3-甲基-5-苯基-4-异噁唑羧酸乙酯 | 92029-29-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-甲基-5-苯基-4-异噁唑羧酸乙酯
• 英文名称: ethyl 3-methyl-5-phenylisoxazole-4-carboxylate
• 英文别名: 3-Methyl-5-phenyl-isoxazol-4-carbonsaeure-aethylester；3-Methyl-5-phenyl-isoxazol-carbonsaeure-(4)-aethylester；3-methyl-5-phenyl-isoxazole-4-carboxylic acid ethyl ester；ethyl 3-methyl-5-phenyl-4-isoxazole carboxylate；Ethyl 3-methyl-5-phenyl-1,2-oxazole-4-carboxylate
• CAS: 92029-29-3
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: MMEZWYVJDPVZAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基-5-苯基-4-异噁唑羧酸乙酯 在 硫酸 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 14.5h， 生成 3-methyl-5-(3-nitro-phenyl)-isoxazole-4-carboxylic acid
  参考文献：
  名称：

  CARADONA; STEIN, Farmaco, Edizione Scientifica, 1960, vol. 15, p. 647 - 654

  摘要：

  DOI：
• 作为产物：
  描述：

  2-benzoyl-3-methylamino-crotonic acid ethyl ester 在 乙醇 、 盐酸羟胺 作用下， 生成 3-甲基-5-苯基-4-异噁唑羧酸乙酯
  参考文献：
  名称：

  Benary, Chemische Berichte, 1909, vol. 42, p. 3919

  摘要：

  DOI：

文献信息

• Design, synthesis and cytotoxic activities of scopoletin-isoxazole and scopoletin-pyrazole hybrids
  作者：Wei Shi、Jinglin Hu、Na Bao、Dongang Li、Li Chen、Jianbo Sun

  DOI：10.1016/j.bmcl.2016.11.089

  日期：2017.1

  12 novel scopoletin-isoxazole and scopoletin-pyrazole hybrids were designed, synthesized and their chemical structures were confirmed by HR-MS, IR, 1H NMR and 13C NMR spectra. The anticancer activities of the newly synthesized compounds were evaluated in vitro against three human cancer cell lines including HCT-116, Hun7 and SW620 by MTT assay. The screening results showed that six compounds (9a, 9c

  设计，合成了12种新颖的草素-异恶唑和草素-吡唑杂化物，并通过HR-MS，IR，1 H NMR和13 C NMR谱图确认了它们的化学结构。通过MTT分析，体外评估了新合成的化合物对三种人类癌细胞系包括HCT-116，Hun7和SW620的抗癌活性。筛选结果表明，六种化合物（9a，9c，9d，12a，18b和18d）显示出有效的细胞毒活性，IC 50为值低于20μM。此外，我们进一步评估了六种化合物对人类正常组织细胞系HFL-1的生长抑制活性。特别是，化合物9d对正常细胞HFL-1表现出显着的抗增殖活性，IC 50值在8.76μM至9.83μM范围内，细胞毒性较弱，IC 50值为90.9μM，这表明基于异恶唑的of草素杂种是有效的化学修饰以提高东碱的抗癌活性。
• Novel isoxazole and thiazole compounds and use thereof as drugs
  申请人：——

  公开号：US20030114505A1

  公开（公告）日：2003-06-19

  The present invention relates to novel isoxazole and thiazole compounds having an excellent lysophosphatidic acid (LPA) receptor antagonistic activity represented by general formula [1] or salts thereof: 1 wherein R1 and R2 represents an optionally substituted alkyl group or the like; R3 represents a hydrogen atom or the like; R4 represent a group selected from the group consisting of (I) optionally substituted phenyl, aryl, or heterocycle, (II) substituted or nonsubstituted alkyl, and (III) substituted or nonsubstituted alkenyl, alternatively, R3 and R4 may form a ring structure together with a carbon atom to which they bind; and X represents an oxygen atom or a sulfur atom, provided that, when R3 is a hydrogen atom, R4 represents a group other than methyl, and the use thereof as a medicine.

  本发明涉及一种新型异噁唑和噻唑化合物，其具有优异的溶血磷脂酸（LPA）受体拮抗活性，通式为[1]或其盐：其中，R1和R2代表可选取代的烷基或类似物；R3代表氢原子或类似物；R4代表从（I）可选取代的苯基、芳基或杂环基，（II）取代或未取代的烷基，以及（III）取代或未取代的烯基中选择的基团，或者R3和R4可以与它们所结合的碳原子一起形成环状结构；X代表氧原子或硫原子，前提是当R3是氢原子时，R4代表甲基以外的基团，以及其作为药物的用途。
• Isoxazole and thiazole compounds and use thereof as medicine
  申请人：Ueno Akihiro

  公开号：US06964975B2

  公开（公告）日：2005-11-15

  The present invention relates to novel isoxazole and thiazole compounds having an excellent lysophosphatidic acid (LPA) receptor antagonistic activity represented by general formula [1] or salts thereof: wherein R1 and R2 represents an optionally substituted alkyl group or the like; R3 represents a hydrogen atom or the like; R4 represent a group selected from the group consisting of (I) optionally substituted phenyl, aryl, or heterocycle, (II) substituted or nonsubstituted alkyl, and (III) substituted or nonsubstituted alkenyl, alternatively, R3 and R4 may form a ring structure together with a carbon atom to which they bind; and X represents an oxygen atom or a sulfur atom, provided that, when R3 is a hydrogen atom, R4 represents a group other than methyl, and the use thereof as a medicine.

  本发明涉及具有卓越的溶血磷脂酸（LPA）受体拮抗活性的新型异噁唑和噻唑化合物，其通式表示为[1]或其盐：其中，R1和R2代表可选取代的烷基或类似物；R3代表氢原子或类似物；R4代表从（I）可选取代的苯基，芳基或杂环，（II）取代或未取代的烷基，以及（III）取代或未取代的烯基的群中选择的群，或者，R3和R4可以与它们结合的碳原子一起形成环结构；X代表氧原子或硫原子，前提是，当R3是氢原子时，R4代表甲基以外的群，以及其作为药物的用途。
• Synthesis of Highly Reactive Ketenimines via Photochemical Rearrangement of Isoxazoles
  作者：Cormac Bracken、Marcus Baumann

  DOI：10.1021/acs.orglett.3c02556

  日期：2023.9.8

  as building blocks in organic synthesis; however, the effective preparation of these versatile entities remains a synthetic challenge. Here we report a continuous photochemical process that generates ketenimines via skeletal rearrangement of trisubstituted isoxazoles. The resulting flow process is noteworthy, as it provides for the first time a straightforward entry into these ketenimines that were

  乙烯酮亚胺是高度亲电子的物质，作为有机合成的基础材料具有多种应用；然而，有效准备这些多功能实体仍然是一项综合挑战。在这里，我们报道了通过三取代异恶唑的骨架重排生成烯酮亚胺的连续光化学过程。由此产生的流动过程值得注意，因为它首次提供了直接进入这些乙烯亚胺的方法，而这些乙烯亚胺以前只能通过光谱观察到。通过可分离的烯酮亚胺将异恶唑转化为药学相关的吡唑，证明了这种杂环转位反应方法的价值。
• Design, Synthesis, and in Vitro Biological Evaluation of 1<i>H</i>-1,2,3-Triazole-4-carboxamide Derivatives as New Anti-influenza A Agents Targeting Virus Nucleoprotein
  作者：Huimin Cheng、Junting Wan、Meng-I Lin、Yingxue Liu、Xiaoyun Lu、Jinsong Liu、Yong Xu、Jianxin Chen、Zhengchao Tu、Yih-Shyun E. Cheng、Ke Ding

  DOI：10.1021/jm2013503

  日期：2012.3.8

  The influenza virus nucleoprotein (NP) is an emerging target for anti-influenza drug development. Nucleozin (1) and its closely related derivatives had been identified as NP inhibitors displaying anti-influenza activity. Utilizing 1 as a lead molecule, we successfully designed and synthesized a series of 1H-1,2,3-triazole-4-carboxamide derivatives as new anti-influenza A agents. One of the most potent compounds, 3b, inhibited the replication of various H3N2 and H1N1 influenza A virus strains with IC50 values ranging from 0.5 to 4.6 mu M. Compound 3b also strongly inhibited the replication of H5N1 (RG14), amantidine-resistant A/WSN/33 (H1N1), and oseltamivir-resistant A/WSN/1933 (H1N1, 274Y) virus strains with IC50 values in sub-mu M ranges. Further computational studies and mechanism investigation suggested that 3b might directly target influenza virus A nucleoprotein to inhibit its nuclear accumulation.