1-(2',4',6'-trihydroxyphenyl)pentan-1-one | 2999-18-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2',4',6'-trihydroxyphenyl)pentan-1-one
• 英文别名: 1-(2,4,6-trihydroxyphenyl)pentan-1-one；valeryl phloroglucinol；1-(2,4,6-trihydroxy-phenyl)-pentan-1-one；1-(2,4,6-Trihydroxy-phenyl)-pentan-1-on
• CAS: 2999-18-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: HPBAQDWUBZVAMF-UHFFFAOYSA-N

物化性质

• 熔点：
  149 °C
• 沸点：
  363.1±22.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1-(2',4',6'-trihydroxyphenyl)pentan-1-one 在 盐酸 、 汞 、 锌 作用下， 以 乙醇 为溶剂， 反应 100.0h， 以49%的产率得到2-pentyl-phloroglucinol
  参考文献：
  名称：

  Mizobuchi, Shigeyuki; Sato, Yuko, Agricultural and Biological Chemistry, 1985, vol. 49, # 3, p. 719 - 724

  摘要：

  DOI：
• 作为产物：
  描述：

  在 水 作用下， 反应 1.5h， 生成 1-(2',4',6'-trihydroxyphenyl)pentan-1-one
  参考文献：
  名称：

  A Test for Homology:  Photoactive Crystalline Assemblies Involving Linear Templates Based on a Homologous Series of Phloroglucinols

  摘要：

  Cocrystallization of trans-1,2-bis(4-pyridyl)ethylene (4,4'-bpe) with eight members of a homologous series of phloroglucinols 1a-h yields molecular solids 2(1a-h)-2(4,4'-bpe) with components held together by four O-H...N hydrogen bonds. In each case, the molecules assemble to form a discrete four-component assembly with olefins preorganized for a [2 + 2] photodimerization. UV irradiation of each member in the series of solids produces rctt-tetrakis(4-pyridyl)cyclobutane (4,4'-tpcb), stereospecifically, in up to 100% yield.

  DOI：

  10.1021/ol0484052

文献信息

• Synthesis of novel flavonoid derivatives as potential HIV- Integrase inhibitors
  作者：Nelly N. Mateeva、Rao N. Kode、Kinfe K. Redda

  DOI：10.1002/jhet.5570390620

  日期：2002.11

  Eighteen novel flavonoid derivatives - substituted chalcones and flavones were synthesized and characterized by using NMR, IR, UV/Vis spectroscopy and elemental analysis. The target compounds were achieved by using a sequence of simple and effective reactions starting from phloroglucinol. The initial hydroxyl groups were protected by methylation and in the final flavones the 5-OH group was selectively

  合成了十八种新的类黄酮衍生物-取代的查耳酮和黄酮，并通过NMR，IR，UV / Vis光谱和元素分析对其进行了表征。通过使用一系列从间苯三酚开始的简单有效的反应，可以实现目标化合物。最初的羟基被甲基化保护，而在最后的黄酮中，5-OH通过AlBr 3选择性地脱甲基。5-甲氧基黄酮显示强荧光，在除去甲基后将其猝灭。
• Probing the Catalytic Promiscuity of a Regio- and Stereospecific C-Glycosyltransferase from<i>Mangifera indica</i>
  作者：Dawei Chen、Ridao Chen、Ruishan Wang、Jianhua Li、Kebo Xie、Chuancai Bian、Lili Sun、Xiaolin Zhang、Jimei Liu、Lin Yang、Fei Ye、Xiaoming Yu、Jungui Dai

  DOI：10.1002/anie.201506505

  日期：2015.10.19

  The catalytic promiscuity of the novel benzophenone C‐glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio‐ and stereospecific C‐glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP‐glucose, and also formed O‐ and N‐glycosides. Moreover, MiCGT was able to

  探索了新型二苯甲酮C-糖基转移酶MiCGT的催化混杂性，该酶参与了印度芒果（Mangifera indica）的芒果苷的生物合成。MiCGT对35种结构多样的药物样支架和带有UDP-葡萄糖的简单酚类化合物具有较强的区域和立体特异性C-糖基化能力，还形成了O-和N-糖苷。而且，MiCGT能够用UDP木糖生成C-木糖苷。还利用MiCGT的OGT可逆性与简单的糖供体一起生成C-葡萄糖苷。三种芳基C-糖苷显示出有效的SGLT2抑制活性，IC 50 值为2.6×，7.6×和7.6×10 -7  M， 分别。这些发现首次证明了通过酶法在药物发现中通过对生物活性天然和非天然产物进行C-糖基化来实现多元化的巨大潜力。
• A Novel Parkinson’s Disease Drug Candidate with Potent Anti-neuroinflammatory Effects through the Src Signaling Pathway
  作者：Ya-Dan Wang、Xiu-Qi Bao、Song Xu、Wen-Wen Yu、Sheng-Nan Cao、Jin-Ping Hu、Yan Li、Xiao-Liang Wang、Dan Zhang、Shi-Shan Yu

  DOI：10.1021/acs.jmedchem.6b00976

  日期：2016.10.13

  mice at a median lethal dose (LD50) >5000 mg/kg. Its in vivo efficacy was demonstrated in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP)- and MPTP/probenecid (prob)-induced subacute and chronic PD models, respectively, and α-synuclein transgenic mice. Mechanistic studies revealed neuroinflammation inhibition by targeting Src/phosphatase and tensin homologue deleted on chromosome 10 (PTEN)/Akt signaling

  帕金森氏病（PD）是一种与年龄有关的神经退行性疾病，目前有许多药物治疗方法，但大多数都会引起严重的副作用。因此，迫切需要能够阻止疾病进展并允许长期给药的新型治疗策略。神经炎症在PD的发病机理中起关键作用。在这里，我们报告发现和优化间苯三酚衍生物，一类新型的抗神经炎化合物。对命中化合物3-甲基-1-（2,4,6-三羟基苯基）丁-1-的结构修饰产生了43种衍生物，包括临床前候选药物（化合物21），具有良好的体外抗神经炎作用，具有良好的体外抗炎性。在中等致死剂量下小鼠血脑屏障穿透力和理想的安全裕度（LD 50）> 5000 mg / kg。分别在1-甲基-4-苯基-1,2,3,6-四氢吡啶（MPTP）-和MPTP / probenecid（prob）诱导的亚急性和慢性PD模型以及α-突触核蛋白转基因模型中证明了其体内功效老鼠。机理研究表明，通过靶向10号染色体（PTEN）/ Akt信号缺失的Src
• Inhibitory Effect of Acylphloroglucinol Derivatives on the Replication of Vesicular Stomatitis Virus
  作者：Kazuhiro Chiba、Takako Takakuwa、Masahiro Tada、Takao Yoshii

  DOI：10.1271/bbb.56.1769

  日期：1992.1

  The antiviral activity of natural phloroglucinols and of synthesized mono- and diacylphloroglucinols, and 2,6-diacyl-4,4-dialkylcyclohexa-1,3,5-triones was investigated. A correlation between the acyl chain length and inhibitory activity against vesicular stomatitis virus (VSV) was observed. Potent antiviral activity was found in di-isovalerylphoroglucinol. 2,6-Diacyl-4,4-dialkylcyclohexa-1,3,5-triones inhibited replication of the virus with low cytotoxicity.

  研究了天然根皮酚类化合物、合成的一元和二元酰基根皮酚类化合物以及2,6-二酰基-4,4-二烷基环己-1,3,5-三酮的抗病毒活性。观察到酰基链长度与对水泡性口炎病毒（VSV）的抑制活性之间的相关性。二异戊酰基根皮酚显示出强大的抗病毒活性。2,6-二酰基-4,4-二烷基环己-1,3,5-三酮具有抑制病毒复制和低细胞毒性的特点。
• Synthesis and antibiotic activity of novel acylated phloroglucinol compounds against methicillin-resistant Staphylococcus aureus
  作者：Navriti Mittal、Haben H. Tesfu、Andrew M. Hogan、Silvia T. Cardona、John L. Sorensen

  DOI：10.1038/s41429-019-0153-4

  日期：2019.5

  The rise in antibiotic resistance among pathogenic microorganisms has created an imbalance in the drugs available for treatment, in part due to the slow development of new antibiotics. Cystic fibrosis (CF) patients are highly susceptible to antibiotic-resistant pathogens, including methicillin-resistant Staphylococcus aureus (MRSA). Phloroglucinols and related polyketide natural products have demonstrated antimicrobial activity against a number of Gram-positive bacteria including S. aureus. In this study, we investigated a series of acylated phloroglucinol derivatives to determine their potential as lead compounds for the design of novel therapeutics. To assess the activity of these compounds, we determined the minimum inhibitory and bactericidal concentration (MIC and MBC, respectively), the minimum biofilm inhibitory and biofilm eradication concentration (MBIC and MBEC, respectively), and evaluated hemolytic activity, as well as their interaction with clinically relevant antibiotics. Of the 12 compounds tested against MRSA and methicillin-susceptible strains, four showed MIC values ranging from 0.125 to 8 µg ml−1 and all of them were bactericidal. However, none of the compounds were able to eradicate biofilms at the concentrations tested. Three of the four did not display hemolytic activity under the conditions tested. Further studies on the interactions of these compounds with clinically relevant antibiotics showed that phlorodipropanophenone displayed synergistic activity when paired with doxycycline. Our results suggest that these acylated phloroglucinols have potential for being further investigated as antibacterial leads.

  病原微生物中抗生素抗性的上升造成了治疗用药物的不平衡，这在一定程度上是由于新抗生素的研发缓慢。囊性纤维化(CF)患者极易感染抗生素抗性病原体，包括耐甲氧西林金黄色葡萄球菌(MRSA)。间苯三酚类及其相关多酮天然产物已显示出对多种革兰氏阳性细菌(包括金黄色葡萄球菌)的抗菌活性。在本研究中，我们调查了一系列酰化间苯三酚衍生物质，以确定它们作为新型治疗药物设计的先导化合物的潜力。为了评估这些化合物的活性，我们测定了最低抑制浓度和杀菌浓度(MIC和MBC)、最低生物膜抑制浓度和生物膜消除浓度(MBIC和MBEC)，并评估了溶血活性，以及它们与临床相关抗生素的相互作用。在针对MRSA和甲氧西林敏感菌株测试的12种化合物中，有4种的MIC值在0.125至8 µg/ml之间，且均为杀菌性。然而，在测试的浓度下，这些化合物均无法消除生物膜。其中3种在测试条件下未显示溶血活性。进一步研究这些化合物与临床相关抗生素的相互作用，结果显示，苯二丙酸苯酮在配伍强力霉素时表现出协同活性。我们的结果表明，这些酰化间苯三酚具有作为抗菌先导物进一步研究的潜力。