2-<(1H-imidazol-1-yl)methyl>-5-formylpyrrole | 118896-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-<(1H-imidazol-1-yl)methyl>-5-formylpyrrole
• 英文别名: 2-[(1H-imidazol-1-yl)methyl]-5-formylpyrrole；5-(1H-Imidazol-1-ylmethyl)-1H-pyrrole-2-carbaldehyde；5-(imidazol-1-ylmethyl)-1H-pyrrole-2-carbaldehyde
• CAS: 118896-48-3
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: JXYMQLUDNFTXSH-UHFFFAOYSA-N

物化性质

• 沸点：
  420.2±35.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-<(1H-imidazol-1-yl)methyl>-5-formylpyrrole 在 disodium hydrogenphosphate 、 sodium amalgam 、 氢溴酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 5.0h， 生成 7-Imidazol-1-ylmethyl-pyrrolo[1,2-c]pyrimidine; hydrobromide
  参考文献：
  名称：

  吡咯并[1,2- c ]嘧啶及其衍生物的改进合成

  摘要：

  描述了一种改进的合成吡咯并[1,2- c ]嘧啶衍生物的方法，该方法是将吡咯-2-羧酸与甲苯磺酰基甲基异氰酸酯进行环缩合，然后将所得的2-甲苯磺酰基吡咯并[1,2 - c ]-嘧啶与汞齐钠进行磺酰化

  DOI：

  10.1016/0040-4039(96)00812-x
• 作为产物：
  描述：

  N,N-二甲基-1-(1H-吡咯-2-基)甲胺 在 三氯氧磷 作用下， 以 xylene 为溶剂， 反应 6.5h， 生成 2-<(1H-imidazol-1-yl)methyl>-5-formylpyrrole
  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

• Pyrrolodiazines. 5. Synthesis, Structure, and Chemistry of Pyrrolo[1,2-<i>c</i>]pyrimidine. Dipolar Cycloaddition of Pyrrolo[1,2-<i>c</i>]pyrimidinium Ylides
  作者：José M. Minguez、Juan J. Vaquero、Julio Alvarez-Builla、Obis Castaño、José L. Andrés

  DOI：10.1021/jo9907080

  日期：1999.10.1

  An improved synthesis of pyrrolo[1,2-c]pyrimidines, including the parent system, was accomplished via sequential condensation of substituted pyrrole-2-carboxaldehydes with tosylmethyl isocyanide (TOSMIC), followed by desulfonylation of the formed tosylpyrrolo[1,2-c]pyrimidines. Based on the ab initio calculations performed on the pyrrolo[1,2-c]pyrimidine 1a, some of the basic chemistry was investigated including electrophilic substitution, addition of organolithium reagents, metalation with lithium diisopropylamide (LDA) and subsequent reaction with electrophiles, and formation of salts by quaternization of the nonbridgehead nitrogen. Azomethine ylides generated from pyrrolo[1,2-c]pyrimidinium salts undergo 1,3-dipolar cycloaddition with suitable dipolarophiles to give new dipyrrolo[1,2-a;1',2'-c]pyrimidine derivatives, with high regio- and stereoselectivity.
• Improved synthesis of pyrrolo[1,2-c]pyrimidine and derivatives
  作者：JoséM. Minguez、Juan J. Vaquero、JoséL. García-Navio、Julio Alvarez-Builla

  DOI：10.1016/0040-4039(96)00812-x

  日期：1996.6

  An improved synthesis of pyrrolo[1,2-c]pyrimidine derivatives by cyclocondensation of pyrrole-2-carboxaldehydes with tosylmethyl isocyanide followed by desulfonylation of the resulting 2-tosylpyrrolo[1,2-c]-pyrimidines with sodium amalgam is described

  描述了一种改进的合成吡咯并[1,2- c ]嘧啶衍生物的方法，该方法是将吡咯-2-羧酸与甲苯磺酰基甲基异氰酸酯进行环缩合，然后将所得的2-甲苯磺酰基吡咯并[1,2 - c ]-嘧啶与汞齐钠进行磺酰化
• [(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.