4-hydroxy-6-methyl-3-octanoyl-2-pyrone | 107617-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-6-methyl-3-octanoyl-2-pyrone
• 英文别名: 4-Hydroxy-6-methyl-3-octanoylpyran-2-one
• CAS: 107617-13-0
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: LKDILUBAHONBOL-UHFFFAOYSA-N

物化性质

• 熔点：
  70 °C
• 沸点：
  381.6±42.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-6-methyl-3-octanoyl-2-pyrone 在 三乙基硅烷 、 lithium perchlorate 作用下， 以 三氟乙酸 为溶剂， 反应 4.0h， 以88%的产率得到4-hydroxy-6-methyl-3-octyl-2-pyrone
  参考文献：
  名称：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

  摘要：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00150-7
• 作为产物：
  描述：

  2,2-dimethyl-5-(3-oxobutyryl)-1,3-dioxane-4,6-dione 以 甲苯 、 三氟乙酸 为溶剂， 反应 5.0h， 生成 4-hydroxy-6-methyl-3-octanoyl-2-pyrone
  参考文献：
  名称：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

  摘要：

  A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2-pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00150-7

文献信息

• Chelation of the Optimal Antifungal Pogostone Analogue with Copper(II) to Explore the Dual Antifungal and Antibacterial Agent
  作者：Delong Wang、Chunxia Yuan、Yunpeng Li、Shuhong Bai、Juntao Feng、Yong Wang、Yali Fang、Zhijia Zhang

  DOI：10.1021/acs.jafc.3c07050

  日期：2024.2.28

  The 3D-QSAR models generated using Topomer comparative molecular field analysis indicated that a shorter alkyl chain (carbon atom number <8), terminal rings, or electron-deficient groups on the alkyl side chain are beneficial for antifungal potency. Further, bioassay results revealed that the component of 21 in complex 34 dominated the antifungal activity, but the introduction of Cu(II) significantly

  在不断探索更有效的抗真菌 pogostone (Po) 类似物的过程中，我们保留了先前确定的 3-乙酰基-4-羟基-2-吡喃酮核心基序，同时合成了一系列烷基侧链发生变化的 Po 类似物。体外生物测定结果表明，化合物21是最有效的抗真菌类似物，对核盘菌( Sclerotinia sclerotiorum (Lib.) de Bary)的EC 50值为1.1 μg/mL。同时，其Cu(II)络合物34对野油菜黄单胞菌( Xanthomonascampestris pvcampestris )( Xcc )的抗菌活性较21 (MIC=700μg/mL)显着增强，最低抑菌浓度(MIC)为300μg/mL。复合物34对油菜叶片中的核盘菌和Xcc具有显着的预防效果，防效分别为98.8%（50 μg/mL）和80.7%（1000 μg/mL）。使用Topomer比较分子场分析生成的3D-QSAR模型表明
• Inhibition of human sputum elastase by substituted 2-pyrones. 2
  作者：Luisa Cook、Bela Ternai、Peter Ghosh

  DOI：10.1021/jm00389a010

  日期：1987.6

  Nineteen 4-hydroxy- and 4-methoxy-2-pyrones related to elasnin (I) have been assayed for in vitro inhibition of human sputum elastase (HSE), porcine pancreatic elastase, alpha-chymotrypsin, and trypsin. Inhibition is reported as Ki and Ki'; percentage inhibition was dependent on [S] in a number of cases, making it unsuitable as a measure of relative inhibition. The 3-(1-oxoalkyl)-4-hydroxy-6-alkyl-2-pyrones were found to be most effective, the octyl homologue 11 being the most potent inhibitor (Ki = 4.6 microM, 30 times better than the lead compound). A further reduction in inhibition was observed when the hitherto hydrophobic 6-substituent was substituted by a branched functionality of hydrophilic nature. Conversely, methylation of the 4-hydroxy group of the 6-alkyl-2-pyrones increased inhibitory activity. The mechanism of inhibition varied from pure noncompetitive to mixed type to uncompetitive and was found to be dependent on the pattern of substitution. We believe that the 4-hydroxy-2-pyrone binds to the S4 subsite, with the 6-substituent extending across the S4-S1 subsites and the 3-substituent occupying the S5 subsite. The length of the inhibitor binding region was calculated to be approximately 24 A. None of the hydrophobic compounds were found to have any appreciable inhibition (less than 10%) with porcine pancreatic elastase, bovine alpha-chymotrypsin, and bovine trypsin when tested at the limit of their solubility. The hydrophilic compounds were nonspecific, inhibiting all four enzymes. Dialysis was used to show that the interaction is fully reversible.
• EP0365539A4
  申请人：——

  公开号：EP0365539A4

  公开（公告）日：1990-12-05
• HUMAN LEUCOCYTE ELASTASE INHIBITOR COMPOUNDS
  申请人：AUSTRALIAN COMMERCIAL RESEARCH & DEVELOPMENT LIMITED

  公开号：EP0365539A1

  公开（公告）日：1990-05-02
• [EN] HUMAN LEUCOCYTE ELASTASE INHIBITOR COMPOUNDS
  申请人：LA TROBE UNIVERSITY

  公开号：WO1988010258A1

  公开（公告）日：1988-12-29

  (EN) A compound of formula (III) or physiologically acceptable salts thereof, wherein: Z is a bond, -O- or -NH-; R1 and R3 are independently selected from C5-12 substituted of unsubstituted hydrocarbon radicals; R2 is hydrogen or a C1-5 substituted or unsubstituted hydrocarbon radical; said substituted hydrocarbon radicals are substituted with physiologically innocuous substituents which do not interfere with the binding of said compound with elastase-type enzymes; provided that: when R1 is oxohexyl and R2 is hydrogen, then R3 cannot be pentyl; when R1 is oxoheptyl and R2 is hydrogen, then R3 cannot be hexyl; when R1 is oxononyl and R2 is hydrogen, then R3 cannot be octyl; when R1 is oxodecyl and R2 is hydrogen, then R3 cannot be nonyl; and when R1 is oxododecyl and R2 is hydrogen, then R3 cannot be undecyl. These compounds are potent and specific inhibitor compounds fo elastase-type enzymes, especially for human leucocytic elastase (HLE) and can be expected to be useful in the treatment of elastase-type implicated diseases such as arthritis, tumor growth and emphysema. Production, method of use and pharmaceutical compositions containing these compounds are disclosed.(FR) La présente invention se rapporte à un composé représenté par la formule (III) ou à des sels physiologiquement acceptables dudit composé, où: Z représente une liaison, -O- ou -NH-; R1 et R3 sont choisis séparément parmi des radicaux d'hydrocarbures substitués ou non substitués de 5 à 12 atomes de carbone; R2 représente un hydrogène ou un radical d'hydrocarbures substitués ou non substitués de 1 à 5 atomes de carbone; lesdits radicaux d'hydrocarbures substitués étant substitués par des substituants physiologiquement inoffensifs qui ne perturbent pas la liaison entre ledit composé et les enzymes du type élastase; à condition que: lorsque R1 représente un oxohexyle et R2 un hydrogène, alors R3 ne peut pas être un pentyle; lorsque R1 représente un oxoheptyle et R2 un hydrogène, alors R3 ne peut pas être un hexyle; lorsque R1 représente un oxononyle et R2 un hydrogène, alors R3 ne peut pas être un octyle; lorsque R1 un oxodécyle et R2 un hydrogène, alors R3 ne peut pas être un nonyle; et lorsque R1 représente un oxodécyle et R2 un hydrogène, alors R3 nepeut pas être un undécyle. Ces composés constituent des composés inhibiteurs puissants et spécifiques pour les enzymes du type élastase, tel que notamment l'élastase leucocytaire humaine, (HLE) et on peut prévoir que ces composés ont une utilité dans le traitement des maladies dans lesquelles sont impliquées des enzymes du type élastase, tel que l'arthrite, la croissance des tumeurs et les emphysèmes. La production et le procédé d'utilisation de ces composés ainsi que des compositions pharmaceutiques les contenant sont également décrits.