MCC-478 | 193681-12-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: MCC-478
• 英文别名: Phosphonic acid,P-[[2-[2-amino-6-[(4-methoxyphenyl)thio]-9H-purin-9-yl]ethoxy]methyl]-,bis(2,2,2-trifluoroethyl) ester；9-[2-[bis(2,2,2-trifluoroethoxy)phosphorylmethoxy]ethyl]-6-phenylsulfanylpurin-2-amine
• CAS: 193681-12-8
• 化学式: C₁₈H₁₈F₆N₅O₄PS
• 分子量: 545.402
• InChiKey: JJLWXCPEQYXFFT-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85℃
• 沸点：
  671.5±65.0 °C(Predicted)
• 密度：
  1.60

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  140
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  bis(trifluoroethyl) (2-iodoethoxy)methylphosphonate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 MCC-478
  参考文献：
  名称：

  2-Amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl]purine Bis(2,2,2-trifluoroethyl) Esters as Novel HBV-Specific Antiviral Reagents

  摘要：

  Novel 2-amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl] purine bis(2,2,2-trifluoroethyl) esters were synthesized and evaluated for antihepatitis B virus (HBV) activity in vitro using HB611, HuH-6 cell line, stably transfected with the HBV genome. Among the compounds synthesized, 2-amino-6-phenylthio-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (8), 2-amino-6-(4-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl] purine bis(2,2,2-trifluoroethyl) ester (16), 2-amino-6-(3-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (17), and 2-amino-6-(2-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (18) showed considerably high anti-HBV activity, as represented by IC50 values of 0.05, 0.03, 0.04, and 0.08 muM, respectively, and exhibited low cytotoxicity, as represented by CC50 values of more than 1000 muM. It was suggested that these compounds did not have anti-HIV activity, and compound 8 showed only weak anti-HSV-1 activity. An antiviral agent, 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), which was used as a control in the present study, showed moderate anti-HBV activity, as represented by an IC50 value of 0.2 muM. Furthermore, compound 16 was administered orally to mice at a dose of 100 mg/kg in order to examine its gastrointestinal absorbability. Consequently, the main active metabolite was observed in mouse plasma, with especially high concentrations in the liver.

  DOI：

  10.1021/jm020036x

文献信息

• USE OF COMPOUNDS FOR THE TREATMENT OF PAIN
  申请人：Akron Molecules AG

  公开号：EP2846788A1

  公开（公告）日：2015-03-18
• [EN] USE OF COMPOUNDS FOR THE TREATMENT OF PAIN<br/>[FR] UTILISATION DE COMPOSÉS POUR LE TRAITEMENT DE LA DOULEUR
  申请人：AKRON MOLECULES GMBH

  公开号：WO2013167743A1

  公开（公告）日：2013-11-14

  The present invention relates to new therapies to treat pain and related diseases, as well as pharmaceutical compounds for use in said therapies.
• 2-Amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl]purine Bis(2,2,2-trifluoroethyl) Esters as Novel HBV-Specific Antiviral Reagents
  作者：Kouichi Sekiya、Hideaki Takashima、Naoko Ueda、Naohiro Kamiya、Satoshi Yuasa、Yoshiyuki Fujimura、Masaru Ubasawa

  DOI：10.1021/jm020036x

  日期：2002.7.1

  Novel 2-amino-6-arylthio-9-[2-(phosphonomethoxy)ethyl] purine bis(2,2,2-trifluoroethyl) esters were synthesized and evaluated for antihepatitis B virus (HBV) activity in vitro using HB611, HuH-6 cell line, stably transfected with the HBV genome. Among the compounds synthesized, 2-amino-6-phenylthio-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (8), 2-amino-6-(4-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl] purine bis(2,2,2-trifluoroethyl) ester (16), 2-amino-6-(3-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (17), and 2-amino-6-(2-methoxyphenylthio)-9-[2-(phosphonomethoxy)ethyl]purine bis(2,2,2-trifluoroethyl) ester (18) showed considerably high anti-HBV activity, as represented by IC50 values of 0.05, 0.03, 0.04, and 0.08 muM, respectively, and exhibited low cytotoxicity, as represented by CC50 values of more than 1000 muM. It was suggested that these compounds did not have anti-HIV activity, and compound 8 showed only weak anti-HSV-1 activity. An antiviral agent, 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), which was used as a control in the present study, showed moderate anti-HBV activity, as represented by an IC50 value of 0.2 muM. Furthermore, compound 16 was administered orally to mice at a dose of 100 mg/kg in order to examine its gastrointestinal absorbability. Consequently, the main active metabolite was observed in mouse plasma, with especially high concentrations in the liver.