(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester
• 英文别名: 3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester；3-(4-Hydroxyphenyl)-4,5-dihydro-5-isoxazole-acetic acid methyl ester；methyl 2-[(5R)-3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetate
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: AIXMJTYHQHQJLU-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,5-二氢-3-(4-羟基苯基)-5-异恶唑乙酸甲酯 在 盐酸 作用下， 以 乙醚 、 氯仿 、 丙酮 为溶剂， 生成 (R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester
  参考文献：
  名称：

  WO2007/112036

  摘要：

  公开号：

文献信息

• MIF MODULATORS
  申请人：Jorgensen William L.

  公开号：US20120040974A1

  公开（公告）日：2012-02-16

  The invention provides novel heterocyclic compounds, pharmaceutical compositions and methods of treatment that modulate levels of MIF expression and treat disorders associated with high or low levels of MIF expression.

  该发明提供了新型杂环化合物、制药组合物和治疗方法，可调节MIF表达水平并治疗与高或低MIF表达水平有关的疾病。
• MIF modulators
  申请人：YALE UNIVERSITY

  公开号：US10202343B2

  公开（公告）日：2019-02-12

  The invention provides novel heterocyclic compounds, pharmaceutical compositions and methods of treatment that modulate levels of MIF expression and treat disorders associated with high or low levels of MIF expression.

  本发明提供了新型杂环化合物、药物组合物和治疗方法，可调节 MIF 的表达水平，治疗与 MIF 表达水平过高或过低有关的疾病。
• Isoxazoline compounds having MIF antagonist activity
  申请人：——

  公开号：US20030008908A1

  公开（公告）日：2003-01-09

  Methods of use and pharmaceutical compositions for a genus of low molecular weight compounds comprising optionally substituted isoxazoline ring systems that act as inhibitors of MIF (macrophage migration inhibitory factor) are disclosed. Specifically, the compounds are useful for treating a variety of diseases involving inflammatory activity or pro-inflammatory cytokine responses, such as autoimmune diseases (including rheumatiod arthritis, insulin-dependent diabetes, multiple sclerosis, graft versus host disease, lupus syndromes), asthma, arthritis, ARDS, psoriasis, interleukin-2 toxicity, proliferative vascular disease, and various forms of sepsis and septic shock, and other conditions characterized by underlying MIF responses including, for instance, tumor growth and neovascularization (angiogenesis).

  本发明公开了一种低分子量化合物的使用方法和药物组合物，该化合物包含可选取代的异噁唑啉环系统，可作为 MIF（巨噬细胞迁移抑制因子）的抑制剂。具体来说，这些化合物可用于治疗多种涉及炎症活动或促炎细胞因子反应的疾病，如自身免疫性疾病（包括风湿性关节炎、胰岛素依赖型糖尿病、多发性硬化症、移植物抗宿主病、狼疮综合征）、慢性肾脏病、糖尿病、高血压、高血脂、高血糖等、狼疮综合征）、哮喘、关节炎、ARDS、银屑病、白细胞介素-2毒性、增生性血管疾病、各种形式的败血症和脓毒性休克，以及其他以潜在的 MIF 反应为特征的疾病，包括肿瘤生长和血管新生（血管生成）等。
• Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity
  作者：Kai Fan Cheng、Yousef Al-Abed

  DOI：10.1016/j.bmcl.2006.04.038

  日期：2006.7

  Based on the scaffold of (S,R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazole acetic acid methyl ester (ISO-1), an inhibitor of the proinflammatory cytokine MIF, two critical modifications and chiral resolution have significantly improved the potency of the inhibition. Compound (R)-17 is 20-fold more potent than ISO-1 and inhibits MIF tautomerase activity with an IC50 of 550 nM. (c) 2006 Elsevier Ltd. All rights reserved.
• ISOXAZOLINE COMPOUNDS HAVING MIF ANTAGONIST ACTIVITY
  申请人：Cytokine Pharmasciences, Inc.

  公开号：EP1411930A2

  公开（公告）日：2004-04-28