3-<4-Heptyloxy-phenyl>-propionsaeure | 79785-54-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 3-<4-Heptyloxy-phenyl>-propionsaeure
• 英文别名: 3-(4-Heptoxyphenyl)propanoic acid；3-(4-heptoxyphenyl)propanoic acid
• CAS: 79785-54-9
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: MSPKVWKPCZFWMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<4-Heptyloxy-phenyl>-propionsaeure 、 C₂₅H₅₂NO₁₀PSi 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.0h， 以93%的产率得到
  参考文献：
  名称：

  Structure–Activity Relationships of Lysophosphatidylserine Analogs as Agonists of G-Protein-Coupled Receptors GPR34, P2Y10, and GPR174

  摘要：

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-attivity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS,receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and L-Serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysolPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.

  DOI：

  10.1021/jm5020082
• 作为产物：
  描述：

  对羟基苯丙酸甲酯 在 水 、 sodium hydride 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-<4-Heptyloxy-phenyl>-propionsaeure
  参考文献：
  名称：

  Structure–Activity Relationships of Lysophosphatidylserine Analogs as Agonists of G-Protein-Coupled Receptors GPR34, P2Y10, and GPR174

  摘要：

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-attivity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS,receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and L-Serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysolPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.

  DOI：

  10.1021/jm5020082

文献信息

• COMPOUND EXHIBITING REGULATORY ACTIVITY ON LYSOPHOSPHATIDYLSERINE RECEPTOR FUNCTION
  申请人：The University of Tokyo

  公开号：EP2952517A1

  公开（公告）日：2015-12-09

  The object of the present invention is to provide a compound having a lysophosphatidylserine receptor function modulation activity or a salt thereof. A compound having a lysophosphatidylserine receptor function modulation activity or a salt thereof, or a pharmaceutical composition or a lysophosphatidylserine receptor function moderator containing such compound or salt is provided by the present invention.

  本发明的目的是提供一种具有溶血磷脂酰丝氨酸受体功能调节活性的化合物或其盐。 本发明提供了一种具有溶血磷脂酰丝氨酸受体功能调节活性的化合物或其盐，或含有这种化合物或盐的药物组合物或溶血磷脂酰丝氨酸受体功能调节剂。
• COMPOUND HAVING LYSOPHOSPHATIDYLSERINE RECEPTOR FUNCTION MODULATION ACTIVITY
  申请人：The University of Tokyo

  公开号：EP2952517B1

  公开（公告）日：2018-03-07
• 3-PHENYL-4-HEXYNOIC ACID DERIVATIVES AS GPR40 AGONISTS
  申请人：CELON PHARMA S.A.

  公开号：EP3737470B1

  公开（公告）日：2022-12-14
• US9469665B2
  申请人：——

  公开号：US9469665B2

  公开（公告）日：2016-10-18
• Structure–Activity Relationships of Lysophosphatidylserine Analogs as Agonists of G-Protein-Coupled Receptors GPR34, P2Y10, and GPR174
  作者：Masaya Ikubo、Asuka Inoue、Sho Nakamura、Sejin Jung、Misa Sayama、Yuko Otani、Akiharu Uwamizu、Keisuke Suzuki、Takayuki Kishi、Akira Shuto、Jun Ishiguro、Michiyo Okudaira、Kuniyuki Kano、Kumiko Makide、Junken Aoki、Tomohiko Ohwada

  DOI：10.1021/jm5020082

  日期：2015.5.28

  Lysophosphatidylserine (LysoPS) is an endogenous lipid mediator generated by hydrolysis of membrane phospholipid phosphatidylserine. Recent ligand screening of orphan G-protein-coupled receptors (GPCRs) identified two LysoPS specific human GPCRs, namely, P2Y10 (LPS2) and GPR174 (LPS3), which, together with previously reported GPR34 (LPS1), comprise a LysoPS receptor family. Herein, we examined the structure-attivity relationships of a series of synthetic LysoPS analogues toward these recently deorphanized LysoPS,receptors, based on the idea that LysoPS can be regarded as consisting of distinct modules (fatty acid, glycerol, and L-Serine) connected by phosphodiester and ester linkages. Starting from the endogenous ligand (1-oleoyl-LysolPS, 1), we optimized the structure of each module and the ester linkage. Accordingly, we identified some structural requirements of each module for potency and for receptor subtype selectivity. Further assembly of individually structure-optimized modules yielded a series of potent and LysoPS receptor subtype-selective agonists, particularly for P2Y10 and GPR174.