2,3-dihydrobenzofuran-5-carbaldehyde oxime | 882287-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2,3-dihydrobenzofuran-5-carbaldehyde oxime
• 英文别名: KM 06460；(E)-N-[(2,3-dihydro-1-benzofuran-5-yl)methylidene]hydroxylamine；N-(2,3-dihydro-1-benzofuran-5-ylmethylidene)hydroxylamine
• CAS: 882287-07-2
• 化学式: C₉H₉NO₂
• mdl: MFCD00113320
• 分子量: 163.176
• InChiKey: KZPPLHLNEOMCIV-UHFFFAOYSA-N

物化性质

• 沸点：
  294.3±29.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3-dihydrobenzofuran-5-carbaldehyde oxime 在 氢气 、 palladium(II) hydroxide 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 生成 2,3-二羟基苯并[B]呋喃-5-基甲胺
  参考文献：
  名称：

  Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate Staphylococcus aureus Infections in Vivo

  摘要：

  Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.

  DOI：

  10.1021/acs.jmedchem.7b00949
• 作为产物：
  描述：

  2,3-二氢苯并呋喃-5-甲醛 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 2,3-dihydrobenzofuran-5-carbaldehyde oxime
  参考文献：
  名称：

  Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate Staphylococcus aureus Infections in Vivo

  摘要：

  Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.

  DOI：

  10.1021/acs.jmedchem.7b00949

文献信息

• Isoxazolines as Therapeutic Agents
  申请人：Calderwood David J.

  公开号：US20130023526A1

  公开（公告）日：2013-01-24

  The present invention provides compound of Formula (I) biologically active metabolites, pro-drugs, isomers, stereoisomers, solvates, hydrates and pharmaceutically acceptable salts thereof wherein the variables are defined herein. The compounds of the invention are useful for treating immunological conditions.

  本发明提供了化合物Formula（I）的生物活性代谢产物、前药、异构体、立体异构体、溶剂合物、水合物和其药学上可接受的盐，其中变量在此处定义。本发明的化合物对治疗免疫状况有用。
• Efficient transformation of electron-rich arenes into diethyl 3-arylisoxazole-4,5-dicarboxylates
  作者：Ryuhta Nakano、Hideo Togo

  DOI：10.1016/j.tet.2020.131255

  日期：2020.6

  Treatment of electron-rich arenes with Tf2O and DMF, followed by the reaction with NH2OH·HCl and then with Oxone® in the presence of diethyl acetylenedicarboxylate generated diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Other alkynes could be also used for the present one-pot transformation of arenes into 3-arylisoxazole derivatives. Click here and insert your abstract text

  用Tf 2 O和DMF处理富电子芳烃，然后与NH 2 OH·HCl反应，然后与Oxone®在乙炔二羧酸二乙酯存在下反应，生成3-乙基异芳基-4,5-二羧酸二乙酯，产率中等至中等。其他炔烃也可用于将芳烃一锅转化为3-芳基异恶唑衍生物。单击此处并插入您的抽象文本。©2020爱思唯尔科学。版权所有。
• A convenient reagent for the conversion of aldoximes into nitriles and isonitriles
  作者：Wei Zhang、Jin-Hong Lin、Pengfei Zhang、Ji-Chang Xiao

  DOI：10.1039/d0cc00188k

  日期：——

  4-nitro-1-((trifluoromethyl)sulfonyl)-imidazole (NTSI), slight modifications of reaction conditions resulted in significantly different reaction paths to provide either nitriles or isonitriles. The challenging conversion of aldoximes into isonitriles was achieved under mild conditions.

  为了用4-硝基-1-（（三氟甲基）磺酰基）-咪唑（NTSI）使醛肟脱羟基，反应条件的轻微改变导致提供腈或异腈的反应路径明显不同。在温和条件下，醛糖肟转化为异腈具有挑战性。
• Inhibitors of serine proteases
  申请人：Cottrell M. Kevin

  公开号：US20070179167A1

  公开（公告）日：2007-08-02

  The present invention relates to compounds of formula I: or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

  本发明涉及式I的化合物：或其药物可接受的盐或混合物，其抑制丝氨酸蛋白酶活性，特别是乙型肝炎病毒NS3-NS4A蛋白酶的活性。
• INHIBITORS OF SERINE PROTEASES
  申请人：Cottrell Kevin M.

  公开号：US20110165120A1

  公开（公告）日：2011-07-07

  The present invention relates to compounds of formula I: or a pharmaceutically acceptable salt or mixtures thereof that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease.

  本发明涉及式I的化合物：或其药学上可接受的盐或混合物，其抑制丝氨酸蛋白酶活性，特别是乙型肝炎病毒NS3-NS4A蛋白酶的活性。