4-acetylamino-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester | 36707-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 4-acetylamino-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester
• 英文别名: ethyl 4-(acetylamino)-2-(methylsulfanyl)-5-oxo-5,8-dihydro[2,3-d]pyrimidino-pyridine-6-carboxylate；ethyl 4-acetamido-2-methylsulfanyl-5-oxo-8H-pyrido[2,3-d]pyrimidine-6-carboxylate
• CAS: 36707-44-5
• 化学式: C₁₃H₁₄N₄O₄S
• 分子量: 322.345
• InChiKey: OAVSQZFIILPOQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  136
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-acetylamino-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 在 sodium hydroxide 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 4-amino-8-ethyl-5,8-dihydro-5-oxo-2-(1-piperazinyl)pyrido<2,3-d>pyrimidine-6-carboxylic acid
  参考文献：
  名称：

  New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay

  摘要：

  A series of 60 newly synthesized and known quinolone antibacterials, including quinoline- and 1,8-naphthyridine-3-carboxylic acids, pyrido[2,3-d]pyrimidine-6-carboxylic acids, and some monocyclic 4-pyridone-3-carboxylic acids, were tested and compared in a newly established, easy to perform, DNA gyrase assay. The results were correlated with minimum inhibitory concentrations (MICs) against a variety of organisms. Among the known quinolones were 14 clinically significant drugs (oxolinic acid, norfloxacin, ciprofloxacin, enoxacin, etc.) which were used as standards and compared side-by-side. The study focused on the changes in DNA gyrase inhibition brought about by certain features of the molecules, namely, the C6-fluorine or the nature of the C7 substituent. The intrinsic gyrase inhibition of the fused parent rings, quinoline vs. naphthyridine vs. pyrido[2,3-d]pyrimidine, was also explored. In all cases, loss of enzyme inhibition produced poor MICs, but some compounds with good DNA gyrase inhibition did not correspondingly inhibit bacterial growth. Possible explanations for this phenomena and the benefits of a DNA gyrase-MIC strategy for developing future structure-activity relationships are discussed.

  DOI：

  10.1021/jm00153a015
• 作为产物：
  描述：

  diethyl 2-((6-amino-2-(methylthio)pyrimidin-4-ylamino)methylene)malonate 在 diphenyl ether-biphenyl eutectic 作用下， 反应 20.0h， 生成 4-acetylamino-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] COMPOUNDS USEFUL AS AKT/PKB MODULATORS AND USES THEREOF
  [FR] COMPOSÉS UTILES EN TANT QUE MODULATEURS AKT/PKB ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2012158197A3

文献信息

• Antibacterial compounds
  申请人：Anderson D. David

  公开号：US20050159423A1

  公开（公告）日：2005-07-21

  Bacterial protein synthesis-inhibiting compounds having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates in the processes, compositions containing the compounds, and methods of using the compounds are disclosed.

  抑制细菌蛋白质合成的化合物具有式(I)及其盐、前药、前药的盐，制备该化合物的方法和制备过程中的中间体，含有该化合物的组合物，以及使用该化合物的方法被披露。
• ANTIBACTERIAL COMPOUNDS
  申请人：Anderson D. David

  公开号：US20070142353A1

  公开（公告）日：2007-06-21

  Bacterial protein synthesis-inhibiting compounds having formula (I) and salts, prodrugs, and salts of prodrugs thereof, processes for making the compounds and intermediates in the processes, compositions containing the compounds, and methods of using the compounds are disclosed.

  本文揭示具有式(I)及其盐，前药及其盐的细菌蛋白质合成抑制化合物，制备该化合物及其中间体的过程，含有该化合物的组合物以及使用该化合物的方法。
• NOVEL COMPOSITIONS AND METHODS OF USE
  申请人：CHEN Huanming

  公开号：US20110269741A1

  公开（公告）日：2011-11-03

  Described herein are novel enzyme inhibitors. In some embodiments the enzyme inhibitors are integrase inhibitors, particularly HIV integrase inhibitors. Also described herein are compositions containing them and methods of using them. Thus, the compounds and compositions described herein are useful for the in vitro and in vivo inhibition of HIV integrase as a method of treating or preventing HIV, AIDS or related disorders.

  本文介绍了新型酶抑制剂。在某些实施例中，酶抑制剂是整合酶抑制剂，特别是HIV整合酶抑制剂。本文还介绍了包含它们的组合物和使用它们的方法。因此，本文所描述的化合物和组合物可用于体外和体内抑制HIV整合酶作为治疗或预防HIV、艾滋病或相关疾病的方法。
• [EN] NOVEL COMPOSITIONS AND METHODS OF USE<br/>[FR] NOUVELLES COMPOSITIONS ET PROCÉDÉS D'UTILISATION
  申请人：ARDEA BIOSCIENCES INC

  公开号：WO2009089263A3

  公开（公告）日：2009-09-17
• [EN] COMPOUNDS USEFUL AS AKT/PKB MODULATORS AND USES THEREOF<br/>[FR] COMPOSÉS UTILES EN TANT QUE MODULATEURS AKT/PKB ET LEURS UTILISATIONS
  申请人：LYNDOR BIOSCIENCES L L C

  公开号：WO2012158197A3

  公开（公告）日：2013-03-14