1-(3-dodecyloxyphenyl)-1-hydroxy-5-[2-(3-hydroxypropyloxy)-2-oxyethyl]-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-5-ium bromide | 1179810-97-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(3-dodecyloxyphenyl)-1-hydroxy-5-[2-(3-hydroxypropyloxy)-2-oxyethyl]-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-5-ium bromide
• 英文别名: 1-[(3-(dodecyloxy)phenyl)-1-hydroxy-5-[2-(3-hydroxypropoxy)-2-oxyethyl]-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-5-ium bromide；3-hydroxypropyl 2-[1-(3-dodecoxyphenyl)-1-hydroxy-3-oxo-2H-pyrrolo[3,4-c]pyridin-5-ium-5-yl]acetate;bromide
• CAS: 1179810-97-9
• 化学式: Br*C₃₀H₄₃N₂O₆
• 分子量: 607.585
• InChiKey: AJIUUVWHAVVQTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3-dodecyloxyphenyl)-1-hydroxy-5-[2-(3-hydroxypropyloxy)-2-oxyethyl]-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-5-ium bromide 在 三乙酰氧基硼氢化钠 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 0.17h， 以44%的产率得到3-hydroxypropyl 3-aminocarbonyl-[4-(3-dodecyloxybenzoyl)-1,4-dihydropyridin-1-yl]acetate
  参考文献：
  名称：

  Development of isoniazid–NAD truncated adducts embedding a lipophilic fragment as potential bi-substrate InhA inhibitors and antimycobacterial agents

  摘要：

  Isoniazid-NAD truncated adducts embedding a lipophilic fragment were designed, synthesized and evaluated as inhibitors of the enoyl-acyl carrier protein (ACP) reductase (InhA) of Mycobacterium tuberculosis and as antimycobacterial agents. These compounds, planned as bi-substrate inhibitors and inspired from the active metabolite of isoniazid, combine both the nicotinamide moiety of the cofactor NAD and a lipophilic hydrocarbon chain mimic of the InhA substrate. The lipophilic fragment was introduced using either Suzuki-Miyaura cross-coupling or a classical nucleophilic substitution reaction. Several compounds developed in this work were indeed able to inhibit the InhA activity and showed promising antimycobacterial activities. However a direct correlation between the expressed activity and the bi-substrate mode of action could not yet be unambiguously demonstrated (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.016
• 作为产物：
  描述：

  3-(bromoacetoxy)propan-1-ol 、 1-(3-dodecyloxyphenyl)-1-hydroxy-1,2-dihydropyrrolo[3,4-c]pyridine-3-one 以 四氢呋喃 为溶剂， 以35%的产率得到1-(3-dodecyloxyphenyl)-1-hydroxy-5-[2-(3-hydroxypropyloxy)-2-oxyethyl]-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-5-ium bromide
  参考文献：
  名称：

  Development of isoniazid–NAD truncated adducts embedding a lipophilic fragment as potential bi-substrate InhA inhibitors and antimycobacterial agents

  摘要：

  Isoniazid-NAD truncated adducts embedding a lipophilic fragment were designed, synthesized and evaluated as inhibitors of the enoyl-acyl carrier protein (ACP) reductase (InhA) of Mycobacterium tuberculosis and as antimycobacterial agents. These compounds, planned as bi-substrate inhibitors and inspired from the active metabolite of isoniazid, combine both the nicotinamide moiety of the cofactor NAD and a lipophilic hydrocarbon chain mimic of the InhA substrate. The lipophilic fragment was introduced using either Suzuki-Miyaura cross-coupling or a classical nucleophilic substitution reaction. Several compounds developed in this work were indeed able to inhibit the InhA activity and showed promising antimycobacterial activities. However a direct correlation between the expressed activity and the bi-substrate mode of action could not yet be unambiguously demonstrated (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.07.016