1-[(4-phenylphenyl)methyl]-6,7-dihydro-5H-pyrrolo[2,3-c]azepine-4,8-dione | 1234505-85-1

• 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: 1-[(4-phenylphenyl)methyl]-6,7-dihydro-5H-pyrrolo[2,3-c]azepine-4,8-dione
• CAS: 1234505-85-1
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: YRIPYXMAUMAQQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  51.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(4-phenylphenyl)methyl]-6,7-dihydro-5H-pyrrolo[2,3-c]azepine-4,8-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以85%的产率得到4-Hydroxy-1-[(4-phenylphenyl)methyl]-4,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one
  参考文献：
  名称：

  Pyrrolo[2,3-c]azepine derivatives: A new class of potent protein tyrosine phosphatase 1B inhibitors

  摘要：

  A series of pyrrolo[2,3-c] azepine derivatives was designed, synthesized, and evaluated as a new class of inhibitors against protein tyrosine phosphatase 1B (PTP1B) in vitro. The results demonstrated that compounds bearing a biphenyl moiety were proved to markedly influence the potency of these inhibitors. Particularly, compounds 29, 35 and 36 showed interesting inhibition with IC50 value of 16.36, 14.93 and 13.92 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.052
• 作为产物：
  描述：

  2-(三氯乙酰)吡咯 在 四磷十氧化物 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 1-[(4-phenylphenyl)methyl]-6,7-dihydro-5H-pyrrolo[2,3-c]azepine-4,8-dione
  参考文献：
  名称：

  Pyrrolo[2,3-c]azepine derivatives: A new class of potent protein tyrosine phosphatase 1B inhibitors

  摘要：

  A series of pyrrolo[2,3-c] azepine derivatives was designed, synthesized, and evaluated as a new class of inhibitors against protein tyrosine phosphatase 1B (PTP1B) in vitro. The results demonstrated that compounds bearing a biphenyl moiety were proved to markedly influence the potency of these inhibitors. Particularly, compounds 29, 35 and 36 showed interesting inhibition with IC50 value of 16.36, 14.93 and 13.92 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.052

文献信息

• Discovery of Aldisine and Its Derivatives as Novel Antiviral, Larvicidal, and Antiphytopathogenic-Fungus Agents
  作者：Wentao Xu、Rongxin Yang、Yanan Hao、Hongjian Song、Yuxiu Liu、Jingjing Zhang、Yongqiang Li、Qingmin Wang

  DOI：10.1021/acs.jafc.2c04256

  日期：2022.10.5

  Based on the widespread use of hydrogen bonds in drug design, a series of aldisine derivatives containing oxime, oxime ether, and hydrazone moieties were designed and synthesized, and their antiviral, larvicidal, and fungicidal activities were evaluated for the first time. The bioassay results showed that most of these derivatives were active against tobacco mosaic virus (TMV). Hydrazone derivative

  基于氢键在药物设计中的广泛应用，设计合成了一系列含有肟、肟醚和腙部分的醛化衍生物，并首次评价了它们的抗病毒、杀幼虫和杀真菌活性。生物测定结果表明，这些衍生物中的大多数对烟草花叶病毒 (TMV) 具有活性。腙衍生物12在 500 mg/L时的体内灭活、治疗和保护活性分别为 52 ± 4、49 ± 1 和 52 ± 3%，与市售抗病毒药物宁南霉素 (57 ± 3, 56 ± 2 和 59 ± 1%）在相同剂量下。抗病毒机制研究表明，化合物12可引起20S CP（涂层蛋白）盘融合和解体，从而影响病毒颗粒的组装。分子对接结果表明化合物12与TMV CP之间存在明显的氢键。大多数衍生物对鳞翅目害虫的幼虫具有活性，例如Mythimna separata、Pyrausta nubilalis和Plutella xylostella。一些化合物还表现出对淡色库蚊的杀幼虫活性；其中化合物9和13的杀幼虫活性分别为
• Design, Synthesis, and Bioactivity of Aldisine Derivatives Containing Oxime and Hydrazine Moieties Based on Hydrogen Bonds
  作者：Wentao Xu、Rongxin Yang、Lixia Liu、Jingjing Zhang、Yuxiu Liu、Yongqiang Li、Lizhong Wang、Hongjian Song、Qingmin Wang

  DOI：10.1021/acs.jafc.3c02480

  日期：2023.7.26

  analysis. The antiviral activity test result showed that most derivatives had antiviral activity against tobacco mosaic virus (TMV), and some compounds had better activity than the commercial antiviral drug ribavirin, especially compounds 2 and 24, which had comparable activity to the most effective commercial antiviral drug ningnanmycin. Preliminary mode of action studies showed that compound 2 could affect

  海洋天然产物以其独特的结构、多样的生物活性、新颖的作用方式在药物研发中越来越受到关注。以抗病毒生物碱阿地辛为先导化合物，利用药物设计中广泛使用的氢键效应，通过在分子中引入具有氢键受体或供体的官能团，设计并合成了含有肟和腙部分的衍生物。通过核欧沃豪瑟效应（NOE）光谱和单晶分析系统地研究了衍生物的构型。抗病毒活性测试结果表明，大多数衍生物对烟草花叶病毒（TMV）具有抗病毒活性，部分化合物的活性优于市售抗病毒药物利巴韦林，特别是化合物2和24，其活性与最有效的市售抗病毒药物相当。宁南霉素。初步作用模式研究表明，化合物2可以通过促进TMV外壳蛋白的聚集和断裂来影响杆状TMV的组装。分子对接实验表明，肟和腙部分的引入确实可以增加分子与靶蛋白之间的氢键。此外，我们还对这些衍生物进行了杀真菌和杀幼虫活性研究。这些衍生物大多对粘虫和小菜蛾具有良好的杀幼虫活性，并表现出广谱杀菌活性。