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(Z)-3-(2-(2-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one | 1257269-08-1

中文名称
——
中文别名
——
英文名称
(Z)-3-(2-(2-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one
英文别名
(3Z)-3-[2-(2-chlorophenyl)-2-oxoethylidene]-4H-1,4-benzoxazin-2-one
(Z)-3-(2-(2-chlorophenyl)-2-oxoethylidene)-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one化学式
CAS
1257269-08-1
化学式
C16H10ClNO3
mdl
——
分子量
299.713
InChiKey
SXAGJLVODPLYNN-LCYFTJDESA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    3.7
  • 重原子数:
    21
  • 可旋转键数:
    2
  • 环数:
    3.0
  • 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:
    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
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文献信息

  • Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: Novel antibacterial agents against Mycobacterium tuberculosis
    作者:Xiaokai Li、Nina Liu、Huaning Zhang、Susan E. Knudson、Richard A. Slayden、Peter J. Tonge
    DOI:10.1016/j.bmcl.2010.08.076
    日期:2010.11
    Menaquinone is an essential component of the electron transport chain in many pathogens and consequently enzymes in the menaquinone biosynthesis pathway are potential drug targets for the development of novel antibacterial agents. In order to identify leads that target MenB, the 1,4-dihydroxy-2-naphthoyl-CoA synthase from Mycobacterium tuberculosis, a high-throughput screen was performed. Several 1,4-benzoxazines were identified in this screen and subsequent SAR studies resulted in the discovery of compounds with excellent antibacterial activity against M. tuberculosis H37Rv with MIC values as low as 0.6 mu g/ml. The 1,4-benzoxazine scaffold is thus a promising foundation for the development of antitubercular agents. (C) 2010 Elsevier Ltd. All rights reserved.
  • Design, synthesis and antimycobacterial activity of benzoxazinone derivatives and open-ring analogues: Preliminary data and computational analysis
    作者:Daniele Zampieri、Maria Grazia Mamolo、Julia Filingeri、Sara Fortuna、Alessandro De Logu、Adriana Sanna、Davide Zanon
    DOI:10.1016/j.bmcl.2019.07.025
    日期:2019.9
    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.
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