2-(8-heptadecenyl)-2-oxazoline | 34900-26-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 2-(8-heptadecenyl)-2-oxazoline
• 英文别名: 2-heptadec-8-enyl-4,5-dihydro-oxazole；((Z)-2-Heptadec-8-enyl)-4,5-dihydro-oxazole；2-[(Z)-heptadec-8-enyl]-4,5-dihydro-1,3-oxazole
• CAS: 34900-26-0
• 化学式: C₂₀H₃₇NO
• 分子量: 307.52
• InChiKey: SOTODSFNXCLCGH-KTKRTIGZSA-N

物化性质

• 沸点：
  405.3±24.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  22
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  油酰乙醇胺 在 氯化亚砜 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 7.5h， 以88%的产率得到2-(8-heptadecenyl)-2-oxazoline
  参考文献：
  名称：

  COMPOSITIONS AND METHODS FOR THE MODULATION OF SPECIFIC AMIDASES FOR N-ACYLETHANOLAMINES FOR USE IN THE THERAPY OF INFLAMMATORY DISEASES

  摘要：

  本发明涉及用于调节能够水解N-酰乙醇胺的酰胺酶的组合物和方法，用于治疗炎症性疾病。具体来说，本发明涉及一般式(I)的化合物：对映体、非对映异构体、消旋体和混合物、多形态、盐、溶剂化合物，其中：(a) R是具有13至19个碳原子的直链烷基基团或具有13至19个碳原子并带有一个双键的烯基基团；(b) X为0或S；(c) Y为2或3个碳原子的烷基烃基残基，可选择地取代一个或两个相等或不同的基团，所述基团选自以下群组中的一种：—CH3、—CH2OH、—COOCH3、—COOH。Y可能更倾向于是：—CH2—CH2—、—CH2—CH2—CH2—、CH(CH3)—CH2—、—CH2—CH(CH3)—、—CH2—C(CH3)2—、—CH2—CH(CH2OH)—、—CH2—C((CH2OH)2—、—CH═CH—、—CH2—CH(COOCH3)—、—CH2—CH(COOH)—，用作药物。

  公开号：

  US20150057269A1

文献信息

• Novel Analogues of Arachidonylethanolamide (Anandamide):  Affinities for the CB1 and CB2 Cannabinoid Receptors and Metabolic Stability
  作者：Sonyuan Lin、Atmaram D. Khanolkar、Pusheng Fan、Andreas Goutopoulos、Ce Qin、Demetris Papahadjis、Alexandros Makriyannis

  DOI：10.1021/jm970257g

  日期：1998.12.1

  Several analogues of the endogenous cannabinoid receptor ligand arachidonylethanolamide (anandamide) were synthesized and evaluated in order to study (a) the structural requirements for high-affinity binding to the CB1 and CB2 cannabinoid receptors and (b) their hydrolytic stability toward anandamide amidase. The series reported here was aimed at exploring structure-activity relationships (SAR) primarily with regard to stereoelectronic requirements of ethanolamido headgroup for interaction with the cannabinoid receptor active site. Receptor affinities, reported as K-i values, were obtained by a standard receptor binding assay using [H-3]CP-55,940 as the radioligand, while stability toward the amidase was evaluated by comparing the K-i of each analogue in the presence and absence of phenylmethanesulfonyl fluoride (PMSF), a serine protease blocker and inhibitor of anandamide amidase. Introduction of a methyl group in the 1'- and 2'-positions or substitution of the ethanolamido headgroup with a butylamido group gave analogues with vastly improved biochemical stability. This is accomplished in some cases with increased receptor affinity. Conversely, oxazolyl and methyloxazolyl headgroups led to low-affinity analogues. Substitution of the hydroxyl group with electronegative substituents such as fluoro, chloro, allyl, and propargyl groups significantly increased receptor affinity but did not influence the biochemical stability. The 2'-chloro analogue of anandamide was found to have the highest affinity for CB1. Additionally, reversing the positions of the carbonyl and NH in the amido group produces retro-anandamides possessing considerably higher metabolic stability. Replacement of the arachidonyl tail with oleyl or linoleyl results in analogues with low affinities for both receptors. All of the analogues in this study showed high selectivity for the CB1 receptor over the peripheral CB2 receptor. The most potent analogues were tested for their ability to stimulate the binding of [S-35]GTP gamma S to G-proteins and were shown to be potent cannabimimetic agonists. The results are discussed in terms of pharmacophoric features affecting receptor affinity and enzymatic stability.
• Witte,H.; Seeliger,W., Justus Liebigs Annalen der Chemie, 1974, p. 996 - 1009
  作者：Witte,H.、Seeliger,W.

  DOI：——

  日期：——
• COMPOSITIONS AND METHODS FOR THE MODULATION OF SPECIFIC AMIDASES FOR N-ACYLETHANOLAMINES FOR USE IN THE THERAPY OF INFLAMMATORY DISEASES
  申请人：Della Valle Francesco

  公开号：US20150057269A1

  公开（公告）日：2015-02-26

  The present invention regards compositions and methods for the modulation of amidases capable of hydrolysing N-acylethanolamines useable in the therapy of inflammatory diseases. In particular, the present invention regards a compound of general formula (I): enantiomers, diastereoisomers, racemes and mixtures, polymorphs, salts, solvates thereof, wherein: (a) R is a linear alkyl radical having 13 to 19 carbon atoms or alkenyl radical having 13 to 19 carbon atoms carrying a double bond; (b) X is 0 or S; (c) Y is a 2 or 3 carbon atom alkylene residue, optionally substituted with one or two groups equal or different from each other and selected from among the group consisting of: —CH 3 , —CH 2 OH, —COOCH 3 , —COOH. Y may preferably be: —CH 2 —CH 2 —, —CH 2 —CH 2 —CH 2 —, CH(CH 3 )—CH 2 —, —CH 2 —CH(CH 3 )—, —CH 2 —C(CH 3 ) 2 —, —CH 2 —CH(CH 2 OH)—, —CH 2 —C((CH 2 OH) 2 )—, —CH═CH—, —CH 2 —CH(COOCH 3 )—, —CH 2 —CH(COOH)—, for use as a medicine.

  本发明涉及用于调节能够水解N-酰乙醇胺的酰胺酶的组合物和方法，用于治疗炎症性疾病。具体来说，本发明涉及一般式(I)的化合物：对映体、非对映异构体、消旋体和混合物、多形态、盐、溶剂化合物，其中：(a) R是具有13至19个碳原子的直链烷基基团或具有13至19个碳原子并带有一个双键的烯基基团；(b) X为0或S；(c) Y为2或3个碳原子的烷基烃基残基，可选择地取代一个或两个相等或不同的基团，所述基团选自以下群组中的一种：—CH3、—CH2OH、—COOCH3、—COOH。Y可能更倾向于是：—CH2—CH2—、—CH2—CH2—CH2—、CH(CH3)—CH2—、—CH2—CH(CH3)—、—CH2—C(CH3)2—、—CH2—CH(CH2OH)—、—CH2—C((CH2OH)2—、—CH═CH—、—CH2—CH(COOCH3)—、—CH2—CH(COOH)—，用作药物。