1-(5-Nitro-furyl)-3-thienyl-propen-(1)-on-(3) | 21494-06-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: 1-(5-Nitro-furyl)-3-thienyl-propen-(1)-on-(3)
• 英文别名: 1--3-<5-nitro-furyl-(2)>-prop-2-en-1-on；3-(5-nitro-furan-2-yl)-1-thiophen-2-yl-propenone；3-(5-Nitrofuran-2-yl)-1-thiophen-2-ylprop-2-en-1-one；3-(5-nitrofuran-2-yl)-1-thiophen-2-ylprop-2-en-1-one
• CAS: 21494-06-4
• 化学式: C₁₁H₇NO₄S
• 分子量: 249.247
• InChiKey: NCJXHQDDCKSBAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-乙酰基噻吩 、 5-硝基糠醛 在 硫酸 、 溶剂黄146 作用下， 生成 1-(5-Nitro-furyl)-3-thienyl-propen-(1)-on-(3)
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives as potent antitubercular agents

  摘要：

  Based on stereoelectronic feature analysis using density functional theory (DFT) at B3LYP/3-21*G level, a series of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives with low LUMO energies (<-0.10 eV); concentrated over the nitro group, furan moiety and alpha,beta-unsaturated carbonyl bridge were envisaged as potential antitubercular agents. The target compounds were prepared by condensation of 5-nitro-2-furaldehyde with various ketones under acidic condition. The compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Rv and their cytotoxicity in VERO cell line. Several synthesized compounds showed good antitubercular activity of <5 mu M along with low cytotoxicity. In particular, compound ((E)-3-(5-nitrofuran-2-yl)-1-(4-(piperidin-1-yl) phenyl) prop-2-en-1-one) (3v) was found to be very potent (MIC: 0.19 mu M) with good selectivity index (MIC90/CC50: > 1800). Thus, this study shows the potential of stereoelectronic property analysis in developing improved nitroaromatics as antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.127

文献信息

• Design, synthesis, and biological evaluation of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives as potent antitubercular agents
  作者：Nilesh R. Tawari、Ranjeet Bairwa、M.K. Ray、M.G.R. Rajan、Mariam S. Degani

  DOI：10.1016/j.bmcl.2010.08.127

  日期：2010.11

  Based on stereoelectronic feature analysis using density functional theory (DFT) at B3LYP/3-21*G level, a series of 4-(5-nitrofuran-2-yl)prop-2-en-1-one derivatives with low LUMO energies (<-0.10 eV); concentrated over the nitro group, furan moiety and alpha,beta-unsaturated carbonyl bridge were envisaged as potential antitubercular agents. The target compounds were prepared by condensation of 5-nitro-2-furaldehyde with various ketones under acidic condition. The compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Rv and their cytotoxicity in VERO cell line. Several synthesized compounds showed good antitubercular activity of <5 mu M along with low cytotoxicity. In particular, compound ((E)-3-(5-nitrofuran-2-yl)-1-(4-(piperidin-1-yl) phenyl) prop-2-en-1-one) (3v) was found to be very potent (MIC: 0.19 mu M) with good selectivity index (MIC90/CC50: > 1800). Thus, this study shows the potential of stereoelectronic property analysis in developing improved nitroaromatics as antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.