oleyl trifluoromethyl ketone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: oleyl trifluoromethyl ketone
• 英文别名: (Z)-1,1,1-trifluorononadec-10-en-2-one
• 化学式: C₁₉H₃₃F₃O
• 分子量: 334.466
• InChiKey: SOJGXPSMVNTNQL-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  23
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  oleyl trifluoromethyl ketone 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 以60%的产率得到(Z)-1,1,1-trifluorononadec-10-en-2-ol
  参考文献：
  名称：

  [EN] OLEIC ACID DERIVATIVES AS TREATMENTS FOR FRIEDREICH ATAXIA AND INHIBITORS OF FERROPTOSIS
  [FR] DÉRIVÉS D'ACIDE OLÉIQUE UTILISÉS COMME TRAITEMENTS DE L'ATAXIE DE FRIEDREICH ET INHIBITEURS DE LA FERROPTOSE

  摘要：

  该发明涉及到Formula I或Formula II的化合物，包括含有这些化合物的组合物，以及利用这些化合物治疗神经退行性疾病，如Friedreich共济失调的方法。

  公开号：

  WO2021097069A1
• 作为产物：
  描述：

  油酸 在 吡啶 、 草酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.75h， 生成 oleyl trifluoromethyl ketone
  参考文献：
  名称：

  [EN] OLEIC ACID DERIVATIVES AS TREATMENTS FOR FRIEDREICH ATAXIA AND INHIBITORS OF FERROPTOSIS
  [FR] DÉRIVÉS D'ACIDE OLÉIQUE UTILISÉS COMME TRAITEMENTS DE L'ATAXIE DE FRIEDREICH ET INHIBITEURS DE LA FERROPTOSE

  摘要：

  该发明涉及到Formula I或Formula II的化合物，包括含有这些化合物的组合物，以及利用这些化合物治疗神经退行性疾病，如Friedreich共济失调的方法。

  公开号：

  WO2021097069A1

文献信息

• Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones
  作者：Xue Liu、Long Liu、Tianzeng Huang、Jingjing Zhang、Zhi Tang、Chunya Li、Tieqiao Chen

  DOI：10.1021/acs.orglett.1c01720

  日期：2021.6.18

  The trifluoromethylation of benzoic acids with TMSCF3 was achieved through nucleophilic substitution with the use of anhydrides as an in situ activating reagent. Under the reaction conditions, a wide range of carboxylic acids including the bioactive ones worked well, thus providing a facile and efficient method for preparing aryl trifluoromethyl ketones from the readily available starting materials

  苯甲酸与 TMSCF 3的三氟甲基化是通过亲核取代实现的，使用酸酐作为原位活化剂。在该反应条件下，包括生物活性羧酸在内的多种羧酸都能很好地发挥作用，从而为从易得的原料制备芳基三氟甲基酮提供了一种简便有效的方法。
• Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: A probe of structural and conformational features contributing to inhibition
  作者：Dale L. Boger、Haruhiko Sato、Aaron E. Lerner、Bryce J. Austin、Jean E. Patterson、Matthew P. Patricelli、Benjamin F. Cravatt

  DOI：10.1016/s0960-894x(98)00734-3

  日期：1999.1

  The examination of a series of trifluoromethyl ketone inhibitors of Fatty Acid Amide Hydrolase (FAAH, oleamide hydrolase, anandamide amidohydrolase) is detailed in efforts that define structural and conformational properties that contribute to enzyme inhibition and substrate binding. The results imply an extended bound conformation, highlight a role for the presence, position, and stereochemistry of

  在确定有助于酶抑制和底物结合的结构和构象特性的努力中，详细检查了一系列脂肪酸酰胺水解酶的三氟甲基酮抑制剂（FAAH，油酰胺水解酶，阿南酰胺酰胺水解酶）。结果暗示了扩展的结合构象，突出了δ-顺式双键的存在，位置和立体化学的作用，并且暗示了脂肪酸酰胺底物的C11-C18 / C22几乎没有明显的作用。
• Modulation of anxiety through blockade of anandamide hydrolysis
  申请人：Piomelli Daniele

  公开号：US20090048337A1

  公开（公告）日：2009-02-19

  Fatty acid amide hydrolase inhibitors of the Formula: I. are provided wherein X is NH, CH 2 , O, or S; Q is O or S; Z is O or N; R is an aromatic moiety selected from the group consisting of substituted or unsubstituted aryl; substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenyl; substituted or unsubstituted terphenylyl; substituted or unsubstituted cycloalkyl, heteroaryl, or alkyl; and R 1 and R 2 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, and substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; with the proviso that if Z is O, one of R 1 and R 2 is absent, and that if Z is N, optionally R 1 and R 2 may optionally be taken together to form a substituted or unsubstituted N-heterocycle or substituted or unsubstituted heteroaryl with the N atom to which they are each attached. Pharmaceutical compositions comprising the compounds of Formula I and methods of using them to inhibit FAAH and/or treat appetite disorders, glaucoma, pain, insomnia, and neurological and psychological disorders including anxiety disorders, epilepsy, and depression are provided.

  提供了公式为I的脂肪酸酰胺水解酶抑制剂，其中X为NH，CH2，O或S; Q为O或S; Z为O或N; R为从取代或未取代芳基; 取代或未取代的联苯基; 取代或未取代的萘基; 取代或未取代的苯基; 取代或未取代的三苯基基; 取代或未取代的环烷基，杂环芳基或烷基中选择的芳香基；R1和R2独立地选择自H，取代或未取代的烷基，取代或未取代的杂环烷基，取代或未取代的苯基，取代或未取代的联苯基，取代或未取代的芳基，取代或未取代的杂环芳基的群体中；但如果Z为O，则R1和R2中的一个不存在，如果Z为N，则可选地将R1和R2结合在一起形成取代或未取代的N-杂环或取代或未取代的杂环芳基，与它们各自连接的N原子。提供了包含公式I化合物的药物组合物以及使用它们抑制FAAH和/或治疗食欲障碍，青光眼，疼痛，失眠以及神经和心理障碍，包括焦虑症，癫痫和抑郁症的方法。
• MODULATION OF ANXIETY THROUGH BLOCKADE OF ANANDAMIDE HYDROLYSIS
  申请人：Piomelli Daniele

  公开号：US20120010283A1

  公开（公告）日：2012-01-12

  Fatty acid amide hydrolase inhibitors of the Formula: are provided wherein X is NH, CH 2 , O, or S; Q is O or S; Z is O or N; R is an aromatic moiety selected from the group consisting of substituted or unsubstituted aryl; substituted or unsubstituted biphenylyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted phenyl; substituted or unsubstituted terphenylyl; substituted or unsubstituted cycloalkyl, heteroaryl, or alkyl; and R 1 and R 2 are independently selected from the group consisting of H, substituted or unsubstituted alkyl, substituted or unsubstituted heteroalkyl, and substituted or unsubstituted phenyl, substituted or unsubstituted biphenylyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl; with the proviso that if Z is O, one of R 1 and R 2 is absent, and that if Z is N, optionally R 1 and R 2 may optionally be taken together to form a substituted or unsubstituted N-heterocycle or substituted or unsubstituted heteroaryl with the N atom to which they are each attached. Pharmaceutical compositions comprising the compounds of Formula I and methods of using them to inhibit FAAH and/or treat appetite disorders, glaucoma, pain, insomnia, and neurological and psychological disorders including anxiety disorders, epilepsy, and depression are provided.

  提供了公式为的脂肪酸酰胺水解酶抑制剂：其中X为NH，CH2，O或S；Q为O或S；Z为O或N；R为从取代或未取代芳基；取代或未取代联苯基；取代或未取代萘基；取代或未取代苯基；取代或未取代三苯基基；取代或未取代环烷基，杂环芳基或烷基中选择的芳香基；R1和R2分别选择自H，取代或未取代烷基，取代或未取代杂环烷基，取代或未取代苯基，取代或未取代联苯基，取代或未取代芳基和取代或未取代杂环芳基的群中；但是如果Z为O，则R1和R2中的一个不存在，如果Z为N，则可选地将R1和R2结合在一起形成取代或未取代的N-杂环或取代或未取代的杂环芳基，与它们各自连接的N原子。提供了包含公式I化合物的制药组合物以及使用它们来抑制FAAH和/或治疗食欲障碍，青光眼，疼痛，失眠以及神经和心理障碍，包括焦虑症，癫痫和抑郁症的方法。
• Inhibitors of fatty acid amide hydrolase
  申请人：The Scripps Research Institute

  公开号：EP2093220A2

  公开（公告）日：2009-08-26

  Improved competitive inhibitors of fatty acid amide hydrolase (FAAH) employ an alpha-keto heterocyclic pharmacophore and a binding subunit having a pi-unsaturation. The alpha-keto heterocyclic pharmacophore and a binding subunit are attached to one another, preferably by a hydrocarbon chain. The improvement lies in the use of a heterocyclic pharmacophore selected from oxazoles, oxadiazoles, thiazoles, and thiadiazoles that have alkyl or aryl substituents at their 4 and/or 5 positions. The improved competitive inhibitors of FAAH display enhanced activity over conventional competitive inhibitors of FAAH.

  改进的脂肪酸酰胺水解酶（FAAH）竞争性抑制剂采用了α-酮杂环药源和具有对不饱和度的结合亚基。α-酮杂环药基和结合亚基彼此连接，最好是通过烃链连接。改进之处在于使用了选自噁唑、噁二唑、噻唑和噻二唑的杂环嗜药体，这些杂环嗜药体的 4 和/或 5 位具有烷基或芳基取代基。与传统的 FAAH 竞争性抑制剂相比，改进的 FAAH 竞争性抑制剂显示出更强的活性。