2,2-Dimethyl-3-nitrooxy-propionic acid 2-(tert-butoxycarbonyl-isopropyl-amino)-1-(naphthalen-1-yloxymethyl)-ethyl ester | 761000-92-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-Dimethyl-3-nitrooxy-propionic acid 2-(tert-butoxycarbonyl-isopropyl-amino)-1-(naphthalen-1-yloxymethyl)-ethyl ester
• CAS: 761000-92-4
• 化学式: C₂₆H₃₆N₂O₈
• 分子量: 504.58
• InChiKey: PBTVGPOWXVARAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.01
• 重原子数：
  36.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  117.44
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-3-nitrooxy-propionic acid 2-(tert-butoxycarbonyl-isopropyl-amino)-1-(naphthalen-1-yloxymethyl)-ethyl ester 在 盐酸 作用下， 以 甲醇 为溶剂， 生成 [3-[(2-Hydroxy-3-naphthalen-1-yloxypropyl)-propan-2-ylamino]-2,2-dimethyl-3-oxopropyl] nitrate
  参考文献：
  名称：

  Synthesis and vasorelaxant properties of hybrid molecules out of NO-donors and the β-receptor blocking drug propranolol

  摘要：

  S-Nitroso-N-acetylpenicillamine (SNAP) and 3-nitrooxypivaloyl acid were combined in the form of the respective amides with propranolol, in order to obtain prodrugs (NO-propranololes) with beta-receptor blocking properties of the latter compound with nitric oxide releasing properties of the former compounds. A respective nitratoester could not be synthesized, because it immediately rearranges to the amide after deprotection of the amino group. In vitro tests on porcine pulmonary arteries showed that both types of hybrid molecules (6, 12) elicited vasorelaxation, but the nitratoamide was less potent by more than one order of magnitude. The vasorelaxant effect of SNAP was more pronounced than that of the SNAP-hybrid (12), on the other hand the nitratoamide 6 was more potent than 3-nitrooxypivaloyl acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.014
• 作为产物：
  描述：

  2,2-二甲基-3-(硝基氧基)丙酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 2,2-Dimethyl-3-nitrooxy-propionic acid 2-(tert-butoxycarbonyl-isopropyl-amino)-1-(naphthalen-1-yloxymethyl)-ethyl ester
  参考文献：
  名称：

  Synthesis and vasorelaxant properties of hybrid molecules out of NO-donors and the β-receptor blocking drug propranolol

  摘要：

  S-Nitroso-N-acetylpenicillamine (SNAP) and 3-nitrooxypivaloyl acid were combined in the form of the respective amides with propranolol, in order to obtain prodrugs (NO-propranololes) with beta-receptor blocking properties of the latter compound with nitric oxide releasing properties of the former compounds. A respective nitratoester could not be synthesized, because it immediately rearranges to the amide after deprotection of the amino group. In vitro tests on porcine pulmonary arteries showed that both types of hybrid molecules (6, 12) elicited vasorelaxation, but the nitratoamide was less potent by more than one order of magnitude. The vasorelaxant effect of SNAP was more pronounced than that of the SNAP-hybrid (12), on the other hand the nitratoamide 6 was more potent than 3-nitrooxypivaloyl acid. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.014