Nonanoic acid, 3-methyl-4-nitro-, methyl ester | 89631-02-7

• 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: Nonanoic acid, 3-methyl-4-nitro-, methyl ester
• 英文别名: methyl 3-methyl-4-nitrononanoate
• CAS: 89631-02-7
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: FBGXUZRTIUKKOR-UHFFFAOYSA-N

物化性质

• 沸点：
  313.5±25.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Nonanoic acid, 3-methyl-4-nitro-, methyl ester 在 镍 氢气 、 氯化铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 55.0 ℃ 、413.69 kPa 条件下， 反应 28.0h， 生成 (4S,5S)-4-Methyl-5-pentyl-pyrrolidin-2-ylideneamine; hydrochloride
  参考文献：
  名称：

  2-Iminopyrrolidines as Potent and Selective Inhibitors of Human Inducible Nitric Oxide Synthase

  摘要：

  A series of substituted 2-iminopyrrolidines has been prepared and shown to be potent and selective inhibitors of the human inducible nitric oxide synthase (hiNOS) isoform versus the human endothelial nitric oxide synthase (heNOS) and the human neuronal nitric oxide synthase (hnNOS). Simple substitutions at the 3-, 4-, or 5-position afforded more potent analogues than the parent 2-iminopyrrolidine 1. The effect of ring substitutions on both potency and selectivity for the different NOS isoforms is described. Substitution at the 4- and 5-positions of the 2-iminopyrrolidine yielded both potent and selective inhibitors of hiNOS. In particular, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine, monohydrochloride (20), displayed potent inhibition of hiNOS (IC50 = 0.25 mu M) and selectivities of 897 (heNOS IC50/hiNOS IC50) and 13 (hnNOS IC50/hiNOS IC50) Example 20 was shown to be an efficacious inhibitor of NO production in the mouse endotoxin assay. Furthermore, 20 displayed in vivo selectivity, versus heNOS isoform, by not elevating blood pressure at multiples of the effective dose in the mouse.

  DOI：

  10.1021/jm970840x
• 作为产物：
  描述：

  巴豆酸甲酯 、 1-硝基己烷 在 甲基三辛基氯化铵 、 potassium carbonate 作用下， 反应 6.0h， 以34%的产率得到Nonanoic acid, 3-methyl-4-nitro-, methyl ester
  参考文献：
  名称：

  2-Iminopyrrolidines as Potent and Selective Inhibitors of Human Inducible Nitric Oxide Synthase

  摘要：

  A series of substituted 2-iminopyrrolidines has been prepared and shown to be potent and selective inhibitors of the human inducible nitric oxide synthase (hiNOS) isoform versus the human endothelial nitric oxide synthase (heNOS) and the human neuronal nitric oxide synthase (hnNOS). Simple substitutions at the 3-, 4-, or 5-position afforded more potent analogues than the parent 2-iminopyrrolidine 1. The effect of ring substitutions on both potency and selectivity for the different NOS isoforms is described. Substitution at the 4- and 5-positions of the 2-iminopyrrolidine yielded both potent and selective inhibitors of hiNOS. In particular, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine, monohydrochloride (20), displayed potent inhibition of hiNOS (IC50 = 0.25 mu M) and selectivities of 897 (heNOS IC50/hiNOS IC50) and 13 (hnNOS IC50/hiNOS IC50) Example 20 was shown to be an efficacious inhibitor of NO production in the mouse endotoxin assay. Furthermore, 20 displayed in vivo selectivity, versus heNOS isoform, by not elevating blood pressure at multiples of the effective dose in the mouse.

  DOI：

  10.1021/jm970840x

文献信息

• 2-Iminopyrrolidines as Potent and Selective Inhibitors of Human Inducible Nitric Oxide Synthase
  作者：Timothy J. Hagen、Arija A. Bergmanis、Steven W. Kramer、Kam F. Fok、Albert E. Schmelzer、Barnett S. Pitzele、Lydia Swenton、Gina M. Jerome、Christine M. Kornmeier、William M. Moore、Linda F. Branson、Jane R. Connor、Pamela T. Manning、Mark G. Currie、E. Ann Hallinan

  DOI：10.1021/jm970840x

  日期：1998.9.1

  A series of substituted 2-iminopyrrolidines has been prepared and shown to be potent and selective inhibitors of the human inducible nitric oxide synthase (hiNOS) isoform versus the human endothelial nitric oxide synthase (heNOS) and the human neuronal nitric oxide synthase (hnNOS). Simple substitutions at the 3-, 4-, or 5-position afforded more potent analogues than the parent 2-iminopyrrolidine 1. The effect of ring substitutions on both potency and selectivity for the different NOS isoforms is described. Substitution at the 4- and 5-positions of the 2-iminopyrrolidine yielded both potent and selective inhibitors of hiNOS. In particular, (+)-cis-4-methyl-5-pentylpyrrolidin-2-imine, monohydrochloride (20), displayed potent inhibition of hiNOS (IC50 = 0.25 mu M) and selectivities of 897 (heNOS IC50/hiNOS IC50) and 13 (hnNOS IC50/hiNOS IC50) Example 20 was shown to be an efficacious inhibitor of NO production in the mouse endotoxin assay. Furthermore, 20 displayed in vivo selectivity, versus heNOS isoform, by not elevating blood pressure at multiples of the effective dose in the mouse.