2-(oxazolo[5,4-b]pyridin-2-yl)phenol | 1276122-45-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(oxazolo[5,4-b]pyridin-2-yl)phenol
• 英文别名: 2-{[1,3]oxazolo[5,4-b]pyridin-2-yl}phenol；2-([1,3]Oxazolo[5,4-b]pyridin-2-yl)phenol；2-([1,3]oxazolo[5,4-b]pyridin-2-yl)phenol
• CAS: 1276122-45-2
• 化学式: C₁₂H₈N₂O₂
• 分子量: 212.208
• InChiKey: PZAHALHTNOSNKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-甲基苄溴 、 2-(oxazolo[5,4-b]pyridin-2-yl)phenol 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 生成 2-(2-((3-methylbenzyl)oxy)phenyl)oxazolo[5,4-b]pyridine
  参考文献：
  名称：

  Discovery of the selective sphingomyelin synthase 2 inhibitors with the novel structure of oxazolopyridine

  摘要：

  Sphingomyelin synthase (SMS) is a key enzyme in sphingomyelin biosynthetic pathway, whose activity is highly related to the atherosclerosis progression. SMS2 could serve as a promising therapeutic target for atherosclerosis. Based on the structure of lead compound D2, a series of oxazolopyridine derivatives were designed, synthesized, and their inhibitory activities against purified SMS1 and SMS2 enzymes were evaluated respectively. The representative molecules QY4 and QY16 possess micromolar inhibitory activities against SMS2 and excellent isoform preferences over SMS1, qualified to be selected as potential molecules in further discovery of specific SMS2 inhibitors. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.05.074
• 作为产物：
  描述：

  邻三氟甲基苯酚 、 3-氨基-2-羟基吡啶 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以76.3%的产率得到2-(oxazolo[5,4-b]pyridin-2-yl)phenol
  参考文献：
  名称：

  2-苄氧苯基噁唑并吡啶类化合物及其药物用 途

  摘要：

  本发明属药物化学领域，涉及式I结构所示的2‑苄氧苯基噁唑并吡啶类化合物及其药物用途，其中所述R,X,Y,Z与发明内容中的详细描述一致。该类化合物能抑制鞘磷脂合酶活性，可用于制备鞘磷脂合酶小分子抑制剂。本发明提了包括如式I结构所示的化合物或以其为有效活性成分的药物组合物及其在制备预防和治疗由于鞘磷脂水平异常增加所引起疾病的药物中的应用；所述由于鞘磷脂水平异常增加所引起的疾病包括动脉粥样硬化、脂肪肝、肥胖和Ⅱ型糖尿病等代谢综合症。（I）。

  公开号：

  CN108329330B

文献信息

• 2-苄氧苯基噁唑并吡啶类化合物及其药物用 途
  申请人：复旦大学

  公开号：CN108329330B

  公开（公告）日：2021-05-04

  本发明属药物化学领域，涉及式I结构所示的2‑苄氧苯基噁唑并吡啶类化合物及其药物用途，其中所述R,X,Y,Z与发明内容中的详细描述一致。该类化合物能抑制鞘磷脂合酶活性，可用于制备鞘磷脂合酶小分子抑制剂。本发明提了包括如式I结构所示的化合物或以其为有效活性成分的药物组合物及其在制备预防和治疗由于鞘磷脂水平异常增加所引起疾病的药物中的应用；所述由于鞘磷脂水平异常增加所引起的疾病包括动脉粥样硬化、脂肪肝、肥胖和Ⅱ型糖尿病等代谢综合症。（I）。
• Transformation of Anionically Activated Trifluoromethyl Groups to Heterocycles under Mild Aqueous Conditions
  作者：Jennifer X. Qiao、Tammy C. Wang、Carol Hu、Jianqing Li、Ruth R. Wexler、Patrick Y. S. Lam

  DOI：10.1021/ol200326u

  日期：2011.4.1

  The (hetero)aromatic trifluoromethyl group is present in many biologically active molecules and is generally considered to be chemically stable. In this paper, a convenient one-step synthesis of C-C linked aryl-heterocycles or heteroaryl-heterocycles In good to excellent yields via the reaction of anionically activated trifluoromethyl groups with amino nucleophiles containing a second NH, OH, or SH nucleophile in 1 N sodium hydroxide is reported. The method has high functional group tolerability and is potentially useful in parallel synthesis.
• US7642358B2
  申请人：——

  公开号：US7642358B2

  公开（公告）日：2010-01-05
• Discovery of the selective sphingomyelin synthase 2 inhibitors with the novel structure of oxazolopyridine
  作者：Xiang-Yu Qi、Yang Cao、Ya-Li Li、Ming-Guang Mo、Lu Zhou、De-Yong Ye

  DOI：10.1016/j.bmcl.2017.05.074

  日期：2017.8

  Sphingomyelin synthase (SMS) is a key enzyme in sphingomyelin biosynthetic pathway, whose activity is highly related to the atherosclerosis progression. SMS2 could serve as a promising therapeutic target for atherosclerosis. Based on the structure of lead compound D2, a series of oxazolopyridine derivatives were designed, synthesized, and their inhibitory activities against purified SMS1 and SMS2 enzymes were evaluated respectively. The representative molecules QY4 and QY16 possess micromolar inhibitory activities against SMS2 and excellent isoform preferences over SMS1, qualified to be selected as potential molecules in further discovery of specific SMS2 inhibitors. (C) 2017 Elsevier Ltd. All rights reserved.