(R)-5-[1,2]dithiolan-3-yl-pentanoic acid methylamide | 1225192-30-2

• 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 methylamide
• 英文别名: 5-[(3R)-dithiolan-3-yl]-N-methylpentanamide
• CAS: 1225192-30-2
• 化学式: C₉H₁₇NOS₂
• 分子量: 219.372
• InChiKey: FUMZEQODHXNVQE-MRVPVSSYSA-N

物化性质

• 沸点：
  398.4±11.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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 methylamide 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

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING FIBROSIS, INFLAMMATION AND CANCER<br/>[FR] COMPOSITIONS ET MÉTHODES POUR INHIBER LA FIBROSE, L'INFLAMMATION ET LE CANCER
  申请人：GEORGIA TECH RES INST

  公开号：WO2022146980A1

  公开（公告）日：2022-07-07

  Provided herein are macrocycle-based compounds or diastereomers, solvate, or a pharmaceutically acceptable salt thereof. Also provided are pharmaceutical compositions and medicaments that include the compounds described herein as well as methods of treating fibrosis, inflammatory disease, and cancer.

  本文提供基于大环化合物或其对映体、溶剂化物或其药学上可接受的盐。还提供包括上述化合物的药物组合物和药物，以及治疗纤维化、炎症性疾病和癌症的方法。
• 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.
• [EN] ALPHA-LIPOIC ACID DERIVATIVES AND THEIR USE IN DRUG PREPARATION<br/>[FR] DÉRIVÉS DE L'ACIDE ALPHA-LIPOÏQUE ET LEUR UTILISATION DANS LA PRÉPARATION DE MÉDICAMENTS
  申请人：SEGIX ITALIA S R L

  公开号：WO2010052310A1

  公开（公告）日：2010-05-14

  The present invention concerns an enantiomer R of a compound of Formula (I), wherein X is -NH-R1 or of Formula (V) or (VI), R1 is -(CH2)n-R2, R2 is a linear, branched or cyclic C1C6 aliphatic group, -O-(CH2)n-CH3, -NH-CO- (CH2)n-CH3, 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 C1C3) and -OCO(alkyl C1C3), or of Formula (V), R3 is H or a C1-C3 aliphatic group and R4 is a linear C1-C3 or a branched C3-C12 aliphatic group, or R3 is a C1-C3 aliphatic group and R4 is a linear C1-C12 aliphatic group, Y is O, CH-(CH2)n-CH3 or N(CO)(CH2)n-CH3, 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.

  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。