3-羟基-2-甲基-1-丙基吡啶-4-酮 | 30652-13-2

• 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: 3-羟基-2-甲基-1-丙基吡啶-4-酮
• 英文名称: 3-hydroxy-2-methyl-1-propyl-4(1H)-pyridinone
• 英文别名: 1-propyl-2-methyl-3-hydroxypyrid-4-one；3-hydroxy-2-methyl-1-propyl-4-pyridinone；N-propyl-3-hydroxy-2-methyl-4-pyridon；3-hydroxy-2-methyl-1-propyl-4-pyridone；3-hydroxy-2-methyl-1-propyl-1H-pyridin-4-one；3-hydroxy-2-methyl-1-propylpyrid-4-one；3-hydroxy-2-methyl-1-propylpyridin-4-one
• CAS: 30652-13-2
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: BFUSTCYJXIZANF-UHFFFAOYSA-N

物化性质

• 沸点：
  266.0±40.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-羟基-2-甲基-1-丙基吡啶-4-酮 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 1,4-dihydro-2-methyl-1-propyl-4-propylimino-3-pyridinol
  参考文献：
  名称：

  Faerber, M.; Osiander, H.; Severin, T., Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 947 - 956

  摘要：

  DOI：
• 作为产物：
  描述：

  O-半乳糖基异麦芽酚 在 almond meal 作用下， 以 甲醇 、 水 为溶剂， 反应 104.0h， 生成 3-羟基-2-甲基-1-丙基吡啶-4-酮
  参考文献：
  名称：

  Efficient Syntheses of N-Alkyl-3-hydroxy-2-methyl-4(1H)-pyridinones From Carbohydrate Precursors

  摘要：

  N-alkyl-3-hydroxy-2-methyl-4(1H)-pyridinohes can be synthesised in reasonable yield from either 1-(3-hydroxy-2-furanyl)ethanone or O-galactosylisomaltol. Since these carbohydrate precursors can be produced from the disaccharide, alpha-D-lactose, a simple and inexpensive transformation into pyridinones is possible.

  DOI：

  10.1080/00397919908086062

文献信息

• Synthesis, characterization, and biological relevance of hydroxypyrone and hydroxypyridinone complexes of molybdenum
  作者：Sarah J Lord、Noah A Epstein、Robert L Paddock、Christopher M Vogels、Tracy L Hennigar、Michael J Zaworotko、Nicholas J Taylor、William R Driedzic、Tom L Broderick、Stephen A Westcott

  DOI：10.1139/v99-111

  日期：1999.7.1

  We have prepared a number of complexes of the type cis-MoO₂L₂ where L represents a hydroxypyronato or hydroxypyridinonato ligand. Both the maltol (3-hydroxy-2-methyl-4-pyrone, Hma) and kojic acid (5-hydroxy-2-hydroxymethyl-4-pyrone, Hka) complexes, cis-MoO₂(ma)₂ (1) and cis-MoO₂(ka)₂ (2), have been characterized by X-ray diffraction studies. The pyrone ligands are bound to molybdenum in a cis bidentate fashion via the deprotonated hydroxyl groups and the ketone moieties. Crystals of 1 are orthorhombic, a = 12.107 (1), b = 8.6169 (8), c = 16.472 (1) Å, Z = 4, space group Pca2₁, and those of 2 are monoclinic, a = 8.4591 (5), b = 16.3453 (10), c = 10.2954 (7) Å, β = 103.0320 (10)°, Z = 4, space group P2₁/c. Hydroxypyridinone molybdenum complexes have been prepared for both maltol and kojic acid derivatives with the substituents Me, n-Pr, CH₂Ph, Ph at the ring nitrogen. Crystals of the 3-hydroxy-2-methyl-1-phenyl-4-pyridinone (Hppp) derivative, MoO₂(ppp)₂ (9), are monoclinic, a = 10.9476 (6), b = 13.5353 (9), c = 17.4877 (10) Å, β = 93.465 (4)°, Z = 4, space group P2₁/n. Initial investigations into the effects molybdenum compounds have on diabetic hearts are presented. Both Na₂MoO₄ (used as a control) and 1 were effective in lowering blood glucose and free fatty acid levels. Diabetic rats treated with molybdate showed significant improvements in postischemic cardiac function.Key words: molybdenum, hydroxypyrones, hydroxypyridinones, heart function.

  我们已经准备了一系列cis-MoO₂L₂类型的配合物，其中L代表羟基吡啶酮或羟基吡啶酮配体。麦芽酮（3-羟基-2-甲基-4-吡喃酮，Hma）和曲酸（5-羟基-2-羟甲基-4-吡喃酮，Hka）配合物，cis-MoO₂(ma)₂（1）和cis-MoO₂(ka)₂（2），已经通过X射线衍射研究进行了表征。吡喃酮配体以顺式双齿方式通过去质子羟基和酮基与钼结合。1的晶体为正交晶系，a = 12.107（1），b = 8.6169（8），c = 16.472（1）埃，Z = 4，空间群Pca2₁，而2的晶体为单斜晶系，a = 8.4591（5），b = 16.3453（10），c = 10.2954（7）埃，β = 103.0320（10）°，Z = 4，空间群P2₁/c。已经为麦芽酮和曲酸衍生物制备了羟基吡啶酮钼配合物，其在环氮原子处具有Me、n-Pr、CH₂Ph、Ph等取代基。3-羟基-2-甲基-1-苯基-4-吡啶酮（Hppp）衍生物MoO₂(ppp)₂（9）的晶体为单斜晶系，a = 10.9476（6），b = 13.5353（9），c = 17.4877（10）埃，β = 93.465（4）°，Z = 4，空间群P2₁/n。首次研究了钼化合物对糖尿病心脏的影响。钼酸钠（用作对照）和1在降低血糖和游离脂肪酸水平方面均有效。接受钼酸盐治疗的糖尿病大鼠在缺血后心脏功能方面表现出显著改善。关键词：钼、羟基吡喃酮、羟基吡啶酮、心脏功能。
• Process for producing pyrid-4-ones
  申请人：THE ROYAL FREE HOSPITAL SCHOOL OF MEDICINE

  公开号：EP0335745A1

  公开（公告）日：1989-10-04

  Substituted-3-hydroxy-pyrid-4-ones, derivatives thereof, and salts thereof are produced by reacting subsituted-3-hydroxypyr-4-one with ammonia or a non-sterically hindered primary amine usually in the presence of a solvent such as water. Also disclosed are novel derivatives of 2-ethyl-3-hydroxypyrid-4-one.

  通过将取代的3-羟基吡啶-4-酮与氨或非立体位阻的一级胺反应，通常在水等溶剂的存在下，可以制备取代的3-羟基吡啶-4-酮、其衍生物和盐类。此外，还披露了2-乙基-3-羟基吡啶-4-酮的新衍生物。
• Synthetic methods and in vitro iron binding studies of the novel 1-alkyl-2-ethyl-3-hydroxypyrid-4-one iron chelators
  作者：G.J. Kontoghiorghes、L. Sheppard、J. Barr

  DOI：10.1016/s0020-1693(00)84951-8

  日期：1988.7

  Abstract Three novel iron chelators namely the 1-methyl-, 1-ethyl- and 1-propyl-2-ethyl-3-hydroxypyrid-4-ones were prepared in high yields from ethyl maltol and the related alkylamine in a one step reaction. These chelators formed 3 chelator:1 iron stable, coloured, neutral complexes at physiological pH and mobilise iron from transferrin, ferritin and haemosiderin. The rate of iron mobilisation from

  摘要用一步法从乙基麦芽酚和相关的烷基胺中高收率地制备了三种新型的铁螯合剂，即1-甲基-，1-乙基-和1-丙基-2-乙基-3-羟基吡啶-4-酮。这些螯合剂形成3种螯合剂：1在生理pH值下稳定的，有色的铁中性复合物，并从运铁蛋白，铁蛋白和血铁蛋白中动员铁。这些蛋白质的铁动员速率为转铁蛋白>血铁蛋白>铁蛋白。1-烷基-2-乙基-3-羟基吡啶-4-酮在生理pH下的廉价合成和强铁结合特性需要进一步研究和开发这些化合物及其同系物，以治疗铁超负荷和铁过剩。铁的其他疾病失衡和毒性。
• 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。
• 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。

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