Trifluoro-methanesulfonic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester | 111727-02-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: Trifluoro-methanesulfonic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester
• 英文别名: [(2R,3S,5S)-2-(6-aminopurin-9-yl)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-yl] trifluoromethanesulfonate
• CAS: 111727-02-7
• 化学式: C₃₂H₃₀F₃N₅O₇S
• 分子量: 685.681
• InChiKey: VUCOZVUPVZLTOE-BRWNIOCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  158
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到9-{(2R,3R,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-fluoro-tetrahydro-furan-2-yl}-9H-purin-6-ylamine
  参考文献：
  名称：

  Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV

  摘要：

  2',3'-Dideoxy purine nucleosides have anti-HIV activity in vitro and the inosine analogue is being clinically evaluated. The instability of these compounds toward acidic conditions complicates oral administration. The effect of the addition of a fluorine atom to the 2'-position was investigated by preparing the fluorine-containing 2'-erythro and 2'-threo isomers of ddA and the threo isomer of ddI. All fluorine-containing compounds were indefinitely stable to acidic conditions which completely decomposed ddI (1) and ddA (2) in minutes. While the fluorine-containing erythro isomer, 5, was inactive, the threo isomers, 2'-F-dd-ara-A (3) and 2'-F-dd-ara-I (4), were just as potent and active in protecting CD4+ ATH8 cells from the cytopathogenic effects of HIV-1 as the parent drugs. Exposure to pH 1 at 37 degrees C prior to testing destroyed the activity of ddA and ddI but left the anti-HIV properties of 3 and 4 unchanged. The fluorinated analogues also protected cells exposed to HIV-2 and inhibited gag gene product expression but not as effectively as the parent compounds. The fluorine-containing analogues appear to be somewhat more toxic in vitro to the antigen- and mitogen-driven proliferation of immunocompetent cells than their corresponding parent compounds.

  DOI：

  10.1021/jm00165a015
• 作为产物：
  描述：

  3'-deoxydenosine 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 作用下， 反应 19.0h， 生成 Trifluoro-methanesulfonic acid (2R,3S,5S)-2-(6-amino-purin-9-yl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV

  摘要：

  2',3'-Dideoxy purine nucleosides have anti-HIV activity in vitro and the inosine analogue is being clinically evaluated. The instability of these compounds toward acidic conditions complicates oral administration. The effect of the addition of a fluorine atom to the 2'-position was investigated by preparing the fluorine-containing 2'-erythro and 2'-threo isomers of ddA and the threo isomer of ddI. All fluorine-containing compounds were indefinitely stable to acidic conditions which completely decomposed ddI (1) and ddA (2) in minutes. While the fluorine-containing erythro isomer, 5, was inactive, the threo isomers, 2'-F-dd-ara-A (3) and 2'-F-dd-ara-I (4), were just as potent and active in protecting CD4+ ATH8 cells from the cytopathogenic effects of HIV-1 as the parent drugs. Exposure to pH 1 at 37 degrees C prior to testing destroyed the activity of ddA and ddI but left the anti-HIV properties of 3 and 4 unchanged. The fluorinated analogues also protected cells exposed to HIV-2 and inhibited gag gene product expression but not as effectively as the parent compounds. The fluorine-containing analogues appear to be somewhat more toxic in vitro to the antigen- and mitogen-driven proliferation of immunocompetent cells than their corresponding parent compounds.

  DOI：

  10.1021/jm00165a015

文献信息

• MARQUEZ, VICTOR E.;TSENG, CHRISTOPHER K. -H.;MITSUYA, HIROAKI;AOKI, SHIZU+, J. MED. CHEM., 33,(1990) N, C. 978-985
  作者：MARQUEZ, VICTOR E.、TSENG, CHRISTOPHER K. -H.、MITSUYA, HIROAKI、AOKI, SHIZU+

  DOI：——

  日期：——