6-amino-9-[5-O-(4,4'-dimethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl]-9H-purine | 111727-01-6

• 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: 6-amino-9-[5-O-(4,4'-dimethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl]-9H-purine
• 英文别名: (2R,3S,5S)-2-(6-aminopurin-9-yl)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]oxolan-3-ol
• CAS: 111727-01-6
• 化学式: C₃₁H₃₁N₅O₅
• 分子量: 553.618
• InChiKey: NOBMIXQDCWEUCH-BRWNIOCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-amino-9-[5-O-(4,4'-dimethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl]-9H-purine 在 四丁基氟化铵 、 sodium hydride 、 三氯乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.58h， 生成 [(2S,4R,5R)-5-(6-氨基嘌呤-9-基)-4-氟四氢呋喃-2-基]甲醇
  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：

  N-[9-((2R,3S,5S)-3-Trimethylsilanyloxy-5-trimethylsilanyloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide 在 氨 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 64.5h， 生成 6-amino-9-[5-O-(4,4'-dimethoxytrityl)-3-deoxy-β-D-threo-pentofuranosyl]-9H-purine
  参考文献：
  名称：

  Synthesis of the antibiotically active part of agrocin 84

  摘要：

  Phosphitylation of bis-O-silylated threo-2,3-dihydroxy-4-methylpentanamide and condensation of the resulting N-acylphosphorodiamidite with 2'-O-acetyl-3'-deoxyarabinoadenosine led, after oxidation and deprotection, to the isolation of the title compound. (C) 1998 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4039(98)00888-0

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：——
• Synthesis of the antibiotically active part of agrocin 84
  作者：Dmitri Filippov、Cornelis M Timmers、Aaron R Roerdink、Gijs A van der Marel、Jacques H van Boom

  DOI：10.1016/s0040-4039(98)00888-0

  日期：1998.7

  Phosphitylation of bis-O-silylated threo-2,3-dihydroxy-4-methylpentanamide and condensation of the resulting N-acylphosphorodiamidite with 2'-O-acetyl-3'-deoxyarabinoadenosine led, after oxidation and deprotection, to the isolation of the title compound. (C) 1998 Elsevier Science Ltd. Ail rights reserved.
• Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV
  作者：Victor E. Marquez、Christopher K. H. Tseng、Hiroaki Mitsuya、Shizuko Aoki、James A. Kelley、Harry Ford、Jeri S. Roth、Samuel Broder、David G. Johns、John S. Driscoll

  DOI：10.1021/jm00165a015

  日期：1990.3

  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.