2-fluoroxanthen-9-one-6-carboxylic acid | 894088-97-2

• 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: 2-fluoroxanthen-9-one-6-carboxylic acid
• 英文别名: 7-fluoro-9-oxo-9H-xanthene-3-carboxylic acid；7-fluoro-9-oxoxanthene-3-carboxylic acid
• CAS: 894088-97-2
• 化学式: C₁₄H₇FO₄
• 分子量: 258.206
• InChiKey: QMTQKOIDOXRRSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-fluoroxanthen-9-one-6-carboxylic acid 在 氯化亚砜 作用下， 反应 1.0h， 生成
  参考文献：
  名称：

  Synthesis and cancer cell cytotoxicity of substituted xanthenes

  摘要：

  A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N, N-diethyl]-9-hydroxy-9( 3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 mu M across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e. g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.018
• 作为产物：
  描述：

  2-(4-fluorophenoxy)terephthalic acid 在 硫酸 作用下， 反应 3.0h， 以62%的产率得到2-fluoroxanthen-9-one-6-carboxylic acid
  参考文献：
  名称：

  Synthesis and cancer cell cytotoxicity of substituted xanthenes

  摘要：

  A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N, N-diethyl]-9-hydroxy-9( 3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 mu M across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e. g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.018
• 作为试剂：
  描述：

  7-fluoro-9-oxo-9H-xanthene-3-carboxylic acid methyl ester 、 9-oxo-xanthene-3-carboxylic acid methyl ester 在 2-fluoroxanthen-9-one-6-carboxylic acid 作用下， 以the title compound 7-fluoro-9-oxo-9H-xanthene-3-carboxylic acid, 3e was obtained的产率得到2-fluoroxanthen-9-one-6-carboxylic acid
  参考文献：
  名称：

  Tricyclic-bridged piperidinyline derivatives as §-opioid modulators

  摘要：

  本发明涉及化合物、组合物和方法，用于治疗各种疾病和病症，包括疼痛。这些化合物由以下式子I所表示：其中A、G、Y、R3、R4和R5在此被定义。

  公开号：

  US07589104B2

文献信息

• Tricyclic delta-opioid modulators
  申请人：Carson R. John

  公开号：US20060135524A1

  公开（公告）日：2006-06-22

  The invention is directed to delta opioid receptor modulators. More specifically, the invention relates to tricyclic δ-opioid modulators. Pharmaceutical and veterinary compositions and methods of treating mild to severe pain and various diseases using compounds of the invention are also described.

  这项发明涉及δ阿片受体调节剂。更具体地，该发明涉及三环δ-阿片调节剂。还描述了利用该发明的化合物治疗轻度至严重疼痛和各种疾病的药用和兽医组合物以及方法。
• TRICYCLIC DELTA-OPIOID MODULATORS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1833825A1

  公开（公告）日：2007-09-19
• US7589104B2
  申请人：——

  公开号：US7589104B2

  公开（公告）日：2009-09-15
• [EN] TRICYCLIC d-OPIOID MODULATORS<br/>[FR] MODULATEURS DES RECEPTEURS OPIOIDES $G(D) TRICYCLIQUES
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2006069277A1

  公开（公告）日：2006-06-29

  [EN] The invention is directed to delta opioid receptor modulators. More specifically, the invention relates to tricyclic d-opioid modulators. Pharmaceutical and veterinary compositions and methods of treating mild to severe pain and various diseases using compounds of the invention are also described.
  [FR] L'invention concerne des modulateurs des récepteurs opioïdes delta. Plus spécifiquement, elle concerne des modulateurs des récepteurs opioïdes d tricycliques. L'invention concerne aussi des compositions pharmaceutiques et vétérinaires et des méthodes utilisant ces composés pour traiter les douleurs modérées à fortes et diverses maladies.
• Synthesis and cancer cell cytotoxicity of substituted xanthenes
  作者：Rajan Giri、John R. Goodell、Chenguo Xing、Adam Benoit、Harneet Kaur、Hiroshi Hiasa、David M. Ferguson

  DOI：10.1016/j.bmc.2010.01.018

  日期：2010.2

  A series of substituted xanthenes was synthesized and screened for activity using DU-145, MCF-7, and HeLa cancer cell growth inhibition assays. The most potent compound, 9g ([N, N-diethyl]-9-hydroxy-9( 3-methoxyphenyl)-9H-xanthene-3-carboxamide), was found to inhibit cancer cell growth with IC50 values ranging from 36 to 50 mu M across all three cancer cell lines. Structure-activity relationship (SAR) data is presented that indicates additional gains in potency may be realized through further derivatization of the compounds (e. g., the incorporation of a 7-fluoro substituent to 9g). Results are also presented that suggest the compounds function through a unique mechanism of action as compared to that of related acridine and xanthone anticancer agents (which have been shown to intercalate into DNA and inhibit topoisomerase II activity). A structural comparison of these compounds suggests the differences in function may be due to the structure of the xanthene heterocycle which adopts a nonplanar conformation about the pyran ring. (C) 2010 Elsevier Ltd. All rights reserved.