(4R)-1-(4-methoxybenzyl)-4-methyl-3,4-dihydropyridin-2-one | 234447-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4R)-1-(4-methoxybenzyl)-4-methyl-3,4-dihydropyridin-2-one
• 英文别名: (4R)-1-[(4-methoxyphenyl)methyl]-4-methyl-3,4-dihydropyridin-2-one
• CAS: 234447-85-9
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: BWEFNFZSJFYSAP-NSHDSACASA-N

物化性质

• 沸点：
  404.4±34.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-1-(4-methoxybenzyl)-4-methyl-3,4-dihydropyridin-2-one 在 sodium hydroxide 、 偶氮二异丁腈 、 三氟化硼乙醚 、 三苯基氢化锡 、 苄基三乙基氯化铵 、 triethyloxonium fluoroborate 作用下， 以 二氯甲烷 、 苯甲醚 、 苯 为溶剂， 生成 (1S,5R,6R,7R)-7-fluoro-5-methyl-2-azabicyclo[4.1.0]heptan-3-imine
  参考文献：
  名称：

  Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines

  摘要：

  Further chemical modification of 2-iminopiperidines fused to cyclopropane rings was performed. Optically active isomers 2 and 13 were synthesized and their biological activity was evaluated. Compound 2 exhibited greater potency and more isoform selectivity than enantiomer 13 in the iNOS inhibition assay. One of the gem-chlorines on the fused cyclopropane moiety of 2 was eliminated to produce 3, which showed reduced potency for iNOS inhibition, as well as 4 with an increased potency. The isoform selectivity of 4 was also much higher than that of 3. This was also true for the corresponding methyl derivatives 6-9. The structure-activity relationship (SAR) study and computer aided docking study of the most optimized structure 4 with human iNOS will also be reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00034-8
• 作为产物：
  描述：

  (3S)-5-hydroxy-N-(4-methoxybenzyl)-3-methylpentanamide 在 三氧化硫吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 4.5h， 生成 (4R)-1-(4-methoxybenzyl)-4-methyl-3,4-dihydropyridin-2-one
  参考文献：
  名称：

  Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines

  摘要：

  Further chemical modification of 2-iminopiperidines fused to cyclopropane rings was performed. Optically active isomers 2 and 13 were synthesized and their biological activity was evaluated. Compound 2 exhibited greater potency and more isoform selectivity than enantiomer 13 in the iNOS inhibition assay. One of the gem-chlorines on the fused cyclopropane moiety of 2 was eliminated to produce 3, which showed reduced potency for iNOS inhibition, as well as 4 with an increased potency. The isoform selectivity of 4 was also much higher than that of 3. This was also true for the corresponding methyl derivatives 6-9. The structure-activity relationship (SAR) study and computer aided docking study of the most optimized structure 4 with human iNOS will also be reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00034-8

文献信息

• Design and Synthesis of Orally Bioavailable Inhibitors of Inducible Nitric Oxide Synthase. Identification of 2-Azabicyclo[4.1.0]heptan-3-imines
  作者：Yasufumi Kawanaka、Kaoru Kobayashi、Shinya Kusuda、Tadashi Tatsumi、Masayuki Murota、Toshihiko Nishiyama、Katsuya Hisaichi、Atsuko Fujii、Keisuke Hirai、Masao Naka、Masaharu Komeno、Yshihiko Odagaki、Hisao Nakai、Masaaki Toda

  DOI：10.1016/s0968-0896(03)00034-8

  日期：2003.4

  Further chemical modification of 2-iminopiperidines fused to cyclopropane rings was performed. Optically active isomers 2 and 13 were synthesized and their biological activity was evaluated. Compound 2 exhibited greater potency and more isoform selectivity than enantiomer 13 in the iNOS inhibition assay. One of the gem-chlorines on the fused cyclopropane moiety of 2 was eliminated to produce 3, which showed reduced potency for iNOS inhibition, as well as 4 with an increased potency. The isoform selectivity of 4 was also much higher than that of 3. This was also true for the corresponding methyl derivatives 6-9. The structure-activity relationship (SAR) study and computer aided docking study of the most optimized structure 4 with human iNOS will also be reported. (C) 2003 Elsevier Science Ltd. All rights reserved.