(E,E)-2,7-bis(4-methoxybenzylidene)cycloheptanone | 140401-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E,E)-2,7-bis(4-methoxybenzylidene)cycloheptanone
• 英文别名: 2,7-Bis(4-methoxybenzylidene)cycloheptanone；2,7-[(E,E)-bis-(4-methoxy-benzylidene)]-cycloheptanone；2,7-[(E,E)-Bis-(4-methoxy-benzyliden)]-cycloheptanon；2,7-Bis-(4-methoxy-benzylidene)-cycloheptanone；(2E,7E)-2,7-bis[(4-methoxyphenyl)methylidene]cycloheptan-1-one
• CAS: 140401-72-5
• 化学式: C₂₃H₂₄O₃
• 分子量: 348.442
• InChiKey: RZRQKHSVCIFCKH-MXWIWYRXSA-N

物化性质

• 熔点：
  95-97 °C(Solv: ethanol (64-17-5))
• 沸点：
  559.1±50.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  (E,E)-2,7-bis(4-methoxybenzylidene)cycloheptanone 在 氢氧化钾 、 sodium hydroxide 、 双氧水 作用下， 以 1,4-二氧六环 、 乙醇 、 丙酮 为溶剂， 反应 11.0h， 生成 4a-Hydroxy-9-[hydroxy-(4-methoxy-phenyl)-methyl]-4-(4-methoxy-phenyl)-1,3,4,4a,5,6,7,8-octahydro-cycloheptapyrimidine-2-thione
  参考文献：
  名称：

  一些用作镇痛、抗惊厥和抗帕金森病药物的新型取代吡啶和嘧啶衍生物的合成与反应

  摘要：

  以化合物1、2、9为起始原料，合成了一系列取代的吡啶和嘧啶衍生物作为镇痛、抗惊厥和抗帕金森病药物。1与四氯邻苯二甲酸酐缩合得到吡啶基-酰亚胺衍生物3，化合物1与1,2,4,5-苯-四羧酸二酐和1,4,5,8反应得到化合物4和5 -萘四甲酸二酐，分别。类似地，化合物 2 与之前的酸酐反应，分别得到相应的酰亚胺 6 和双酰亚胺衍生物 7 和 8。双-芳基亚甲基衍生物9用过氧化氢处理得到相应的双-环氧乙烷环烷酮衍生物10，再与硫脲缩合得到相应的硫代嘧啶衍生物11。在无水乙酸钠存在下用氯乙酸处理化合物11得到相应的噻唑并嘧啶衍生物12，其在乙酸/乙酸酐中与芳香醛缩合得到芳基亚甲基衍生物13。此外，化合物13可以通过化合物11的反应制备与氯乙酸、芳香醛和乙酸钠在乙酸和乙酸酐的混合物中反应。药理筛选表明，这些获得的化合物中有许多具有与作为参比药物的伐地昔布、卡马西平和苯扎托品相当的镇痛、抗惊厥和抗帕金森病活性。

  DOI：

  10.1002/ardp.200500982
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (E,E)-2,7-bis(4-methoxybenzylidene)cycloheptanone
  参考文献：
  名称：

  Synthesis and antitumor activity of certain new thiazolo[2,3-b]quinazoline and thiazolo[3,2-a]pyrimidine analogs

  摘要：

  A novel series of thiazolo[2,3-b]quinazoline (16-19, 25-28, and 34-37) and cyclohepta[d]thiazolo[3,2-a]pyrimidine (20-23, 29-32, and 38-41) analogs was designed and synthesized. Structure elucidation of the synthesized compounds was attained by the use of H-1 NMR, C-13 NMR, and mass spectrometry. The obtained compounds were evaluated for their in vitro antitumor activity using the National Cancer Institute's 60 cell lines' panel assay that included nine tumor subpanels, namely, leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast cancer cells. Most of the investigated compounds showed a remarkable broad-spectrum antitumor activity. Compounds 19, 28, 32, and 34 proved to be 10-, 15-, 2-, and 7-fold more active than 5-FU, with GI(50) MG-MID values of 2.4, 1.5, 11.2, and 3.1 mu M, respectively.

  DOI：

  10.1007/s00044-013-0649-6

文献信息

• Synthesis of Curcumin Analogues as Potential Antioxidant, Cancer Chemopreventive Agents
  作者：Khairia M. Youssef、Magda A. El-Sherbeny、Faiza S. El-Shafie、Hassan A. Farag、Omar A. Al-Deeb、Sit Albanat A. Awadalla

  DOI：10.1002/ardp.200300763

  日期：2004.1

  New series of 3, 5‐bis(substituted benzylidene)‐4‐piperidones, 2, 7‐bis(substituted benzylidene)cycloheptanones, 1, 5‐bis(substituted phenyl)‐1, 4‐pentadien‐3‐ones, 1, 7‐bis(substituted phenyl)‐1, 6‐heptadien‐3, 5‐diones, 1, 1‐bis(substituted cinnamoyl)‐cyclopentanes, and 1, 1‐bis(substituted cinnamoyl)cyclohexanes have been synthesized and tested for their antioxidant activity. Among the tested compounds

  新系列 3, 5-双（取代苯亚甲基）-4-哌啶酮，2, 7-双（取代苯亚甲基）环庚酮，1, 5-双（取代苯基）-1，4-戊二烯-3-，1， 7-双（取代苯基）-1, 6-庚二烯-3, 5-二酮，1, 1-双（取代肉桂酰基）-环戊烷和1, 1-双（取代肉桂酰基）环己烷已合成并测试其性能抗氧化活性。在被测化合物中，化合物II4、II9、II10、II11、V1和V4表现出较高的自由基清除活性，%抑制率分别为90.71、91.24、96.91、94.26、99.23和99.85%。此外，化合物 V1 是外周多核中性粒细胞 (PMN) 的安全成员，存活率为 91%。报告了详细的合成、光谱和生物学数据。
• Synthesis and biological evaluation of new curcumin derivatives as antioxidant and antitumor agents
  作者：Said M. Bayomi、Hassan A. El-Kashef、Mahmoud B. El-Ashmawy、Magda N. A. Nasr、Magda A. El-Sherbeny、Farid A. Badria、Laila A. Abou-zeid、Mariam A. Ghaly、Naglaa I. Abdel-Aziz

  DOI：10.1007/s00044-012-0116-9

  日期：2013.3

  Twenty-four new compounds were prepared, taking curcumin as a lead, in order to explore their antioxidant and antitumor properties. The capacities of these derivatives to scavenge the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) radical cation (ABTS(.+)), and to protect human red blood cells (RBCs) from oxidative haemolysis were investigated. In addition, the percentage viability of different cell lines (Hep G2, WI38, VERO and MCF-7) was tested. The result of the antitumor testing was generally in accordance with those of the antioxidant assays. Compounds which bear o-methoxy substitution to the 4-hydroxy function in the phenyl ring (7g, 5g and 3g) exhibited significantly higher ABTS(.+)-scavenging, antihaemolysis, and antitumor activities than other derivatives. In addition, molecular modelling studies were carried out for biologically active and inactive compounds, to study the structure-activity relationship, with the aim to elucidate which portions of the molecules are critical for the antioxidant and antitumor activity.
• A facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations
  作者：Nimisha Singh、Jyoti Pandey、Amit Yadav、Vinita Chaturvedi、Shalini Bhatnagar、Anil N. Gaikwad、Sudhir Kumar Sinha、Awaneet Kumar、P.K. Shukla、Rama P. Tripathi

  DOI：10.1016/j.ejmech.2008.09.026

  日期：2009.4

  An economical and facile synthesis of alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanones was achieved by the reaction of cycloalkanones with different aromatic aldehydes using ethanolic KOH in good yields. Few of the selected compounds were reduced with NaBH4 to the respective alpha,alpha'-(EE)-bis(benzylidene)-cycloalkanols. All these compounds and our earlier synthesized cyclohexyl phenyl methanols were evaluated for their antitubercular, antifungal and antibacterial activities. Several compounds displayed moderate antitubercular activity with MIC = 12.5-1.56 mu g/mL. However, none of the compounds displayed any significant antifungal activity. (c) 2008 Elsevier Masson SAS. All rights reserved.
• Matsunaga, Y.; Miyamoto, S., Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1993, vol. 237, p. 311 - 318
  作者：Matsunaga, Y.、Miyamoto, S.

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• Mattu; Manca, Annali di Chimica, 1956, vol. 46, p. 1173,1177,1182
  作者：Mattu、Manca

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