9-thiophen-2-yl-nonanoic acid | 21010-08-2

• 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: 9-thiophen-2-yl-nonanoic acid
• 英文别名: 9-[2]thienyl-nonanoic acid；9-[2]Thienyl-nonansaeure；9-(2-Thienyl)-nonanoic acid；9-thiophen-2-ylnonanoic acid
• CAS: 21010-08-2
• 化学式: C₁₃H₂₀O₂S
• 分子量: 240.367
• InChiKey: LWHWQCIYPUKQCV-UHFFFAOYSA-N

物化性质

• 熔点：
  35 °C(Solvent: Benzene ; Ligroine)
• 沸点：
  217 °C(Press: 10.2 Torr)
• 密度：
  1.083±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-thiophen-2-yl-nonanoic acid 在 哌啶 、 sodium hydroxide 、 氯化亚砜 、 三氯氧磷 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 4.5h， 生成 9-[5-((E)-2-Carboxy-vinyl)-thiophen-2-yl]-nonanoic acid
  参考文献：
  名称：

  Inverse agonists at the polyamine-sensitive modulatory site of the NMDA receptor: 50-fold increase in potency by insertion of an aromatic ring into an alkanediamine chain

  摘要：

  Polyamines like spermine and spermidine increase the opening frequency of the NMDA receptor associated ion channel and, as a consequence, specific binding of non-saturating concentrations of the channel radioligand [H-3]MK-801. Compounds exhibiting the contrary effect have been described as polyamine inverse agonists, with 1,12-dodecanediamine (N-12-N) being one of the most specific ones (IC50 16.5 mu M). Here we describe the synthesis of a series of long-chain alkanediamines, with a thiophene nucleus inserted at various positions, and report the discovery of 5-(4-aminobutyl)-2-thiopheneoctanamine (N-4-T-8-N), which inhibited specific binding of [H-3]MK-801 by 50 % at 0.33 mu M. In the presence of 100 mu M of spermine, 4.0 mu M N-4-T-8-N was necessary to achieve the same degree of inhibition. N-4-T-8-N is the most potent polyamine inverse agonist presently known and should be a useful tool to elucidate the physiological significance of the polyamine regulatory site of the NMDA receptor complex. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80070-1
• 作为产物：
  描述：

  8-(2-Thienyl)octanonitrile 在 氢氧化钾 作用下， 以 甘油 为溶剂， 反应 7.0h， 以60%的产率得到9-thiophen-2-yl-nonanoic acid
  参考文献：
  名称：

  Ring-closure reactions. 16. An improved procedure for the synthesis of (2,5)thiophenophan-1-ones and its application to a convenient preparation of dl-muscone

  摘要：

  DOI：

  10.1021/jo01298a029

文献信息

• Method of inhibiting parasitic activity
  申请人：Washington University

  公开号：US05747537A1

  公开（公告）日：1998-05-05

  A method of inhibiting parasitic activity is disclosed in which the biosynthesis, structure and/or function of the glycosyl phosphatidylinositol (GPI) anchor of said parasite may be affected by incorporating into said GPI anchor selected analogs of myristic acid containing various heteroatoms, substituents and unsaturated bonds, including ester-containing analogs, ketocarbonyl-containing analogs, sulfur-containing analogs, double bond- and triple bond-containing analogs, aromatic moiety-containing analogs, nitrated analogs and halogenated analogs.

  公开了一种抑制寄生活动的方法，其中可以通过将含有各种杂原子、取代基和不饱和键的肉豆蔻酸选择性类似物纳入所述寄生物的磷脂酰肌醇糖基磷脂酰肌醇（GPI）锚中来影响所述寄生物的生物合成、结构和/或功能，其中包括酯含类似物、酮羰基含类似物、硫含类似物、双键和三键含类似物、芳香基含类似物、硝基类似物和卤代类似物。
• Thienyl-containing fatty acid glycosyl phosphatidylinosital analogues
  申请人：Washington University

  公开号：US05998642A1

  公开（公告）日：1999-12-07

  A method of inhibiting parasitic activity is disclosed in which the biosynthesis, structure and/or function of the glycosyl phosphatidylinositol (GPI) anchor of said parasite may be affected by incorporating into said GPI anchor selected analogs of myristic acid containing various heteroatoms, substituents and unsaturated bonds, including ester-containing analogs, ketocarbonyl-containing analogs, sulfur-containing analogs, double bond- and triple bond-containing analogs, aromatic moiety-containing analogs, nitrated analogs and halogenated analogs.

  本发明揭示了一种抑制寄生虫活动的方法，其中可以通过将所述GPI锚中选择的肉豆蔻酸类似物包含其中来影响所述寄生虫的生物合成、结构和/或功能，所述肉豆蔻酸类似物包括含有各种杂原子、取代基和不饱和键的酯类类似物、酮羰基类类似物、含硫类类似物、双键和三键含有类类似物、芳香基含有类类似物、硝基类类似物和卤代类类似物。
• Tetradecadienoic acid, a glycosyl phosphatidylinositol (GPI) analogue
  申请人：Washington University

  公开号：US05760259A1

  公开（公告）日：1998-06-02

  A method of inhibiting parasitic activity is disclosed in which the biosynthesis, structure and/or function of the glycotyl phosphatidylinositol (GPI) anchor of said parasite may be affected by incorporating into said GPI anchor selected analogs of myristic acid containing various heteroatoms, substituents and unsaturated bonds, including ester-containing analogs, ketocarbonyl-containing analogs, sulfur-containing analogs, double bond- and triple bond-containing analogs, aromatic moiety-containing analogs, nitrated analogs and halogenated analogs.

  本发明揭示了一种抑制寄生活动的方法，其中可以通过将所选肉豆蔻酸的类似物包含到所述寄生物的糖脂磷酰肌醇（GPI）锚中，影响所述 GPI 锚的生物合成、结构和/或功能，其中所选肉豆蔻酸的类似物包括含有各种杂原子、取代基和不饱和键的酯类类似物、酮基含量类似物、硫含量类似物、双键和三键含量类似物、芳香基团含量类似物、硝基类似物和卤代类似物。
• Furyl containing fatty acids, glycosyl phosphatidylinositol (GPI)
  申请人：Washington University

  公开号：US06048989A1

  公开（公告）日：2000-04-11

  A method of inhibiting parasitic activity is disclosed in which the biosynthesis, structure and/or function of the glycosyl phosphatidylinositol (GPI) anchor of said parasite may be affected by incorporating into said GPI anchor selected analogs of myristic acid containing various heteroatoms, substituents and unsaturated bonds, including ester-containing analogs, ketocarbonyl-containing analogs, sulfur-containing analogs, double bond- and triple bond-containing analogs, aromatic moiety-containing analogs, nitrated analogs and halogenated analogs.

  本发明揭示了一种抑制寄生活动的方法，其中通过将所选肉豆蔻酸的类似物纳入所述寄生物的磷脂酰肌醇醇磷脂（GPI）锚定物中，影响所述寄生物的GPI锚定物的生物合成、结构和/或功能，所述类似物包括含有各种杂原子、取代基和不饱和键的肉豆蔻酸酯类似物、酮羰基含有类似物、含硫类似物、双键和三键含有类似物、芳香基团含有类似物、硝化类似物和卤代类似物。
• Ring-closure reactions. 14. Kinetics of macrocyclization by the intramolecular acylation of thiophene and benzothiophene compounds
  作者：C. Galli、G. Illuminati、L. Mandolini

  DOI：10.1021/jo01290a022

  日期：1980.1