14-methylthio-tetradecanoic acid | 307924-54-5

• 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: 14-methylthio-tetradecanoic acid
• 英文别名: S-methyl-14-thiomyristic acid；14-Methylsulfanyltetradecanoic acid
• CAS: 307924-54-5
• 化学式: C₁₅H₃₀O₂S
• 分子量: 274.468
• InChiKey: XUGPBGGPVQTVBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  14-methylthio-tetradecanoic acid 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以88%的产率得到14-methylsulfonyltetradecanoic acid
  参考文献：
  名称：

  Evaluation of Methylthio-, Methylsulfinyl-, and Methylsulfonyl-Analogs of Alkanes and Alkanoic Acids as Cardiac Inotropic and Antifungal Agents

  摘要：

  A group of alkane and alkanoic acid compounds of general formula MeS(O)m(CH2)nR [m = 0-2; n = 1, 5, 13; R = Me, CO2H(Na)] were synthesized for evaluation as cardiac inotropic and antifungal agents. Inotropic activity was determined as the ability of the test compound to modulate in vitro guinea pig atrium contractility. The oxidation state of the S-atom was an important determinant of inotropic modulation since the thio (m = 0) analogs exhibited a positive inotropic effect. In contrast, the sulfinyl (m = 1) and sulfonyl (m = 2) analogs exhibited a negative inotropic effect. A pentyl spacer (n = 5) provided the largest positive or negative inotropic effect. The relative positive, and negative, inotropic potency orders with respect to the R-substituent were Me > or = CO2H, and CO2Na > or = Me, respectively. The most potent positive inotrope MeS(CH2)5Me (EC50 = 4.49 x 10(-6) M) could serve as a useful lead-compound for the design of a new class of positive inotropic agents. In a broad spectrum antifungal screen, the minimal inhibitory concentration (MIC) range for the five most active compounds was MeSO2(CH2)5Me (0.46-1.83 mM), MeS(CH2)13Me (0.31-1.23 mM), MeSO(CH2)13Me (< 0.009-1.87 mM), MeSO2(CH2)13Me (0.27-1.09 mM), and MeS(CH2)13CO2H (0.27-1.09 mM), relative to the reference drug Ampotericin B (< 0.0002-0.002 mM). The most active antifungal agent MeSO(CH2)13Me was selective against C. guillermondi, C. neoformans, S. cerevisiae, and A. fumigatus (strain TIMM 1776).

  DOI：

  10.1002/1521-4184(20009)333:9<293::aid-ardp293>3.0.co;2-2
• 作为产物：
  描述：

  14-溴十四烷酸 、 sodium thiomethoxide 以 甲醇 为溶剂， 反应 12.0h， 以71.8%的产率得到14-methylthio-tetradecanoic acid
  参考文献：
  名称：

  Development of 11C-Labeled ω-sulfhydryl fatty acid tracer for myocardial imaging with PET

  摘要：

  [C-11]-S-methyl-16-thiopalmitic acid (a) was developed with excellent heart-to-background uptake ratios and higher retention in heart. Myocardial uptake and metabolism of the tracer is markedly higher CPT I dependent. When compared to [C-11]-S-methyl-14-thiomyristic acid (b), [C-11]-S-methyl-12-thiododecanoic acid (c) and [C-11]-palmitate, a showed an early high uptake and a significantly slower late clearance in heart and a prolonged myocardial elimination half-life (30 min). Analysis of heart tissue and urine samples showed that a was metabolized via beta-oxidation in myocardium. Small animal PET images of the accumulation of a in the rat myocardium were clearly superior to [C-11]-palmitate. These initial studies suggest that a could be a potentially useful clinical PET tracer to assess myocardial fatty acid metabolism. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.062

文献信息

• Development of 11C-Labeled ω-sulfhydryl fatty acid tracer for myocardial imaging with PET
  作者：Xiangxiang Wu、Peizhi Wang、Ruixin Liu、Huahui Zeng、Fangfang Chao、Hao Liu、Caiyun Xu、Haifeng Hou、Qiong Yao

  DOI：10.1016/j.ejmech.2017.10.062

  日期：2018.1

  [C-11]-S-methyl-16-thiopalmitic acid (a) was developed with excellent heart-to-background uptake ratios and higher retention in heart. Myocardial uptake and metabolism of the tracer is markedly higher CPT I dependent. When compared to [C-11]-S-methyl-14-thiomyristic acid (b), [C-11]-S-methyl-12-thiododecanoic acid (c) and [C-11]-palmitate, a showed an early high uptake and a significantly slower late clearance in heart and a prolonged myocardial elimination half-life (30 min). Analysis of heart tissue and urine samples showed that a was metabolized via beta-oxidation in myocardium. Small animal PET images of the accumulation of a in the rat myocardium were clearly superior to [C-11]-palmitate. These initial studies suggest that a could be a potentially useful clinical PET tracer to assess myocardial fatty acid metabolism. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Evaluation of Methylthio-, Methylsulfinyl-, and Methylsulfonyl-Analogs of Alkanes and Alkanoic Acids as Cardiac Inotropic and Antifungal Agents
  作者：Nadeem Iqbal、Carol-Anne McEwen、Soroush Sardari、Mohsen Daneshtalab、Edward E. Knaus

  DOI：10.1002/1521-4184(20009)333:9<293::aid-ardp293>3.0.co;2-2

  日期：2000.9

  A group of alkane and alkanoic acid compounds of general formula MeS(O)m(CH2)nR [m = 0-2; n = 1, 5, 13; R = Me, CO2H(Na)] were synthesized for evaluation as cardiac inotropic and antifungal agents. Inotropic activity was determined as the ability of the test compound to modulate in vitro guinea pig atrium contractility. The oxidation state of the S-atom was an important determinant of inotropic modulation since the thio (m = 0) analogs exhibited a positive inotropic effect. In contrast, the sulfinyl (m = 1) and sulfonyl (m = 2) analogs exhibited a negative inotropic effect. A pentyl spacer (n = 5) provided the largest positive or negative inotropic effect. The relative positive, and negative, inotropic potency orders with respect to the R-substituent were Me > or = CO2H, and CO2Na > or = Me, respectively. The most potent positive inotrope MeS(CH2)5Me (EC50 = 4.49 x 10(-6) M) could serve as a useful lead-compound for the design of a new class of positive inotropic agents. In a broad spectrum antifungal screen, the minimal inhibitory concentration (MIC) range for the five most active compounds was MeSO2(CH2)5Me (0.46-1.83 mM), MeS(CH2)13Me (0.31-1.23 mM), MeSO(CH2)13Me (< 0.009-1.87 mM), MeSO2(CH2)13Me (0.27-1.09 mM), and MeS(CH2)13CO2H (0.27-1.09 mM), relative to the reference drug Ampotericin B (< 0.0002-0.002 mM). The most active antifungal agent MeSO(CH2)13Me was selective against C. guillermondi, C. neoformans, S. cerevisiae, and A. fumigatus (strain TIMM 1776).