N-(4-mercaptophenyl)-2-oxo-2H-chromene-3-carboxamide | 1001015-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-mercaptophenyl)-2-oxo-2H-chromene-3-carboxamide
• 英文别名: 2-oxo-N-(4-sulfanylphenyl)chromene-3-carboxamide
• CAS: 1001015-64-0
• 化学式: C₁₆H₁₁NO₃S
• 分子量: 297.334
• InChiKey: MJVFEGXEAKADPF-UHFFFAOYSA-N

物化性质

• 熔点：
  256-258 °C
• 沸点：
  585.9±50.0 °C(Predicted)
• 密度：
  1.441±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基苯硫酚 在 N-甲基吗啉 、 recombinant L1 B3-type dinuclear Zn(II)-containing metallo-β-lactamase 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 苯酚 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.5h， 生成 N-(4-mercaptophenyl)-2-oxo-2H-chromene-3-carboxamide
  参考文献：
  名称：

  A novel fluorogenic substrate for dinuclear Zn(II)-containing metallo-β-lactamases

  摘要：

  In an effort to prepare a fluorogenic substrate to be used in activity assays with metallo-beta-lactamases, (6R,7R)-8-oxo-7-(2-oxo-2H-chromene-3-carboxamido)-3-((4-(2-oxo-2H-chromene-3-carboxamido)-phe nylthio)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CA) was synthesized and characterized. CA exhibited a fluorescence quantum yield (phi) of 0.0059, two fluorescence lifetimes of 3.63 x 10 (-10) and 5.38 x 10(-9) s, and fluorescence intensity that is concentration-dependent. Steady-state kinetic assays revealed that CA is a substrate for metallo-beta-lactamases (M beta Ls) L1 and CcrA, exhibiting K-m and k(cat) values of 18 mu M and 5 s(-1) and 11 mu M and 17 s(-1), respectively. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.071

文献信息

• Synthesis of novel coumarin and benzocoumarin derivatives and their biological and photophysical studies
  作者：Alaa S. Abd-El-Aziz、Hany M. Mohamed、Shawkat Mohammed、Shamsulhaq Zahid、Athar Ata、Ahmed H. Bedair、Ahmed M. El-Agrody、Pierre D. Harvey

  DOI：10.1002/jhet.5570440610

  日期：2007.11

  The reaction of 1-chloromethylbenzo[f]coumarins (36) with cyanide anion under different reaction conditions was also investigated in order to assess its suitability for nucleophilic substitution reactions as well as ring transformation products (43-49). Synthesis of 1-((benzo[d]thiazol-2-yl)methyl)-9-hydroxybenzo[f]coumarin (50) represented the first example of methylene bridge-head heterocyclecontaining

  通过香豆素-3-羰基氯（1）与许多亲核试剂的反应已经制备了香豆素-3 N-羧酰胺的几种衍生物（3-21）。还使用相同的方法制备了新型双头香豆素-3 N-羧酰胺（26-33）。应用Pechmann-Duisberg反应制备新的苯并[ f ]-苯并[ h ]香豆素和4-（氯甲基）-吡喃并[3,2 - c ]香豆素-2-酮（36-42）。1-氯甲基苯并[ f ]香豆素的反应（36）还研究了在不同反应条件下与氰化物阴离子形成的阴离子，以评估其对亲核取代反应以及环转化产物的适用性（43-49）。1-（（苯并[ d ]噻唑-2-基）甲基）-9-羟基苯并[ f ]香豆素（50）的合成代表了含亚甲基桥头杂环的苯并[ f ]香豆素的第一个实例。一些新制备的香豆素对革兰氏阳性和革兰氏阴性细菌表现出抗菌活性。发现化合物36d对所有经筛选的细菌具有活性。对选定的荧光苯并[ f ]-和苯并[ h ]进行了光物理研究
• Novel fluorescent cephalosporins: Synthesis, antimicrobial activity and photodynamic inactivation of antibiotic resistant bacteria
  作者：Jian-Min Xiao、Lei Feng、Li-Sheng Zhou、Hui-Zhou Gao、Yi-Lin Zhang、Ke-Wu Yang

  DOI：10.1016/j.ejmech.2012.11.019

  日期：2013.1

  Two novel fluorescent cephalosporins, TCA and TBCA, were synthesized and characterized by H-1 NMR, C-13 NMR, UV-vis, and fluorescence spectroscopies. Biological activity assays demonstrated that TCA inactivated a Klebsiella pneumonia strain that expressed extended-spectrum beta-lactamases. Incubation of 6 mu M TCA with K. pneumonia cultures resulted in cell death for 84% of the cells after 126 J/cm(2) of light irradiation. In vitro, TCA exhibited a MIC = 0.5 mu g/mL with Staphylococcus aureus. Kinetic evaluation revealed that TCA and TBCA were substrates for B1 and B3 subclass metallo-beta-lactamases. TBCA exhibited stronger binding affinities to the Gram-positive bacterial strains MRSA1, MRSA2, and S. aureus with value of 2.95-6.59 mu M per 10(8) cells/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.
• A novel fluorogenic substrate for dinuclear Zn(II)-containing metallo-β-lactamases
  作者：Yin-Lin Zhang、Jian-Min Xiao、Ji-Li Feng、Ke-Wu Yang、Lei Feng、Li-Sheng Zhou、Michael W. Crowder

  DOI：10.1016/j.bmcl.2013.01.071

  日期：2013.3

  In an effort to prepare a fluorogenic substrate to be used in activity assays with metallo-beta-lactamases, (6R,7R)-8-oxo-7-(2-oxo-2H-chromene-3-carboxamido)-3-((4-(2-oxo-2H-chromene-3-carboxamido)-phe nylthio)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CA) was synthesized and characterized. CA exhibited a fluorescence quantum yield (phi) of 0.0059, two fluorescence lifetimes of 3.63 x 10 (-10) and 5.38 x 10(-9) s, and fluorescence intensity that is concentration-dependent. Steady-state kinetic assays revealed that CA is a substrate for metallo-beta-lactamases (M beta Ls) L1 and CcrA, exhibiting K-m and k(cat) values of 18 mu M and 5 s(-1) and 11 mu M and 17 s(-1), respectively. (C) 2013 Elsevier Ltd. All rights reserved.