(2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone
• 英文别名: 2,5-bis(o-methoxybenzylidene)cyclopentanone；2,5-Bis(2-methoxybenzylidene)cyclopentanone；(2E,5E)-2,5-bis[(2-methoxyphenyl)methylidene]cyclopentan-1-one
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: IOYDQEKSUHPMDT-HBKJEHTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-甲苯磺酰乙腈 、 (2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone 在 水 、 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以91%的产率得到1,2-bis(4-(2-methoxyphenyl)-1H-pyrrol-3-yl)ethane
  参考文献：
  名称：

  Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

  摘要：

  本报告介绍了一种通过二烯酮衍生物与 TosMIC 反应获得 3,3-联吡咯衍生物的简单而高效的合成策略。该反应涉及 van Leusen 的吡咯合成，然后在温和的条件下，在有水存在的情况下进行不寻常的 CâC 键裂解。

  DOI：

  10.1039/c3ob42570c
• 作为产物：
  描述：

  环戊酮 、 邻甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以85 %的产率得到(2E,5E)-2,5-bis(2-methoxybenzylidene)cyclopentanone
  参考文献：
  名称：

  铱催化2,5-二亚烷基环戊酮双不对称氢化合成手性环戊酮

  摘要：

  在此，我们报道了一种有效的铱催化双不对称氢化 2,5-二亚烷基环戊酮，以优异的收率和立体选择性提供手性 2,5-二取代环戊酮。动力学实验和对照实验的结果表明，两个C=C键是逐步加氢的，第二个立体中心是由手性催化剂和单加氢产物的手性协同控制的。氢化产物可以以克级制备并且易于衍生化。

  DOI：

  10.1021/acs.orglett.2c02656

文献信息

• New diarylpentanoids and chalcones as potential antimicrobial adjuvants
  作者：Joana Moreira、Fernando Durães、Joana Freitas-Silva、Nikoletta Szemerédi、Diana I.S.P. Resende、Eugenia Pinto、Paulo Martins da Costa、Madalena Pinto、Gabriella Spengler、Honorina Cidade、Emília Sousa

  DOI：10.1016/j.bmcl.2022.128743

  日期：2022.7

  efflux pumps (EPs) one of the most worrisome. In bacteria, EPs can also play important roles in virulence, quorum-sensing (QS) and biofilm formation. To identify new potential antimicrobial adjuvants, a library of diarylpentanoids and chalcones was synthesized and tested. These compounds presented encouraging results in potentiating the activity of antimicrobials, being diarylpentanoid 13 the most promising

  抗菌素耐药性的产生是由于几种适应机制，外排泵 (EPs) 的过度表达是最令人担忧的机制之一。在细菌中，EPs 还可以在毒力、群体感应 (QS) 和生物膜形成中发挥重要作用。为了确定新的潜在抗菌佐剂，合成并测试了二芳基戊烷和查耳酮文库。这些化合物在增强抗微生物剂的活性方面表现出令人鼓舞的结果，其中二芳基戊烷13是最有希望的。化合物9、13、16、19、22和23表现出 EP 抑制作用，主要在金黄色葡萄球菌272123中。图13、19、22和23对金黄色葡萄球菌272,123中的生物膜形成具有抑制作用，而 13 和22抑制少动鞘氨醇Ezf 10-17 和紫色色杆菌CV026对中的 QS 。总体结果表明，二芳基戊烷13和查耳酮22对所有测试的耐药机制均具有活性，表明它们具有作为抗菌佐剂的潜力。
• Ananthakrishna Nadar; Renuga, Journal of the Indian Chemical Society, 2006, vol. 83, # 12, p. 1219 - 1222
  作者：Ananthakrishna Nadar、Renuga

  DOI：——

  日期：——
• Amberlyst-15 and Amberlite-200C: Efficient catalysts for aldol and cross-aldol condensation under ultrasound irradiation
  作者：Achraf Lahyani、Manef Chtourou、Mohamed Hédi Frikha、Mahmoud Trabelsi

  DOI：10.1016/j.ultsonch.2013.01.017

  日期：2013.9

  This paper presents an improved synthesis of trans-chalcones and alpha,alpha '-bis(arylmethylidene) cycloalkanones under ultrasound irradiation in the presence of commercial acid-resins as catalysts in solvent free conditions. Several trans-chalcones and alpha,alpha '-bis(arylmethylidene) cycloalkanones were synthesized in good yields and excellent selectivity in a short reaction time. (C) 2013 Elsevier B.V. All rights reserved.
• Exploration and synthesis of curcumin analogues with improved structural stability both in vitro and in vivo as cytotoxic agents
  作者：Guang Liang、Lili Shao、Yi Wang、Chengguang Zhao、Yanhui Chu、Jian Xiao、Yu Zhao、Xiaokun Li、Shulin Yang

  DOI：10.1016/j.bmc.2008.10.044

  日期：2009.3

  Curcumin has a surprisingly wide range of chemo-preventive and chemo-therapeutic activities and is under investigation for the treatment of various human cancers. However, the clinical application of curcumin has been significantly limited by its instability and poor metabolic property. Although a number of synthetic modi. cations of curcumin have been studied intensively in order to develop a molecule with enhanced bioactivities, few synthetic studies were done for the improvement of pharmacokinetic profiles. In the present study, a series of mono-carbonyl analogues of curcumin were designed and synthesized by deleting the reactive beta-diketone moiety, which was considered to be responsible for the pharmacokinetic limitation of curcumin. The results of the in vitro stability studies and in vivo pharmacokinetic studies indicated that the stability of these mono-carbonyl analogues was greatly enhanced in vitro and their pharmacokinetic profiles were also significantly improved in vivo. Furthermore, the cytotoxic activities of mono-carbonyl analogues were evaluated in seven different tumor cell lines by MTT assay and the structure-activity relation (SAR) was discussed and concluded. The results suggest that the five-carbon linker-containing analogues of curcumin may be favorable for the curcumin-based drug development both pharmacokinetically and pharmacologically. (C) 2009 Published by Elsevier Ltd.