5,8-dimethoxytetralin-2-carboxylic acid | 68569-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,8-dimethoxytetralin-2-carboxylic acid
• 英文别名: 5,8-dimethoxy-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid
• CAS: 68569-97-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: CPWCICMLTNTXCU-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,8-dimethoxytetralin-2-carboxylic acid 在 盐酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 三氯化铝 、 偶氮二异丁腈 、 potassium tert-butylate 、 氧气 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 四氯化碳 、 二氯甲烷 、 硝基苯 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 21.5h， 生成 (7S,9S)9-乙酰基-7,8,9,10-四氢-6,7,9,11-四羟基-5,12-并四苯二酮
  参考文献：
  名称：

  Facile Total Syntheses of Idarubicinone‐7‐β‐D‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives

  摘要：

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.

  DOI：

  10.1081/scc-120030758
• 作为产物：
  描述：

  对苯二甲醚 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 0.67h， 生成 5,8-dimethoxytetralin-2-carboxylic acid
  参考文献：
  名称：

  Facile Total Syntheses of Idarubicinone‐7‐β‐D‐glucuronide: Convenient Preparations of AB‐Ring Synthon Using Some Carboxylic Acid Derivatives

  摘要：

  Regiospecific syntheses of idarubicinone coupled with D-glucuronic acid are described. Cyclization of dimethoxybenzene with carboxylic acid derivatives in polyphosphoric acid (PPA) in one step afforded the naphthalenones 7, which were transformed to the (+/-)-idarubicinone 3b by general methods. Esterification of (+/-)-3b with (S)-(+)-O-acetylmandelic acid with subsequent separation and deprotection gave (+)-3b and (-)-3b. Reaction of separated two stereoisomers with acetobromo-alpha-D-glucuronic acid methyl ester respective followed by hydrolysis using lithium hydroxide and amberite cation exchange resin furnished two kinds of idarubicinone-7-beta-D-glucuronide (20 and 21) that are coupled at C-7 position of idarubicinone.

  DOI：

  10.1081/scc-120030758

文献信息

• Composition for treatment of pathogens that are resistant to tetracyclines
  申请人：Bioversys AG

  公开号：EP2762134A1

  公开（公告）日：2014-08-06

  The invention relates to compounds and pharmaceutical compositions useful in combination with tetracyclines in the treatment of bacterial infections caused by Gram-positive and Gram-negative pathogens, with particular efficacy in tetracycline resistant strains. These compounds specifically bind to TetR and therefore prevent the transcriptional activation of tet resistance genes. The compounds have a potentiating effect on the activity of members of the tetracycline family, in particular of tetracycline, minocycline, doxycycline and tigecycline, in the treatment of tetracycline susceptible, intermediate and tetracycline resistant pathogens.

  该发明涉及与四环素结合在一起用于治疗由革兰氏阳性和革兰氏阴性病原体引起的细菌感染的化合物和药物组合物，对四环素耐药菌株尤为有效。这些化合物特异性地结合到TetR，从而阻止tet耐药基因的转录激活。这些化合物对四环素家族成员的活性具有增强作用，尤其对四环素、米诺环素、多西环素和替加环素在治疗四环素敏感、中间和四环素耐药病原体方面具有增强作用。
• [EN] COMPOSITION FOR TREATMENT OF PATHOGENS THAT ARE RESISTANT TO TETRACYCLINES<br/>[FR] COMPOSITION POUR LE TRAITEMENT DE PATHOGÈNES QUI SONT RÉSISTANTS AUX TÉTRACYCLINES
  申请人：BIOVERSYS AG

  公开号：WO2014118361A1

  公开（公告）日：2014-08-07

  The invention relates to compounds and pharmaceutical compositions useful in combination with tetracyclines in the treatment of bacterial infections caused by Gram- positive and Gram-negative pathogens, with particular efficacy in tetracycline resistant strains. These compounds specifically bind to TetR and therefore prevent the transcriptional activation of tet resistance genes. The compounds have a potentiating effect on the activity of members of the tetracycline family, in particular of tetracycline, minocycline, doxycycline and tigecycline, in the treatment of tetracycline susceptible, intermediate and tetracycline resistant pathogens.

  该发明涉及与四环素联合使用的化合物和药物组合物，用于治疗由革兰氏阳性和革兰氏阴性病原体引起的细菌感染，特别在四环素耐药菌株中具有显著疗效。这些化合物特异性地结合到TetR，从而阻止tet耐药基因的转录激活。这些化合物对四环素家族成员（特别是四环素、米诺环素、多西环素和替吉环素）的活性具有增强作用，在治疗四环素敏感、中间和四环素耐药病原体方面表现出效果。
• COMPOSITION FOR TREATMENT OF PATHOGENS THAT ARE RESISTANT TO TETRACYCLINES
  申请人：BIOVERSYS AG

  公开号：US20150359791A1

  公开（公告）日：2015-12-17

  The invention relates to compounds and pharmaceutical compositions useful in combination with tetracyclines in the treatment of bacterial infections caused by Gram-positive and Gram-negative pathogens, with particular efficacy in tetracycline resistant strains. These compounds specifically bind to TetR and therefore prevent the transcriptional activation of tet resistance genes. The compounds have a potentiating effect on the activity of members of the tetracycline family, in particular of tetracycline, minocycline, doxycycline and tigecycline, in the treatment of tetracycline susceptible, intermediate and tetracycline resistant pathogens.

  本发明涉及化合物和药物组合物，可用于与四环素联合治疗由革兰氏阳性和革兰氏阴性病原体引起的细菌感染，对四环素耐药菌株具有特殊疗效。这些化合物特异性结合TetR，从而防止tet耐药基因的转录激活。这些化合物对四环素家族成员的活性具有增强作用，特别是对四环素、米诺环素、多西环素和替加环素在四环素敏感、中间和四环素耐药病原体治疗中的活性具有增强作用。
• Rao, M. Vishnumurthi; Bhatt, M. Vivekananda, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 6, p. 487 - 488
  作者：Rao, M. Vishnumurthi、Bhatt, M. Vivekananda

  DOI：——

  日期：——
• Synthesis and redox properties of chromophore modified glycosides related to anthracyclines
  作者：J. William Lown、Sham M. Sondhi、Sukhendu B. Mandal、John Murphy

  DOI：10.1021/jo00143a026

  日期：1982.10