5-Pyridin-2-ylbenzene-1,3-diol | 1448788-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-Pyridin-2-ylbenzene-1,3-diol
• CAS: 1448788-46-2
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: QUHMQXDPZHYQQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Pyridin-2-ylbenzene-1,3-diol 在 potassium tert-butylate 、 sodium methylate 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.33h， 生成 6-[3-(4-methylsulfonylphenoxy)-5-propan-2-yloxyphenyl]-1H-pyridin-2-one
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036
• 作为产物：
  描述：

  2-(3,5-dimethoxyphenyl)pyridine 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以46%的产率得到5-Pyridin-2-ylbenzene-1,3-diol
  参考文献：
  名称：

  Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif

  摘要：

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.036

文献信息

• 1,3-Dihydroxybenzene derivatives and colorants containing said compounds
  申请人：——

  公开号：US20040016063A1

  公开（公告）日：2004-01-29

  1,3-Dihydroxybenzene derivatives of general formula (I) or (Ia) or physiologically tolerated, water-soluble thereof 1 wherein R′1 denotes substituted pyridyl group, a pyrimidyl group, a group of formula (IIa) or (IIIa) 2 and the dyeing agents for keratin fibers containing these compounds.

  一般式(I)或(Ia)的1,3-二羟基苯衍生物，或其生理耐受性、水溶性的衍生物，其中R′1代表取代吡啶基、嘧啶基、式(IIa)或(IIIa)的基团，以及含有这些化合物的角蛋白纤维染料剂。
• US7125428B2
  申请人：——

  公开号：US7125428B2

  公开（公告）日：2006-10-24
• Pyrimidone-based series of glucokinase activators with alternative donor–acceptor motif
  作者：Kevin J. Filipski、Angel Guzman-Perez、Jianwei Bian、Christian Perreault、Gary E. Aspnes、Mary T. Didiuk、Robert L. Dow、Richard F. Hank、Christopher S. Jones、Robert J. Maguire、Meihua Tu、Dongxiang Zeng、Shenping Liu、John D. Knafels、John Litchfield、Karen Atkinson、David R. Derksen、Francis Bourbonais、Ketan S. Gajiwala、Michael Hickey、Theodore O. Johnson、Paul S. Humphries、Jeffrey A. Pfefferkorn

  DOI：10.1016/j.bmcl.2013.06.036

  日期：2013.8

  Glucokinase activators are a class of experimental agents under investigation as a therapy for Type 2 diabetes mellitus. An X-ray crystal structure of a modestly potent agent revealed the potential to substitute the common heterocyclic amide donor-acceptor motif for a pyridone moiety. We have successfully demonstrated that both pyridone and pyrimidone heterocycles can be used as a potent donor-acceptor substituent. Several sub-micromolar analogs that possess the desired partial activator profile were synthesized and characterized. Unfortunately, the most potent activators suffered from sub-optimal pharmacokinetic properties. Nonetheless, these donor-acceptor motifs may find utility in other glucokinase activator series or beyond. (C) 2013 Elsevier Ltd. All rights reserved.