beta,gamma-二氢维他命K1 | 64236-23-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: beta,gamma-二氢维他命K1
• 英文名称: 2-methyl-3-(1',2'-dihydrophytyl)-1,4-naphthoquinone
• 英文别名: 2-methyl-3-(3,7,11,15-tetramethylhexadecyl)naphthalene-1,4-dione；Dihydrophyllochinon；2-Methyl-3-(3,7,11,15-tetramethylhexadecyl)-1,4-naphthalenedione
• CAS: 64236-23-3
• 化学式: C₃₁H₄₈O₂
• 分子量: 452.721
• InChiKey: XOQNYHSBHIIJMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  543.8±50.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  beta,gamma-二氢维他命K1 在 双氧水 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以83%的产率得到2-methyl-3-(1',2'-dihydrophytyl)-1,4-naphthoquinone 2,3-epoxide
  参考文献：
  名称：

  Substituted vitamin K epoxide analogs. New competitive inhibitors and substrates of vitamin K1 epoxide reductase

  摘要：

  2- and 3-substituted vitamin K 2,3-epoxide analogues were synthesized and tested as inactivators, inhibitors, and substrates for beef liver microsomal vitamin K1 epoxide reductase. 2-(X)-3-phytyl-1,4-naphthoquinone 2,3-epoxides, where X is hydroxymethyl, chloromethyl, fluoromethyl, difluoromethyl, and formyl were all competitive inhibitors, but none was an inactivator. Only the 2-hydroxymethyl analogue was reduced to a quinone that was stable enough under the conditions of the experiment to be detected. Vitamin K1 epoxide analogues with modified phytyl chains (1'-hydroxy, 3'-fluoro with isomerized double bond, 1'-hydroxy and 1'-fluoro with saturated double bond, and the corresponding unsubstituted chains) were synthesized. All of the analogues were competitive inhibitors of vitamin K1 epoxide reductase. The nonfluorinated analogues also were shown to be substrates, being reduced to the corresponding quinone without enzyme inactivation. At least one other enzyme besides vitamin K1 epoxide reductase in beef liver microsomes also metabolizes all of these analogues.

  DOI：

  10.1021/jm00168a038
• 作为产物：
  描述：

  phytenal 在 palladium on activated charcoal silver(II) oxide 、 正丁基锂 、 氢气 、 硝酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 20.66h， 生成 beta,gamma-二氢维他命K1
  参考文献：
  名称：

  Substituted vitamin K epoxide analogs. New competitive inhibitors and substrates of vitamin K1 epoxide reductase

  摘要：

  2- and 3-substituted vitamin K 2,3-epoxide analogues were synthesized and tested as inactivators, inhibitors, and substrates for beef liver microsomal vitamin K1 epoxide reductase. 2-(X)-3-phytyl-1,4-naphthoquinone 2,3-epoxides, where X is hydroxymethyl, chloromethyl, fluoromethyl, difluoromethyl, and formyl were all competitive inhibitors, but none was an inactivator. Only the 2-hydroxymethyl analogue was reduced to a quinone that was stable enough under the conditions of the experiment to be detected. Vitamin K1 epoxide analogues with modified phytyl chains (1'-hydroxy, 3'-fluoro with isomerized double bond, 1'-hydroxy and 1'-fluoro with saturated double bond, and the corresponding unsubstituted chains) were synthesized. All of the analogues were competitive inhibitors of vitamin K1 epoxide reductase. The nonfluorinated analogues also were shown to be substrates, being reduced to the corresponding quinone without enzyme inactivation. At least one other enzyme besides vitamin K1 epoxide reductase in beef liver microsomes also metabolizes all of these analogues.

  DOI：

  10.1021/jm00168a038

文献信息

• TREATMENT OF MITOCHONDRIAL DISEASES WITH NAPHTHOQUINONES
  申请人：Edison Pharmaceuticals, Inc.

  公开号：EP2600857A2

  公开（公告）日：2013-06-12
• US5215924A
  申请人：——

  公开号：US5215924A

  公开（公告）日：1993-06-01
• [EN] TREATMENT OF MITOCHONDRIAL DISEASES WITH NAPHTHOQUINONES<br/>[FR] TRAITEMENT DE MALADIES MITOCHONDRIALES PAR DES NAPHTOQUINONES
  申请人：EDISON PHARMACEUTICALS INC

  公开号：WO2012019029A2

  公开（公告）日：2012-02-09

  Methods of treating, preventing or suppressing symptoms associated with mitochondrial diseases, such as Friedreich's ataxia (FRDA), Leber's Hereditary Optic Neuropathy (LHON), dominant optic atrophy (DOA); mitochondrial myopathy, encephalopathy, lactacidosis, stroke (MELAS), Leigh syndrome or Kearns-Sayre Syndrome (KSS) with compounds of Formula (I) are disclosed. Methods of modulating, normalizing, or enhancing energy biomarkers, as well as compounds useful for such methods are also disclosed.
• [EN] THERAPEUTIC COMPOSITIONS INCLUDING NAPHTHOQUINONES AND USES THEREOF<br/>[FR] COMPOSITIONS THÉRAPEUTIQUES COMPRENANT DES NAPHTHOQUINONES ET LEURS UTILISATIONS
  申请人：STEALTH PEPTIDES INT INC

  公开号：WO2015183985A2

  公开（公告）日：2015-12-03

  Disclosed herein are methods and compositions for the treatment and/or prevention of diseases or conditions comprising administration of naphthoquinones, and/or naturally or artificially occurring derivatives, analogues, or pharmaceutically acceptable salts thereof, alone or in combination with one or more active agents (e.g., an aromatic-cationic peptide). The present technology provides compositions related to aromatic-cationic peptides linked to naphthoquinones and uses of the same. In some embodiments, the aromatic-cationic peptide comprises 2',6'-dimethyl-Tyr-D-Arg-Phe-Lys-NH2, Phe-D-Arg-Phe-Lys-NH2, or D-Arg-2',6'-Dmt-Lys-Phe-NH2.
• Substituted vitamin K epoxide analogs. New competitive inhibitors and substrates of vitamin K1 epoxide reductase
  作者：Robert P. Ryall、Dhirendra L. Nandi、Richard B. Silverman

  DOI：10.1021/jm00168a038

  日期：1990.6

  2- and 3-substituted vitamin K 2,3-epoxide analogues were synthesized and tested as inactivators, inhibitors, and substrates for beef liver microsomal vitamin K1 epoxide reductase. 2-(X)-3-phytyl-1,4-naphthoquinone 2,3-epoxides, where X is hydroxymethyl, chloromethyl, fluoromethyl, difluoromethyl, and formyl were all competitive inhibitors, but none was an inactivator. Only the 2-hydroxymethyl analogue was reduced to a quinone that was stable enough under the conditions of the experiment to be detected. Vitamin K1 epoxide analogues with modified phytyl chains (1'-hydroxy, 3'-fluoro with isomerized double bond, 1'-hydroxy and 1'-fluoro with saturated double bond, and the corresponding unsubstituted chains) were synthesized. All of the analogues were competitive inhibitors of vitamin K1 epoxide reductase. The nonfluorinated analogues also were shown to be substrates, being reduced to the corresponding quinone without enzyme inactivation. At least one other enzyme besides vitamin K1 epoxide reductase in beef liver microsomes also metabolizes all of these analogues.