5-(2',3'-O,O-isopropylidene-1'-deoxy-β-D-ribofuranosyl)thiophene-2-carbonitrile | 763139-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2',3'-O,O-isopropylidene-1'-deoxy-β-D-ribofuranosyl)thiophene-2-carbonitrile
• 英文别名: 2,2-dimethyl-4-(2-cyanothiophen-5-yl)-6-hydroxymethyltetrahydrofuro[3,4-a][1,3]dioxole；5-[(3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]thiophene-2-carbonitrile
• CAS: 763139-81-7
• 化学式: C₁₃H₁₅NO₄S
• 分子量: 281.332
• InChiKey: ZXFBWGTTXULQTE-KXGXSXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2',3'-O,O-isopropylidene-1'-deoxy-β-D-ribofuranosyl)thiophene-2-carbonitrile 在 磷酸三乙酯 、 magnesium sulfate 、 manganese(ll) chloride 、 三氯氧磷 作用下， 以 formamide 为溶剂， 反应 96.0h， 生成 [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(5-cyanothiophen-2-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
  参考文献：
  名称：

  Novel nicotinamide adenine dinucleotide analogues as selective inhibitors of NAD+-dependent enzymes

  摘要：

  Three novel dinucleotide analogues of nicotinamide adenine dinucleotide (NAD(+)) have been synthesised from D-ribonolactone. These compounds incorporate a thiophene moiety in place of nicotinamide and are hydrolytically stable. They have been evaluated as inhibitors of adenosine diphosphate ribosyl cyclase, glutamate dehydrogenase and Sir2 acyltransferase activities. Enzyme specificity and a high level of inhibition was observed for the dehydrogenase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.091
• 作为产物：
  描述：

  卡培他滨杂质25 在 三乙基硅烷 、 4-二甲氨基吡啶 、 potassium permanganate 、 正丁基锂 、 三氟甲磺酸三甲基硅酯 、 HCR-W₂ H⁺-Dowex resin 、 三乙胺 、 二异丙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 、 正戊烷 为溶剂， 反应 17.5h， 生成 5-(2',3'-O,O-isopropylidene-1'-deoxy-β-D-ribofuranosyl)thiophene-2-carbonitrile
  参考文献：
  名称：

  Novel nicotinamide adenine dinucleotide analogues as selective inhibitors of NAD+-dependent enzymes

  摘要：

  Three novel dinucleotide analogues of nicotinamide adenine dinucleotide (NAD(+)) have been synthesised from D-ribonolactone. These compounds incorporate a thiophene moiety in place of nicotinamide and are hydrolytically stable. They have been evaluated as inhibitors of adenosine diphosphate ribosyl cyclase, glutamate dehydrogenase and Sir2 acyltransferase activities. Enzyme specificity and a high level of inhibition was observed for the dehydrogenase. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.091