quinoline-2,4-dicarboxaldehyde | 52287-46-4

• 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: quinoline-2,4-dicarboxaldehyde
• 英文别名: 2,4-diformylquinoline；quinoline-2,4-dicarbaldehyde；Chinolin-2,4-dicarbaldehyd；2,4-Diformyl-chinolin；2,4-Diformylchinolin
• CAS: 52287-46-4
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: HWLOAAFCSVWBDQ-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C
• 沸点：
  386.5±27.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  quinoline-2,4-dicarboxaldehyde 在 sodium tetrahydroborate 、 zinc(II) oxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (4-formylquinolin-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：

  2-methyl-4-(1,3,5-trioxan-2-yl)quinolone 在 盐酸 、 selenium(IV) oxide 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成 quinoline-2,4-dicarboxaldehyde
  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

• Godard,A. et al., Bulletin de la Societe Chimique de France, 1976, p. 789 - 792
  作者：Godard,A. et al.

  DOI：——

  日期：——
• Seyhan, Istanbul Universitesi Fen Fakultesi Mecmuasi, Seri A: Matematik-Fizik-Kimya, 1951, vol. 16, p. 252
  作者：Seyhan

  DOI：——

  日期：——
• Vismara, Elena; Fontana, Francesca; Minisci, Francesco, Gazzetta Chimica Italiana, 1987, vol. 117, # 2, p. 135 - 136
  作者：Vismara, Elena、Fontana, Francesca、Minisci, Francesco

  DOI：——

  日期：——
• GODARD A.; DUBALLET P.; QUEQUINER G.; PASTOUR P., BULL. SOC. CHIM. FRANCE <BSCF-AS>, 1976, NO 5-6, PART. 2, 789-792
  作者：GODARD A.、 DUBALLET P.、 QUEQUINER G.、 PASTOUR P.

  DOI：——

  日期：——
• VISMARA E.; FONTANA F.; MINISCI F., GAZZ. CHIM. ITAL., 117,(1987) N 2, 135-136
  作者：VISMARA E.、 FONTANA F.、 MINISCI F.

  DOI：——

  日期：——