2-(5-methylfuran-2-yl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)quinoline-4-carboxamide | 713118-53-7

• 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-(5-methylfuran-2-yl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)quinoline-4-carboxamide
• 英文别名: 2-(5-methyl-2-furyl)-N-[5-(4-pyridyl)-1,3,4-thiadiazol-2-yl]-4-quinolinecarboxamide；2-(5-methylfuran-2-yl)-N-(5-pyridin-4-yl-1,3,4-thiadiazol-2-yl)quinoline-4-carboxamide
• CAS: 713118-53-7
• 化学式: C₂₂H₁₅N₅O₂S
• mdl: MFCD05999580
• 分子量: 413.459
• InChiKey: ZXRTUBHUTXPXNM-UHFFFAOYSA-N

物化性质

• 密度：
  1.404±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(5-methylfuran-2-yl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)quinoline-4-carboxamide 在 sodium periodate 、 ruthenium(IV) oxide hydrate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 16.0h， 以29%的产率得到4-((5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)carbamoyl)quinoline-2-carboxylic acid
  参考文献：
  名称：

  Oxidative Reactivities of 2-Furylquinolines: Ubiquitous Scaffolds in Common High-Throughput Screening Libraries

  摘要：

  High-throughput screening (HTS) was employed to discover APOBEC3G inhibitors, and multiple 2-furylquinolines (e.g., 1) were found. Dose response assays with 1 from the HTS sample, as well as commercial material, yielded similar confirmatory results. Interestingly, freshly synthesized and DMSO-solubilized 1 was inactive. Repeated screening of the DMSO aliquot of synthesized 1 revealed increasing APOBEC3G inhibitory activity with age, suggesting that 1 decomposes into an active inhibitor. Laboratory aging of 1 followed by analysis revealed that 1 undergoes oxidative decomposition in air, resulting from a [4 + 2] cycloaddition between the furan of 1 and O-1(2). The resulting endoperoxide then undergoes additional transformations, highlighted by Baeyer-Villager rearrangements, to deliver lactam, carboxylic acid, and aldehyde products. The endoperoxide also undergoes hydrolytic opening followed by further transformations to a bis-enone. Eight structurally related analogues from HTS libraries were similarly reactive. This study constitutes a cautionary tale to validate 2-furylquinolines for structure and stability prior to chemical optimization campaigns.

  DOI：

  10.1021/acs.jmedchem.5b00930
• 作为产物：
  描述：

  异烟酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.0h， 生成 2-(5-methylfuran-2-yl)-N-(5-(pyridin-4-yl)-1,3,4-thiadiazol-2-yl)quinoline-4-carboxamide
  参考文献：
  名称：

  [EN] CYTOSINE DEAMINASE MODULATORS FOR ENHANCEMENT OF DNA TRANSFECTION
  [FR] MODULATEURS DE LA CYTOSINE DÉSAMINASE POUR L'AMÉLIORATION DE LA TRANSFECTION D'ADN

  摘要：

  公开号：

  WO2013074059A3

文献信息

• [EN] SMALL MOLECULE INHIBITORS OF APOBEC3G AND APOBEC3B<br/>[FR] INHBITEURS DE PETITES MOLÉCULES D'APOBEC3G ET D'APOBEC3B
  申请人：HARKI DANIEL A

  公开号：WO2015106272A1

  公开（公告）日：2015-07-16

  The present invention is directed to compositions and methods for inhibition of APOBEC-related DNA cytosine deaminase enzymes, and to methods of using the compounds for treatment of a disease in a patient, such as an infectious disease or a cancer. The infectious disease can be a viral disease, e.g., HIV, or can be a cancer, such as a breast, bladder, cervical, head, or neck cancer, or a lung squamous cell carcinoma or lung adenocarcinoma.

  本发明涉及抑制APOBEC相关的DNA胞嘧啶脱氨酶酶的组合物和方法，以及使用这些化合物治疗患者的疾病的方法，例如感染性疾病或癌症。感染性疾病可以是病毒性疾病，例如HIV，也可以是癌症，例如乳腺癌、膀胱癌、宫颈癌、头颈部肿瘤或肺鳞状细胞癌或肺腺癌。
• STAT3 INHIBITOR CONTAINING QUINOLINECARBOXAMIDE DERIVATIVE AS ACTIVE INGREDIENT
  申请人：General Incorporated Association Pharma Valley Project Supporting Organization

  公开号：EP2325181B1

  公开（公告）日：2017-03-29
• US20140275224A1
  申请人：——

  公开号：——

  公开（公告）日：——
• CYTOSINE DEAMINASE MODULATORS FOR ENHANCEMENT OF DNA TRANSFECTION
  申请人：Regents of the University of Minnesota

  公开号：EP2635280A2

  公开（公告）日：2013-09-11
• US8466290B2
  申请人：——

  公开号：US8466290B2

  公开（公告）日：2013-06-18