5-hydroxy-2-methyl-thiopyran-4(1H)-one | 30717-77-2

• 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: 5-hydroxy-2-methyl-thiopyran-4(1H)-one
• 英文别名: 5-hydroxy-2-methyl-4H-pyran-4-thione；5-hydroxy-2-methylpyran-4(1H)-thione；5-hydroxy-2-methylpyran-4-thione；thioallomaltol；allothiomaltol；5-hydroxy-2-methyl-pyran-4-thione
• CAS: 30717-77-2
• 化学式: C₆H₆O₂S
• 分子量: 142.178
• InChiKey: FKPXXEKBFZKNPV-UHFFFAOYSA-N

物化性质

• 熔点：
  99.5-100.5 °C(Solv: carbon tetrachloride (56-23-5))
• 沸点：
  207.3±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-methyl-thiopyran-4(1H)-one 在 sodium acetate 、 乙酸酐 、 三乙胺 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 5-methyl-2H-furo[2,3-c]pyran-2-one
  参考文献：
  名称：

  Preparation of 2H-Furo[2,3-c]pyran-2-one Derivatives and Evaluation of Their Germination-Promoting Activity

  摘要：

  The butenolide, 3-methyl-2H-furo[2,3-c]pyran-2-one (1), has recently been identified as the germination stimulant present in smoke that promotes the germination of seeds from a wide range of plant species. In this paper, we describe the preparation of a number of analogues of 2 and compare their efficacy in promoting seed germination of three highly smoke-responsive plant species, Lactuca sativa L. cv. Grand Rapids (Asteraceae), Emmenanthe penduliflora Benth. (Hydrophyllaceae), and Solanum orbiculatum Poir. (Solanaceae). The results show that the methyl substituent at C-3 in 1 is important for germination-promoting activity while substitution at C-7 reduces activity. In contrast, bioactivity is mostly retained with analogues substituted at C-4 or C-5.

  DOI：

  10.1021/jf0633241
• 作为产物：
  描述：

  曲酸 在 劳森试剂 、 盐酸 、 氯化亚砜 、 锌 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 5-hydroxy-2-methyl-thiopyran-4(1H)-one
  参考文献：
  名称：

  Organometallic complexes of (thio)allomaltol-based Mannich-products: Synthesis, stability and preliminary biological investigations

  摘要：

  Organometallic complexes with (thio) pyrone-based ligands have been shown to possess promising cytotoxic properties. To extend the class of potential metallodrugs, the (thio) pyrone backbone was modified via Mannich reaction with morpholine, N-methylpiperazine and piperidine as cyclic amine. The ligands and organometallic complexes were characterized by means of 1D and 2D NMR, ESI MS and also in one case by X-ray diffraction analysis. Due to the high aqueous solubility, the behavior and stability in aqueous solution of the synthesized complexes was studied by 1H NMR spectroscopy. In addition, the influence of these modifications on cytotoxicity in human cancer cell lines was investigated by means of the MTT assay. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.10.044

文献信息

• ‘Unconventional’ Coordination Chemistry by Metal Chelating Fragments in a Metalloprotein Active Site
  作者：David P. Martin、Patrick G. Blachly、Amy R. Marts、Tessa M. Woodruff、César A. F. de Oliveira、J. Andrew McCammon、David L. Tierney、Seth M. Cohen

  DOI：10.1021/ja500616m

  日期：2014.4.9

  strength of the metal–ligand binding. Collectively, these data demonstrate that the mode of binding by small metal-binding groups can be significantly influenced by the protein active site. Diminishing the strength of the metal–ligand bond results in unconventional modes of metal coordination not found in typical coordination compounds or even carefully engineered active site models, and understanding

  三个密切相关的螯合剂的结合：5-羟基-2-甲基-4H-吡喃-4-硫酮（allothiomaltol，ATM），3-羟基-2-甲基-4H-吡喃-4-硫酮（thiomaltol，TM），和 3-羟基-4H-吡喃-4-硫酮 (thiopyromeconic acid, TPMA) 对人碳酸酐酶 II (hCAII) 的活性位点进行了研究。这些配体中的两个显示出与 hCAII 中的活性位点 Zn2+ 离子的单齿配位模式，在酶活性位点的模型复合物中没有概括。hCAII-硫代麦芽酚复合物中这种前所未有的结合模式已通过 X 射线晶体学和 X 射线光谱学进行表征。此外，与无机模型复合物相比，活性位点的空间限制迫使配体进入“扁平”配位模式。密度函数计算表明几何结构的这种变化显着降低了金属-配体结合的强度。总的来说，这些数据表明小金属结合基团的结合模式可以受到蛋白质活性位点的显着影响。降低金属-配体键的强度会
• Maltol-Derived Ruthenium-Cymene Complexes with Tumor Inhibiting Properties: The Impact of Ligand-Metal Bond Stability on Anticancer Activity In Vitro
  作者：Wolfgang Kandioller、Christian G. Hartinger、Alexey A. Nazarov、Caroline Bartel、Matthias Skocic、Michael A. Jakupec、Vladimir B. Arion、Bernhard K. Keppler

  DOI：10.1002/chem.200901939

  日期：2009.11.16

  behavior investigated as well as their tumor‐inhibiting potency. The aquation behavior of pyrone systems with electron‐donating substituents and of thiopyrone complexes was found to be significantly different from that of the maltol‐type complex reported previously. However, the formation of the dimer can be excluded as the primary reason for the inactivity of the complex because some of the stable compounds

  带有麦芽酚配体的有机金属钌-芳烃化合物在体外抗癌试验中几乎没有活性，大概是由于在水溶液中形成了二聚Ru II类。在试图稳定这种复合物，的[Ru（η 6 - p[cymene]（XY）Cl]（XY =吡喃酮或噻吩并吡喃酮）配合物具有不同的（硫）吡喃酮配体取代模式合成，对其结构进行了光谱表征，并研究了其水合行为以及其抑制肿瘤的能力。发现带有供电子取代基的吡喃酮体系和噻喃酮配合物的水合行为与先前报道的麦芽酚型配合物的水合行为有显着差异。然而，由于某些稳定的化合物在癌细胞系中也不具有活性，因此可以排除二聚体的形成作为复合物失活的主要原因。相反，对氨基酸的反应性研究表明，吡喃酮和噻喃酮复合物的反应性不同，
• The First Anticancer Tris(pyrazolyl)borate Molybdenum(IV) Complexes: Tested in Vitro and in Vivo—A Comparison of <i>O,O</i> ‐, <i>S,O</i> ‐, and <i>N</i> , <i>N‐</i> Chelate Effects
  作者：Iker Berasaluce、Klaudia Cseh、Alexander Roller、Michaela Hejl、Petra Heffeter、Walter Berger、Michael A. Jakupec、Wolfgang Kandioller、Michael S. Malarek、Bernhard K. Keppler

  DOI：10.1002/chem.201903605

  日期：2020.2.17

  The synthesis, characterization and biological activity of molybdenum(IV) complexes containing Trofimenko's scorpionato ligand, hydrotris(3-isopropylpyrazolyl)borate (TpiPr ), in addition to varying biologically active as well as other conventional ligands is described. Ligands employed include (O,O-) (S,O-) (N,N-) donors that have been successfully coordinated to the molybdenum center by means of

  描述了除具有不同的生物活性以及其他常规配体以外，还含有特罗菲缅科的蝎子配体，氢三（3-异丙基吡唑基）硼酸酯（TpiPr）的钼（IV）配合物的合成，表征和生物学活性。使用的配体包括（O，O-）（S，O-）（N，N-）供体，这些供体已通过已知MoVI起始材料TpiPr的氧原子转移（OAT）反应成功地与钼中心配位MoO 2 Cl。合成的配合物通过标准分析方法进行表征，并在可能的情况下通过X射线衍射分析进行表征。通过UV / Vis光谱研究了化合物的水稳定性，并且通过循环伏安法研究了连接的配体支架对氧化电位（MoIV至MoV）的影响。使用聚乙烯吡咯烷酮（PVP）作为增溶剂，可获得足够的水溶性以进行生物学测试。已经在体外和体内进行了抗癌活性测试和初步的作用方式研究。
• METALLOPROTEIN INHIBITORS
  申请人：Puerta David T.

  公开号：US20120041032A1

  公开（公告）日：2012-02-16

  The present invention relates to metalloprotein inhibitors comprising: a. an organic substituent and at least one zinc binding group (ZBG) covalently attached thereto; or b. a ZBG substituted by a side chain wherein the ZBG is of formula (I): wherein X is O or S and each R 1 , R 2 , R 3 , and R 4 is individually hydrogen or an organic radical. The metalloprotein inhibitors are useful for preventing or treating a pathological disease, condition, or symptom that is associated with pathological metalloprotein activity and/or that is alleviated by inhibition of said activity.

  本发明涉及金属蛋白酶抑制剂，包括：a. 有机取代基和至少一个与其共价结合的锌结合基（ZBG）；或b. 由侧链取代的ZBG，其中ZBG的化学式为（I）：其中X为O或S，每个R1、R2、R3和R4分别为氢或有机基团。这些金属蛋白酶抑制剂可用于预防或治疗与病理性金属蛋白酶活性相关的病理性疾病、症状或病情，并且通过抑制该活性缓解。
• Synthesis of sulfur karrikin bioisosteres as potential neuroprotectives
  作者：Martin Pošta、Václav Zima、Lenka Poštová Slavětínská、Marika Matoušová、Petr Beier

  DOI：10.3762/bjoc.18.57

  日期：——

  extremely efficient neuroprotective butenolide. Herein, we report the targeted synthesis of this compound as well as new synthetic protocols toward a class of compounds derived from 2H-furo[2,3-c]pyran-2-ones (karrikins) via bioisosteric exchange of oxygen with sulfur. In particular, we present synthetic procedures toward bioisosteres of karrikins with one or two sulfur heteroatoms incorporated into the core

  唯一已知的含硫 karrikin，3-methyl-2 H - thiopyrano[3,4- b ]furan-2-one，最近已被确定为一种极其有效的神经保护性丁烯内酯。在此，我们报告了该化合物的靶向合成以及针对通过氧与硫的生物等排交换衍生自 2 H-呋喃[2,3 - c ]吡喃-2-酮（karrikins）的一类化合物的新合成方案。特别是，我们提出了对 karrikins 生物等排体的合成程序，其中一个或两个硫杂原子掺入核心骨架中，并评估了它们在抑制乙酰胆碱酯酶方面的生物活性。