rac-α-methylene-6-phenylhexanoic acid | 195071-00-2

• 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: rac-α-methylene-6-phenylhexanoic acid
• 英文别名: 2-methylene-6-phenylhexanoic acid；2-methylene-6-phenyl-hexanoic acid；2-Methylidene-6-phenylhexanoic acid
• CAS: 195071-00-2
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: OTZLCBROLNYWPX-UHFFFAOYSA-N

物化性质

• 沸点：
  381.0±31.0 °C(Predicted)
• 密度：
  1.051±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  rac-α-methylene-6-phenylhexanoic acid 在 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 以48%的产率得到2-(bromomethyl)-6-phenylhexanoic acid
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of N-(2-Oxo-3-oxetanyl)amides as N-Acylethanolamine-hydrolyzing Acid Amidase Inhibitors

  摘要：

  The fatty acid ethanolamides (FAEs) are a family of bioactive lipid mediators that include the endogenous agonist of peroxisome proliferator-activated receptor-alpha, palmitoylethanolamide (PEA). FAEs are hydrolyzed intracellularly by either fatty acid amide hydrolase or N-acylethanolamine-hydrolyzing acid amidase (NAAA). Selective inhibition of NAAA by (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide [(S)-OOPP, 7a] prevents PEA degradation in mouse leukocytes and attenuates responses to proinflammatory stimuli. Starting from the structure of 7a, a series of beta-lactones was prepared and tested on recombinant rat NAAA to explore structure-activity relationships (SARs) for this class of inhibitors and improve their in vitro potency. Following the hypothesis that these compounds inhibit NAAA by acylation of the catalytic cysteine, we identified several requirements for recognition at the active site and obtained new potent inhibitors. In particular, (S)-N-(2-oxo-3-oxetanyl)biphenyl-4-carboxamide (7h) was more potent than 7a at inhibiting recombinant rat NAAA activity (7a, IC(50) = 420 nM; 7h, IC(50) = 115 nM) in vitro and at reducing carrageenan-induced leukocyte infiltration in vivo.

  DOI：

  10.1021/jm100582w
• 作为产物：
  描述：

  4-苯基-1-丁基溴 在 氢氧化钾 、 二乙胺盐酸盐 、 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 反应 22.0h， 生成 rac-α-methylene-6-phenylhexanoic acid
  参考文献：
  名称：

  Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.

  DOI：

  10.1021/jm010272s

文献信息

• .beta.-thiopropionyl-aminoacid derivatives and their use as
  申请人：SmithKline Beecham p.l.c.

  公开号：US06048852A1

  公开（公告）日：2000-04-11

  A method of treatment of bacterial infections in humans or animals which comprises administering, in combination with a .beta.-lactam antibiotic, a therapeutically effective amount of an amino acid derivative of Formula (I) or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, ##STR1## wherein: R is hydrogen, a salt forming cation or an in vivo hydrolysable ester-forming group; R.sub.1 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms or by a mercapto, (C.sub.1-6)alkoxy, hydroxy, amino, nitro, carboxy, (C.sub.1-6)alkylcarbonyloxy, (C.sub.1-6)alkoxycarbonyl, formyl or (C.sub.1-6)alkylcarbonyl group, (C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl(C.sub.1-6)alkyl, heterocyclyl or heterocyclyl(C.sub.1-6)alkyl; R.sub.2 is hydrogen, (C.sub.1-6)alkyl or aryl(C.sub.1-6)alkyl; R.sub.3 is hydrogen, (C.sub.1-6)alkyl optionally substituted by up to three halogen atoms, (C.sub.3-7)cycloalkyl, fused aryl(C.sub.3-7)cycloalkyl, (C.sub.3-7)cycloalkyl(C.sub.2-6)alkyl, (C.sub.2-6)alkenyl, (C.sub.2-6)alkynyl, aryl, aryl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, heterocyclyl or heterocyclyl-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n, where m is 0 to 3, n is 1 to 3, each R.sub.10 and R.sub.11 is independently hydrogen or (C.sub.1-4)alkyl and X is O, S(O).sub.x where x is 0-2, or a bond; R.sub.4 is hydrogen, or an in vivo hydrolysable acyl group; and R.sub.5 and R.sub.6 are independently hydrogen and (C.sub.1-6)alkyl or together represent (CH.sub.2).sub.p where p is 2 to 5. Some compounds are claimed per se.

  一种治疗人类或动物细菌感染的方法，包括与β-内酰胺类抗生素联合给药，给予公式(I)的氨基酸衍生物的治疗有效量或其药用可接受的盐、溶剂化合物或体内可水解酯的治疗有效量，其中：R为氢、形成盐的阳离子或体内可水解酯形成基团；R.sub.1为氢、(C.sub.1-6)烷基，可选地被高达三个卤素原子或巯基、(C.sub.1-6)烷氧基、羟基、氨基、硝基、羧基、(C.sub.1-6)烷基羰氧基、(C.sub.1-6)烷氧羰基、甲酰基或(C.sub.1-6)烷基羰基取代，(C.sub.3-7)环烷基，(C.sub.3-7)环烷基(C.sub.2-6)烷基，(C.sub.2-6)烯基，(C.sub.2-6)炔基，芳基，芳基(C.sub.1-6)烷基，杂环烷基或杂环烷基(C.sub.1-6)烷基；R.sub.2为氢，(C.sub.1-6)烷基或芳基(C.sub.1-6)烷基；R.sub.3为氢，(C.sub.1-6)烷基，可选地被高达三个卤素原子取代，(C.sub.3-7)环烷基，融合的芳基(C.sub.3-7)环烷基，(C.sub.3-7)环烷基(C.sub.2-6)烷基，(C.sub.2-6)烯基，(C.sub.2-6)炔基，芳基，芳基-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n，杂环烷基或杂环烷基-(CHR.sub.10).sub.m --X--(CHR.sub.11).sub.n，其中m为0至3，n为1至3，每个R.sub.10和R.sub.11独立地为氢或(C.sub.1-4)烷基，X为O，S(O).sub.x，其中x为0-2，或键；R.sub.4为氢，或体内可水解的酰基；R.sub.5和R.sub.6独立地为氢和(C.sub.1-6)烷基，或一起代表(CH.sub.2).sub.p，其中p为2至5。一些化合物本身被要求。
• Carbodiimides comprising thiocarbamide acid ester groups
  申请人：Burghardt Andre

  公开号：US20070179226A1

  公开（公告）日：2007-08-02

  Thiocarbamides comprising at least one carbodiimide group and at least one thiocarbamic ester group of the formula

  含有至少一个异氰酸酯基团和至少一个硫代氨基酸酯基团的硫代氨基甲酸酯，化学式为：
• Foldable ophthalmic and otorhinolaryngological device materials
  申请人：——

  公开号：US20030130460A1

  公开（公告）日：2003-07-10

  Disclosed are soft, high refractive index, acrylic materials having an elongation of at least 150%. These materials, especially useful as intraocular lens materials, contain an aryl acrylic hydrophobic monomer as the single principal device-forming monomer. In addition to their use as intraocular lens materials, the present materials are also suitable for use in other ophthalmic or otorhinolaryngological devices, such as contact lenses, keratoprostheses, corneal inlays or rings; otological ventilation tubes and nasal implants.

  本发明揭示了具有至少150％伸长率的软性高折射率丙烯酸材料。这些材料尤其适用于作为人工晶体材料，其中含有芳基丙烯酸疏水单体作为唯一的主要器件成形单体。除了作为人工晶体材料之外，本材料还适用于其他眼科或鼻喉科设备的使用，例如隐形眼镜、角膜假体、角膜植入物或环;耳科通气管和鼻部植入物。
• Polymere Phenylalkyl-acrylsäureester, deren Herstellung und deren Verwendung
  申请人：HÜLS AKTIENGESELLSCHAFT

  公开号：EP0093855A1

  公开（公告）日：1983-11-16

  Beansprucht werden polymere Phenylalkyl-acrylsäureester der Formel in der R einen geradkettigen oder verzweigten Alkylenrest mit 3 bis 4 Kohlenstoffatomen bedeutet, der gegebenenfalls durch ein Ethersauerstoffatom unterbrochen sein kann, und deren Verwendung als schlagzäh machende Komponente in hochtransparenten schlagzähen Formmassen auf der Basis von Polyvinylchlorid.

  所述聚合物苯基烷基丙烯酸酯的化学式为 其中 R 表示具有 3 至 4 个碳原子的直链或支链亚烷基，可选择以一个醚氧原子作为间 断，它们可用作以聚氯乙烯为基础的高透明度抗冲击模塑组合物中的抗冲击模塑成分。
• Hochtransparente schlagzähe Formmassen auf der Basis von Polyvinylchlorid
  申请人：HÜLS AKTIENGESELLSCHAFT

  公开号：EP0093854A2

  公开（公告）日：1983-11-16

  Hochtransparente schlagzähe Formmassen auf der Basis von Polyvinylchlorid enthalten als schlagzäh machende Komponente Polymerisate von Monomeren der folgenden Formel R einen geradkettigen oder verzweigten Alkylenrest mit 3 bis 8 Kohlenstoffatomen bedeutet, welcher gegebenenfalls 1 bis 3 Ethersauerstoffatome enthält.

  以聚氯乙烯为基础的高透明抗冲击模塑化合物含有下式单体聚合物作为抗冲击成分 R 是具有 3 至 8 个碳原子的直链或支链亚烷基，可选择含有 1 至 3 个醚氧原子。