ethyl 13-oxotridecanoate | 1119-77-3

• 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: ethyl 13-oxotridecanoate
• 英文别名: 12-Formyl-laurinsaeure-ethylester；Ethyl 12-formyl-laurat；13-oxo-tridecanoic acid ethyl ester；13-Oxo-tridecansaeure-aethylester
• CAS: 1119-77-3
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: VBUFDQHNGGVOEO-UHFFFAOYSA-N

物化性质

• 沸点：
  155-161 °C(Press: 0.8 Torr)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 13-oxotridecanoate 在 水 、 sodium hexamethyldisilazane 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 顺式-13-十八碳烯酸
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105
• 作为产物：
  描述：

  12-溴十二烷酸 在 sodium phosphinate 、 乙酰氯 作用下， 反应 24.0h， 生成 ethyl 13-oxotridecanoate
  参考文献：
  名称：

  Synthesis and Characterization of Novel Acyl-Glycine Inhibitors of GlyT2

  摘要：

  It has been demonstrated previously that the endogenous compound N-arachidonyl-glycine inhibits the glycine transporter GlyT2, stimulates glycinergic neurotransmission, and provides analgesia in animal models of neuropathic and inflammatory pain. However, it is a relatively weak inhibitor with an IC50, of 9 mu M and is subject to oxidation via cyclooxygenase, limiting its therapeutic value. In this paper we describe the synthesis and testing of a novel series of monounsaturated C18 and C16 acyl-glycine molecules as inhibitors of the glycine transporter GIyT2. We demonstrate that they are up to 28 fold more potent that N-arachidonyl-glycine with no activity at the closely related GlyT1 transporter at concentrations up to 30 mu M. This novel class of compounds show considerable promise as a first generation of GIyT2 transport inhibitors.

  DOI：

  10.1021/acschemneuro.7b00105

文献信息

• [EN] NOVEL GLYCINE TRANSPORT INHIBITORS FOR THE TREATMENT OF PAIN<br/>[FR] NOUVEAUX INHIBITEURS DE TRANSPORT DE GLYCINE POUR LE TRAITEMENT DE LA DOULEUR
  申请人：UNIV SYDNEY

  公开号：WO2018132876A1

  公开（公告）日：2018-07-26

  The present invention relates to novel glycine transport inhibitor compounds and their use for treating pain.

  本发明涉及新型甘氨酸转运抑制剂化合物及其用于治疗疼痛的用途。
• Synthèses de produits macrocycliques à odeur musquée. 13e communication Sur une nouvelle méthode de préparation de l'acide méthyl-2-pentadécane-dioïque
  作者：Max Stoll

  DOI：10.1002/hlca.19510340230

  日期：——

  On a décrit une méthode pour transformer l'ester érucique ou brassidique en méthyl-2-pentadécane-dioate d'éthyle.

  在décritune和méthode上倒入m'thyl-2-pentadécane-dioated'éthyle的éérécécé或brasidique变压器。
• Antiproliferative and Antimigratory Actions of Synthetic Long Chain n-3 Monounsaturated Fatty Acids in Breast Cancer Cells That Overexpress Cyclooxygenase-2
  作者：Pei H. Cui、Tristan Rawling、Kirsi Bourget、Terry Kim、Colin C. Duke、Munikumar R. Doddareddy、David E. Hibbs、Fanfan Zhou、Bruce N. Tattam、Nenad Petrovic、Michael Murray

  DOI：10.1021/jm300673z

  日期：2012.8.23

  Cyclooxygenase-2 (COX-2) is overexpressed in many human cancers and converts the n-6 polyunsaturated fatty acid (PUFA) arachidonic acid to prostaglandin E-2 (PGE(2)), which drives tumorigenesis; in contrast, n-3 PUFA inhibit tumorigenesis. We tested the hypothesis that these antitumor actions of n-3 PUFA may involve the n-3 olefinic bond. n-3 Monounsaturated fatty acids (MUFAs) of chain length C16-C22 were synthesized and evaluated in MDA-MB-468 breast cancer cells that stably overexpressed COX-2 (MDA-COX-2 cells). Longer chain (C19-C22) n-3 MUFAs inhibited proliferation, activated apoptosis, decreased PGE2 formation, and decreased cell invasion; C16-C18 analogues were less active. Molecular modeling showed that interactions of Arg120, Tyr355, and several hydrophobic amino acid residues in the COX-2 active site with C19-C22 MUFA analogues were favored. Thus, longer-chain n-3 MUFAs may be prototypes of novel anticancer agents that decrease the formation of PGE2 in tumor cells that contain high levels of COX-2.
• Tirodkar,S.V. et al., Indian Journal of Chemistry, 1968, vol. 6, p. 184 - 186
  作者：Tirodkar,S.V. et al.

  DOI：——

  日期：——
• Dhekne,V.V. et al., Indian Journal of Chemistry, 1966, vol. 4, p. 524 - 526
  作者：Dhekne,V.V. et al.

  DOI：——

  日期：——