3-oxo-4-thiofuro[3,4-c]pyridine | 178970-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-oxo-4-thiofuro[3,4-c]pyridine
• 英文别名: 6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]-pyridin-3(1)-one；6-methyl-4-thioxo-4,5-dihydrofuro[3,-c]pyridin-3(1H)-one；6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-one；6-methyl-4-sulfanylidene-1,5-dihydrofuro[3,4-c]pyridin-3-one
• CAS: 178970-86-0
• 化学式: C₈H₇NO₂S
• mdl: MFCD00541961
• 分子量: 181.215
• InChiKey: CFMFFLDDOANTMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  70.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘乙酸 、 3-oxo-4-thiofuro[3,4-c]pyridine 在 potassium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到[(6-methyl-3-oxo-1,3-dihydrofuro[3,4-c]pyridin-4-yl)sulfanyl]acetic acid
  参考文献：
  名称：

  Synthesis of novel 6-methyl-4-sulfanylfuro[3,4-с]pyridin-3(1H)-ones

  摘要：

  Alkylation of 6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-one in an alkaline medium proceeds regioselectively at the sulfur atom to form sulfanyl derivatives.

  DOI：

  10.1007/s10593-019-02584-5
• 作为产物：
  描述：

  4-chloro-6-methyl-1H-furo<3,4-c>pyridin-3-one 在 硫脲 作用下， 以 正丁醇 为溶剂， 反应 10.0h， 以66%的产率得到3-oxo-4-thiofuro[3,4-c]pyridine
  参考文献：
  名称：

  Kaigorodova, E. A.; Kvak, S. N.; Ugrak, B. I., Russian Journal of Organic Chemistry, 1995, vol. 31, # 12, p. 1650 - 1652

  摘要：

  DOI：

文献信息

• Dihydrofuro[3,4<i>-c</i>]pyridinones as Inhibitors of the Cytolytic Effects of the Pore-Forming Glycoprotein Perforin
  作者：Gersande Lena、Joseph A. Trapani、Vivien R. Sutton、Annette Ciccone、Kylie A. Browne、Mark J. Smyth、William A. Denny、Julie A. Spicer

  DOI：10.1021/jm801063n

  日期：2008.12.11

  Dihydrofuro[3,4-c]pyridinones are the first class of small molecules reported to inhibit the cytolytic effects of the lymphocyte toxin perforin. A lead structure was identified from a high throughput screen, and a series of analogues were designed and prepared to explore structure-activity relationships around the core bicyclic thioxofuropyridinone and pendant furan ring. This resulted in the identification of a submicromolar inhibitor of the perforin-induced lysis of Jurkat T-lymphoma cells.
• Synthesis and anti-influenza virus activity of 4-oxo- or thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-ones
  作者：Ye Jin Jang、Raghavendra Achary、Hye Won Lee、Hyo Jin Lee、Chong-Kyo Lee、Soo Bong Han、Young-Sik Jung、Nam Sook Kang、Pilho Kim、Meehyein Kim

  DOI：10.1016/j.antiviral.2014.04.013

  日期：2014.7

  A target-free approach was applied to discover anti-influenza viral compounds, where influenza infected Madin-Darby canine kidney cells were treated 7500 different small organic chemicals individually and reduction of virus-induced cytopathic effect was measured. One of the hit compounds was (Z)-1-((5-fluoro-1H-indol-3-yl)methylene)-6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-one (15a) with half-maximal effective concentrations of 17.4-21.1 mu M against influenza A/H1N1, A/H3N2 and B viruses without any cellular toxicity at 900 mu M. To investigate the structure-activity relationships, two dozens of the hit analogs were synthesized. Among them, 15g, 15j, 15q, 15s, 15t and 15x had anti-influenza viral activity comparable or superior to that of the initial hit. The anti-influenza viral compounds efficiently suppressed not only viral protein level of the infected cells but also production of viral progeny in the culture supernatants in a dose-dependent manner. Based on a mode-of-action study, they did not affect virus entry or RNA replication. Instead, they suppressed viral neuraminidase activity. This study is the first to demonstrate that dihydrofuropyridinones could serve as lead compounds for the discovery of alternative influenza virus inhibitors. (C) 2014 Elsevier B.V. All rights reserved.
• Investigation of furopyridines. Part 7. Synthesis and antibacterial activity of 1-arylidene-3-oxo-4-thioxofuro[3,4-c]-pyridines
  作者：E. A. Kaigorodova、S. N. Mikhailichenko、V. K. Vasilin、V. I. Terekhov、V. G. Kul'nevich

  DOI：10.1007/bf02464207

  日期：1998.4
• Synthesis of novel 6-methyl-4-sulfanylfuro[3,4-с]pyridin-3(1H)-ones
  作者：Elena А. Kaigorodova、Natal’ya M. Gantsgorn、Leonid D. Konyushkin、Gennady D. Krapivin

  DOI：10.1007/s10593-019-02584-5

  日期：2019.11

  Alkylation of 6-methyl-4-thioxo-4,5-dihydrofuro[3,4-c]pyridin-3(1H)-one in an alkaline medium proceeds regioselectively at the sulfur atom to form sulfanyl derivatives.
• Kaigorodova, E. A.; Kvak, S. N.; Ugrak, B. I., Russian Journal of Organic Chemistry, 1995, vol. 31, # 12, p. 1650 - 1652
  作者：Kaigorodova, E. A.、Kvak, S. N.、Ugrak, B. I.、Zaplishnyi, V. N.、Kul'nevich, V. G.

  DOI：——

  日期：——