(Z)-3-(2-([1,1'-biphenyl]-4-yl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one

• 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: (Z)-3-(2-([1,1'-biphenyl]-4-yl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
• 英文别名: (3Z)-3-[2-oxo-2-(4-phenylphenyl)ethylidene]-4H-1,4-benzoxazin-2-one
• 化学式: C₂₂H₁₅NO₃
• 分子量: 341.366
• InChiKey: JWFOQOMSQMVDEB-RGEXLXHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  联苯单乙酮 在 sodium 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 (Z)-3-(2-([1,1'-biphenyl]-4-yl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activity of benzoxazinone derivatives and open-ring analogues: Preliminary data and computational analysis

  摘要：

  This study examines in depth benzoxazine nucleus for antimycobacterial property. We synthesized some benzoxazin-2-one and benzoxazin-3-one derivatives, which were tested for activity against a panel of Mycobacterium tuberculosis (Mtb) strains, including H37Ra, H37Rv and some resistant strains. Several compounds displayed a high antimycobacterial activity and the three isoniazid analogue derivatives 8a-c exhibited a MIC range of 0.125-0.250 mu g/mL (0.37-0.75 mu M) against strain H37Ra, therefore lower than the isoniazid reference drug. Two benzoxazin-2-one derivatives, 1c and 5j, together with isoniazid-analogue compound 8a, also revealed low MIC values against resistant strains and proved highly selective for mycobacterial cells, compared to mammalian Vero cells. To predict whether molecule 8a is able to interact with the active site of InhA, we docked it into the crystal structure; indeed, during the molecular dynamic simulation the compound never left the protein pocket. The more active compounds were predicted for ADME properties and all proved to be potentially orally active in humans.

  DOI：

  10.1016/j.bmcl.2019.07.025

文献信息

• Synthesis, antimicrobial activity, structure-activity relationship and cytotoxic studies of a new series of functionalized (Z)-3-(2-oxo-2-substituted ethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ones
  作者：Ritu Sharma、Lalit Yadav、Jaggi Lal、Pradeep K. Jaiswal、Manas Mathur、Ajit K. Swami、Sandeep Chaudhary

  DOI：10.1016/j.bmcl.2017.08.017

  日期：2017.9

  ethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ones 23–26, incorporating pharmaceutically privileged substructures such as cyclopropyl, naphthyl, biphenyl and cyclohexylphenyl were synthesized in excellent yields. All the synthesized compounds were screened for their in vitro antibacterial activity against gram-(+)ve and gram-(−)ve bacterial species i.e. S. griseus, S. aureus, B. subtillis and E. coli as

  一系列新的官能化（Z）-3-（2-氧-2-取代亚乙基）-3,4-二氢-2 H-苯并[ b ] [1,4]恶嗪-2-酮23 – 26，以优异的产率合成了药学上优先的亚结构，例如环丙基，萘基，联苯和环己基苯基。所有合成的化合物筛选它们体外抗革兰氏抗菌活性- （+）ve和克- （ - ）已经细菌物种即灰色链霉菌，金黄色葡萄球菌，枯草芽孢杆菌和大肠杆菌以及体外抗真菌对真菌物种，即氧化枯萎病菌的活性，A。niger，P。funiculosum和T. reesei。在这项研究中，与标准药物，氨苄青霉素和氯霉素以及酮康唑相比，含有环丙基和环己基苯基亚结构的化合物被确定为有前途的抗菌剂。SAR研究表明，吸电子基团增加了2-氧代-苯并[1,4]恶嗪的抗菌和抗真菌活性，反之亦然。该系列中活性最高的化合物23e和26e比氨苄青霉素和氯霉素显示出令人鼓舞的抗菌活性。此外，化合物26d与酮康唑相比，它显示出有希望的抗真菌效力。使用MTT分析法对3T