6-chloro-7-hydroxy-3-phenyl-4H-chromen-4-one | 97340-30-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-chloro-7-hydroxy-3-phenyl-4H-chromen-4-one
• 英文别名: 6-chloro-7-hydroxy-3-phenyl-chromen-4-one；6-chloro-7-hydroxy-3-phenylchromen-4-one；6-Chlor-7-hydroxy-isoflavon
• CAS: 97340-30-2
• 化学式: C₁₅H₉ClO₃
• 分子量: 272.688
• InChiKey: BHBOHGGOQLWYSZ-UHFFFAOYSA-N

物化性质

• 熔点：
  270-271 °C
• 沸点：
  468.5±45.0 °C(Predicted)
• 密度：
  1.437±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-chloro-7-hydroxy-3-phenyl-4H-chromen-4-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以168.7 mg的产率得到4-chloro-6-(4-phenyl-1H-pyrazol-3-yl)benzene-1,3-diol
  参考文献：
  名称：

  Repurposing Hsp90 inhibitors as antibiotics targeting histidine kinases

  摘要：

  To address the growing need for new antimicrobial agents, we explored whether inhibition of bacterial signaling machinery could inhibit bacterial growth. Because bacteria rely on two-component signaling systems to respond to environmental changes, and because these systems are both highly conserved and mediated by histidine kinases, inhibiting histidine kinases may provide broad spectrum antimicrobial activity. The histidine kinase ATP binding domain is conserved with the ATPase domain of eukaryotic Hsp90 molecular chaperones. To find a chemical scaffold for compounds that target histidine kinases, we leveraged this conservation. We screened ATP competitive Hsp90 inhibitors against CckA, an essential histidine kinase in Caulobacter crescentus that controls cell growth, and showed that the diaryl pyrazole is a promising scaffold for histidine kinase inhibition. We synthesized a panel of derivatives and found that they inhibit the histidine kinases C. crescentus CckA and Salmonella PhoQ but not C. crescentus DivJ; and they inhibit bacterial growth in both Gram-negative and Gram-positive bacterial strains. (C) 2017 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.10.036
• 作为产物：
  描述：

  苯乙酸 、 4-氯间苯二酚 、 N,N-二甲基甲酰胺 在 三氟化硼乙醚 、 五氯化磷 作用下， 反应 9.0h， 以13%的产率得到6-chloro-7-hydroxy-3-phenyl-4H-chromen-4-one
  参考文献：
  名称：

  Repurposing Hsp90 inhibitors as antibiotics targeting histidine kinases

  摘要：

  To address the growing need for new antimicrobial agents, we explored whether inhibition of bacterial signaling machinery could inhibit bacterial growth. Because bacteria rely on two-component signaling systems to respond to environmental changes, and because these systems are both highly conserved and mediated by histidine kinases, inhibiting histidine kinases may provide broad spectrum antimicrobial activity. The histidine kinase ATP binding domain is conserved with the ATPase domain of eukaryotic Hsp90 molecular chaperones. To find a chemical scaffold for compounds that target histidine kinases, we leveraged this conservation. We screened ATP competitive Hsp90 inhibitors against CckA, an essential histidine kinase in Caulobacter crescentus that controls cell growth, and showed that the diaryl pyrazole is a promising scaffold for histidine kinase inhibition. We synthesized a panel of derivatives and found that they inhibit the histidine kinases C. crescentus CckA and Salmonella PhoQ but not C. crescentus DivJ; and they inhibit bacterial growth in both Gram-negative and Gram-positive bacterial strains. (C) 2017 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.10.036

文献信息

• [EN] ANTIGIARDIAL AGENTS AND USE THEREOF<br/>[FR] AGENTS ANTI-GIARDIASE ET LEUR UTILISATION
  申请人：UNIV MISSISSIPPI

  公开号：WO2004014886A1

  公开（公告）日：2004-02-19

  The present invention provides a method of preventing or treating one or more of the following medical conditions, or treating symptoms of one or more of the following medical conditions: amebic infections, giardiasis, estrogen deficient states, osteoporosis, cardiovascular heart disease, high cholesterol levels, hyperlipidemia, cancer by administering to a subject having, or predisposed to, one or more of the conditions, a therapeutically effective amount of a compound of the present invention and a pharmaceutically acceptable carrier.

  本发明提供了一种预防或治疗以下一种或多种医疗状况，或治疗以下一种或多种医疗状况的症状的方法：阿米巴感染、贾第虫病、雌激素缺乏状态、骨质疏松症、心血管疾病、高胆固醇水平、高脂血症、癌症，通过向具有或易于患上一种或多种这些疾病的受试者施用本发明化合物的治疗有效量和药学上可接受的载体。
• [EN] 3,4-DIARYLPYRAZOLES AND THEIR USE IN THE THERAPY OF CANCER<br/>[FR] 3,4-DIARYLPYRAZOLES ET LEUR UTILISATION EN THERAPIE ANTI-CNCEREUSE
  申请人：RIBOTARGETS LTD

  公开号：WO2003055860A1

  公开（公告）日：2003-07-10

  The present invention pertains to the use of certain 3,4-diarylpyrazoles of formula (I), both in vitro and in vivo, to inhibit heat shock protein 90 (HSP90), and in the treatment of conditions mediated by HSP90, including, for example, cancer; wherein: Ar3 is independently: a C5-20aryl group, and is optionally substituted; Ar4 is independently: a C5-20aryl group, and is optionally substituted; R5 is independently: hydrogen; halo; hydroxy; ether; formyl; acyl; carboxy; ester; acyloxy; oxycarbonyloxy; amido; acylamido; aminocarbonyloxy; tetrazolyl; amino; nitro; cyano; azido; sulfhydryl; thioether; sulfonamido; C1-7alkyl; C3-20heterocycyl; or C5-20aryl; RN is independently: -H; C1-7alkyl; C3-20heterocycyl; or, C5-20aryl; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to such compounds, pharmaceutical compositions comprising such compounds, such compounds for medical use, such compounds for use in the treatment of conditions mediated by HSP90, including, for example, cancer, and use of such compounds in the preparation of medicaments for such treatments.

  本发明涉及使用式(I)的特定3,4-二芳基吡唑化合物，无论是体外还是体内，以抑制热休克蛋白90（HSP90）的作用，并用于治疗由HSP90介导的疾病，例如癌症；其中：Ar3独立地表示：C5-20芳基基团，且可选地被取代；Ar4独立地表示：C5-20芳基基团，且可选地被取代；R5独立地表示：氢；卤素；羟基；醚；甲酰基；酰基；羧基；酯基；酰氧基；氧羰基氧基；酰胺基；酰胺氧基；氨基羰氧基；四唑基；氨基；硝基；氰基；偶氮基；硫醇基；硫醚基；磺酰胺基；C1-7烷基；C3-20杂环基；或C5-20芳基；RN独立地表示：-H；C1-7烷基；C3-20杂环基；或C5-20芳基；以及其药学上可接受的盐，溶剂化合物，酰胺，酯，醚，化学保护形式和前药。本发明还涉及这些化合物，包含这些化合物的制药组合物，用于医疗用途的这些化合物，用于治疗由HSP90介导的疾病，例如癌症的这些化合物，以及使用这些化合物制备此类治疗药物的用途。
• 3,4-diarylpyrazoles and their use in the therapy of cancer
  申请人：Drysdale James Martin

  公开号：US20050222230A1

  公开（公告）日：2005-10-06

  The present invention pertains to the use of certain 3,4-diarylpyrazoles of formula (I), both in vitro and in vivo, to inhibit heat shock protein 90 (HSP90), and in the treatment of conditions mediated by HSP90, including, for example, cancer; wherein: Ar 3 is independently: a C 5-20 aryl group, and is optionally substituted; Ar 4 is independently: a C 5-20 aryl group, and is optionally substituted; R 5 is independently: hydrogen; halo; hydroxy; ether; formyl; acyl; carboxy; ester, acyloxy; oxycarbonyloxy; amido; acylamido; aminocarbonyloxy; tetrazolyl; amino; nitro; cyano; azido; sulfhydryl; thioether; sulfonamido; C 1-7 alkyl; C 3-20 heterocycyl; or C 5-20 aryl; RN is independently: —H; C 1-7 alkyl; C 3-20 heterocycyl; or, C 5-20 aryl; and pharmaceutically acceptable salts, solvates, amides, esters, ethers, chemically protected forms, and prodrugs thereof. The present invention also pertains to such compounds, pharmaceutical compositions comprising such compounds, such compounds for medical use, such compounds for use in the treatment of conditions mediated by HSP90, including, for example, cancer, and use of such compounds in the preparation of medicaments for such treatments.

  本发明涉及使用公式（I）中的某些3,4-二芳基吡唑化合物，无论是在体内还是体外，用于抑制热休克蛋白90（HSP90），以及用于治疗由HSP90介导的疾病，包括癌症等；其中：Ar3独立地表示：C5-20芳基基团，可选地取代；Ar4独立地表示：C5-20芳基基团，可选地取代；R5独立地表示：氢；卤素；羟基；醚；甲酰基；酰基；羧基；酯，酰氧基；氧羰酰氧基；酰胺；酰胺基；氨基羰酰氧基；四唑基；氨基；硝基；氰基；偶氮基；磺酰基；硫醚基；磺酰胺基；C1-7烷基；C3-20杂环基；或C5-20芳基；R N 独立地表示：-H；C1-7烷基；C3-20杂环基；或C5-20芳基；以及其药学上可接受的盐，溶剂化合物，酰胺，酯，醚，化学保护形式和前药。本发明还涉及这种化合物，包含这种化合物的制药组合物，用于医学用途的这种化合物，用于治疗由HSP90介导的疾病，包括癌症的这种化合物，以及使用这种化合物制备这种治疗药物的用途。
• Antigiardial agents and use thereof
  申请人：Avery Mitchell

  公开号：US20060106091A1

  公开（公告）日：2006-05-18

  The present invention provides a method of preventing or treating one or more of the following medical conditions, or treating symptoms of one or more of the following medical conditions: amebic infections, giardiasis, estrogen deficient states, osteoporosis, cardiovascular heart disease, high cholesterol levels, hyperlipidemia, cancer by administering to a subject having, or predisposed to, one or more of the conditions, a therapeutically effective amount of a compound of the present invention and a pharmaceutically acceptable carrier.

  本发明提供了一种预防或治疗下列一种或多种病症，或治疗下列一种或多种病症的症状的方法：阿米巴感染、贾第鞭毛虫病、雌激素缺乏状态、骨质疏松症、心血管心脏病、高胆固醇水平、高脂血症、癌症，其方法是向患有或易患上述一种或多种病症的受试者施用治疗有效量的本发明化合物和药学上可接受的载体。
• ISOFLAVONE DERIVATIVES
  申请人：CHINOIN LTD.

  公开号：EP0710234A1

  公开（公告）日：1996-05-08