4-hydroxy-3-((2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoyl)-6-methyl-2H-pyran-2-one | 1084815-96-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-hydroxy-3-((2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoyl)-6-methyl-2H-pyran-2-one
• 英文别名: 4-hydroxy-3-[(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoyl]-6-methyl-pyran-2-one；4-hydroxy-3-[(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoyl]-6-methylpyran-2-one
• CAS: 1084815-96-2
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: HQKLBPYALIMCPG-GGWOSOGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-[(2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoyl]-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate 在 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以74%的产率得到4-hydroxy-3-((2E,4E)-5-(4-methoxyphenyl)penta-2,4-dienoyl)-6-methyl-2H-pyran-2-one
  参考文献：
  名称：

  脱水乙酸二氟硼烷配合物的合成与反应

  摘要：

  Dehydracetic acid difluoroborane complex, 3-acetyl-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate, was synthesized and characterized. The complex was involved into condensation reactions at the acetyl group with various aromatic and heterocyclic aldehydes, and with the 4-dimethylaminobenzaldehyde it reacted also at the methyl group in the position 6.

  DOI：

  10.1134/s107042800807018x

文献信息

• Drug design based on pentaerythritol tetranitrate reductase: synthesis and antibacterial activity of Pogostone derivatives
  作者：Biao Wang、Wei Huang、Jin Zhou、Xue Tang、Yang Chen、Cheng Peng、Bo Han

  DOI：10.1039/c7ob01429e

  日期：——

  Pogostone with potent antibacterial activity, we performed molecular docking studies of Pogostone with PETNR and analyzed structure–activity relationships, which guided the structure design and the subsequent facile organocatalytic synthesis of Pogostone derivatives under mild reaction conditions. Several of the synthesized compounds showed antibacterial activity in vitro, including one compound (3h)

  我们以前的工作表明，Pogostone通过靶向季戊四醇四硝酸酯还原酶（PETNR）发挥抗菌作用。为了开发具有强抗菌活性的Pogostone衍生物，我们进行了PETGO与Pogostone的分子对接研究，并分析了结构与活性之间的关系，这指导了结构设计以及随后在温和的反应条件下轻松进行有机催化合成Pogostone衍生物的工作。几种合成的化合物在体外均显示出抗菌活性，其中一种化合物（3h）对耐甲氧西林的金黄色葡萄球菌非常有效。这些结果表明，在侧链上带有官能团的Pogostone衍生物可能是抗菌药物开发的良好线索。
• Cytotoxic and antibacterial activities of the analogues of pogostone
  作者：Zheng-wei Tang、Cheng Peng、Min Dai、Bo Han

  DOI：10.1016/j.fitote.2015.08.003

  日期：2015.10

  Six new (A5-A6, A8-A11) and six known (A1-A4, A7, PO) et-pyrone compounds were synthesized with dehydroacetate and aldehydes in tetrahydrofuran at room temperature. And their structures were determined by H-1-NMR, C-13-NMR and mass spectroscopy. In the bioscreening experiments, ten compounds (A1-A5, PO, A7-A10) exhibited antibacterial activities against Staphylococcus aureus ATCC 25923 with minimum inhibitory concentration (MIC) values of 4-512 mg/L, and nine compounds (Al-AS, PO, A7-A8, A10) exhibited antibacterial activities against Methicillin-resistant S. aureus (MRSA) ATCC 43300 with MIC values of 4-256 mg/L. Moreover, compound A10 showed the highest antibacterial activity against S. aureus ATCC 25923 and MRSA with MIC values of 4 mg/L, while the MIC values of Amoxicillin were 8 mg/I. and >256 mg/L, respectively. Two compounds (A8 and PO) exhibited antibacterial activities against Escherichia coli ATCC 25922 with MIC values of 32-512 mg/L However, only one compound (A8) exhibited significant antibacterial activity against Pseudomonas aeruginosa CVCC 3360 with MIC value of 256 mg/L. Moreover, A10 exhibited significant inhibition of proliferation in the four cell lines MCF-10, A549, A2780 and MFC, and showed stronger inhibitive activity of these four selected cell lines than cisplatin in the cytotoxic assay. Thus, this study suggests that pogostone analogues, especially A10, represented a kind of promising antibacterial and antineoplastic agents. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis and reactions of dehydracetic acid difluoroborane complex
  作者：A. V. Manaev、K. V. Tambov、V. F. Traven’

  DOI：10.1134/s107042800807018x

  日期：2008.7

  Dehydracetic acid difluoroborane complex, 3-acetyl-6-methyl-2-oxo-2H-pyran-4-yl difluoridoborate, was synthesized and characterized. The complex was involved into condensation reactions at the acetyl group with various aromatic and heterocyclic aldehydes, and with the 4-dimethylaminobenzaldehyde it reacted also at the methyl group in the position 6.
• Discovery of 3-acetyl-4-hydroxy-2-pyranone derivatives and their difluoridoborate complexes as a novel class of HIV-1 integrase Inhibitors
  作者：Kavya Ramkumar、Konstantin V. Tambov、Rambabu Gundla、Alexandr V. Manaev、Vladimir Yarovenko、Valery F. Traven、Nouri Neamati

  DOI：10.1016/j.bmc.2008.08.067

  日期：2008.10

  HIV-1 integrase (IN) has emerged as an important therapeutic target for anti-HIV drug development. Its uniqueness to the virus and its critical role in the viral life cycle makes IN suitable for selective inhibition. The recent approval of Raltegravir (MK-0518) has created a surge in interest and great optimism in the field. In our ongoing IN drug design research, we herein report the discovery of substituted analogs of 3-acetyl-4-hydroxy-2-pyranones and their difluoridoborate complexes as novel IN inhibitors. In many of these compounds, complexation with boron difluoride increased the potency and selectivity of IN inhibition. Compound 9 was most active with an IC50 value of 9 mu M and 3 mu M for 3'-processing and strand transfer inhibition, respectively. (C) 2008 Elsevier Ltd. All rights reserved.