5-phenyloxymethylisoxazole-3-carboxylic acid | 932801-86-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-phenyloxymethylisoxazole-3-carboxylic acid
• 英文别名: 5-(Phenoxymethyl)-1,2-oxazole-3-carboxylic acid
• CAS: 932801-86-0
• 化学式: C₁₁H₉NO₄
• 分子量: 219.197
• InChiKey: SQQNUTPYPNFZLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-phenyloxymethylisoxazole-3-carboxylic acid 、 甲基2-(苯基氨基)乙酸酯 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 methyl (2S)-2-[[5-(phenoxymethyl)isoxazole-3-carbonyl]amino]-2-phenyl-acetate
  参考文献：
  名称：

  Searching for New Cures for Tuberculosis: Design, Synthesis, and Biological Evaluation of 2-Methylbenzothiazoles

  摘要：

  The actual development and clinical use of new therapeutics for tuberculosis (TB) have remained stagnant for years because of the complexity of the disease process, the treatment of which at present requires the administration of drug combinations over a 6 month period. There is thus all urgent need for the discovery and development of novel, more active, and less toxic anti-TB agents. In this study, we report on the chemistry and biology of a series of potent 5-(2-methylbenzothiazol-5-yloxy-methyl)isoxazole-3-carboxamide derivatives, which proved to be active against replicating Mycobacterium tuberculosis (Mtb) H(37)Rv. The most potent compounds 7j and 7s were found to inhibit Mtb growth at micromolar concentrations, with MIC values of 1.4 and 1.9 mu M, respectively. Impressively, all active compounds were nontoxic toward Vero cells (IC50 > 128 mu M). Moreover, the best of these compounds were also tested against protozoan parasites, and some of these compounds were found to show activity, especially against Plasmodium falciparum. These studies thus suggest that certain 2-methylbenzothiazole based compounds may serve as promising lead scaffolds for further elaboration as anti-TB drugs and as possible antimalaria drugs.

  DOI：

  10.1021/jm901112f
• 作为产物：
  描述：

  苯基炔丙基醚 在 三乙烯二胺 、 水 、 potassium hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 24.0h， 生成 5-phenyloxymethylisoxazole-3-carboxylic acid
  参考文献：
  名称：

  Amide compound, an arthropod pest control agent and a method for controlling arthropod pest

  摘要：

  公开号：

  EP2952096B1

文献信息

• METHOD FOR CONTROLLING ARTHROPOD PEST
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US20150344466A1

  公开（公告）日：2015-12-03

  An amide compound represented by formula (I): [wherein A represents a 3- to 7-membered saturated heterocyclic ring which contains, as ring-forming component(s), one or more atoms or groups selected from the group consisting of an oxygen atom and —S(O) t —, t represents 0, etc., R 1 and R 2 are the same or different and represent a hydrogen atom, etc., n represents 0, etc., the following formula (II): represents a 5-membered aromatic ring, in which Z represents a nitrogen atom or a carbon atom and X 1 , X 2 and X 3 are the same or different and represent a nitrogen atom, etc., R 3 and R 4 are the same or different and represent a hydrogen atom, etc., m represents 0 to 2, Q represents one group selected from group A or a C1 to C8 chain hydrocarbon group optionally having one group selected from group A, Y represents an oxygen atom, etc., u represents 0, etc., and v represents 0, etc.] has excellent arthropod pest controlling effects.

  化合物式(I)所代表的酰胺化合物：[其中A代表一个3到7个成员的饱和杂环环，该环包含作为环构成组分之一或多个原子或基团，所选自氧原子和—S（O）t—群，t代表0等；R1和R2相同或不同，代表氢原子等；n代表0等；下列式子(II)代表一个5个成员的芳香环，在该环中Z代表一个氮原子或一个碳原子，X1、X2和X3相同或不同，代表氮原子等，R3和R4相同或不同，代表氢原子等，m代表0到2，Q代表从群A中选择的一个群或一个C1到C8链烃基团，该基团可以选择从群A中选择的一个群，Y代表氧原子等，u代表0等，v代表0等]具有优良的节肢动物害虫控制效果。
• JP2015/51963
  申请人：——

  公开号：——

  公开（公告）日：——
• Isoxazole derivatives and methods of treating diseases
  申请人：Shaw Jiajiu

  公开号：US20080085912A1

  公开（公告）日：2008-04-10

  A series of isoxazole derivatives and methods of treating immune-mediated diseases by isoxazole derivatives are described.
• US9814235B2
  申请人：——

  公开号：US9814235B2

  公开（公告）日：2017-11-14
• [EN] ISOXAZOLE DERIVATIVES AND METHODS OF TREATING DISEASES<br/>[FR] DÉRIVÉS D'ISOXAZOLE ET MÉTHODES THÉRAPEUTIQUES
  申请人：DOU DEXIAN

  公开号：WO2008043263A1

  公开（公告）日：2008-04-17

  [EN] A series of isoxazole derivatives and methods of treating immune-mediated diseases by isoxazole derivatives are described.
  [FR] L'invention concerne une série de dérivés d'isoxazole et de méthodes thérapeutiques pour maladies liées à l'immunité par les dérivés d'isoxazole.