(R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid | 478336-90-2

• 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
• 英文别名: 2-[(5R)-3-(4-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetic acid
• CAS: 478336-90-2
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: WXEFTTZSUKSHIG-SECBINFHSA-N

物化性质

• 沸点：
  448.2±51.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  79.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid 、 甲醇 在 三甲基氯硅烷 作用下， 生成 (R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid methyl ester
  参考文献：
  名称：

  Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.04.038
• 作为产物：
  描述：

  2-[(5R)-3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-3-(4-hydroxyphenyl)-4,5-dihydro-5-isoxazoleacetic acid
  参考文献：
  名称：

  Critical modifications of the ISO-1 scaffold improve its potent inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2006.04.038

文献信息

• 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。
• ISOXAZOLINE COMPOUNDS HAVING MIF ANTAGONIST ACTIVITY
  申请人：Cytokine Pharmasciences, Inc.

  公开号：EP1411930A2

  公开（公告）日：2004-04-28
• EP1411930A4
  申请人：——

  公开号：EP1411930A4

  公开（公告）日：2007-04-04
• Isoxazoline Compounds Having MIF Antagonist Activity
  申请人：Al-Abed Yousef

  公开号：US20100016391A1

  公开（公告）日：2010-01-21

  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 rheumatoid 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).
• ISOXAZOLINE COMPOUNDS IN TYPE 2 DIABETES AND OTHER MALADIES
  申请人：Satoskar Abhay

  公开号：US20130123261A1

  公开（公告）日：2013-05-16

  Methods for treating diabetes in a subject, reducing the blood glucose level of a subject suffering from diabetes, and reducing or preventing an increase in the level of resistin in a subject, comprising administering to said subject a compound having the following formula: wherein R 1 , R 2 , R 3 , R 4 , R 5 , X, Y, and R 16 are described herein; or salt thereof, prodrug thereof, or combination thereof, optionally in contact with one or more pharmaceutical carrier.