2-[3-(4-chlorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl]acetic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2-[3-(4-chlorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl]acetic acid
• 英文别名: [3-(4-chlorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl]acetic acid；2-[3-(4-chlorophenyl)-5,9-dimethyl-7-oxofuro[3,2-g]chromen-6-yl]acetic acid
• 化学式: C₂₁H₁₅ClO₅
• mdl: MFCD03661308
• 分子量: 382.8
• InChiKey: LSZYWBGRRKAHPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[3-(4-chlorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl]acetic acid 在 水 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 lithium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (2R)-1-[2-[3-(4-chlorophenyl)-5,9-dimethyl-7-oxofuro[3,2-g]chromen-6-yl]acetyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Antibiotic That Inhibits the ATPase Activity of an ATP-Binding Cassette Transporter by Binding to a Remote Extracellular Site

  摘要：

  Antibiotic-resistant strains of Staphylococcus aureus pose a major threat to human health and there is an ongoing need for new antibiotics to treat resistant infections. In a high throughput screen (HTS) of 230 000 small molecules designed to identify bioactive wall teichoic acid (WTA) inhibitors, we identified one hit, which was expanded through chemical synthesis into a small panel of potent compounds. We showed that these compounds target TarG, the transmembrane component of the two-component ATP-binding cassette (ABC) transporter TarGH, which exports WTA precursors to the cell surface for attachment to peptidoglycan. We purified, for the first time, a WTA transporter and have reconstituted ATPase activity in proteoliposomes.' We showed that this new compound series inhibits TarH-catalyzed ATP hydrolysis even though the binding site maps to TarG near the opposite side of the membrane. These are the first ABC transporter inhibitors shown to block ATPase activity by binding to the transmembrane domain. The compounds have potential as, therapeutic agents to treat S. aureus infections, and purification of the transmembrane transporter will enable further development.

  DOI：

  10.1021/jacs.7b04726
• 作为产物：
  描述：

  2,6-二羟基甲苯 在 硫酸 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 异丙醇 、 丙酮 为溶剂， 反应 18.0h， 生成 2-[3-(4-chlorophenyl)-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl]acetic acid
  参考文献：
  名称：

  2H-色烯和 7H-呋喃色烯衍生物选择性抑制肿瘤相关的人碳酸酐酶 IX 和 XII 亚型

  摘要：

  肿瘤相关碳酸酐酶 (CA) IX 和 XII 已被认为是治疗缺氧肿瘤的潜在靶标。因此，考虑到它的高药理潜力...

  DOI：

  10.1080/14756366.2023.2270183

文献信息

• Modified Coumarins. 33. Synthesis of Furo- and Dihydropyranocoumarins Containing a Lupinine Moiety
  作者：Yu. A. Nikitina、A. I. Galaev、Ya. L. Garazd、M. M. Garazd、V. G. Kartsev

  DOI：10.1007/s10600-015-1423-4

  日期：2015.9

  New coumarin derivatives containing a lupinine moiety were synthesized via amidation of furocoumarinylacetic, furocoumarinylpropionic, and dihydropyranocoumarinyloxyacetic acids with lupinylamine.

  通过呋喃香豆素乙酸、呋喃香豆素丙酸和二氢吡喃香豆素氧乙酸与羽扇豆胺的酰胺化反应，合成了含有羽扇豆碱分子的新型香豆素衍生物。
• ——
  作者：I. V. Nagorichna、I. P. Dubovik、M. M. Garazd、V. P. Khilya

  DOI：10.1023/a:1025466317733

  日期：——

  Substituted 2-(7-oxofuro[3,2-g]chromen-6-yl) acetic acids, modified psoralen analogs, were synthesized by linear fusion of a furan ring to the coumarin system.
• Antibiotic That Inhibits the ATPase Activity of an ATP-Binding Cassette Transporter by Binding to a Remote Extracellular Site
  作者：Leigh M. Matano、Heidi G. Morris、Anthony R. Hesser、Sara E. S. Martin、Wonsik Lee、Tristan W. Owens、Emaline Laney、Hidemasa Nakaminami、David Hooper、Timothy C. Meredith、Suzanne Walker

  DOI：10.1021/jacs.7b04726

  日期：2017.8.9

  Antibiotic-resistant strains of Staphylococcus aureus pose a major threat to human health and there is an ongoing need for new antibiotics to treat resistant infections. In a high throughput screen (HTS) of 230 000 small molecules designed to identify bioactive wall teichoic acid (WTA) inhibitors, we identified one hit, which was expanded through chemical synthesis into a small panel of potent compounds. We showed that these compounds target TarG, the transmembrane component of the two-component ATP-binding cassette (ABC) transporter TarGH, which exports WTA precursors to the cell surface for attachment to peptidoglycan. We purified, for the first time, a WTA transporter and have reconstituted ATPase activity in proteoliposomes.' We showed that this new compound series inhibits TarH-catalyzed ATP hydrolysis even though the binding site maps to TarG near the opposite side of the membrane. These are the first ABC transporter inhibitors shown to block ATPase activity by binding to the transmembrane domain. The compounds have potential as, therapeutic agents to treat S. aureus infections, and purification of the transmembrane transporter will enable further development.