1-丁基-3-羟基-2-甲基吡啶-4-酮 | 30652-15-4

• 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: 1-丁基-3-羟基-2-甲基吡啶-4-酮
• 英文名称: 1,n-butyl-3-hydroxy-2-methylpyrid-4-one
• 英文别名: CP24；1-Butyl-3-hydroxy-2-methylpyrid-4-one；4(1H)-Pyridinone, 1-butyl-3-hydroxy-2-methyl-；1-butyl-3-hydroxy-2-methylpyridin-4-one
• CAS: 30652-15-4
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: YYJBZFVEZYRNEW-UHFFFAOYSA-N

物化性质

• 沸点：
  282.5±40.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(benzyloxy)-1-butyl-2-methylpyridin-4(1H)-one 在 10% palladium on carbon 、 氢气 作用下， 生成 1-丁基-3-羟基-2-甲基吡啶-4-酮
  参考文献：
  名称：

  Synthesis, antimicrobial evaluation and QSAR study of some 3-hydroxypyridine-4-one and 3-hydroxypyran-4-one derivatives

  摘要：

  A series of Mannich bases of 2-alkyl-3-hydroxy-pyridine-4-ones, namely 2-alkyl-3-hydroxy-5-N-piperidylmethyl or N,N-dialkylaminomethyl pyridine-4-ones 9, 10 and 15-18, two derivatives of N-aryl-2methyl-3-hydroxy-pyridine-4-ones 19, 20 and two N-alkyl derivatives of maltol, 21 and 22 were prepared. They were screened for their antibacterial and antifungal activities against a variety of microorganisms using micro plate Alamar Blues assay (MABA) method. Multiple linear regressions (MLR) analysis was performed for the synthesized compounds as well as a series of pyridinone and pyranone derivatives 23-43 which have been synthesized and evaluated for antimicrobial activity by other researchers previously. Studied compounds showed a better quantitative structure-activity relationship (QSAR) model for the antimicrobial activity against Candida albicans and Staphylococcus aureus in comparison with other tested microorganisms. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.10.022

文献信息

• Synthesis of Oxovanadium Complexes and Their Apoptosis-Inducing Activity in Leukemia Cells
  作者：Tomoko Yamaguchi、Shinya Watanabe、Yuriko Matsumura、Yoshikazu Tokuoka、Akihiro Yokoyama

  DOI：10.1248/cpb.60.508

  日期：——

  Vanadium complexes with different ligands were synthesized and evaluated for antiproliferative activity on U937 cells. The alkyl chain length of the ligands affected the antiproliferative activity, and two complexes—3b and 4—exhibited strong activities with IC50 values of 6.02 and 3.90 μM respectively. Annexin V staining and DNA ladder formation indicated that these complexes induced apoptosis in U937 cells.

  不同配体的钒复合物被合成并评估对U937细胞的抗增殖活性。配体的烷基链长度影响抗增殖活性，其中两个复合物——3b和4——展现出强活性，IC50值分别为6.02和3.90 μM。Annexin V染色和DNA梯带形成表明这些复合物诱导了U937细胞的凋亡。
• VICINAL PRIMARY DIAMINES ASSOCIATED WITH METAL AND/OR FREE RADICAL CHELATION MOTIFS, AND ACTIVE AGAINST CARBONYL AND OXIDATIVE STRESS, AND USE THEREOF
  申请人：UNIVERSITE AMIENS PICARDIE JULES VERNE

  公开号：US20180201602A1

  公开（公告）日：2018-07-19

  The invention relates to compounds of Formula I: or the salts thereof, as well as the use thereof in the pharmaceutical, cosmetic or agrofood industry.

  该发明涉及公式I的化合物：或其盐，以及在制药、化妆品或农业食品工业中的使用。
• Boronic-Acid-Accelerated Electrophilic Activation of Unprotected Maltols to N-Substituted Hydroxypyridinones in Water
  作者：Di Ke、Lei Zhang、Xiuwen Zhong、Jiaan Shao、Yongping Yu、Wenteng Chen

  DOI：10.1021/acs.orglett.1c03833

  日期：2022.2.18

  3,4-Hydroxypyridinone (3,4-HOPO) is a vital metal-chelating pharmacophore. However, the efficient synthesis has been a long-standing problem in drug development. In this paper, we report an efficient electrophilic activation of unprotected maltols via reversible covalent bonds between boronic acid and 3-hydroxyl/4-carbonyl. This one-pot reaction proceeded well on a gram scale in water with excellent

  3,4-Hydroxypyridinone (3,4-HOPO) 是一种重要的金属螯合药效团。然而，高效合成一直是药物开发中长期存在的问题。在本文中，我们报告了通过硼酸和 3-羟基/4-羰基之间的可逆共价键对未受保护的麦芽酚进行有效的亲电活化。这种一锅法反应在水中以克级进行良好，效率高达 97%。此外，利用通过瞬时硼酸盐的共价相互作用，大多数以前坚韧的胺供体，包括空间位阻胺、芳香胺、氨基酸和氨基醇，都具有良好的耐受性。重要的是，这一战略在制药行业的潜力通过成功合成 3、
• Iron(III) complexes as contrast agents for image enhancement in magnetic resonance imaging
  申请人：The University of Toledo

  公开号：US06294152B1

  公开（公告）日：2001-09-25

  A compound of formula (I): wherein, R1 is independently selected from methyl and ethyl and R2 is independently selected from hydrogen, alkyl, and substituted alkyl. The compound is capable of functioning as a ligand and complexing with paramagnetic Fe(III) ion for use as a second-sphere contrast enhancing agent for magnetic resonance imaging of tissue. The present invention also relates to a method of administering the second sphere contrast agent.

  化合物的化学式为（I）：其中，R1独立选择自甲基和乙基，R2独立选择自氢、烷基和取代烷基。该化合物能够作为配体并与顺磁性Fe（III）离子形成络合物，用作组织的第二球半对比增强剂的磁共振成像。本发明还涉及一种给予第二球半对比剂的方法。
• Exploiting Natural Maltol for Synthesis of Novel Hydroxypyridone Derivatives as Promising Anti-Virulence Agents in Bactericides Discovery
  作者：Wan-Lin Xiao、Na Wang、Lin-Li Yang、Yu-Mei Feng、Pan-Long Chu、Jiao-Jiao Zhang、Shuai-Shuai Liu、Wu-Bin Shao、Xiang Zhou、Li-Wei Liu、Song Yang

  DOI：10.1021/acs.jafc.3c00465

  日期：2023.5.3

  pathogenic bacteria. The antibacterial mechanism showed that it could considerably reduce various virulence factors (such as extracellular enzymes, biofilm, and T3SS effectors) and inhibit the expression of virulence factor-related genes. In addition, the control efficiency of compound B6 against rice bacterial leaf blight at 200 μg mL–1 was 46.15–49.15%, and their control efficiency was improved by approximately

  基于抑制细菌毒力因子的抗感染策略是开发新型抗菌药物以解决传统药物/农药杀菌活性引发的耐药性的重要方向。为了识别和获得更有效和多样化的毒力靶向分子，我们制备了一系列 3-hydroxy-2-methyl-1-pyridin-4-(1 H )-one衍生物并评估了它们的抗菌行为。化合物B 6表现出最高的生物活性，半数最大有效浓度 (EC 50 ) 值范围为 9m 10.03 至 30.16 μg mL –1对抗三种植物病原菌。抗菌机制表明它可以显着降低各种毒力因子（如细胞外酶、生物膜和T3SS效应子）并抑制毒力因子相关基因的表达。此外，复方B 6在200 μg·mL -1浓度下对水稻细菌性叶枯病的防效为46.15～49.15%，添加农药助剂后防效提高约12%。因此，开发了一类新的靶向细菌毒力因子的候选杀菌剂来控制植物细菌病害。