methyl 18-bromo-4-thiaoctadecanoate | 83518-11-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 18-bromo-4-thiaoctadecanoate
• 英文别名: methyl β-(14-bromotetradecylthio)-propionate；Methyl 3-(14-bromotetradecylsulfanyl)propanoate
• CAS: 83518-11-0
• 化学式: C₁₈H₃₅BrO₂S
• 分子量: 395.445
• InChiKey: IFWYTGXLMJTFMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  22
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 18-bromo-4-thiaoctadecanoate 在 四丁基氟化铵 、 水 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 74.0h， 以61.6%的产率得到18-fluoro-4-thiaoctadecanoic acid
  参考文献：
  名称：

  Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

  摘要：

  In vivo imaging of regional fatty acid oxidation (FAO) rates would have considerable potential for evaluation of mammalian diseases. We have synthesized and evaluated F-18-labeled thia fatty acid analogues as metabolically trapped FAO probes to understand the effect of chain length, degree of unsaturation, and placement of the thia substituent on myocardial uptake and retention. 18-[F-18]Fluoro-4-thia-(9Z)-octadec-9-enoic acid (3) showed excellent heart/background radioactivity concentration ratios along with highest retention in heart and liver. Pretreatment of rats with the CPT-1 inhibitor, POCA, caused >80% reduction in myocardial uptake of 16-[F-18]fluoro-4-thiahexadecanoic acid (2) and 3, indicating high specificity for FAO. In contrast, 18-[F-18]fluoro-4-thiaoctadecanoic acid (4) showed dramatically reduced myocardial uptake and blunted response to POCA. 18-[F-18]Fluoro-6-thiaoctadecanoic acid (5) showed moderate myocardial uptake and no sensitivity of myocardial uptake to POCA. The results demonstrate relationships between structures of F-18-labeled thia fatty acid and uptake and their utility as FAO probes in various tissues.

  DOI：

  10.1021/jm301345v
• 作为产物：
  描述：

  十四烷二酸 在 硫酸 、 氢溴酸 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.75h， 生成 methyl 18-bromo-4-thiaoctadecanoate
  参考文献：
  名称：

  Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes

  摘要：

  In vivo imaging of regional fatty acid oxidation (FAO) rates would have considerable potential for evaluation of mammalian diseases. We have synthesized and evaluated F-18-labeled thia fatty acid analogues as metabolically trapped FAO probes to understand the effect of chain length, degree of unsaturation, and placement of the thia substituent on myocardial uptake and retention. 18-[F-18]Fluoro-4-thia-(9Z)-octadec-9-enoic acid (3) showed excellent heart/background radioactivity concentration ratios along with highest retention in heart and liver. Pretreatment of rats with the CPT-1 inhibitor, POCA, caused >80% reduction in myocardial uptake of 16-[F-18]fluoro-4-thiahexadecanoic acid (2) and 3, indicating high specificity for FAO. In contrast, 18-[F-18]fluoro-4-thiaoctadecanoic acid (4) showed dramatically reduced myocardial uptake and blunted response to POCA. 18-[F-18]Fluoro-6-thiaoctadecanoic acid (5) showed moderate myocardial uptake and no sensitivity of myocardial uptake to POCA. The results demonstrate relationships between structures of F-18-labeled thia fatty acid and uptake and their utility as FAO probes in various tissues.

  DOI：

  10.1021/jm301345v

文献信息

• Neue schwefelhaltige Phospholipide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
  申请人：BOEHRINGER MANNHEIM GMBH

  公开号：EP0050327B1

  公开（公告）日：1984-06-20
• US4444766A
  申请人：——

  公开号：US4444766A

  公开（公告）日：1984-04-24
• Structure Dependence of Long-Chain [¹⁸F]Fluorothia Fatty Acids as Myocardial Fatty Acid Oxidation Probes
  作者：Mukesh K. Pandey、Anthony P. Belanger、Shuyan Wang、Timothy R. DeGrado

  DOI：10.1021/jm301345v

  日期：2012.12.13

  In vivo imaging of regional fatty acid oxidation (FAO) rates would have considerable potential for evaluation of mammalian diseases. We have synthesized and evaluated F-18-labeled thia fatty acid analogues as metabolically trapped FAO probes to understand the effect of chain length, degree of unsaturation, and placement of the thia substituent on myocardial uptake and retention. 18-[F-18]Fluoro-4-thia-(9Z)-octadec-9-enoic acid (3) showed excellent heart/background radioactivity concentration ratios along with highest retention in heart and liver. Pretreatment of rats with the CPT-1 inhibitor, POCA, caused >80% reduction in myocardial uptake of 16-[F-18]fluoro-4-thiahexadecanoic acid (2) and 3, indicating high specificity for FAO. In contrast, 18-[F-18]fluoro-4-thiaoctadecanoic acid (4) showed dramatically reduced myocardial uptake and blunted response to POCA. 18-[F-18]Fluoro-6-thiaoctadecanoic acid (5) showed moderate myocardial uptake and no sensitivity of myocardial uptake to POCA. The results demonstrate relationships between structures of F-18-labeled thia fatty acid and uptake and their utility as FAO probes in various tissues.