methyl 4-iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate | 138787-01-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡唑核糖核苷和核糖核苷酸
• 英文名称: methyl 4-iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate
• 英文别名: N-(beta-d-ribofuranosyl) 3-carbomethoxy-4-iodopyrazole；methyl 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-iodopyrazole-3-carboxylate
• CAS: 138787-01-6
• 化学式: C₁₀H₁₃IN₂O₆
• 分子量: 384.128
• InChiKey: WFWXOSGVJSTSOE-ZOQUXTDFSA-N

物化性质

• 沸点：
  567.5±50.0 °C(Predicted)
• 密度：
  2.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 4-iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate 在 咪唑 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 49.0h， 生成 1-[(2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-4-iodo-1H-pyrazole-3-carboxylic acid butyl ester
  参考文献：
  名称：

  Manfredini, Stefano; Bazzanini, Rita; Baraldi, Pier Giovanni, Medicinal Chemistry Research, 1996, vol. 6, # 5, p. 293 - 311

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 1-(β-D-2',3',5'-tri-O-benzoylribofuranosyl)-4-iodo-pyrazole-3-carboxylate 在 sodium methylate 作用下， 以75%的产率得到methyl 4-iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate
  参考文献：
  名称：

  Design, synthesis and antiproliferative activity of methyl 4-Iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate and related compounds

  摘要：

  In a SAR study on azole-related nucleosides we have designed some pyrazole-nucleoside analogs characterised, for the first time, by a carboxylic ester moiety. 4-Iodo-1-beta-D-ribofuranosyl-pyrazole-3-carboxylate showed a wide spectrum of antiproliferative activity and a particularly low cytotoxicity against resting PBL, being, unlike the other azole nucleosides, more active than the corresponding primary amide. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00216-8

文献信息

• Design, synthesis and antiproliferative activity of methyl 4-Iodo-1-β-D-ribofuranosyl-pyrazole-3-carboxylate and related compounds
  作者：Stefano Manfredini、Rita Bazzanini、Pier Giovanni Baraldi、Daniele Simoni、Silvia Vertuani、Alessandra Pani、Elisabetta Pinna、Franca Scintu、Donatella Lichino、Paolo La Colla

  DOI：10.1016/0960-894x(96)00216-8

  日期：1996.6

  In a SAR study on azole-related nucleosides we have designed some pyrazole-nucleoside analogs characterised, for the first time, by a carboxylic ester moiety. 4-Iodo-1-beta-D-ribofuranosyl-pyrazole-3-carboxylate showed a wide spectrum of antiproliferative activity and a particularly low cytotoxicity against resting PBL, being, unlike the other azole nucleosides, more active than the corresponding primary amide. Copyright (C) 1996 Elsevier Science Ltd
• Manfredini, Stefano; Bazzanini, Rita; Baraldi, Pier Giovanni, Medicinal Chemistry Research, 1996, vol. 6, # 5, p. 293 - 311
  作者：Manfredini, Stefano、Bazzanini, Rita、Baraldi, Pier Giovanni、Simoni, Daniele、Vertuani, Silvia、Pani, Alessandra、Pinna, Elisabetta、Scintu, Franca、De Montis, Antonella、La Colla, Paolo

  DOI：——

  日期：——