methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylate | 438467-08-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylate
• 英文别名: methyl 3-[(biphenyl-4-ylcarbonyl)amino]thiophene-2-carboxylate；methyl 3-[(4-phenylbenzoyl)amino]thiophene-2-carboxylate
• CAS: 438467-08-4
• 化学式: C₁₉H₁₅NO₃S
• mdl: MFCD03070826
• 分子量: 337.399
• InChiKey: JZGINTNMHKJHNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylate 在 lithium hydroxide monohydrate 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Pyrimidinone Derivatives and Their Use as a Drug

  摘要：

  本申请涉及新的嘧啶酮衍生物。这些产品对某些亚型的大麻素受体，特别是CB2受体具有良好的亲和力。它们特别适用于治疗涉及一个或多个大麻素受体的病理状况和疾病。本发明还涉及含有上述产品的药物组合物及其用于制备药物的用途。

  公开号：

  US20090325933A1
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 42.0h， 生成 methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylate
  参考文献：
  名称：

  Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections

  摘要：

  Targeting PqsD is a promising novel approach to disrupt bacterial cell-to-cell-communication in Pseudomonas aeruginosa. In search of selective PqsD inhibitors, two series of benzamidobenzoic acids - one published as RNAP inhibitors and the other as PqsD inhibitors - were investigated for inhibitory activity toward the respective other enzyme. Additionally, novel derivatives were synthesized and biologically evaluated. By this means, the structural features needed for benzamidobenzoic acids to be potent and, most notably, selective PqsD inhibitors were identified. The most interesting compound of this study was the 3-Cl substituted compound 5 which strongly inhibits PqsD (IC50 6.2 mu M) while exhibiting no inhibition of RNAP. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.02.014
• 作为试剂：
  描述：

  单水氢氧化锂 、 methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylate 在 乙酸乙酯 、 水 、 溶剂黄146 、 Sodium sulfate-III 、 methyl 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylate 作用下， 以 水 、 四氢呋喃 为溶剂， 反应 3.0h， 生成 3-([1,1'-biphenyl]-4-ylcarboxamido)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Pyrimidinone Derivatives and Their Use as a Drug

  摘要：

  本申请涉及新的嘧啶酮衍生物。这些产物对于某些亚型的大麻素受体，尤其是CB2受体具有良好的亲和力。它们特别适用于治疗一个或多个大麻素受体参与的病理条件和疾病。该发明还涉及含有所述产物的制药组合物及其用于制备药物的用途。

  公开号：

  US20090325933A1

文献信息

• DERIVES DE PYRIMIDINONE ET LEUR UTILISATION COMME MEDICAMENT
  申请人：Societe de Conseils de Recherches et d'Applications Scientifique

  公开号：EP2054419A2

  公开（公告）日：2009-05-06
• [EN] PYRIMIDINONE DERIVATIVES AND THEIR USE AS A DRUG<br/>[FR] DERIVES DE PYRIMIDINONE ET LEUR UTILISATION COMME MEDICAMENT
  申请人：SOD CONSEILS RECH APPLIC

  公开号：WO2008012413A2

  公开（公告）日：2008-01-31

  [EN] The present application relates to new pyrimidinone derivatives. These products have a good affinity for certain sub-types of cannabinoid receptors, especially the CB2 receptors. They are particularly attractive for treating pathological conditions and diseases in which one or more cannabinoid receptors are involved. The invention also relates to pharmaceutical compositions containing said products and their use for the preparation of a drug.
  [FR] La présente demande a pour objet de nouveaux dérivés pyrimidinone. Ces produits ont une bonne affinité pour certains sous-types de récepteurs de cannabinoides, en particulier les récepteurs CB2. Ils sont particulièrement intéressants pour traiter les états pathologiques et les maladies dans lesquels un ou plusieurs récepteurs des cannabinoides sont impliqués. L'invention concerne également des compositions pharmaceutiques contenant lesdits produits et leur utilisation pour la préparation d'un médicament.
• Benzamidobenzoic acids as potent PqsD inhibitors for the treatment of Pseudomonas aeruginosa infections
  作者：Stefan Hinsberger、Johannes C. de Jong、Matthias Groh、Jörg Haupenthal、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2014.02.014

  日期：2014.4

  Targeting PqsD is a promising novel approach to disrupt bacterial cell-to-cell-communication in Pseudomonas aeruginosa. In search of selective PqsD inhibitors, two series of benzamidobenzoic acids - one published as RNAP inhibitors and the other as PqsD inhibitors - were investigated for inhibitory activity toward the respective other enzyme. Additionally, novel derivatives were synthesized and biologically evaluated. By this means, the structural features needed for benzamidobenzoic acids to be potent and, most notably, selective PqsD inhibitors were identified. The most interesting compound of this study was the 3-Cl substituted compound 5 which strongly inhibits PqsD (IC50 6.2 mu M) while exhibiting no inhibition of RNAP. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Pyrimidinone Derivatives and Their Use as a Drug
  申请人：Poitout Lydie

  公开号：US20090325933A1

  公开（公告）日：2009-12-31

  The present application relates to new pyrimidinone derivatives. These products have a good affinity for certain sub-types of cannabinoid receptors, especially the CB2 receptors. They are particularly attractive for treating pathological conditions and diseases in which one or more cannabinoid receptors are involved. The invention also relates to pharmaceutical compositions containing said products and their use for the preparation of a drug.

  本申请涉及新的嘧啶酮衍生物。这些产品对某些亚型的大麻素受体，特别是CB2受体具有良好的亲和力。它们特别适用于治疗涉及一个或多个大麻素受体的病理状况和疾病。本发明还涉及含有上述产品的药物组合物及其用于制备药物的用途。