6,8-Dichloro-4-oxo-4H-chromene-3-carboxylic acid | 72798-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,8-Dichloro-4-oxo-4H-chromene-3-carboxylic acid
• 英文别名: 6,8-Dichlorochromone-3-carboxylic acid；6,8-dichloro-4-oxochromene-3-carboxylic acid
• CAS: 72798-31-3
• 化学式: C₁₀H₄Cl₂O₄
• 分子量: 259.045
• InChiKey: WVQVJUOBWKULAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-Dichloro-4-oxo-4H-chromene-3-carboxylic acid 在 copper(l) iodide 、 氯化亚砜 作用下， 生成 Ethyl 6,8-dichloro-2-(4-fluorophenyl)-4-oxo-2,3-dihydrochromene-3-carboxylate
  参考文献：
  名称：

  Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection

  摘要：

  Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.

  DOI：

  10.1021/jm400786q
• 作为产物：
  描述：

  3',5'-二氯-2'-羟基苯乙酮 在 sodium chlorite 、 三氯氧磷 作用下， 生成 6,8-Dichloro-4-oxo-4H-chromene-3-carboxylic acid
  参考文献：
  名称：

  Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against Helicobacter pylori Infection

  摘要：

  Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.

  DOI：

  10.1021/jm400786q

文献信息

• Penicillins and their antibacterial use
  申请人：Sandoz Ltd.

  公开号：US04320133A1

  公开（公告）日：1982-03-16

  The invention provides novel penicillins and cephalosporins of formula I, ##STR1## methods for their production and their anti-bacterial use.

  本发明提供了公式I的新型青霉素和头孢菌素，以及它们的生产方法和抗菌用途。##STR1##
• Penicillins, per se and for use as antibacterially active antibiotics and their production
  申请人：SANDOZ AG

  公开号：EP0003115A1

  公开（公告）日：1979-07-25

  Penicillins and cephalosporins of formula I, in which R, is hydrogen or pivaloyloxymethyl, R2 is phenyl, 4-hydroxyphenyl or 1,4-cyclohexadien-1-yl, R3 is hydrogen, lower alkyl or lower alkylthio, R4 and R5, which may be the same or different, are hydrogen, lower alkyl, hydroxy, lower alkoxy, carboxyl, lower alkoxycarbonyl, lower alkoxycarbonylmethyl, carboxymethyl or halogen, A is the group in which Rs is hydrogen or lower alkyl, B is oxygen of sulphur, X is a group of formula IIa or IIb, in which R7 is hydrogen, acetoxy or a group of formula IIc, and Ring D is a 5- or 6-membered, unsaturated ring, which may contain one or more hetero atoms, and salts of compounds of formula I, in which R, is hydrogen, methods for their production and their anti-bacterial use.

  式 I 的青霉素和头孢菌素 其中 R 为氢或新戊酰氧基甲基、 R2 是苯基、4-羟基苯基或 1,4-环己二烯-1-基、 R3 是氢、低级烷基或低级烷硫基、 R4 和 R5（可以相同或不同）是氢、低级烷基、羟基、低级烷氧基、羧基、低级烷氧羰基、低级烷氧羰基甲基、羧甲基或卤素、 A 是以下基团 其中 Rs 为氢或低级烷基、 B 是硫的氧、 X 是式 IIa 或 IIb、 其中 R7 是氢、乙酰氧基或式 IIc、 环 D 是 5 或 6 元不饱和环、 以及式 I 化合物的盐（其中 R 为氢）、其生产方法和抗菌用途。
• Synthesis of 3-(3-Alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl)aminocarbonylchromones
  作者：Linghua Cao、Lin Zhang、Pengyuan Cui

  DOI：10.1023/b:cohc.0000037320.27881.27

  日期：2004.5
• US4320133A
  申请人：——

  公开号：US4320133A

  公开（公告）日：1982-03-16
• Improved Flavodoxin Inhibitors with Potential Therapeutic Effects against <i>Helicobacter pylori</i> Infection
  作者：Juan J. Galano、Miriam Alías、Reyes Pérez、Adrian Velázquez-Campoy、Paul S. Hoffman、Javier Sancho

  DOI：10.1021/jm400786q

  日期：2013.8.8

  Helicobacter pylori (Hp) infection affects one-half of the human population and produces a variety of diseases from peptic ulcer to cancer. Current eradication therapies achieve modest success rates (around 70%), resistance to the antibiotics of choice is on the rise, and vaccination has not proved to be successful yet. Using an essential Hp protein, flavodoxin, as target, we identified three low-molecular-weight flavodoxin inhibitors with bactericidal anti-Hp properties. To improve their therapeutic indexes, we have now identified and tested 123 related compounds. We have first tested similar compounds available. Then we have designed, synthesized, and tested novel variants for affinity to flavodoxin, MIC for Hp, cytotoxicity, and bactericidal effect. Some are novel bactericidal inhibitors with therapeutic indexes of 9, 38 and 12, significantly higher than those of their corresponding leads. Developing novel Hp-specific antibiotics will help fighting Hp resistance and may have the advantage of not generally perturbing the bacterial flora.