1,1'-(2,4,6-三羟基-1,3-亚苯基)二(1-丙酮) | 3145-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1'-(2,4,6-三羟基-1,3-亚苯基)二(1-丙酮)
• 英文名称: 1,1'-(2,4,6-trihydroxy-1,3-phenylene)bis(propan-1-one)
• 英文别名: 1,3-dipropanoyl-2,4,6-trihydroxy benzene；di-propanoylphloroglucinol；dipropionyl phloroglucinol；2,4-dipropionyl-phloroglucinol；2,4-Dipropionyl-phloroglucin；1-Propanone, 1,1'-(2,4,6-trihydroxy-m-phenylene)di-；1-(2,4,6-trihydroxy-3-propanoylphenyl)propan-1-one
• CAS: 3145-11-7
• 化学式: C₁₂H₁₄O₅
• 分子量: 238.24
• InChiKey: MAULNQUCMOQLDU-UHFFFAOYSA-N

物化性质

• 熔点：
  152–154°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  1,1'-(2,4,6-三羟基-1,3-亚苯基)二(1-丙酮) 、 2-(2-hydroxy-2-methylpropyl)cyclohex-2-enone 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以91%的产率得到1,1'-(5,7-dihydroxy-2,2-dimethyl-2,3,3a,4-tetrahydro-4,9a-propanofuro[2,3-b]chromene-6,8-diyl)bis(propan-1-one)
  参考文献：
  名称：

  仿生莫拉莫司酮和Myrtucommulone J的仿生启发性合成

  摘要：

  在生物启发和结构欣赏的推动下，通过生物合成的半缩醛化/脱水/ [3 + 3]型环加成多米诺序列实现了具有仿生功能的酰基间苯二酚Myrtucommulone J和myrtucommuacetalone的结构仿生的第一个仿生全合成。步进效率高。这些合成导致Myrtucommulone J的结构更正。

  DOI：

  10.1021/acs.orglett.7b02159
• 作为产物：
  描述：

  夫洛丙酮 、 丙酰氯 在 三氯化铝 作用下， 生成 1,1'-(2,4,6-三羟基-1,3-亚苯基)二(1-丙酮)
  参考文献：
  名称：

  Murata, Masatsune; Yamakoshi, Yoko; Homma, Seiichi, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 12, p. 2062 - 2063

  摘要：

  DOI：

文献信息

• <i>ortho</i>-Amidoalkylation of Phenols via Tandem One-Pot Approach Involving Oxazine Intermediate
  作者：Ramesh Mudududdla、Shreyans K. Jain、Jaideep B. Bharate、Ajai P. Gupta、Baldev Singh、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1021/jo3017132

  日期：2012.10.5

  phenols via Mannich-type condensation with formaldehyde and lactams using recyclable solid acid catalyst is described. This is the first report for ortho-amidoalkylation of phenols by lactams via Mannich-type condensation. LC-ESI-MS/MS based mechanistic study revealed that reaction proceeds through o-quinone methide (o-QM) and an oxazine intermediate via tandem Knoevenagel condensation, formal [4 +

  描述了一种新的有效方法，该方法通过使用可循环使用的固体酸催化剂，通过曼尼希型缩合与甲醛和内酰胺进行苯酚的邻位酰胺基烷基化。这是关于内酰胺通过曼尼希型缩合对苯酚进行邻氨基烷基烷基化的首次报道。基于LC-ESI-MS / MS的机理研究表明，反应是通过串联Knoevenagel缩合，[4 + 2] -Diels-Alder环加成和酸催化的恶嗪环-通过邻甲基苯醌（o- QM）和恶嗪中间体进行的开幕。
• 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。
• Biocatalytic Friedel-Crafts Acylation and Fries Reaction
  作者：Nina G. Schmidt、Tea Pavkov-Keller、Nina Richter、Birgit Wiltschi、Karl Gruber、Wolfgang Kroutil

  DOI：10.1002/anie.201703270

  日期：2017.6.19

  The Friedel-Crafts acylation is commonly used for the synthesis of aryl ketones, and a biocatalytic version, which may benefit from the chemo- and regioselectivity of enzymes, has not yet been introduced. Described here is a bacterial acyltransferase which can catalyze Friedel-Crafts C-acylation of phenolic substrates in buffer without the need of CoA-activated reagents. Conversions reach up to >99 %

  弗里德尔-克来福特酰化通常用于芳基酮的合成，并且尚未引入可能受益于酶的化学和区域选择性的生物催化版本。这里描述的是一种细菌酰基转移酶，它可以催化缓冲液中酚类底物的 Friedel-Crafts C-酰化，而不需要 CoA 激活试剂。转化率高达 >99%，并且该酶接受各种 C-或 O-酰基供体，例如 DAPG 或乙酸异丙烯酯。此外，该酶能够使间苯二酚衍生物发生类似弗里斯重排的反应。这些发现为开发替代性和选择性 CC 键形成方法开辟了道路。
• Synthesis and P-glycoprotein induction activity of colupulone analogs
  作者：Jaideep B. Bharate、Yazan S. Batarseh、Abubakar Wani、Sadhana Sharma、Ram A. Vishwakarma、Amal Kaddoumi、Ajay Kumar、Sandip B. Bharate

  DOI：10.1039/c5ob00554j

  日期：——

  treatment of AD. Colupulone, a prenylated phloroglucinol isolated from Humulus lupulus, is known to activate pregnane-X-receptor (PXR), which is a nuclear receptor controlling P-gp expression. In the present work, we aimed to synthesize and identify analogs of colupulone that are potent P-gp inducer(s) with an ability to enhance Aβ transport across the BBB. A series of colupulone analogs were synthesized

  脑淀粉样蛋白（Aβ）斑块是与阿尔茨海默氏病（AD）病理相关的主要标志之一。据报道，位于血脑屏障（BBB）的外排泵蛋白在清除大脑Aβ中起重要作用，其中P-糖蛋白（P-gp）外排转运泵已显示出至关重要的作用。因此，P-gp已被认为是治疗AD的潜在治疗靶标。Colupulone，一种从Hum草中分离的烯丙基间苯三酚已知其激活孕烷-X-受体（PXR），后者是控制P-gp表达的核受体。在目前的工作中，我们旨在合成和鉴定具有强大的P-gp诱导剂能力的colupulone类似物，并具有增强Aβ通过BBB转运的能力。通过在异戊二烯基和酰基域上的修饰合成了一系列的colupulone类似物。在过表达P-gp的人腺癌LS-180细胞中，使用基于若丹明123的外排试验筛选所有化合物的P-gp诱导活性，其中所有化合物在5μM下显示出显着的P-gp诱导活性。在LS-180细胞中的蛋白质印迹研究中，化合物3k和5f能