2-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-1,3-噻唑-4-甲腈 | 144660-78-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-1,3-噻唑-4-甲腈
• 英文名称: 4-cyanotiazofurin
• 英文别名: 2-(β-D-ribofuranosyl)thiazole-4-carbonitrile；2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,3-thiazole-4-carbonitrile
• CAS: 144660-78-6
• 化学式: C₉H₁₀N₂O₄S
• 分子量: 242.255
• InChiKey: WCYKZVKCGIDDBF-WCTZXXKLSA-N

物化性质

• 沸点：
  547.1±50.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-1,3-噻唑-4-甲腈 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 27.0h， 生成 2-(β-D-ribofuranosyl)thiazole-4-N-methylcarboxamidine hydrochloride
  参考文献：
  名称：

  Synthesis and Antiviral (RNA) Evaluation of Nucleoside Analogs of Tiazofurin Modified at the Carboxamide Moiety

  摘要：

  The carboxamide functionality of tiazofurin la has been modified to produce the following analogs: carboximidates 5a,b, carboxamidines 6, 10, tetrahydropyrimidine 7, N-glycine 8 and N-glutamine 9. These structural modifications abolished the in vitro antiviral (RNA) activity exhibited by tiazofurin against the flaviviruses (yellow fever and Japanese encephalitis viruses), bunyavirus (Punta Toro virus) and togavirus (Venezuelan equine encephalomyelitis virus). Only carboximidates 5a,b retained marginal activity against bunyaviruses.

  DOI：

  10.1080/15257779508010693
• 作为产物：
  描述：

  2-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)thiazole-4-carbonitrile 在 二甲胺 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以87%的产率得到2-[(2R,3R,4S,5R)-3,4-二羟基-5-(羟基甲基)四氢呋喃-2-基]-1,3-噻唑-4-甲腈
  参考文献：
  名称：

  Synthesis and Antiviral (RNA) Evaluation of Nucleoside Analogs of Tiazofurin Modified at the Carboxamide Moiety

  摘要：

  The carboxamide functionality of tiazofurin la has been modified to produce the following analogs: carboximidates 5a,b, carboxamidines 6, 10, tetrahydropyrimidine 7, N-glycine 8 and N-glutamine 9. These structural modifications abolished the in vitro antiviral (RNA) activity exhibited by tiazofurin against the flaviviruses (yellow fever and Japanese encephalitis viruses), bunyavirus (Punta Toro virus) and togavirus (Venezuelan equine encephalomyelitis virus). Only carboximidates 5a,b retained marginal activity against bunyaviruses.

  DOI：

  10.1080/15257779508010693

文献信息

• Synthesis and Antiviral (RNA) Evaluation of Nucleoside Analogs of Tiazofurin Modified at the Carboxamide Moiety
  作者：Michael J. Phelan、Bjarne Gabrielsen、Jorma J. Kirsi、William M. Shannon、Michael A. Ussery、Louis Barthel-Rosa、Ernst M. Schubert、Ganesh D. Kini、Roland K. Robins

  DOI：10.1080/15257779508010693

  日期：1995.8

  The carboxamide functionality of tiazofurin la has been modified to produce the following analogs: carboximidates 5a,b, carboxamidines 6, 10, tetrahydropyrimidine 7, N-glycine 8 and N-glutamine 9. These structural modifications abolished the in vitro antiviral (RNA) activity exhibited by tiazofurin against the flaviviruses (yellow fever and Japanese encephalitis viruses), bunyavirus (Punta Toro virus) and togavirus (Venezuelan equine encephalomyelitis virus). Only carboximidates 5a,b retained marginal activity against bunyaviruses.