Donald R. Hirschfeld、Patrick J. Maloney、Diana S. Yang、Roberto P. Rosenkranz、K. A. M. Walker

  DOI：10.1021/jm00124a027

  日期：1989.4

  Several [(1H-imidazol-1-yl)methyl]- and [(3-pyridinyl)methyl] pyrroles were prepared and evaluated in vitro as thromboxane synthetase inhibitors in human platelet aggregation studies. A number of structures, e.g. 10b,f,g,i (respective IC50 values: 1 microM, 50 nM, 42 nM, 44 nM) showed superior in vitro inhibition of TXA2 synthetase when compared to the standard dazoxiben (1). However, it was found that in vitro potency did not translate into nor correlate with in vivo activity when these compounds were evaluated in mice in a collagen-epinephrine-induced pulmonary thromboembolism model. (E)-1-Methyl-2-[(1H-imidazol-1-yl)methyl]-5-(2-carboxyprop-1-enyl) pyrrole (10b) was found to offer protection against collagen-epinephrine-induced mortality in mice, thereby demonstrating that oral administration is an effective route for absorption of this drug. Additional evidence for the oral effectiveness of 10b in lowering serum TXB2 levels was obtained by performing ex vivo radioimmunoassay experiments with rats. A 13-week study of 10b in rats with reduced renal mass was conducted in order to evaluate the role of TXA2 production in hypertension and renal dysfunction. Although serum and urinary TXB2 levels in rats were found to be lowered during this study by 10b, the levels of urinary protein excretion remained comparable to that of the control group.