4-hydroxybutyric acid pentyl ester | 852240-70-1

• 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: 4-hydroxybutyric acid pentyl ester
• 英文别名: Pentyl 4-hydroxybutanoate
• CAS: 852240-70-1
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: WHIDWSQGWSRLMR-UHFFFAOYSA-N

物化性质

• 沸点：
  260.5±23.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxybutyric acid pentyl ester 在 TEA 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.0h， 生成 4-(3-Chloro-phenoxycarbonyloxy)-butyric acid pentyl ester
  参考文献：
  名称：

  Optimization of Amide-Based Inhibitors of Soluble Epoxide Hydrolase with Improved Water Solubility

  摘要：

  Soluble epoxide hydrolase (sEH) plays an important role in the metabolism of endogenous chemical mediators involved in the regulation of blood pressure and inflammation. 1,3-Disubstituted ureas with a polar group located on the fifth atom from the carbonyl group of urea function are active inhibitors of sEH both in vitro and in vivo. However, their limited solubility in water and relatively high melting point lead to difficulties in formulating the compounds and poor in vivo efficacy. To improve these physical properties, the effect of structural modification of the urea pharmacophore on the inhibition potencies, water solubilities, octanol/water partition coefficients (log P), and melting points of a series of compounds was evaluated. For murine sEH, no loss of inhibition potency was observed when the urea pharmacophore was modified to an amide function, while for human sEH 2.5-fold decreased inhibition was obtained in the amide compounds. In addition, a NH group on the right side of carbonyl group of the amide pharmacophore substituted with an adamantyl group (such as compound 14) and a methylene carbon present between the adamantyl and amide groups were essential to produce potent inhibition of sEH. The resulting amide inhibitors have 10-30-fold better solubility and lower melting point than the corresponding urea compounds. These findings will facilitate synthesis of sEH inhibitors that are easier to formulate and more bioavailable.

  DOI：

  10.1021/jm0500929
• 作为产物：
  描述：

  butanedioic acid n-pentyl monoester 在 硼烷四氢呋喃络合物 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以90%的产率得到4-hydroxybutyric acid pentyl ester
  参考文献：
  名称：

  Optimization of Amide-Based Inhibitors of Soluble Epoxide Hydrolase with Improved Water Solubility

  摘要：

  Soluble epoxide hydrolase (sEH) plays an important role in the metabolism of endogenous chemical mediators involved in the regulation of blood pressure and inflammation. 1,3-Disubstituted ureas with a polar group located on the fifth atom from the carbonyl group of urea function are active inhibitors of sEH both in vitro and in vivo. However, their limited solubility in water and relatively high melting point lead to difficulties in formulating the compounds and poor in vivo efficacy. To improve these physical properties, the effect of structural modification of the urea pharmacophore on the inhibition potencies, water solubilities, octanol/water partition coefficients (log P), and melting points of a series of compounds was evaluated. For murine sEH, no loss of inhibition potency was observed when the urea pharmacophore was modified to an amide function, while for human sEH 2.5-fold decreased inhibition was obtained in the amide compounds. In addition, a NH group on the right side of carbonyl group of the amide pharmacophore substituted with an adamantyl group (such as compound 14) and a methylene carbon present between the adamantyl and amide groups were essential to produce potent inhibition of sEH. The resulting amide inhibitors have 10-30-fold better solubility and lower melting point than the corresponding urea compounds. These findings will facilitate synthesis of sEH inhibitors that are easier to formulate and more bioavailable.

  DOI：

  10.1021/jm0500929

文献信息

• Heteroaryloxy nitrogenous saturated heterocyclic derivative
  申请人：Ohtake Norikazu

  公开号：US20060178375A1

  公开（公告）日：2006-08-10

  Compound of the formula: (I) [wherein each of X 1 , X 2 , and X 3 independently represents N or CH, W represents the formula (II):(II) or the formula (III):(III) and Y represents a group of the formula (IV):(IV)], or a pharmacologically acceptable salt thereof. This compound exhibits histamine receptor H3 antagonist or inverse agonist activity and is useful of the treatment and/or prevention of obesity, diabetes, hormonal secretion abnormality, sleep, disorder, etc.

  该化合物的化学式为（I），其中X1、X2和X3分别独立地代表N或CH，W代表式（II）：（II）或式（III）：（III），Y代表式（IV）的基团：（IV），或其药学上可接受的盐。该化合物表现出组胺H3受体拮抗剂或倒向激动剂活性，可用于治疗和/或预防肥胖症、糖尿病、激素分泌异常、睡眠障碍等疾病。
• Inhibitors for the soluble epoxide hydrolase
  申请人：Hammock D. Bruce

  公开号：US20060270609A1

  公开（公告）日：2006-11-30

  Inhibitors of the soluble epoxide hydrolase (sEH) are provided that incorporate multiple pharmacophores and are useful in the treatment of diseases.

  提供了可用于治疗疾病的可溶性环氧酶（sEH）抑制剂，其中包含多个药效团。
• HETEROARYLOXY NITROGENOUS SATURATED HETEROCYCLIC DERIVATIVE
  申请人：Ohtake Norikazu

  公开号：US20100210637A1

  公开（公告）日：2010-08-19

  Provided are compounds of a formula (I) and their pharmaceutically-acceptable salts: wherein X1, X2 and X3 each independently represent N or CH; W represents the following formula (II): or the following formula (III): Y represents a group of a formula (IV): The compounds have a histamine-H3 receptor antagonistic or inverse-agonistic activity and are useful for remedy and/or prevention of obesity, diabetes, hormone secretion disorders, sleep disorders, etc.

  提供的是公式（I）的化合物及其药学上可接受的盐： 其中，X1、X2和X3各自独立表示N或CH；W表示以下公式（II）： 或以下公式（III）： Y表示以下公式（IV）的基团： 这些化合物具有组胺H3受体拮抗或反拮抗活性，可用于治疗和/或预防肥胖症、糖尿病、激素分泌障碍、睡眠障碍等。
• Molecular Healing of Polymeric Materials, Coatings, Plastics, Elastomers, Composites, Laminates, Adhesives, and Sealants by Active Enzymes
  申请人：McDaniel C. Steven

  公开号：US20100210745A1

  公开（公告）日：2010-08-19

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peotide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文公开了一些聚合材料，如涂层、塑料、层压板、复合材料、弹性体、粘合剂或密封剂；一种表面处理，如纺织品涂层或蜡；一种填料，用于这样的聚合材料或表面处理，其中包括一种酶，如酯酶（例如，脂肪水解酶，硫酸酯水解酶，有机磷化合物降解酶），降解细胞壁和/或细胞膜成分的酶（例如，溶菌酶，裂解转糖基酶），生物杀菌或生物静态肽，以及/或肽酶。本文还公开了通过将酶纳入可通过脂肪水解酶、水解酶和/或脲酶的活性交联材料中来改变材料性能，如使用寿命、柔韧性或刚度的方法。
• Anti-fouling Paints and Coatings
  申请人：Reactive Surfaces LTD

  公开号：US20150191607A1

  公开（公告）日：2015-07-09

  Disclosed herein are polymeric materials such as a coating, a plastic, a laminate, a composite, an elastomer, an adhesive, or a sealant; a surface treatment such as a textile finish or a wax; a filler for such a polymeric material or a surface treatment that includes an enzyme such as an esterase (e.g., a lipolytic enzyme, a sulfuric ester hydrolase, an organophosphorus compound degradation enzyme), an enzyme (e.g., a lysozyme, a lytic transglycosylase) that degrades a cell wall and/or a cell membrane component, a biocidal or biostatic peptide, and/or a peptidase. Also disclosed herein are methods of altering a material's property such as service life, flexability, or rigidity, by incorporation of an enzyme into a material capable of being chemically crosslinked by the activity of a lipolytic enzyme, a hydrolase, and/or a urease.

  本文披露了聚合材料，例如涂层、塑料、层压材料、复合材料、弹性体、粘合剂或密封剂；表面处理，例如纺织品整理或蜡；填充剂，用于这种聚合材料或表面处理，包括酯酶（例如脂肪水解酶、硫酸酯水解酶、有机磷化合物降解酶）的酶，降解细胞壁和/或细胞膜成分的酶（例如溶菌酶、裂解转葡糖苷酶），生物杀菌或生物稳定肽，和/或肽酶。本文还披露了通过将酶并入能够通过脂肪水解酶、水解酶和/或脲酶的活性进行化学交联的材料中，改变材料性能（例如使用寿命、柔韧性或刚度）的方法。