7-(2-phenyl)ethoxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester | 745033-20-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(2-phenyl)ethoxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester
• 英文别名: methyl 2-oxo-7-(2-phenylethoxy)chromene-3-carboxylate
• CAS: 745033-20-9
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: PTOOFHMLSHXKID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(2-phenyl)ethoxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester 在 palladium 10% on activated carbon 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 以95%的产率得到7-(2-phenyl)ethoxyl-3,4-dihydro-2-oxo-4H-1-benzopyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  EP1598345

  摘要：

  公开号：
• 作为产物：
  描述：

  2,4-二羟基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 7-(2-phenyl)ethoxyl-2-oxo-2H-1-benzopyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of carboxycoumarins as a new antitumor treatment targeting lactate transport in cancer cells

  摘要：

  Under hypoxia, cancer cells consume glucose and release lactate at a high rate. Lactate was recently documented to be recaptured by oxygenated cancer cells to fuel the TCA cycle and thereby to support tumor growth. Monocarboxylate transporters (MCT) are the main lactate carriers and therefore represent potential therapeutic targets to limit cancer progression. In this study, we have developed and implemented a stepwise in vitro screening procedure on human cancer cells to identify new potent MCT inhibitors. Various 7-substituted carboxycoumarins and quinolinone derivatives were synthesized and pharmacologically evaluated. Most active compounds were obtained using a palladium-catalyzed Buchwald-Hartwig type coupling reaction, which proved to be a quick and efficient method to obtain aminocarboxycoumarin derivatives. Inhibition of lactate flux revealed that the most active compound 19 (IC50 11 nM) was three log orders more active than the CHC reference compound. Comparison with warfarin, a conventional anticoagulant coumarin, further showed that compound 19 did not influence the prothrombin time which, together with a good in vitro ADME profile, supports the potential of this new family of compounds to act as anticancer drugs through inhibition of lactate flux. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.010

文献信息

• Benzopyran compounds, process for preparing the same and their use
  申请人：Yang Yushe

  公开号：US20060178405A1

  公开（公告）日：2006-08-10

  The invention relates to the benzopyran compounds of formula (I), or the salts thereof, in which, the bond between 3 and 4 positions is a single or double bond; R 1 represents a hydrogen atom or a C 1-6 alkyl that can be substituted; R 2 represents a hydrogen atom, a C 1-6 alkyl that can be substituted or an aromatic carbocyclic or aromatic heterocyclic group that can be substituted. The invention also relates to a process for preparing such compounds or their salts as well as the use of such compounds or their salts in the preparation of the medicine against type II diabetes mellitus.

  本发明涉及式（I）的苯并吡喃化合物或其盐，其中3和4位置之间的键为单键或双键；R1表示氢原子或可被取代的C1-6烷基；R2表示氢原子，可被取代的C1-6烷基或可被取代的芳香环烷基或芳香杂环基。本发明还涉及制备这种化合物或其盐的方法，以及使用这种化合物或其盐制备针对II型糖尿病的药物。
• 3-CARBOXY SUBSTITUTED COUMARIN DERIVATIVES WITH A POTENTIAL UTILITY FOR THE TREATMENT OF CANCER DISEASES
  申请人：UNIVERSITE CATHOLIQUE DE LOUVAIN

  公开号：US20160115146A1

  公开（公告）日：2016-04-28

  The present invention relates to novel compounds. The present invention also relates to the compounds for use as a medicine, more in particular for the prevention or treatment of cancer, more in particular cancers expressing MCT1 and/or MCT4. The present invention also relates to a method for the prevention or treatment of cancer in animals or humans by using the novel compounds. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the novel compounds and to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of cancer. The present invention also relates to processes for the preparation of the compounds.

  本发明涉及新颖化合物。本发明还涉及用于药物的化合物，更具体地用于预防或治疗癌症，更具体地用于表达MCT1和/或MCT4的癌症。本发明还涉及使用新颖化合物预防或治疗动物或人类癌症的方法。本发明还涉及新颖化合物的制药组合物或复方制剂，以及用于药物的组合物或制剂，更优选用于预防或治疗癌症。本发明还涉及制备这些化合物的方法。
• BENZOPYRAN COMPOUNDS, PROCESS FOR PREPARING THE SAME AND THEIR USE
  申请人：SHANGHAI INSTITUTE OF MATERIA MEDICA, CHINESE ACADEMY OF SCIENCES

  公开号：EP1598345A1

  公开（公告）日：2005-11-23

  The invention relates to the benzopyran compounds of formula (I), or the salts thereof, in which, the bond between 3 and 4 positions is a single or double bond; R1 represents a hydrogen atom or a C1-6 alkyl that can be substituted; R2 represents a hydrogen atom, a C1-6 alkyl that can be substituted or an aromatic carbocyclic or aromatic heterocyclic group that can be substituted. The invention also relates to a process for preparing such compounds or their salts as well as the use of such compounds or their salts in the preparation of the medicine against type II diabetes mellitus.

  本发明涉及式（I）的苯并吡喃化合物或其盐，其中，3-4位之间的键为单键或双键；R1代表氢原子或可被取代的C1-6烷基；R2代表氢原子、可被取代的C1-6烷基或可被取代的芳香碳环或芳香杂环基团。本发明还涉及制备此类化合物或其盐的工艺，以及此类化合物或其盐在制备 II 型糖尿病药物中的用途。
• US7456205B2
  申请人：——

  公开号：US7456205B2

  公开（公告）日：2008-11-25
• EP1598345
  申请人：——

  公开号：——

  公开（公告）日：——