3-hydroxy-2-methyl-4H-pyran-4-selenone | 1058259-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-hydroxy-2-methyl-4H-pyran-4-selenone
• 英文别名: 3-hydroxy-2-methylpyran-4-selone
• CAS: 1058259-18-9
• 化学式: C₆H₆O₂Se
• 分子量: 189.072
• InChiKey: ZZDGGVDRJYOZCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-methyl-4H-pyran-4-selenone 、 zinc(II) sulfate 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到bis(3-hydroxy-2-methyl-4H-pyran-4-seleno) zinc(II)
  参考文献：
  名称：

  血糖降下作用を持つセレン含有新規亜鉛（ＩＩ）有機錯体

  摘要：

  Type 1 diabetes currently relies solely on subcutaneous insulin injections for treatment, with no alternative medication available. The solution involves providing therapeutic materials that can be orally administered as an alternative to insulin. The proposed solution is a zinc (II) organic complex containing compounds with a 3-hydroxy-4H-pyran-4-selenone structure with a γ-pyrone ring and its derivatives as ligands, which exhibit insulin-like action and blood glucose-lowering effects. These materials have the potential to replace existing diabetes treatment drugs. No figures are included in the text.

  公开号：

  JP2017031078A
• 作为产物：
  描述：

  麦芽醇 在 Woollins 试剂 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以57%的产率得到3-hydroxy-2-methyl-4H-pyran-4-selenone
  参考文献：
  名称：

  有机硫属元素（硫和硒）锌配合物与羟基吡喃酮衍生物对瘦素缺乏型2型糖尿病ob / ob小鼠的抗糖尿病作用

  摘要：

  自从发现锌（Zn）复合物的抗糖尿病作用以来，我们合成了几种Zn复合物，并使用KKAy 2型糖尿病小鼠模型评估了它们的作用。最近，我们证明了有机硫属元素（硫和硒）Zn络合物具有很强的抗糖尿病作用。在这项研究中，我们用有机硫属元素锌复合物治疗了瘦素缺陷型ob / ob小鼠，并评估了其在糖尿病小鼠模型中由与KKAy小鼠不同的致病机理引起的抗糖尿病作用。C57BL / 6J ob / ob小鼠口服接受双（3-羟基-2-甲基-4（H）-吡喃-4-硫代）Zn，[Zn（hmpt）2]或双（3-羟基-2-甲基-4（H）-吡喃-4-硒基）Zn，[Zn（hmps）2]，每天28天。两种锌配合物均可引起有效的降血糖作用并改善HbA1c值。而且，口服葡萄糖耐量试验证明，葡萄糖耐量有所改善，并且两种锌配合物治疗的小鼠的空腹血浆胰岛素水平均降低。[Zn（hmps）2]处理的小鼠的肝脏和胰腺中的锌浓度和[Zn（hmps

  DOI：

  10.3390/ijms18122647

文献信息

• Synthesis of first row transition metal selenomaltol complexes
  作者：Michael T. Spiegel、Amanda Hoogerbrugge、Shamus Truksa、Andrew G. Smith、Kevin L. Shuford、Kevin K. Klausmeyer、Patrick J. Farmer

  DOI：10.1039/c8dt01170b

  日期：——

  We report an efficient, one-step synthesis of the chelator 3-hydroxy-2-methyl-4-selenopyrone (selenomaltol). Complexes of selenomaltol with Fe(III), Ni(II), Cu(II) and Zn(II) have been prepared and studied by NMR, X-ray crystallography, cyclic voltammetry, EPR and electronic absorption. The Ni(II) and Cu(II) complexes show chemically reversible oxidations which are suggested to be ligand-based. Nuclear

  我们报告了一种有效的一步合成螯合剂3-羟基-2-甲基-4-硒代吡喃酮（硒代诺尔醇）的方法。制备了硒烯诺醇与Fe（III），Ni（II），Cu（II）和Zn（II）的配合物，并通过NMR，X射线晶体学，循环伏安法，EPR和电子吸收进行了研究。Ni（II）和Cu（II）配合物显示出化学可逆的氧化作用，这被认为是基于配体的。核独立化学位移（NICS）分析用于比较硒烯麦醇及其螯合物的杂环的芳香性。本文所述的化合物应显着扩大不常见的O，Se供体螯合物的范围和实用性。
• Investigating the target organs of novel anti-diabetic zinc complexes with organo‑selenium ligands
  作者：Takayuki Nishiguchi、Yutaka Yoshikawa、Hiroyuki Yasui

  DOI：10.1016/j.jinorgbio.2018.05.002

  日期：2018.8

  Diabetes mellitus (DM) is a serious problem worldwide and is becoming increasingly prevalent. Previously, we reported the use of various zinc (Zn) complexes as new anti-diabetic agents. In this study, we synthesized novel organo-selenium (Se) Zn complexes with hydroxy-pyrone derivatives that have a Zn(Se2O2) coordination mode. The results of in vitro insulin-mimetic analyses showed that the compound bis(3-hydroxy-2-methyl-4(H)-pyran-4- seleno)Zn ([Zn(hmps)(2)]) exhibited the strongest activity among all the complexes. In the in vivo studies of Zn complexes with 3-hydroxy-2-methyl-4(H)-pyran-4-one, maltol, (hmpo) derivatives, [Zn(hmps)(2)] exhibited a stronger anti-diabetic effect than bis(3-hydroxy-2-methyl-4(H)-pyran-4-one)Zn ([Zn(hmpo)(2)]), which had a Zn (O-4) coordination mode. Additionally, we investigated the organ distribution of both Zn and Se by determining the amounts of these elements in the organs of [Zn(hmps)(2)]-administered mice. We then evaluated the effect of treatment with Zn complexes on hepatic lipid accumulation and pancreatic islet hypertrophy by hematoxylin and eosin (HE) histological staining. Zn complexes were found to improve the hypertrophy in the pancreas. There were some reports that Se-contaming Zn complexes such as di(2-selenopyridine-N-oxidato)Zn(II) ([ZPS]) were effective for treating diabetes mellitus, so in this study, we examined different types of zinc complexes with organo-selenium ligands.
• Selenomaltol — Synthesis, Spectroscopy and Theoretical Calculations
  作者：Waldemar Tejchman、Krzysztof Zborowski、Wieslaw Lasocha、Leonard M. Proniewicz

  DOI：10.3987/com-08-11337

  日期：——

  Synthesis and structure of the seleno derivative of maltol (selenomaltol) is described. Structural and energetical properties of possible selenomaltol structures have been calculated at the B1LYP/6-311++G(d,p) level. The lowest energies are always predicted for the keto-enol tautomer. To verify obtained results several standard experimental methods, namely: elemental analysis, mass spectrometry, infrared and NMR spectroscopies and X-ray crystallography have been used. Investigation of IR and NMR spectra clearly indicate that the oxygen atom of exocyclic keto group oil maltol was replaced by selenium. Experimental crystallographic results support this conclusion.