5-(2-胺苯基)-2,3-二氢-1,3,4-噁二唑-2-酮 | 86601-73-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-(2-胺苯基)-2,3-二氢-1,3,4-噁二唑-2-酮
• 英文名称: 5-(2-aminophenyl)-1,3,4-oxadiazol-2(3H)-one
• 英文别名: 5-(2-aminophenyl)-3H-1,3,4-oxadiazol-2-one；5-(2-aminophenyl)-1,3,4-oxadiazole-2(3H)-one
• CAS: 86601-73-2
• 化学式: C₈H₇N₃O₂
• mdl: MFCD20309075
• 分子量: 177.162
• InChiKey: TXCJPLZFJGBEJM-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(2-胺苯基)-2,3-二氢-1,3,4-噁二唑-2-酮 以86%的产率得到3-氨基-1H-喹唑烷-2,4-二酮
  参考文献：
  名称：

  The preparation of 5-(2-aminophenyl)-1,3,4-oxadiazole-2(3H)-one and its rearrangement to 3-amino-2,4(1H,3H)-quinazolinedione

  摘要：

  DOI：

  10.1007/bf00799164
• 作为产物：
  描述：

  2-硝基亚苯基肼 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 反应 0.5h， 生成 5-(2-胺苯基)-2,3-二氢-1,3,4-噁二唑-2-酮
  参考文献：
  名称：

  The preparation of 5-(2-aminophenyl)-1,3,4-oxadiazole-2(3H)-one and its rearrangement to 3-amino-2,4(1H,3H)-quinazolinedione

  摘要：

  DOI：

  10.1007/bf00799164

文献信息

• Substituted phenyl derivatives, their preparation and use
  申请人：——

  公开号：US20020037905A1

  公开（公告）日：2002-03-28

  The present invention discloses compounds having the formula 1 wherein the substituents are defined in the application. The compounds are useful as chloride channel blockers.

  本发明公开了具有以下结构的化合物，其中取代基在申请中定义。这些化合物可用作氯离子通道阻滞剂。
• Synthesis and Pharmacological Evaluation of Fenamate Analogues: 1,3,4-Oxadiazol-2-ones and 1,3,4-Oxadiazole-2-thiones
  作者：Aida El-Azzouny、Yousreya Maklad、Herbert Bartsch、Wafaa Zaghary、Waleed Ibrahim、Mosaad Mohamed

  DOI：10.3797/scipharm.aut-03-28

  日期：——

  A series of fenamate pyridyl or quinolinyl analogues of 1,3,4-oxadiazol-2-ones 5a-d and 6a-r, and 1,3,4-oxadiazole-2-thiones 5e-g and 6s-v, respectively, have been synthesized and evaluated for their analgesic (hot-plate) , antiinflammatory (carrageenin induced rat's paw edema) and ulcerogenic effects as well as plasma prostaglandin E2 (PGE2) level. The highest analgesic activity was achieved with compound 5a (0.5 ,0.6 ,0.7 mrnolkg b.wt.) in respect with mefenamic acid (0.4 mmollkg b.wt.). Compounds 6h, 6l and 5g showed 93, 88 and 84% inhibition, respectively on the carrageenan-induced rat's paw edema at dose level of 0.1rnrnol/kg b.wt, compared with 58% inhibition of mefenamic acid (0.2mmoll kg b.wt.). Moreover, the highest inhibitory activity on plasma PGE2 level was displayed also with 6h, 6l and 5g (71, 70,68.5% respectively, 0.lmmolkg b.wt.) compared with indomethacin (60%, 0.01 mmolkg b.wt.) as a reference drug. In addition 6i, 6k, 6p, 6r, 6t and 6v were devoid of any ulcerogenicity.

  一系列的苯酰胺吡啶或喹啉类似物，包括1,3,4-噁二唑-2-酮5a-d和6a-r，以及1,3,4-噁二唑-2-硫酮5e-g和6s-v，已经合成并评估了它们的镇痛（热板法）、抗炎症（卡拉胶诱导的大鼠爪肿胀）和溃疡原性效应以及血浆前列腺素E2（PGE2）水平。化合物5a（0.5、0.6、0.7 mmol/kg体重）在镇痛方面表现最好，相对于美非那酸（0.4 mmol/kg体重）。化合物6h、6l和5g在剂量为0.1 mmol/kg体重时对卡拉胶诱导的大鼠爪肿胀分别显示出93%、88%和84%的抑制作用，相对于美非那酸（0.2 mmol/kg体重）的58%抑制作用。此外，化合物6h、6l和5g在抑制血浆PGE2水平方面也表现出最高的活性（分别为71%、70%和68.5%，0.1 mmol/kg体重），相对于参考药物消炎痛（60%，0.01 mmol/kg体重）。此外，6i、6k、6p、6r、6t和6v没有任何溃疡原性。
• PENTADIENAMIDE DERIVATIVE
  申请人：Kyowa Hakko Kirin Co., Ltd.

  公开号：EP2050734A1

  公开（公告）日：2009-04-22

  The present invention provides a pentadienamide derivative represented by the formula (I): (wherein R1 represents substituted or unsubstituted aryl or a substituted or unsubstituted aromatic heterocyclic group; R2 represents substituted or unsubstituted aryl, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted heteroalicyclic group, or the like; R3 represents a hydrogen atom or is combined together with R4 and the adjacent nitrogen atom thereto to form a substituted or unsubstituted heterocyclic group; R4 represents substituted or unsubstituted aryl, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted heteroalicyclic group, or the like, or is combined together with R3 and the adjacent nitrogen atom thereto to form a substituted or unsubstituted heterocyclic group; and R5, R6, and R7 may be the same or different, and each represents a hydrogen atom or methyl) or a pharmaceutically acceptable salt thereof, and the like.

  本发明提供了一种由式(I)表示的戊二烯酰胺衍生物:(其中R1代表取代或未取代的芳基或取代或未取代的芳香族杂环基；R2代表取代或未取代的芳基、取代或未取代的芳香族杂环基、取代或未取代的杂环螺环基或类似物；R3代表氢原子或与R4及其相邻的氮原子结合形成取代或未取代的杂环基；R4代表取代或未取代的芳基、取代或未取代的芳香族杂环基、取代或未取代的杂环螺环基或类似物，或与R3及其相邻的氮原子结合形成取代或未取代的杂环基；R5、R6和R7可以相同也可以不同，每个代表氢原子或甲基)或其药学上可接受的盐等。
• PENTADIENAMIDE DERIVATIVES
  申请人：NAKASATO Yoshisuke

  公开号：US20090203667A1

  公开（公告）日：2009-08-13

  The present invention provides a pentadienamide derivative represented by the formula (I): (wherein R 1 represents substituted or unsubstituted aryl or a substituted or unsubstituted aromatic heterocyclic group; R 2 represents substituted or unsubstituted aryl, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted heteroalicyclic group, or the like; R 3 represents a hydrogen atom or is combined together with R 4 and the adjacent nitrogen atom thereto to form a substituted or unsubstituted heterocyclic group; R 4 represents substituted or unsubstituted aryl, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted heteroalicyclic group, or the like, or is combined together with R 3 and the adjacent nitrogen atom thereto to form a substituted or unsubstituted heterocyclic group; and R 5 , R 6 , and R 7 may be the same or different, and each represents a hydrogen atom or methyl) or a pharmaceutically acceptable salt thereof, and the like.

  本发明提供了一种由以下公式（I）表示的五二烯酰胺衍生物：（其中，R1代表取代或未取代的芳基或取代或未取代的芳香杂环基；R2代表取代或未取代的芳基，取代或未取代的芳香杂环基，取代或未取代的杂环螺环基或类似物；R3代表氢原子或与R4及其相邻的氮原子结合形成取代或未取代的杂环基；R4代表取代或未取代的芳基，取代或未取代的芳香杂环基，取代或未取代的杂环螺环基或类似物，或与R3及其相邻的氮原子结合形成取代或未取代的杂环基；R5、R6和R7可以相同也可以不同，每个代表氢原子或甲基）或其药学上可接受的盐等。
• Synthesis and Biological Evaluation of New Quinoline and Anthranilic Acid Derivatives as Potential Quorum Sensing Inhibitors
  作者：Ivana Perković、Tanja Poljak、Kirsi Savijoki、Pekka Varmanen、Gordana Maravić-Vlahoviček、Maja Beus、Anja Kučević、Ivan Džajić、Zrinka Rajić

  DOI：10.3390/molecules28155866

  日期：——

  pre-formed biofilms, and inhibit virulence using pyocyanin as a representative marker. Compound 15 displayed the most potent antibiofilm effect, reducing biofilm formation by nearly 50% and pre-formed biofilm masses by 25%. On the other hand, compound 23 exhibited the most significant antivirulence effect, reducing pyocyanin synthesis by over 70%. Thus, our study highlights the potential of 1,3,4-oxadiazoles

  抑制群体感应（QS）是一种中央通信系统，是一种无需抗生素即可对抗细菌病原体的有前途的策略。在这里，我们设计了针对铜绿假单胞菌 PQS（假单胞菌喹诺酮信号）依赖性群体感应（QS）的新型混合化合物，铜绿假单胞菌是一种多重耐药性和高毒力病原体，迫切需要新的抗菌策略。我们使用标准程序将卤素取代的邻氨基苯甲酸与 4-(2-氨基乙基/4-氨基丁基)氨基-7-氯喹啉通过 1,3,4-恶二唑连接，合成了 12 种化合物。首先使用基于革兰氏阴性紫罗兰色杆菌的报告基因对它们的抗生物膜活性进行预筛选，该报告基因在一次实验中鉴定出化合物 15-19 和 23 具有最高的抗 QS 作用和最小的杀菌作用。然后针对铜绿假单胞菌 PAO1 评估这五种化合物，以评估它们防止生物膜形成、根除预先形成的生物膜以及使用绿脓素作为代表性标记物抑制毒力的能力。化合物 15 显示出最有效的抗生物膜作用，将生物膜形成减少近 50%，将预形成的生物膜质量减少