2-heptyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamide | 1593849-57-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-heptyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamide
• 英文别名: 2-heptyl-6-nitro-4-oxo-1H-quinoline-3-carboxamide
• CAS: 1593849-57-0
• 化学式: C₁₇H₂₁N₃O₄
• 分子量: 331.371
• InChiKey: ZYYNLKCPTZVIPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-氧代癸酸甲酯 在 sodium hydride 、 N,N'-羰基二咪唑 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-heptyl-6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  The requirements at the C-3 position of alkylquinolones for signalling in Pseudomonas aeruginosa

  摘要：

  细菌对抗生素的耐药性越来越强，而新抗生素的发现却越来越少，这种 "完美风暴 "使得我们必须寻找新的创新策略来治疗细菌感染。

  DOI：

  10.1039/c6ob01930g

文献信息

• [EN] NOVEL PqsR INVERSE AGONISTS<br/>[FR] NOUVEAUX AGONISTES INVERSES DE PQSR
  申请人：HELMHOLTZ ZENTRUM INFEKTIONSFORSCHUNG GMBH

  公开号：WO2021136805A1

  公开（公告）日：2021-07-08

  The present invention relates to a compound according to general formula (I), which acts as an inverse agonist of PqsR (the currently only known receptor for the Pseudomonas Quinolone Signal (PQS), sometimes also referred to as MvfR); to a pharmaceutical composition containing one or more of the compound(s) of the invention: to a combination preparation containing at least one compound of the invention and at least one further active pharmaceutical ingredient; and to uses of said compound(s), including the use as a medicament, e.g. the use in the treatment or prophylaxis of a bacterial infection, especially a Pseudomonas aeruginosa or Burkholderia infection.

  本发明涉及一种化合物，其通式为（I），作为PqsR的反向激动剂（目前已知的Pseudomonas Quinolone Signal（PQS）受体，有时也称为MvfR）；一种含有该化合物的药物组合物；至少包含本发明化合物之一和至少一种其他活性药物成分的组合制剂；以及该化合物的用途，包括作为药物的用途，例如用于治疗或预防细菌感染，特别是铜绿假单胞菌或伯克霍尔德氏菌感染。
• [EN] PQSR MODULATORS<br/>[FR] MODULATEURS DU PQSR
  申请人：HELMHOLTZ ZENTRUM FÜR INFEKTIONSFORSCHUNG GMBH

  公开号：WO2015149821A1

  公开（公告）日：2015-10-08

  The present invention relates to compounds according to general formula (I); to pharmaceutical compositions comprising one or more of the compound(s); and to the use of the compound(s) as anti-infectives.

  本发明涉及一般式（I）的化合物；含有一种或多种化合物的制药组合物；以及将该化合物用作抗感染剂的用途。
• [EN] NEW PqsR INVERSE AGONISTS<br/>[FR] NOUVEAUX AGONISTES INVERSES DE PQSR
  申请人：HELMHOLTZ ZENTRUM INFEKTIONSFORSCHUNG GMBH

  公开号：WO2021136803A1

  公开（公告）日：2021-07-08

  The present invention relates to a compounds according to general formula (I), which acts as an inverse agonist of PqsR (the currently only known receptor for the Pseudomonas Quinolone Signal (PQS), sometimes also referred to as MvfR); to a pharmaceutical composition containing one or more of the compound(s) of the invention; to a combination preparation containing at least one compound of the invention and at least one further active pharmaceutical ingredient; and to uses of said compound(s), including the use as a medicament, e.g. the use in the treatment or prophylaxis of a bacterial infection, especially a Pseudomonas aeruginosa or Burkholderia infection.

  本发明涉及一种符合通式（I）的化合物，其作为PqsR的反向激动剂（目前已知的Pseudomonas Quinolone Signal（PQS）的唯一受体，有时也称为MvfR）；一种含有本发明化合物中的一种或多种化合物的制药组合物；一种含有本发明化合物中至少一种化合物和至少一种其他活性药物成分的联合制剂；以及本发明化合物的用途，包括作为药物的用途，例如用于治疗或预防细菌感染，特别是铜绿假单胞菌或布氏杆菌感染。
• Overcoming the Unexpected Functional Inversion of a PqsR Antagonist in<i>Pseudomonas aeruginosa</i>: An In Vivo Potent Antivirulence Agent Targeting<i>pqs</i>Quorum Sensing
  作者：Cenbin Lu、Christine K. Maurer、Benjamin Kirsch、Anke Steinbach、Rolf W. Hartmann

  DOI：10.1002/anie.201307547

  日期：2014.1.20

  The virulence regulator PqsR of Pseudomonas aeruginosa is considered as an attractive target for attenuating the bacterial pathogenicity without eliciting resistance. However, despite efforts and desires, no promising PqsR antagonist has been discovered thus far. Now, a surprising functionality change of a highly affine PqsR antagonist in P. aeruginosa is revealed, which is mediated by a bacterial

  铜绿假单胞菌的毒力调节剂PqsR被认为是在不引起耐药性的情况下减弱细菌致病性的诱人靶标。然而，尽管作出了努力和期望，迄今为止尚未发现有希望的PqsR拮抗剂。现在，揭示了铜绿假单胞菌中一种高度亲和力的PqsR拮抗剂的功能发生了令人惊讶的变化，这是由细菌信号分子合酶介导的，并导致细胞效力低下。易感位置的封锁导致发现了第一种在体内有效并靶向PqsR的抗毒化合物，因此为这种新型抗毒疗法提供了概念验证。
• AMINOGLYCOSIDE DERIVATIVES AND NANO-ASSEMBLIES THEREOF, INCLUDING THOSE WITH QUORUM SENSING INHIBITORY FUNCTION
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP3421050A1

  公开（公告）日：2019-01-02

  The present invention relates to conjugates of aminoglycosides and terpenoids, in particular sesquiterpenoids. Furthermore, the present invention relates to nano-assemblies formed by the inventive conjugates and to a method for producing the conjugates and/or the nano-assemblies. The present invention also relates to the inventive conjugates and nano-assemblies for use in therapy, in particular for use in the treatment of infectious diseases. Particularly preferred embodiments of the present invention relate to farnesylated aminoglycosides and nano-assemblies thereof, in which farnesol and its derivatives do not only function as carrier for the aminoglycosides but do themselves have pharmaceutical activity upon cleavage of the conjugate, in particular quorum sensing inhibitory activity.

  本发明涉及氨基糖苷类和萜类，特别是倍半萜类的共轭物。此外，本发明还涉及由本发明共轭物形成的纳米组合物，以及生产共轭物和/或纳米组合物的方法。本发明还涉及用于治疗的本发明共轭物和纳米组合物，特别是用于治疗传染性疾病的共轭物和纳米组合物。本发明特别优选的实施方案涉及法呢醇化氨基糖苷类化合物及其纳米组合物，其中法呢醇及其衍生物不仅作为氨基糖苷类化合物的载体，而且在共轭物裂解后本身也具有药物活性，特别是定量感应抑制活性。