3-(3-(5-nitrofuran-2-yl)acryloyl)-2H-chromen-2-one | 140399-56-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(3-(5-nitrofuran-2-yl)acryloyl)-2H-chromen-2-one
• 英文别名: 3-[3-(5-nitrofuran-2-yl)prop-2-enoyl]chromen-2-one
• CAS: 140399-56-0
• 化学式: C₁₆H₉NO₆
• 分子量: 311.251
• InChiKey: XMMBXFCEJFZLLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.56
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  磷,[2-羰基-2-(2-羰基-2H-1-苯并吡喃-3-基)乙基]三苯基-,溴化 在 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 3-(3-(5-nitrofuran-2-yl)acryloyl)-2H-chromen-2-one
  参考文献：
  名称：

  Yagodinets, P. I.; Skripskaya, O. V.; Chernyuk, I. N., Journal of general chemistry of the USSR, 1991, vol. 61, # 8.2, p. 1714 - 1719

  摘要：

  DOI：

文献信息

• Microwave-assisted synthesis and evaluation of antimicrobial activity of 3-{3-(s-aryl and s-heteroaromatic)acryloyl}-2<i>H</i>-chromen-2-one derivatives
  作者：Olayinka O. Ajani、Obinna C. Nwinyi

  DOI：10.1002/jhet.298

  日期：——

  analytical and spectral data. All the synthesized compounds were screened for their antibacterial activity and 3-3-(4-dimethylaminophenyl)acryloyl}-2H-chromen-2-one () was discovered to be the most active at minimum inhibitory concentration (MIC) value of 7.8 μg/mL. J. Heterocyclic Chem., (2010).

  在本文中，利用缩合反应的方法对微波作为杂环合成能源的潜在利用进行了探索。3-乙酰香豆素（）与芳族和杂芳族醛形成相应的芳族查耳酮（）和杂芳族查耳酮（ 和 ）分别在1-3分钟内达到良好或优异的产量。化学结构通过分析和光谱数据证实。所有合成的化合物筛选它们的抗菌活性和3- 3-（4-二甲基氨基苯基）丙烯酰基} -2- ħ -色烯-2-酮（发现）在7.8μg/ mL的最小抑菌浓度（MIC）值下活性最高。J.杂环化​​学。（2010）。
• 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.
• Yagodinets, P. I.; Skripskaya, O. V.; Chernyuk, I. N., Journal of general chemistry of the USSR, 1991, vol. 61, # 8.2, p. 1714 - 1719
  作者：Yagodinets, P. I.、Skripskaya, O. V.、Chernyuk, I. N.、Shevchuk, M. I.

  DOI：——

  日期：——