2-(hydroxymethyl)quinoline-4-carboxaldehyde | 1376142-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(hydroxymethyl)quinoline-4-carboxaldehyde
• 英文别名: 2-(Hydroxymethyl)quinoline-4-carbaldehyde；2-(hydroxymethyl)quinoline-4-carbaldehyde
• CAS: 1376142-73-2
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: SCGRGWVZOJMSLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)quinoline-4-carboxaldehyde 在 sodium cyanoborohydride 、 溶剂黄146 、 zinc(II) oxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 4-(((2-((5aS,7S)-methyl-1-oxo-1,5a,6,7,8,9-hexahydropyrano[4,3-b]chromen-7-yl)propylamino)methyl)quinolin-2-yl)methyl acetate
  参考文献：
  名称：

  Synthesis and anti-norovirus activity of pyranobenzopyrone compounds

  摘要：

  During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 mu M and TD50 values of >200 and 96.4 mu M, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.084
• 作为产物：
  描述：

  quinoline-2,4-dicarboxaldehyde 在 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以32%的产率得到2-(hydroxymethyl)quinoline-4-carboxaldehyde
  参考文献：
  名称：

  Synthesis and anti-norovirus activity of pyranobenzopyrone compounds

  摘要：

  During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 mu M and TD50 values of >200 and 96.4 mu M, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.084

文献信息

• Synthesis and anti-norovirus activity of pyranobenzopyrone compounds
  作者：Laxman Pokhrel、Yunjeong Kim、Thi D.T. Nguyen、Allan M. Prior、Jianyu Lu、Kyeong-Ok Chang、Duy H. Hua

  DOI：10.1016/j.bmcl.2012.03.084

  日期：2012.5

  During the last decade, noroviruses have gained media attention as the cause of large scale outbreaks of gastroenteritis on cruise ships, dormitories, nursing homes, etc. Although noroviruses do not multiply in food or water, they can cause large outbreaks because approximately 10-100 virions are sufficient to cause illness in a healthy adult. Recently, it was shown that the activity of acyl-coenzyme A:cholesterol acyltransferase-1 (ACAT1) enzyme may be important in norovirus infection. In search of anti-noroviral agents based on the inhibition of ACAT1, we synthesized and evaluated the inhibitory activities of a class of pyranobenzopyrone molecules containing amino, pyridine, substituted quinolines, or 7,8-benzoquinoline nucleus. Three of the sixteen evaluated compounds possess ED50 values in the low micrometer range. 2-Quinolylmethyl derivative 3A and 4-quinolylmethyl derivative 4A showed ED50 values of 3.4 and 2.4 mu M and TD50 values of >200 and 96.4 mu M, respectively. The identified active compounds are suitable for further modification for the development of anti-norovirus agents. (C) 2012 Elsevier Ltd. All rights reserved.