3-(3-chlorophenyl)-isoxazole-4-carboxylic acid ethyl ester

• 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-(3-chlorophenyl)-isoxazole-4-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-(3-Chlorophenyl)-4-Isoxazolecarboxylate；Ethyl 3-(3-chlorophenyl)-1,2-oxazole-4-carboxylate
• 化学式: C₁₂H₁₀ClNO₃
• 分子量: 251.669
• InChiKey: AFZVTLMTWNXSLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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-(3-chlorophenyl)-isoxazole-4-carboxylic acid ethyl ester 在 盐酸 、 叠氮磷酸二苯酯 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 41.5h， 生成 3-(3-chlorophenyl)-isoxazol-4-ylamine hydrochloride
  参考文献：
  名称：

  Discovery of Potent and Selective Pyrazolopyrimidine Janus Kinase 2 Inhibitors

  摘要：

  The discovery of somatic Jak2 mutations in patients with chronic myeloproliferative neoplasms has led to significant interest in disc-ova-ring selective Jak2 inhibitors for use in treating these disorders. A high-throughput screening effort identified the pyrazolo[1,5-a]pyrimidine scaffold as a potent inhibit-or of Jak2. Optimization of lead compounds 7a-b and 8 in this chemical series for activity against Jak2, selectivity against other Jak family kinases, and good in vivo pharmacokinetic properties led to the discovery of 7j. In a SET2 xenograft model that is dependent on Jak2 for growth, 7j demonstrated a time-dependent knock-down of pSTAT5, a downstream target of Jak2.

  DOI：

  10.1021/jm3012239
• 作为产物：
  描述：

  丙酸乙酯 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 34.0h， 生成 3-(3-chlorophenyl)-isoxazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of Potent and Selective Pyrazolopyrimidine Janus Kinase 2 Inhibitors

  摘要：

  The discovery of somatic Jak2 mutations in patients with chronic myeloproliferative neoplasms has led to significant interest in disc-ova-ring selective Jak2 inhibitors for use in treating these disorders. A high-throughput screening effort identified the pyrazolo[1,5-a]pyrimidine scaffold as a potent inhibit-or of Jak2. Optimization of lead compounds 7a-b and 8 in this chemical series for activity against Jak2, selectivity against other Jak family kinases, and good in vivo pharmacokinetic properties led to the discovery of 7j. In a SET2 xenograft model that is dependent on Jak2 for growth, 7j demonstrated a time-dependent knock-down of pSTAT5, a downstream target of Jak2.

  DOI：

  10.1021/jm3012239

文献信息

• 3-Aryl-4-isoxazolecarboxylic acids as plant growth regulants
  申请人：Monsanto Company

  公开号：US04144047A1

  公开（公告）日：1979-03-13

  3-Aryl-4-isothiazolecarboxylic acids as well as 3-aryl-4-isoxazolecarboxylic acids have been found to be effective plant growth regulants especially when applied to soybean plants.

  3-芳基-4-异噻唑羧酸以及3-芳基-4-异噁唑羧酸已被发现是有效的植物生长调节剂，尤其是在应用于大豆植物时。
• 3-Aryl-4-isothiazolecarboxylic acid and 3-aryl-4-isoxazolecarboxylic
  申请人：Monsanto Company

  公开号：US04187099A1

  公开（公告）日：1980-02-05

  Carboxylic acid derivatives having the formula ##STR1## have been found to be effective herbicides. They are especially effective when applied as a pre-emergent herbicide.

  具有式##STR1##的羧酸衍生物已被发现是有效的除草剂。它们作为芽前除草剂使用时尤为有效。
• Discovery of 4-nitro-3-phenylisoxazole derivatives as potent antibacterial agents derived from the studies of [3 + 2] cycloaddition
  作者：Yan Zhang、Zhiwu Long、Longjia Yan、Li Liu、Lan Yang、Yi Le

  DOI：10.1039/d2ra05009a

  日期：——

  Polysubstituted phenylisoxazoles were designed and synthesized to discover new antibacterial agents via [3 + 2] cycloaddition. Thirty-five compounds with a phenylisoxazole scaffold were characterized by NMR, HRMS, and X-ray techniques. After being evaluated against Xanthomonas oryzae (Xoo), Pseudomonas syringae (Psa), and Xanthomonas axonopodis (Xac), 4-nitro-3-phenylisoxazole derivatives were found

  设计并合成了多取代的苯基异恶唑，以通过[3 + 2] 环加成发现新的抗菌剂。通过 NMR、HRMS 和 X 射线技术对 35 种具有苯基异恶唑支架的化合物进行了表征。在针对米黄单胞菌( Xoo )、丁香假单胞菌( Psa ) 和轴突黄单胞菌( Xac )进行评估后，发现 4-硝基-3-苯基异恶唑衍生物具有更好的抗菌活性。进一步的研究表明，这些化合物的 EC 50值远优于阳性对照双汞噻唑。
• US4144047A
  申请人：——

  公开号：US4144047A

  公开（公告）日：1979-03-13
• US4187099A
  申请人：——

  公开号：US4187099A

  公开（公告）日：1980-02-05