Oxetan-2-yl-acetaldehyde | 928758-02-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Oxetan-2-yl-acetaldehyde
• 英文别名: 2-(Oxetan-2-yl)acetaldehyde
• CAS: 928758-02-5
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: VRKBXGVCHFUJEU-UHFFFAOYSA-N

物化性质

• 沸点：
  161.3±13.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Oxetan-2-yl-acetaldehyde 在 sodium hydroxide 、 Hydroquinone 1,4-phthalazinediyl diether 、 次氯酸叔丁酯 、 三乙胺 作用下， 生成 3-Benzyloxycarbonylamino-2-hydroxy-4-oxetan-2-yl-butyric acid tert-butyl ester
  参考文献：
  名称：

  Discovery of (1R,5S)-N-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]- 3-[2(S)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]- 6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(S)-carboxamide (SCH 503034), a Selective, Potent, Orally Bioavailable Hepatitis C Virus NS3 Protease Inhibitor:  A Potential Therapeutic Agent for the Treatment of Hepatitis C Infection

  摘要：

  Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-alpha or polyethylene glycol (PEG)-interferon-alpha alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.

  DOI：

  10.1021/jm060325b

文献信息

• Discovery of (1<i>R</i>,5<i>S</i>)-<i>N</i>-[3-Amino-1-(cyclobutylmethyl)-2,3-dioxopropyl]- 3-[2(<i>S</i>)-[[[(1,1-dimethylethyl)amino]carbonyl]amino]-3,3-dimethyl-1-oxobutyl]- 6,6-dimethyl-3-azabicyclo[3.1.0]hexan-2(<i>S</i>)-carboxamide (SCH 503034), a Selective, Potent, Orally Bioavailable Hepatitis C Virus NS3 Protease Inhibitor:  A Potential Therapeutic Agent for the Treatment of Hepatitis C Infection
  作者：Srikanth Venkatraman、Stéphane L. Bogen、Ashok Arasappan、Frank Bennett、Kevin Chen、Edwin Jao、Yi-Tsung Liu、Raymond Lovey、Siska Hendrata、Yuhua Huang、Weidong Pan、Tejal Parekh、Patrick Pinto、Veljko Popov、Russel Pike、Sumei Ruan、Bama Santhanam、Bancha Vibulbhan、Wanli Wu、Weiying Yang、Jianshe Kong、Xiang Liang、Jesse Wong、Rong Liu、Nancy Butkiewicz、Robert Chase、Andrea Hart、Sony Agrawal、Paul Ingravallo、John Pichardo、Rong Kong、Bahige Baroudy、Bruce Malcolm、Zhuyan Guo、Andrew Prongay、Vincent Madison、Lisa Broske、Xiaoming Cui、Kuo-Chi Cheng、Yunsheng Hsieh、Jean-Marc Brisson、Danial Prelusky、Walter Korfmacher、Ronald White、Susan Bogdanowich-Knipp、Anastasia Pavlovsky、Prudence Bradley、Anil K. Saksena、Ashit Ganguly、John Piwinski、Viyyoor Girijavallabhan、F. George Njoroge

  DOI：10.1021/jm060325b

  日期：2006.10.1

  Hepatitis C virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 170 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-alpha or polyethylene glycol (PEG)-interferon-alpha alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only about 40% of the patients showing sustained virological response. Herein, the SAR leading to the discovery of 70 (SCH 503034), a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been advanced to clinical trials in human beings for the treatment of hepatitis C viral infections is described. X-ray structure of inhibitor 70 complexed with the NS3 protease and biological data are also discussed.