N-[5-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl)-4-phenyl-thiazol-2-yl]-benzamide | 952612-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-[5-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl)-4-phenyl-thiazol-2-yl]-benzamide
• 英文别名: N-(5-(4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)-4-phenylthiazol-2-yl)benzamide；N-[5-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl)-4-phenyl-thiazole-2-yl]benzamide；N-[5-(4-oxo-3-phenylquinazolin-2-yl)-4-phenyl-1,3-thiazol-2-yl]benzamide
• CAS: 952612-54-3
• 化学式: C₃₀H₂₀N₄O₂S
• 分子量: 500.58
• InChiKey: WXWGZIFOXZNBIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N,N-diethylbenzamidine 以 丙酮 、 乙腈 为溶剂， 反应 1.0h， 生成 N-[5-(4-oxo-3-phenyl-3,4-dihydro-quinazolin-2-yl)-4-phenyl-thiazol-2-yl]-benzamide
  参考文献：
  名称：

  取代的4-苯基噻唑：开发有效和选择性的A1，A3和双重A1 / A3腺苷受体拮抗剂。

  摘要：

  腺苷通过四个不同的G蛋白偶联受体（称为A1，A2A，A2B和A3腺苷受体（ARs））充当强大的信号分子。A2A和A2B ARs是Gs偶联的，而A1和A3 ARs通过Gi蛋白抑制cAMP的产生。A1和A3 ARs的拮抗剂可用于治疗（神经）炎性疾病，包括急性肾损伤和肾衰竭，肺部疾病和阿尔茨海默氏病。在本研究中，我们通过在N2和C5处引入取代基来获得包括双重靶标化合物的A1和A3 AR拮抗剂，从而优化了通用的2-氨基-4-苯基噻唑支架。产生了具有（亚）纳摩尔效价的选择性A1拮抗剂，例如11和13。这些化合物显示，与人的A1 AR相比，物种差异在大鼠处的效价明显更高，并且被表征为反向激动剂。制备了几种有效的和选择性的A3 AR拮抗剂，例如7、8、17和22（人A3 AR的Ki值为5-9 nM），它们在大鼠直系同源物上的效力要低得多。此外，开发了双重A1 / A3拮抗剂（10、18），显示Ki值在8到42

  DOI：

  10.1016/j.ejmech.2019.111879

文献信息

• Synthesis and evaluation of quinazolinone derivatives as inhibitors of NF-κB, AP-1 mediated transcription and eIF-4E mediated translational activation: Inhibitors of multi-pathways involve in cancer
  作者：Rajan S. Giri、Hardik M. Thaker、Tony Giordano、Bing Chen、Sam Nuthalapaty、Kamala K. Vasu、Vasudevan Sudarsanam

  DOI：10.1016/j.ejmech.2010.04.038

  日期：2010.9

  In our effort to discover and develop small molecule multi-pathway inhibitors which may be useful as tools for treating cancerous conditions, we have synthesized a small library of 2-thiazole-5-yl-3H-quinazolin-4-one derivatives. Synthesized compounds were evaluated as inhibitors of NF-kappa B and AP-1 mediated transcriptional and eIF-4E mediated translational activation as these transcription and translation factors are known to play a pivotal role in initiation and progression of cancer. The results from the study suggest the utility of the 2-thiazole-5-yl-3H-quinazolin-4-one scaffold as a promising scaffold for the design of novel multi-pathway inhibitors, which can be explored as anti-cancer agents. (C) 2010 Elsevier Masson SAS. All rights reserved.
• THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS
  申请人：Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College

  公开号：EP2007393A2

  公开（公告）日：2008-12-31
• Thiazole and Thiophene Analogues, and Their Use in Treating Autoimmune Diseases and Cancers
  申请人：Giordano Anthony

  公开号：US20090306073A1

  公开（公告）日：2009-12-10

  Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.
• US8217037B2
  申请人：——

  公开号：US8217037B2

  公开（公告）日：2012-07-10
• [EN] THIAZOLE AND THIOPHENE ANALOGUES, AND THEIR USE IN TREATING AUTOIMMUNE DISEASES AND CANCERS<br/>[FR] THIAZOLE ET THIOPHENE ANALOGUES ET LEUR UTILISATION POUR TRAITER DES MALADIES AUTO-IMMUNES ET DES CANCERS
  申请人：UNIV LOUISIANA STATE

  公开号：WO2007118149A2

  公开（公告）日：2007-10-18

  [EN] Thiazole and thiophene compounds are disclosed having utility in treating inflammatory conditions, immunoinflammatory conditions, autoimmune diseases, and cancers. Methods for the synthesis of these compounds are also disclosed.
  [FR] La présente invention concerne des composés de thiazole et de thiophène utilisables pour traiter des inflammations, des états immuno-inflammatoires, des maladies auto-immunes et des cancers. L'invention concerne également des procédés de synthèse de ces composés.