(R)-5-[1,2]dithiolan-3-yl-pentanoic acid propylamide | 1225192-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: (R)-5-[1,2]dithiolan-3-yl-pentanoic acid propylamide
• 英文别名: 5-[(3R)-dithiolan-3-yl]-N-propylpentanamide
• CAS: 1225192-32-4
• 化学式: C₁₁H₂₁NOS₂
• 分子量: 247.426
• InChiKey: NZIVQUUUIHFGAI-SNVBAGLBSA-N

物化性质

• 沸点：
  419.6±14.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-[1,2]dithiolan-3-yl-pentanoic acid propylamide 在 protein extract of mouse liver homogenate 水 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 R-(+)-硫辛酸
  参考文献：
  名称：

  [EN] ALPHA-LIPOIC ACID DERIVATIVES AND THEIR USE IN DRUG PREPARATION
  [FR] DÉRIVÉS DE L'ACIDE ALPHA-LIPOÏQUE ET LEUR UTILISATION DANS LA PRÉPARATION DE MÉDICAMENTS

  摘要：

  本发明涉及化合物Formula (I)的对映异构体R，其中X为-NH-R1或Formula (V)或(VI)，R1为-(CH2)n-R2，R2为线性、支链或环状的C1-C6脂肪族基团，-O-(CH2)n-CH3，-NH-CO-(CH2)n-CH3，一个含有杂原子的5-或6-成员脂肪族或芳香环，或者一个被一个或两个取代基取代的5-或6-成员芳香环，所述取代基选自-OH，-O(烷基C1-C3)和-OCO(烷基C1-C3)，或Formula (V)，R3为H或C1-C3脂肪族基团，R4为线性C1-C3或支链C3-C12脂肪族基团，或者R3为C1-C3脂肪族基团，R4为线性C1-C12脂肪族基团，Y为O，CH-(CH2)n-CH3或N(CO)(CH2)n-CH3，n为0到6的整数。已经发现，本发明的对映异构体能够释放(R)-α-硫辛酸，确保药理活性原则在体内比直接给药获得的更长持续时间，或者模拟硫辛酸本身的药理作用，同时表现出更强烈和持久的活性。

  公开号：

  WO2010052310A1

文献信息

• ALPHA-LIPOIC ACID DERIVATIVES AND THEIR USE IN DRUG PREPARATION
  申请人：Brufani Mario

  公开号：US20110212954A1

  公开（公告）日：2011-09-01

  The present invention concerns an enantiomer R of a compound of Formula (I), wherein X is —NH—R 1 or of Formula (V) or (VI), R 1 is —(CH 2 ) n —R 2 , R 2 is a linear, branched or cyclic C 1 C 6 aliphatic group, —O—(CH 2 ) n —CH 3 , —NH—CO—(CH 2 ) n —CH 3 , a 5- or 6-membered aliphatic or aromatic ring optionally comprising a heteroatom, a 5- or 6-membered aromatic ring substituted by one or two substituents, said substituents being selected from the group consisting of —OH, —O(alkyl C 1 C 3 ) and —OCO(alkyl C 1 C 3 ), or of Formula (V), R 3 is H or a C 1 -C 3 aliphatic group and R 4 is a linear C 1 -C 3 or a branched C 3 -C 12 aliphatic group, or R 3 is a C 1 -C 3 aliphatic group and R 4 is a linear C 1 -C 12 aliphatic group, Y is O, CH—(CH 2 ) n —CH 3 or N(CO)(CH 2 ) n —CH 3 , and n is an integer from O to 6. It has been found that the enantiomers of the invention are able to release (R)-alpha-lipoic acid, ensuring a longer permanence in the body for the pharmacologically active principle than that obtainable by its direct administration, or to simulate the pharmacological action of alpha-lipoic acid itself, while exhibiting a much more intense and lasting activity.
• Lipoyl Compounds And Their Use for Treating Ischemic Injury
  申请人：Baguisi Alexander B.

  公开号：US20130237483A1

  公开（公告）日：2013-09-12

  The present invention relates, in various embodiments, to a compound represented by Structural Formula (I), pharmaceutically acceptable salts or prodrugs thereof, and compositions comprising said compounds, or pharmaceutically acceptable salts or prodrugs thereof. Methods of using compounds of Structural Formulas (I) and (la) or compositions comprising compounds of Structural Formulas (I) and (la), or pharmaceutically acceptable salts or prodrugs thereof, to treat ischemia or ischemia-reperfusion injury are also disclosed.
• LIPOYL COMPOUNDS AND METHODS FOR TREATING ISCHEMIC INJURY
  申请人：Ischemix LLC

  公开号：US20150065564A1

  公开（公告）日：2015-03-05

  The present invention relates, in various embodiments, to a compound represented by Structural Formula (I), pharmaceutically acceptable salts or prodrugs thereof, and compositions comprising said compounds, or pharmaceutically acceptable salts or prodrugs thereof. Methods of using compounds of Structural Formulas (I) and (Ia) or compositions comprising compounds of Structural Formulas (I) and (Ia), or pharmaceutically acceptable salts or prodrugs thereof, to treat ischemia or ischemia-reperfusion injury are also disclosed.
• US8815937B2
  申请人：——

  公开号：US8815937B2

  公开（公告）日：2014-08-26
• US9359325B2
  申请人：——

  公开号：US9359325B2

  公开（公告）日：2016-06-07