5-羟甲基-2-甲基-吡啶-3,4-二醇 | 700-73-2

• 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
• 中文名称: 5-羟甲基-2-甲基-吡啶-3,4-二醇
• 英文名称: 2-Methyl-3,4-dihydroxy-5-hydroxymethyl-pyridin
• 英文别名: 4-Norpyridoxol；5-hydroxymethyl-2-methyl-pyridine-3,4-diol；5-Hydroxymethyl-2-methyl-pyridin-3,4-diol；3,4-Dihydroxy-2-methylpyridine-5-methanol；3-hydroxy-5-(hydroxymethyl)-2-methyl-1H-pyridin-4-one
• CAS: 700-73-2
• 化学式: C₇H₉NO₃
• mdl: MFCD18802611
• 分子量: 155.153
• InChiKey: ZHTYLJBFAGOFTI-UHFFFAOYSA-N

物化性质

• 熔点：
  225.5-226.5 °C (decomp)
• 沸点：
  567.1±45.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-羟甲基-2-甲基-吡啶-3,4-二醇 在 咪唑 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 3,4-bis(benzyloxy)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2-methylpyridine
  参考文献：
  名称：

  Rational design, synthesis and evaluation of first generation inhibitors of the Giardia lamblia fructose-1,6-biphosphate aldolase

  摘要：

  Inhibitors of the Giardia lamblia fructose 1,6-bisphosphate aldolase (GlFBPA), which transforms fructose 1,6-bisphosphate (FBP) to dihydroxyacetone phosphate and glyceraldehyde 3-phosphate, were designed based on 3-hydroxy-2-pyridone and 1,2-dihydroxypyridine scaffolds that position two negatively charged tetrahedral groups for interaction with substrate phosphate binding residues, a hydrogen bond donor to the catalytic Asp83, and a Zn2+ binding group. The inhibition activities for the GlFBPA catalyzed reaction of FBP of the prepared alkyl phosphonate/phosphate substituted 3-hydroxy-2-pyridinones and a dihydroxypyridine were determined. The 3-hydroxy-2-pyridone inhibitor 8 was found to bind to GlFBPA with an affinity (K-i = 14 mu M) that is comparable to that of FBP (K-m = 2 mu m) or its inert analog TBP (K-i = 1 mu M). The X-ray structure of the GlFBPA-inhibitor 8 complex (2.3 angstrom) shows that 8 binds to the active site in the manner predicted by in silico docking with the exception of coordination with Zn2+. The observed distances and orientation of the pyridone ring O=C-C-OH relative to Zn2+ are not consistent with a strong interaction. To determine if Zn2+ coordination occurs in the GIFBPA-inhibitor 8 complex in solution, EXAFS spectra were measured. A four coordinate geometry comprised of the three enzyme histidine ligands and an oxygen atom from the pyridone ring O=C-C-OH was indicated. Analysis of the Zn2+ coordination geometries in recently reported structures of class II FBPAs suggests that strong Zn2+ coordination is reserved for the enediolate-like transition state, accounting for minimal contribution of Zn2+ coordination to binding of 8 to GlFBPA. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.jinorgbio.2010.12.012
• 作为产物：
  描述：

  吡哆醛 在 sodium hydroxide 、 水 、 双氧水 作用下， 生成 5-羟甲基-2-甲基-吡啶-3,4-二醇
  参考文献：
  名称：

  Phosphates of the Vitamin B₆ Group. IV. An Oxidation Product of Codecarboxylase

  摘要：

  DOI：

  10.1021/ja01151a129

文献信息

• Dual antiplatelet/anticoagulant pyridoxine analogs
  申请人：Haque Wasimul

  公开号：US20060094761A1

  公开（公告）日：2006-05-04

  Compounds with antiplatelet aggregation and anticoagulant characteristics for the treatment of cardiovascular, cerebrovascular, and cardiovascular related diseases and symptoms, are described. The methods are directed to administering pharmaceutical compositions comprising aryl sulfonic pyridoxine and/or substituted pyridoxine analogs.

  描述了具有抗血小板聚集和抗凝血特性的化合物，用于治疗心血管、脑血管和与心血管相关的疾病和症状。该方法涉及给药含有芳基磺酸吡ridoxine和/或取代吡ridoxine类似物的药物组合物。
• DUAL ANTIPLATELET/ANTICOAGULANT PYRIDOXINE ANALOGS
  申请人：Medicure International Inc.

  公开号：EP1817288A1

  公开（公告）日：2007-08-15
• EP1817288A4
  申请人：——

  公开号：EP1817288A4

  公开（公告）日：2009-08-26
• US7812037B2
  申请人：——

  公开号：US7812037B2

  公开（公告）日：2010-10-12
• [EN] DUAL ANTIPLATELET/ANTICOAGULANT PYRIDOXINE ANALOGS<br/>[FR] ANALOGUES DE PYRIDOXINE À DOUBLE ACTIVITÉ ANTI-PLAQUETTES ET ANTI-COAGULANTES
  申请人：MEDICURE INT INC

  公开号：WO2006050598A1

  公开（公告）日：2006-05-18

  [EN] Pyridoxine analogs , particularly bis-amidine pyridoxine analogs with antiplatelet and anticoagulant characteristics for the treatment of cardiovascular, cerebrovascular and cardiovascular related diseases and symptoms are described. The methods are directed to administering pharmaceutical compositions comprising substituted bis-amidine pyridoxine analogs having the following formulas:(I),(II),(III). wherein at least two of substituents R¹- R⁶ have amidine groups.
  [FR] La présente invention a pour objet des analogues de pyridoxine, plus particulièrement des analogues de pyridoxine de type bis-amidine, qui présentent des propriétés anti-plaquettes et anti-coagulantes. Lesdits analogues sont destinés au traitement de maladies ou de symptômes de maladies cardiovasculaires et apparentées, ainsi que de maladies ou de symptômes de maladies cérébro-vasculaires. Lesdites méthodes consistent en l'administration de préparations pharmaceutiques comprenant des analogues de bis-amidine pyridoxine substitués de formules suivantes : (I), (II), (III), où au moins deux des substituants R¹-R⁶ portent des groupements amidine.