ethyl 5-phenoxymethylisoxazole-3-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-phenoxymethylisoxazole-3-carboxylate
• 英文别名: Ethyl 5-phenoxymethylisoxazole-3-carboxylate；ethyl 5-(phenoxymethyl)-1,2-oxazole-3-carboxylate
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: FSLDBDBWMYPKNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 5-phenoxymethylisoxazole-3-carboxylate 在 lithium hydroxide monohydrate 、 水 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 5-phenyloxymethylisoxazole-3-carboxylic acid
  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：

  BF₄^(1-)*C₁₉H₂₄N₃O₅⁽¹⁺⁾ 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到ethyl 5-phenoxymethylisoxazole-3-carboxylate
  参考文献：
  名称：

  使用离子液体作为可溶性载体合成乙基异恶唑-3-羧酸酯

  摘要：

  离子液体负载的乙烯基醚的区域选择性1,3-偶极环加成反应，由离子液体负载的α-苯基硒代甲基醚与氰基甲酸乙酯N-氧化物形成，得到负载的异恶唑啉衍生物，然后在温和的酸性条件下从离子液体载体上裂解下来。提供异恶唑-3-羧酸乙酯的条件。这种新的合成方法简单有效，可以高收率获得产品。

  DOI：

  10.1002/jhet.1673

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。
• Amide compound, an arthropod pest control agent and a method for controlling arthropod pest
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2952096B1

  公开（公告）日：2018-04-04
• New N-aryl isoxazolecarboxamides and N-isoxazolylbenzamides as anticonvulsant agents
  作者：F Lepage、F Tombret、G Cuvier、A Marivain、JM Gillardin

  DOI：10.1016/0223-5234(92)90137-p

  日期：1992.9

  We prepared a series of N-aryl isoxazolecarboxamide, N-isoxazolylbenzamide compounds and derivatives and studied their anticonvulsant action in MES and MMS tests. Some of these reveal considerable activity, especially with respect to MES test. The disubstitution in the 2.6-position on the phenyl ring by two methyl groups would appear to be of primary importance for the activity. The amide bridge between the phenyl and isoxazolic rings, whether of the anilide or benzamide type, seems to show similar anticonvulsant behavior. We have selected the derivatives 8 (N-(2.6-dimethylphenyl)-5-methyl-3-isoxazolecarboxamide, 12 (N-(2,6-dimethylphenyl)-5-hydroxymethyl-3-isoxazolecarboxamide) and 51 (N-(5-methyl-3-isoxazolyl)-2.6-dimethylbenzamide) which are presently being studied in more extended pharmacological tests.
• US9814235B2
  申请人：——

  公开号：US9814235B2

  公开（公告）日：2017-11-14
• [EN] METHOD FOR CONTROLLING ARTHROPOD PEST<br/>[FR] PROCÉDÉ DE LUTTE CONTRE LES ARTHROPODES NUISIBLES
  申请人：SUMITOMO CHEMICAL CO

  公开号：WO2014119696A1

  公开（公告）日：2014-08-07

  式（Ｉ） 〔式中、 Ａは、酸素原子及び－Ｓ（Ｏ）ｔ－からなる群より選ばれる１個以上の原子又は基を環構成成分として含む３－７員飽和へテロ環を表し、ｔは０等を表し、Ｒ１及びＲ２は同一又は相異なり、水素原子等を表し、ｎは、０等を表し、下式（ＩＩ）は、５員芳香環を表し、Ｚが窒素原子又は炭素原子を表し、Ｘ１、Ｘ２、及びＸ３は各々同一又は相異なり、窒素原子等を表し、Ｒ３及びＲ４は同一又は相異なり、水素原子等を表し、ｍは０～２を表し、 Ｑは、群Ａより選ばれる１個の基又は群Ａより選ばれる１個の基を有してもよいＣ１－Ｃ８鎖式炭化水素基を表し、Ｙは、酸素原子等を表し、ｕは０等を表し、ｖは１等を表す。〕 で示されるアミド化合物は優れた有害節足動物防除効果を有する。