3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamide | 53013-51-7

• 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: 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamide
• 英文别名: 5-Methyl-4-carbamoyl-3-(2-chlor-phenyl)-isoxazol；3-(2-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid amide；3-(2-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxamide
• CAS: 53013-51-7
• 化学式: C₁₁H₉ClN₂O₂
• mdl: MFCD00118579
• 分子量: 236.658
• InChiKey: OZFANALXKZFARG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamide 、 三氯乙醛 以85%的产率得到
  参考文献：
  名称：

  BARCZYNSKI D. Z.; ECKSTEIN Z., PRZ. CHEM., 1978, 57, NO 4, 176-177

  摘要：

  DOI：
• 作为产物：
  描述：

  2-chloro-N-hydroxybenzimidoyl chloride 在 氢氧化钾 、 ammonium hydroxide 、 氯化亚砜 作用下， 以 乙醇 、 丙酮 为溶剂， 生成 3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamide
  参考文献：
  名称：

  1112. 6-氨基青霉烯酸的衍生物。第六部分 3-和5-苯基异恶唑-4-羧酸的青霉素及其烷基和卤素衍生物

  摘要：

  DOI：

  10.1039/jr9630005838

文献信息

• Synthesis, biological evaluation, molecular docking, and ADMET studies of some isoxazole-based amides
  作者：Sushama Kauthale、Sunil Tekale、Manoj Damale、Jaiprakash Sangshetti、Rajendra Pawar

  DOI：10.1007/s00044-017-2070-z

  日期：2018.2

  Some isoxazole-based amides were synthesized by the reaction of 3-(2-chlorophenyl)-5-methylisoxazole-4-carbonyl chloride with various aliphatic, aromatic and heterocyclic amines; characterized by analysis of spectroscopic data and evaluated for in vivo anti-inflammatory, ulcerogenic, and antimicrobial activity. Compounds A1, A7, and A10 were identified as the potent anti-inflammatory agents in carrageenan-induced

  通过3-（2-氯苯基）-5-甲基异恶唑-4-羰基氯与各种脂肪族，芳香族和杂环胺的反应合成了一些基于异恶唑的酰胺。通过分析光谱数据进行表征，并评估其体内抗炎，促溃疡和抗菌活性。在角叉菜胶诱发的白化病大鼠爪水肿试验中，化合物A1，A7和A10被确定为有效的消炎药，在5小时后显示92.85–93.57％的水肿抑制作用，溃疡指数（2.5）比标准双氯芬酸钠（6.15）低。对大肠杆菌，铜绿假单胞菌，金黄色葡萄球菌和在最小抑制浓度值方面，发现枯草芽孢杆菌与标准氨苄青霉素比较好。分子对接（可能的结合模式，相互作用以及标题化合物与环氧合酶2酶的活性位点对接分数）支持抗炎活性结果。在硅吸收，分布，代谢和排泄毒性方面，还进行了研究，以预测合成抗炎药的初步药理，药代动力学和毒性特征，这表明这些衍生物具有良好的口服药如行为和无毒性质。
• Isoxazolone derivatives and production thereof
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP0250096A1

  公开（公告）日：1987-12-23

  The present invention related to a compound of the formula : wherein R1 is hydrogen, isonitrile or an organic residue bonded through nitrogen ; R is hydrogen, alkyl ' which may be substituted, alkylthio in which sulfur atom may be oxidized or azido, or forms a double bond together with the adjacent carbon atom; provided that when R1 is an organic residue bonded through nitrogen, R is not hydrogen; R2 is carboxyl or a group derivable therefrom, and a salt thereof, and a method for producing the same. The Compound (I) of the present invention has, among others, an excellent anitimicrobial activity and is useful as an antimicrobial agent, etc.

  本发明涉及一种具有以下结构的化合物：其中R1是氢、异腈或通过氮原子键合的有机残基；R是氢、可以被取代的烷基、硫代烷基（其中硫原子可能被氧化）或偶氮基，或者与相邻碳原子形成双键；但是当R1是通过氮原子键合的有机残基时，R不是氢；R2是羧基或可由其衍生的基团，以及其盐，以及生产该化合物的方法。本发明的化合物（I）具有优异的抗微生物活性，可用作抗微生物剂等。
• Epoxy-azetidinones, preparation and use thereof
  申请人：PLIVA farmaceutska, kemijska, prehrambena i kozmeticka industrija, dionicko drustvo

  公开号：EP0864570A1

  公开（公告）日：1998-09-16

  The present invention relates to new epoxy-azetidinones of the general formula I, which are prepared by epoxidizing azetidinones of the general formula II. These compounds are useful intermediates for the prepararion of new potential inhibitors of β-lactamases.

  本发明涉及一种新的环氧-氮杂丙酮类化合物，其一般式为I，其制备方法是通过将一般式为II的氮杂丙酮环氧化得到。这些化合物是制备新的潜在β-内酰胺酶抑制剂的有用中间体。
• Beta-lactam antibiotics, their preparation and their use in pharmaceutical compositions
  申请人：BEECHAM GROUP PLC

  公开号：EP0028497A1

  公开（公告）日：1981-05-13

  The present invention provides the compounds of the formula (II): and pharmaceutically acceptable salts and esters thereof wherein R3 is a hydrogen atom, a group HO3S- or a group R5CO wherein R5 is C1-6 alkyl, C2-6 alkenyl, aryl, aryl(C1-6)alkyl or aryloxy(C1-6) alkyl; and R4 is an organic group other than methyl bonded to the -CO-NH-moiety via a carbon atom; with the proviso that when R3 is a hydrogen atom or a group R5CO the stereochemical configuration at the a-carbon atom of the C-6 substituent is S, and with the further proviso that when R' is a group HO2S- the hydrogen atoms at C-5 and C-6 are cis. Their use is described as are processes for their preparation. Compounds wherein the R'CO-moiety is replaced by a hydrogen atom are also prepared.

  本发明提供了式(II)化合物： 及其药学上可接受的盐和酯 其中 R3 是氢原子、基团 HO3S- 或基团 R5CO，其中 R5 是 C1-6 烷基、C2-6 烯基、芳基、芳基(C1-6)烷基或芳氧基(C1-6)烷基；以及 R4 是通过一个碳原子与-CO-NH-分子键合的除甲基以外的有机基团；但条件是，当 R3 是氢原子或基团 R5CO 时，C-6 取代基 a 碳原子上的立体化学构型为 S，而且当 R' 是基团 HO2S- 时，C-5 和 C-6 上的氢原子为顺式。本文介绍了这些化合物的用途及其制备工艺。还制备了 R'CO 原子被氢原子取代的化合物。
• Beta-lactam antibacterial compounds, their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0034443A2

  公开（公告）日：1981-08-26

  The present invention provides the compounds of the formula (II): and pharmaceutically acceptable salts and cleavable esters thereof wherein RCONH is an organic acylamino group and E is a carboxy group or pharmaceutically acceptable salt or ester thereof or is a cyano group. Their preparation is described as is their use in compositions containing them. Compounds wherein RCONH is replaced by an azido group are described as useful intermediates.

  本发明提供了式(II)化合物： 及其药学上可接受的盐和可裂解酯 其中 RCONH 是有机酰氨基，E 是羧基或其药学上可接受的盐或酯或氰基。本文介绍了它们的制备方法以及在含有它们的组合物中的用途。RCONH 被叠氮基团取代的化合物被描述为有用的中间体。