(3E,5E)-3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one | 877608-37-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3E,5E)-3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one
• 英文别名: 3,5-Bis-(4-methoxy-benzylidene)-tetrahydro-pyran-4-one；(3E,5E)-3,5-bis[(4-methoxyphenyl)methylidene]oxan-4-one
• CAS: 877608-37-2
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: ADOXGRPZVZXSKQ-JYFOCSDGSA-N

物化性质

• 熔点：
  170-172 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  565.4±50.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3E,5E)-3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one 以33%的产率得到
  参考文献：
  名称：

  ROYNYAK G.; SHU V.; SHWARTZ J., J. HETEROCYCL. CHEM., 1981, 18, NO 2, 327-331

  摘要：

  DOI：
• 作为产物：
  描述：

  四氢吡喃酮 、 4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 以79%的产率得到(3E,5E)-3,5-bis(4-methoxybenzylidene)-tetrahydropyran-4-one
  参考文献：
  名称：

  具有 p53 通路潜在激活作用的二芳基戊烷：结合计算机筛选研究、合成和生物活性评估

  摘要：

  计算机对二芳基戊烷库的研究使我们发现了潜在的新 MDM2/X 配体。随后合成了符合药物相似性和 ADMET 预测特性的最佳对接分数的二芳基戊烷类化合物，并评估了它们对结肠癌 HCT116 和成纤维细胞 HFF-1 细胞的抗增殖活性。对 p53-MDM2/X 相互作用的影响通过基于酵母的试验评估了化合物在 HCT116 细胞中显示出有效的抗增殖活性和在正常细胞中的低毒性，从而确定了一种潜在的双重抑制剂。此外，在不存在 p53 和表达突变 p53 形式的 MDA-MB-231 细胞中，其抗增殖作用显着降低。该化合物的抗增殖作用与诱导细胞周期停滞、细胞凋亡、PARP 在 HCT116 细胞中切割并增加 p53 及其转录靶标 p21 和 PUMA。通过对接研究预测了参与抑制 p53-MDM2/X 相互作用的对接姿势和残基。

  DOI：

  10.1002/cmdc.202100337

文献信息

• A highly efficient method for solvent-free synthesis of bisarylmethylidenes of pyranones and thiopyranones
  作者：M. Saeed Abaee、Mohammad M. Mojtahedi、M. Mehdi Zahedi、Roholah Sharifi

  DOI：10.1002/hc.20252

  日期：——

  A remarkable efficient double crossed aldol condensation of heterocyclic ketones with a variety of aromatic aldehydes is described at room temperature in the presence of magnesium bromide ethyl etherate, triethylamine, and methanol under solvent-free conditions. Excellent yields of 3,5-bisarylmethylidenes of pyranones and thiopyranones are achieved in a facile one-pot general procedure. © 2007 Wiley

  在室温下，在溴化镁乙基醚合物、三乙胺和甲醇的存在下，在无溶剂条件下，描述了杂环酮与各种芳香醛的显着有效的双交叉羟醛缩合反应。吡喃酮和噻喃酮的 3,5-二芳基亚甲基的优异产率是通过简单的一锅通用程序实现的。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:44–49, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20252
• New MD2 inhibitors derived from curcumin with improved anti-inflammatory activity
  作者：Yali Zhang、Zhiguo Liu、Jianzhang Wu、Bin Bai、Hongjin Chen、Zhongxiang Xiao、Lingfeng Chen、Yunjie Zhao、Hazel Lum、Yi Wang、Hong Zhang、Guang Liang

  DOI：10.1016/j.ejmech.2018.02.008

  日期：2018.3

  An overactive Toll-like receptor (TLR) signaling complex is a significant pathogenic factor of acute and chronic inflammatory diseases. The natural product curcumin is reported to inhibit the TLR4 co-receptor, MD2 (myeloid differentiation protein 2), but its low in vivo bioavailability limits its therapeutic potential. We developed new curcumin analogs (MACs) with removal of the beta-diketone moiety and substituted residues in benzene rings, and identify these as potential MD2 inhibitors with improved inhibition potency and stability over that of curcumin. Specifically, MAC 17 and 28 showed the highest anti-inflammatory activity, with >90% inhibition of LPS-stimulated cytokine secretion from macrophages, and protected against LPS-induced acute lung injury and sepsis. The MACs inhibited the TLR4-MD2 signaling complex through competition with LPS for binding on MD2, likely at Arg(90). Our findings indicated that MAC 17 and 28 are promising candidates for future development as therapeutic drugs for inflammatory diseases with an endotoxin etiology. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Synthesis and evaluation of curcumin-related compounds for anticancer activity
  作者：Xingchuan Wei、Zhi-Yun Du、Xi Zheng、Xiao-Xing Cui、Allan H. Conney、Kun Zhang

  DOI：10.1016/j.ejmech.2012.04.005

  日期：2012.7

  Sixty-one curcumin-related compounds were synthesized and evaluated for their anticancer activity toward cultured prostate cancer PC-3 cells, pancreas cancer Panc-1 cells and colon cancer HT-29 cells. Inhibitory effects of these compounds on the growth of PC-3. Panc-1 and HT-29 cells were determined by the MTT assay. Compounds E10, F10, FN1 and FN2 exhibited exceptionally potent inhibitory effects on the growth of cultured PC-3, Panc-1 and HT-29 cells. The IC50 for these compounds was lower than 1 mu M in all three cell lines. E10 was 72-, 46- and 117-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. F10 was 69-, 34- and 72-fold more active than curcumin for inhibiting the growth of PC-3, Panc-1 and HT-29 cells, respectively. FN1 and FN2 had about the same inhibitory effect as E10 and F10 toward Panc-1 cells but were less active than E10 and F10 toward PC-3 and HT-29 cells. The active compounds were potent stimulators of apoptosis. The present study indicates that E10, F10, FN1 and FN2 may have useful anticancer activity. (C) 2012 Elsevier Masson SAS. All rights reserved.
• The synthesis of highly functionalised pyridines using Ghosez-type reactions of dihydropyrazoles
  作者：Federica Catti、Paula S. Kiuru、Alexandra M.Z. Slawin、Nicholas J. Westwood

  DOI：10.1016/j.tet.2008.07.063

  日期：2008.9

  The aza-Diels-Alder reaction of alpha beta-unsaturated hydrazones is a general methodology that has been applied both to the synthesis of natural products and to the development of multicomponent reactions. Trends have emerged as to the effect of substituents on the efficiency of this reaction with substituents at the C2 and C4-positions of the aza-diene in general suppressing the reaction. Here we report that 4,5-dihydropyrazoles can function as substrates in this process despite the presence of substituents at both of these positions. A one pot, four chemical step sequence carried out under standard thermal or microwave conditions results in the formation of the corresponding pyridine-containing compounds. The scope of the reaction is explored and additional insights into the proposed mechanism of this reaction are provided. (C) 2008 Elsevier Ltd. All rights reserved.