(S)-Propylisopropylacetic Acid | 247182-97-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-Propylisopropylacetic Acid
• 英文别名: (S)-2-isopropyl-2-propyl-acetic acid；(2S)-propylisopropyl acetic acid；Pentanoic acid, 2-(1-methylethyl)-, (2S)-；(2S)-2-propan-2-ylpentanoic acid
• CAS: 247182-97-4
• 化学式: C₈H₁₆O₂
• 分子量: 144.214
• InChiKey: ODPKTGAWWHZBOY-ZETCQYMHSA-N

物化性质

• 沸点：
  230.6±8.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-Propylisopropylacetic Acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S)-2-propan-2-ylpentanoyl chloride
  参考文献：
  名称：

  Potent Anticonvulsant Urea Derivatives of Constitutional Isomers of Valproic Acid

  摘要：

  Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential, candidates to become new, potent AEDs.

  DOI：

  10.1021/jm7009233

文献信息

• [EN] PROPYLISOPROPYL ACETIC ACID AND PROPYLISOPROPYL ACETAMIDE STEREOISOMERS, A METHOD FOR THEIR SYNTHESIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] STEREOISOMERES D'ACIDE ACETIQUE PROPYLISOPROPYLIQUE ET D'ACETAMIDE PROPYLISOPROPYLIQUE, LEUR METHODE DE SYNTHESE ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY

  公开号：WO1999054282A1

  公开（公告）日：1999-10-28

  (EN) The present invention relates to recemic propylisopropyl acetic acid and propylisopropyl acetamide and their isomers in their racemic and stereospecific forms, for use in treatment of neurological and psychotic disorders, and affective disorders and to treat pain, headaches and migraines. The isomers are of the compound formula (I) wherein R1 is a methyl or ethyl group; R2 is H, methyl or an ethyl group; R3 is ethyl or a propyl group; and R4 is a hydroxyl or amide group, and the total number of carbon atoms in said compound is 8, provided that when R1 is a methyl group and R4 is an amide group, R2 and R3 are not ethyl, further provided that when R1 is an ethyl and R4 a hydroxy group, only stereoisomers of the compound are referred to. The present invention further relates to a method for the stereoselective synthesis of the 2R stereoisomer of PID and PIA. The present invention also relates to pharmaceutical compositions containing as an active ingredient a racemic mixture or stereoisomers of the compounds of general formula (I), which are useful for the treatment of neurological and psychotic disorders, and affective disorders and to treat pain, headaches and migraines.(FR) L'invention concerne de l'acide acétique propylisopropylique racémique et de l'acétamide propylisopropylique ainsi que leurs isomères sous leurs formes racémique et stéréospécifiques, à utiliser dans le traitement de troubles neurologiques et psychotiques, de trouble affectifs, de la douleur, des maux de tête et des migraines. Les isomères de l'invention sont constitués du composé représenté par la formule (I) dans laquelle R1 représente un groupe éthyle ou méthyle; R2 représente H, un groupe éthyle ou méthyle ; R3 représente un groupe propyle ou éthyle ; et R4 représente un groupe amide ou hydroxyle, le nombre total d'atomes de carbone dans ledit composé étant de 8, à condition que lorsque R1 représente un groupe méthyle et R4 un groupe amide, R2 et R3 ne représentent pas éthyle, et encore à condition que lorsque R1 représente un groupe éthyle et R4 un groupe hydroxyle, seuls les stéréoisomères du composé sont concernés. L'invention porte aussi sur une méthode de synthèse stéréo sélective du stéréoisomère 2R d'acétamide propylisopropylique (PID) et d'acide acétique propylisopropylique (PIA). Elle se rapporte encore à des compositions pharmaceutiques contenant, comme principe actif, un mélange racémique ou des stéréoisomères des composés de formule générale (I), utiles pour le traitement de troubles neurologiques et psychotiques, de troubles affectifs et de la douleur, des maux de tête ainsi que des migraines.

  本发明涉及到丙基异丙醋酸和丙基异丙醯胺及其立体异构体的外消旋形式，用于治疗神经和精神障碍、情感障碍以及治疗疼痛、头痛和偏头痛。该化合物的异构体的化学式为(I)，其中R1为甲基或乙基基团；R2为氢、甲基或乙基基团；R3为乙基或丙基基团；R4为羟基或酰胺基团，所述化合物中的碳原子总数为8，但当R1为甲基基团且R4为酰胺基团时，R2和R3不能为乙基。此外，当R1为乙基且R4为羟基时，仅涉及该化合物的立体异构体。本发明还涉及一种制备PID和PIA的2R立体异构体的立体选择性合成方法。本发明还涉及含有外消旋或化合物的立体异构体的药物组合物，其作为活性成分，用于治疗神经和精神障碍、情感障碍以及治疗疼痛、头痛和偏头痛。
• Propylisopropyl acetic acid and propylisopropyl acetamide stereoisomers, a method for their synthesis and pharmaceutical compositions containing them
  申请人：——

  公开号：US20030212131A1

  公开（公告）日：2003-11-13

  The present invention relates to racemic propylisopropyl acetic acid and propylisopropyl acetamide and their isomers in their racemic and stereospecific forms, for use in treatment of neurological and psychotic disorders, and affective disorders and to treat pain, headaches and migraines. The isomers are of the compound formula I 1 R 1 is a methyl or ethyl group; R 2 is H, methyl or an ethyl group; R 3 is ethyl or a propyl group; and R 4 is a hydroxyl or amide group, and the total number of carbon atoms in said compound is 8, provided that when R1 is a methyl group and R4 is an amide group, R2 and R3 are not ethyl, further provided that when R1 is an ethyl and R4 a hydroxyl group, only stereoisomers of the compound are referred to. The present invention further relates to a method for the stereoselective synthesis of the 2R stereoisomer of PID and PIA. The present invention also relates to pharmaceutical compositions containing as an active ingredient a racemic mixture or stereoisomers of the compounds of the general formula (I), which are useful for the treatment of neurological and psychotic disorders, and affective disorders and to treat pain, headaches and migraines.

  本发明涉及外消旋丙基异丙醋酸和丙基异丙醯胺及其立体异构体，用于治疗神经和精神障碍、情感障碍以及治疗疼痛、头痛和偏头痛。该化合物的公式为I，其立体异构体的公式为I，其中R1是甲基或乙基基团；R2是H、甲基或乙基基团；R3是乙基或丙基基团；R4是羟基或酰胺基团，所述化合物中的碳原子总数为8，但当R1为甲基基团且R4为酰胺基团时，R2和R3不为乙基；当R1为乙基基团且R4为羟基基团时，仅涉及该化合物的立体异构体。本发明还涉及一种2R立体异构体的PID和PIA的立体选择性合成方法。本发明还涉及含有外消旋混合物或化合物的立体异构体的药物组合物，其作为活性成分，对神经和精神障碍、情感障碍以及治疗疼痛、头痛和偏头痛具有用途。
• ACYL-UREA DERIVATIVES AND USES THEREOF
  申请人：Bialer Meir

  公开号：US20100280124A1

  公开（公告）日：2010-11-04

  Novel acyl-urea containing compounds, processes of preparing same, compositions containing same and uses thereof in the treatment of neurological diseases and disorders such as epilepsy, neuropathic pain, bipolar disorder, status epilepticus, chemically-induced convulsions and/or seizure disorders, febrile convulsions conditions, metabolic disturbances and a sustenance withdrawal conditions, are provided. Also provided are uses of these and other acyl-urea containing compounds in the treatment of neurological diseases and disorders.

  提供了含有新型酰基脲的化合物、制备该化合物的方法、含有该化合物的组合物以及在治疗神经系统疾病和障碍（如癫痫、神经病性疼痛、躁郁症、持续性癫痫、化学诱导的惊厥和/或癫痫障碍、热性惊厥病症、代谢紊乱和戒断症状）中使用该化合物的方法。还提供了这些和其他含酰基脲的化合物在治疗神经系统疾病和障碍中的用途。
• PROPYLISOPROPYL ACETAMIDE STEREOISOMERS, A METHOD FOR THEIR SYNTHESIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM

  公开号：EP1077926B1

  公开（公告）日：2005-02-23
• PROPYLISOPROPYL ACETIC ACID AND PROPYLISOPROPYL ACETAMIDE STEREOISOMERS, A METHOD FOR THEIR SYNTHESIS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM

  公开号：EP1077926A1

  公开（公告）日：2001-02-28