3,3-Dimethyl-4-nitro-nonanoic acid methyl ester | 185120-75-6

• 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: 3,3-Dimethyl-4-nitro-nonanoic acid methyl ester
• 英文别名: Methyl 3,3-dimethyl-4-nitrononanoate
• CAS: 185120-75-6
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: IRHAYMIBDLKZAM-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±25.0 °C(Predicted)
• 密度：
  1.008±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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：

  3,3-Dimethyl-4-nitro-nonanoic acid methyl ester 在 镍 氢气 作用下， 以 甲醇 为溶剂， 55.0 ℃ 、413.68 kPa 条件下， 反应 24.0h， 以60%的产率得到5-pentyl-4,4-dimethylpyrrolidin-2-one
  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：

  3,3-二甲基丙烯酸甲酯 、 1-硝基己烷 在 四丁基氟化铵 作用下， 反应 24.0h， 以67%的产率得到3,3-Dimethyl-4-nitro-nonanoic acid 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

• NITRIC OXIDE SYNTHASE INHIBITORS DERIVED FROM CYCLIC AMIDINES
  申请人：G.D. Searle & Co.

  公开号：EP0824523A1

  公开（公告）日：1998-02-25
• [EN] NITRIC OXIDE SYNTHASE INHIBITORS DERIVED FROM CYCLIC AMIDINES<br/>[FR] INHIBITEURS DE LA SYNTHASE D'OXYDE NITRIQUE DERIVES DES AMIDINES CYCLIQUES
  申请人：G.D. SEARLE & CO.

  公开号：WO1996035677A1

  公开（公告）日：1996-11-14

  (EN) Compounds having formula (I) wherein R1, R5, R6 and R7 are hydrogen or certain specified substituents; R8 and R9 are independently hydrogen, hydroxy or alkoxy; and X, A and B are independently NR2, O, S, SO, SO2, CH=CH or (CH2)p, p being 0-6; are useful as nitric oxide synthase inhibitors.(FR) L'invention concerne les composés présentant la formule (I) dans laquelle, R1, R5, R6 et R7 sont de l'hydrogène ou des substituants spécifiés; R8 et R9 sont indépendamment de l'hydrogène, de l'hydroxy ou de l'alkoxy; et X, A et B sont indépendamment du NR2, O, S, SO, SO2, CH=CH ou (CH2)p, p étant compris entre 0 et 6. Ces composés peuvent être utilisés comme inhibiteurs de la synthase d'oxyde nitrique.
• 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.