(5Z,8Z,11Z,14Z)-N-(1-羟基丙-2-基)二十碳-5,8,11,14-四烯酰胺 | 150314-39-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (5Z,8Z,11Z,14Z)-N-(1-羟基丙-2-基)二十碳-5,8,11,14-四烯酰胺
• 英文名称: methanandamide
• 英文别名: (R)-methanandamide；(5Z,8Z,11Z,14Z)-N-(1-hydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide
• CAS: 150314-39-9
• 化学式: C₂₃H₃₉NO₂
• 分子量: 361.568
• InChiKey: SQKRUBZPTNJQEM-ZKWNWVNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S7
• 危险类别码：
  R11
• 危险品运输编号：
  UN 1170 3/PG 2

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 Candida antarctica B lipase 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 (5Z,8Z,11Z,14Z)-N-(1-羟基丙-2-基)二十碳-5,8,11,14-四烯酰胺
  参考文献：
  名称：

  用于合成 Anandamide 和 N-脂肪酰基烷醇胺类似物的改进酶促方法：抗肿瘤活性的组合策略

  摘要：

  通过南极念珠菌 B 脂肪酶催化的酯化和氨解反应，以非常好的收率和高化学选择性获得了来自亚麻酸和花生四烯酸的 20 种 N-脂肪酰胺，其中 15 种是新化合物。通过研究反应参数（温度、E/S比、醇和链烷醇胺/脂肪酸比、时间、溶剂、游离溶剂体系等）获得最佳反应条件。为了确定产生链烷醇酰胺的理想酶促方法，我们在三个程序中评估了酶的性能：i) 乙酯的氨解，ii) 脂肪酸和链烷醇胺之间的直接缩合，以及 iii) 脂肪的一锅/两步转化通过原位形成乙酯和随后由链烷醇胺氨解，将酸转化为链烷醇酰胺。酶促方法的优点，如温和的反应条件和低环境影响，强调生物催化是制备报告化合物的便捷方式。在大鼠神经胶质瘤 C6 细胞中评估了所有化合物和 anandamide 及其类似物的混合物的细胞毒活性。这些研究表明，一些 anandamide 类似物增强了 anandamide 的抗肿瘤作用，表明它们可能作为治疗工具用于癌症治疗。

  DOI：

  10.1002/ejoc.201501263

文献信息

• Pharmacological and behavioral evaluation of alkylated anandamide analogs
  作者：Irma B. Adams、William Ryan、Michael Singer、Raj K. Razdan、David R. Compton、Billy R. Martin

  DOI：10.1016/0024-3205(95)00187-b

  日期：1995.5

  examined structure-activity relationships in alkylated anandamide analogs. The analogs were evaluated for their ability to displace [3H]CP-55,940 in a filtration binding assay using rat brain membranes in the presence and absence of the enzyme inhibitor phenylmethylsulfonyl fluoride (PMSF). Behavioral activity was assessed by the ability of the analogs to produce hypomotility and antinociception. Methylations

  从猪脑中分离出的Anandamide（花生四烯基乙醇酰胺）已在药理学分析中与大麻素受体结合并产生大麻素活性。这项研究检查了烷基化的anandamide类似物的构效关系。在存在和不存在酶抑制剂苯基甲基磺酰氟（PMSF）的情况下，使用大鼠脑膜在过滤结合试验中评估了类似物置换[3H] CP-55,940的能力。通过类似物产生动力不足和抗伤害感受的能力来评估行为活性。在不存在PMSF的情况下，碳2和1处的甲基化可稳定形成化合物，其亲和力和行为活性与Anandamide类似。在这些位置或氮甲基化处添加较大的烷基会降低受体亲和力和行为能力。这些结果表明在anandamide的特定碳甲基化赋予体外稳定性。
• Verwendung von Agonisten des zentralen Cannabinoid-Rezeptors CB1
  申请人：Bayer HealthCare AG

  公开号：EP0860168B1

  公开（公告）日：2007-08-08
• UTILISATION DE COMPOSÉS CANNABINOÏDES POUR STIMULER LA MÉLANOGÉNÈSE
  申请人：L'OREAL

  公开号：EP2739260B1

  公开（公告）日：2017-09-27
• INHIBITORS OF ANOREXIC LIPID HYDROLYSIS FOR THE TREATMENT OF EATING DISORDERS
  申请人：Hansen Harald S.

  公开号：US20090054526A1

  公开（公告）日：2009-02-26

  Compounds, pharmaceuticals, cosmetic or dietary supplements for the treatment of overweight, obesity and/or type II diabetes in a mammal (e.g. human) comprising a compound with formula I or formula II for example ceramidase-inhibitor, such as (1S,2R)-D-ery-thro-2-(N-myristoylamino)-1-phenyl-1-propanol, alone or in combination with an anorexic lipid (or other appetite-inhibiting acylamides or oleoyl-estrone), and methods of treatment comprising administration of said compounds, pharmaceuticals, cosmetic or a dietary supplements. The compounds, pharmaceuticals, cosmetic or dietary supplements and methods of the invention may further be used in modifying the feeding behaviour, suppression of hunger, enhancement of satiety, reduction of energy intake, reduction of fat tissue mass/lean mass ratio in a mammal (e.g. human).
• USE OF CANNABINOID COMPOUNDS FOR STIMULATING MELANOGENESIS
  申请人：Zuccolo Michela

  公开号：US20140193349A1

  公开（公告）日：2014-07-10

  The invention relates to the nontherapeutic cosmetic use of at least one cannabinoid compound chosen from the compounds corresponding to general formula (I): and also the geometric isomers and optical isomers thereof, the cosmetically acceptable acid or base salts thereof, and the hydrates thereof; in which compounds of formula (I): R 1 represents a hydrogen atom or a C 1 -C 30 alkyl group; it being possible for said alkyl group to be optionally substituted with a hydroxyl (OH) group; R 2 represents a halogen atom or a group chosen from hydroxyl, thiol (SH), and amino optionally substituted with one or two C 1 -C 6 alkyl groups; R 3 and R 4 form, together with the carbon atom which bears them, an oxo group or else R 3 and R 4 represent a hydrogen atom; R 5 represents a hydrogen atom or a C 1 -C 6 alkyl group; X represents a heteroatom chosen from oxygen and sulfur atoms and the divalent group —N(R 6 )—, with R 6 representing a hydrogen atom or a C 1 -C 6 alkyl group; represents a single or double bond; n is 1, 2 or 3, preferentially 1 or 2; it being understood that, when R 3 and R 4 together form an oxo group with the carbon atom which bears them and X represents an oxygen atom, then R 1 cannot represent a hydroxymethyl group, as an agent for coloring keratin materials. It also relates to one of these specific cannabinoid compounds for use thereof in the treatment of vitiligo or pityriasis versicolor, to nontherapeutic cosmetic processes for coloring the skin or for treating canities, comprising the topical application to the skin and/or head hair, or the oral administration, of a composition comprising, in a physiologically acceptable medium, one of these cannabinoid compounds, and to a process for selecting an active agent which promotes the pigmentation of keratin materials.