5-cyclopropyl-4-[(1-naphthyl)methyl]-2-oxo-8-(1H-1,2,3-triazol-4-yl)-7-thia-1-azabicyclo[4.3.0]nona-3,5,8-triene-9-carboxylic acid | 1394135-87-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-cyclopropyl-4-[(1-naphthyl)methyl]-2-oxo-8-(1H-1,2,3-triazol-4-yl)-7-thia-1-azabicyclo[4.3.0]nona-3,5,8-triene-9-carboxylic acid
• 英文别名: 8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(1H-1,2,3-triazol-4-yl)-5H-thiazolo[3,2-a]pyridine-3-carboxylic acid；8-cyclopropyl-7-(1-naphthylmethyl)-5-oxo-2-(1H-triazol-4-yl)thiazolo[3,2-a]pyridine-3-carboxylic acid；8-cyclopropyl-7-(naphthalen-1-ylmethyl)-5-oxo-2-(2H-triazol-4-yl)-[1,3]thiazolo[3,2-a]pyridine-3-carboxylic acid
• CAS: 1394135-87-5
• 化学式: C₂₄H₁₈N₄O₃S
• 分子量: 442.498
• InChiKey: DRTGIFGVIWTJLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  125
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 8-cyclopropyl-2-ethynyl-7-(naphthalen-1-ylmethyl)-5-oxo-5H-thiazolo[3,2-a]pyridine-3-carboxylate 在 sodium azide 、 四丁基氟化铵 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 21.0h， 生成 5-cyclopropyl-4-[(1-naphthyl)methyl]-2-oxo-8-(1H-1,2,3-triazol-4-yl)-7-thia-1-azabicyclo[4.3.0]nona-3,5,8-triene-9-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and evaluation of triazole functionalized ring-fused 2-pyridones as antibacterial agents

  摘要：

  Antibacterial resistance is today a worldwide problem and the demand for new classes of antibacterial agents with new mode of action is enormous. In the strive for new antibacterial agents that inhibit pilus assembly, an important virulence factor, routes to introduce triazoles in position 8 and 2 of ring-fused bicyclic 2-pyridones have been developed. This was made via Sonogashira couplings followed by Huisgen 1,3-dipolar cycloadditions. The method development made it possible to introduce a diverse series of substituted triazoles and their antibacterial properties were tested in a whole cell pili-dependent biofilm assay. Most of the twenty four candidates tested showed low to no activity but interestingly three compounds, one 8-substituted and two 2-substituted, showed promising activities with EC50's between 9 and 50 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.06.018

文献信息

• [EN] RING-FUSED THIAZOLINO 2-PYRIDONES, METHODS FOR PREPARATION THEREOF AND THEIR USE IN THE TREATMENT AND/OR PREVENTION OF TUBERCULOSIS<br/>[FR] THIAZOLINO 2-PYRIDONES À CYCLES FUSIONNÉS, LEURS PROCÉDÉS DE PRÉPARATION ET LEUR UTILISATION DANS LE TRAITEMENT ET/OU LA PRÉVENTION DE LA TUBERCULOSE
  申请人：QURETECH BIO AB

  公开号：WO2017175182A1

  公开（公告）日：2017-10-12

  The present disclosure provides a combination comprising: (i) a drug against tuberculosis, or a pharmaceutically acceptable salt thereof, and (ii) a compound of Formula (II), or a pharmaceutically acceptable combination thereof. The combination may be used in the treatment and/or prevention of tuberculosis.

  本公开提供了一种组合物，包括：（i）用于治疗结核病的药物或其药用盐，以及（ii）式（II）的化合物，或其药用可接受的组合物。该组合物可用于治疗和/或预防结核病。
• [EN] RING-FUSED THIAZOLINO 2-PYRIDONES IN COMBINATION WITH A DRUG AGAINST TUBERCULOSIS<br/>[FR] THIAZOLINO 2-PYRIDONES À CYCLE FUSIONNÉ EN COMBINAISON AVEC UN MÉDICAMENT CONTRE LA TUBERCULOSE
  申请人：QURETECH BIO AB

  公开号：WO2019068910A1

  公开（公告）日：2019-04-11

  The present disclosure provides a combination comprising: (i). a drug against tuberculosis inhibiting the cytochrome b subunit of the bc1 complex, said cytochrome b subunit being encoded by the gene qcrB,in Mycobacterium tuberculosis, or a pharmaceutically acceptable salt thereof, and (ii) a compound of Formula (II), or a pharmaceutically acceptable salt thereof.

  本公开提供一种组合物，包括：(i) 抗结核药物，抑制bc1复合物的细胞色素b亚基，所述细胞色素b亚基由Mycobacterium tuberculosis的qcrB基因编码，或其药用盐，以及(ii) 公式(II)的化合物，或其药用盐。
• Ring-fused thiazolino 2-pyridones, methods for preparation thereof and their use in the treatment and/or prevention of tuberculosis
  申请人：QURETECH BIO AB

  公开号：US10945999B2

  公开（公告）日：2021-03-16

  The present disclosure provides a combination comprising: (i) a drug against tuberculosis, or a pharmaceutically acceptable salt thereof, and (ii) a compound of Formula II, or a pharmaceutically acceptable combination thereof. The combination may be used in the treatment and/or prevention of tuberculosis.

  本公开提供了一种组合物，包括：(i) 抗结核药物或其药学上可接受的盐；(ii) 式 II.化合物或其药学上可接受的组合物、 或其药学上可接受的组合物。 该组合物可用于治疗和/或预防结核病。
• Ring-fused thiazolino 2-pyridones in combination with a drug against tuberculosis
  申请人：QURETECH BIO AB

  公开号：US11129816B2

  公开（公告）日：2021-09-28

  Described is a composition that includes: (i) a drug against tuberculosis inhibiting the cytochrome b subunit of the bc1 complex, said cytochrome b subunit being encoded by the gene qcrB, in Mycobacterium tuberculosis, or a pharmaceutically acceptable salt thereof, and (ii) a compound of Formula II, or a pharmaceutically acceptable salt thereof.

  所述组合物包括 (i) 一种抑制 bc1 复合物细胞色素 b 亚基的抗结核药物，所述细胞色素 b 亚基由结核分枝杆菌中的 qcrB 基因编码，或其药学上可接受的盐，和 (ii) 式 II 的化合物、 或其药学上可接受的盐。
• RING-FUSED THIAZOLINO 2-PYRIDONES, METHODS FOR PREPARATION THEREOF AND THEIR USE IN THE TREATMENT AND/OR PREVENTION OF TUBERCULOSIS
  申请人：Quretech Bio AB

  公开号：EP3439655B1

  公开（公告）日：2021-03-03