2,6-bis(4-hydroxybenzylidene)cyclohexanone | 18977-35-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 2,6-bis(4-hydroxybenzylidene)cyclohexanone
• 英文别名: 2,6-bis(4-hydroxyphenylmethylene)cyclohexanone；2,6-bis (4-hydroxybenzylidene)cyclohexanone；2,6-bis(4-hydroxybenzylidene)-cyclohexanone；2,6-bis-(4-hydroxybenzylidene)cyclohexanone；2,6-di(4-hydroxybenzylidene)cyclohexanone；2,6-bis-(4-hydroxy-benzylidene)-cyclohexanone；2,6-bis[(4-hydroxyphenyl)methylidene]cyclohexan-1-one
• CAS: 18977-35-0
• 化学式: C₂₀H₁₈O₃
• 分子量: 306.361
• InChiKey: MGXGEFQCJBBKND-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C
• 沸点：
  555.7±50.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis(4-hydroxybenzylidene)cyclohexanone 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 0.02h， 以65%的产率得到4-[7-(4-hydroxybenzylidene)-3,3a,4,5,6,7-hexahydro-2H-indazol-3-yl]phenol
  参考文献：
  名称：

  Microwave-Assisted In Situ Cyclization of Curcumin Derivatives as Dominant Chemotherapeutic Agents for Leukemia and Colon Cancer

  摘要：

  DOI：

  10.1134/s1070428022030150
• 作为产物：
  描述：

  2,6-Bis-[4-(tetrahydro-pyran-2-yloxy)-benzylidene]-cyclohexanone 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 2,6-bis(4-hydroxybenzylidene)cyclohexanone
  参考文献：
  名称：

  Synthesis, crystal structure and anti-inflammatory properties of curcumin analogues

  摘要：

  Curcuminoids have been reported to possess multifunctional bioactivities, especially the ability to inhibit proinflammatory induction. Since it has been suggested that the seven-carbon beta-diketone linker in curcumin is responsible for its instability, nine mono-carbonyl five-carbon linker containing analogues were designed and synthesized. Their bioactivity against lipopolysaccharide-induced TNF-alpha amd IL-6 secretion was evaluated by using mouse J774.1 macrophages. The results showed that the 3'-methoxyl plays an important role in bioactivity and cyclohexanone containing analogues exhibited stronger inflammatory inhibition than acetone and cyclopentanone analogues. Subsequently the most active analogue 3c was determined using single-crystal X-ray diffraction. X-ray analysis and comparison with curcumin reveals that the presence of cyclohexanone in 3c, which remotely resembles the 6-membered ring in the enol tautomer in curcumin, may play an important role in the bioactivity. It is suggested that five-carbon linker analogues containing a cyclohexane ring which are synthetically assessable may be pharmacologically important. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.01.031

文献信息

• Effects of diarylpentanoid analogues of curcumin on chemiluminescence and chemotactic activities of phagocytes
  作者：Ibrahim Jantan、Syed Nasir Abbas Bukhari、Nordin Haji Lajis、Faridah Abas、Lam Kok Wai、Malina Jasamai

  DOI：10.1111/j.2042-7158.2011.01423.x

  日期：2012.2.6

  A series of 43 curcumin diarylpentanoid analogues were synthesized and evaluated for their inhibitory effects on the chemiluminescence and chemotactic activity of phagocytes in vitro.

  The effects of the compounds on the respiratory burst of human whole blood and isolated human polymorphonuclear leukocytes (PMNs) were evaluated using a luminol-based chemiluminescence assay and their effect on chemotactic migration of PMNs was investigated using the Boyden chamber technique.

  Compounds 6, 17, 25 and 30 exhibited significant inhibitory activity on the oxidative burst of PMNs. The presence of methoxy groups at positions 2 and 5, and methoxylation and fluorination at positions 4 and 2 of both phenyl rings, respectively, may contribute significantly to their reactive oxygen species inhibition activity. Compounds 7, 17, 18, 24 and 32 showed strong inhibition of the chemotaxis migration of PMNs. Chlorination at various positions of both phenyl rings of cyclohexanone diarylpentanoid resulted in compounds with potent inhibitory effects on PMN migration.

  The results suggest that some of these diarylpentanoid analogues are able to modulate the innate immune response of phagocytes at different steps, emphasizing their potential as a source of new immunomodulatory agents.

  摘要 目的 合成了一系列43个姜黄素二芳基戊酮类似物，并评估它们对体外吞噬细胞化学发光和趋化活性的抑制作用。 方法 使用基于流明的化学发光测定法评估化合物对人全血和分离的人多形核白细胞（PMNs）呼吸爆发的影响，并利用Boyden室技术研究它们对PMNs趋化迁移的影响。 主要发现 化合物6、17、25和30在PMNs的氧化爆发上表现出显著的抑制活性。在两个苯环的2和5位置有甲氧基基团，以及在4和2位置分别有甲氧化和氟化基团的存在，可能会显著促进它们对活性氧化物种的抑制活性。化合物7、17、18、24和32显示出对PMNs趋化迁移的强烈抑制作用。在环己酮二芳基戊酮类似物的两个苯环的不同位置进行氯化，导致化合物对PMN迁移具有强效抑制作用。 结论 结果表明，这些二芳基戊酮类似物中的一些能够调节吞噬细胞的先天免疫反应的不同步骤，强调它们作为新的免疫调节剂来源的潜力。
• Synthesis and biological evaluation of asymmetrical diarylpentanoids as antiinflammatory, anti-α-glucosidase, and antioxidant agents
  作者：Sze Wei Leong、Tahani Awin、Siti Munirah Mohd Faudzi、M. Maulidiani、Khozirah Shaari、Faridah Abas

  DOI：10.1007/s00044-019-02430-5

  日期：2019.11

  poor antioxidant potential of desired diarylpentanoid structure. Structure-activity relationship (SAR) study disclosed that the existence of meta-hydroxyphenyl and bromo groups is crucial for antiinflammatory and anti-α-glucosidase activities, respectively. Molecular docking study showed that bromo moiety could form additional hydrophobic contacts with α-glucosidase, thereby increased the inhibition

  新的一系列七（1，3，6，7，10，12，和13）和6个（2，4，5，8，9，和11已知diarylpentanoid类似物）被合成并评估它们的一氧化氮（NO ）和α-葡萄糖苷酶的抑制活性及其抗氧化能力。九种化合物（2，3，4，5，6，8，11，12，和发现13）具有与姜黄素相当的活性（IC 50 ＝13.0μM），其中化合物8显示出最强的NO抑制活性，IC 50值为17.5μM。同时，四种化合物（1，7，12，和13被发现），以具有比，姜黄素（30.9μM）的更好的α葡萄糖苷酶抑制活性，与IC 50值范围从19.4至24.9 µM。另一方面，没有一种合成的化合物具有比姜黄素更好的清除DPPH的活性，表明所需的二芳基戊烷结构的抗氧化能力较差。结构-活性关系（SAR）研究表明，间位羟基苯基和溴基的存在分别对抗炎和抗α-葡萄糖苷酶活性至关重要。分子对接研究表明，溴部分可以与α-葡萄糖苷酶形成额
• Synthesis and antioxidant properties of enone core based dendrimers with carbazole as surface group
  作者：Perumal Rajakumar、Nagarathinam Venkatesan、Karuppannan Sekar、Subramani Nagaraj、Ramasamy Rengasamy

  DOI：10.1016/j.ejmech.2009.11.051

  日期：2010.3

  Synthesis of enone core based dendrimers with carbazole as surface group has been achieved. All the synthesized dendrimers showed excellent antioxidant behavior with commercially available 1,1-diphenyl-2-picryl hydrazyl (DPPH).

  已经实现了以咔唑为表面基团的基于烯酮核的树枝状大分子的合成。所有合成的树枝状聚合物均具有可商购的1,1-二苯基-2-吡啶基肼基（DPPH）的优异抗氧化性能。
• Synthesis and biological evaluation of new curcumin analogues as antioxidant and antitumor agents: Molecular modeling study
  作者：Said M. Bayomi、Hassan A. El-Kashef、Mahmoud B. El-Ashmawy、Magda N.A. Nasr、Magda A. El-Sherbeny、Naglaa I. Abdel-Aziz、Magda A.-A. El-Sayed、Ghada M. Suddek、Shahenda M. El-Messery、Mariam A. Ghaly

  DOI：10.1016/j.ejmech.2015.07.014

  日期：2015.8

  New curcumin analogues have been synthesized and their antioxidant activities were investigated by measuring their free radical scavenging capacities. The in vitro and in vivo antitumor activities of the synthesized compounds on Ehrlich ascites carcinoma (EAC) cell line were evaluated. 4-(4-Chlorophenyl)-2-(5-ethyl-7-(4-methoxybenzylidene)-3-(4-methoxyphenyl)-3,3a,4,5,6,7-hexahydro-2H-pyrazolo[4,3-c]

  已经合成了新的姜黄素类似物，并通过测量其清除自由基的能力来研究其抗氧化活性。在体外和体内对艾氏腹水癌的合成的化合物的抗肿瘤活性（EAC）细胞系进行了评价。4-（4-氯苯基）-2-（5-乙基-7-（4-甲氧基亚苄基）-3-（4-甲氧基苯基）-3,3a，4,5,6,7-六氢-2 H-吡唑并[ 4,3- ç ]吡啶-2-基）噻唑7H表明在兼具优异的抗肿瘤活性在体外和体内研究中更重要的是试验化合物和参考药，顺铂。进行了不同的分子建模研究，其中化合物的对接端粒酶活性位点7h提示其可以通过抑制端粒酶发挥其抗肿瘤作用。
• A Convenient Synthesis of α,α’-Bis(substituted benzylidene)cycloalkanones Catalyzed by Y(TFA)₃
  作者：Genxiang Luo、Runxia Wang、Chunsheng Liu

  DOI：10.1080/15533174.2011.613882

  日期：2012.4.1

  Aromatic aldehydes undergo crossed aldol condensation with cyclic ketones in the presence of Y(TFA)3 under solvent-free conditions to afford the corresponding α,α’-bis(substituted benzylidene)cycloalkanones in satisfactory yields. Furthermore, the catalyst can be recovered conveniently and reused several times in the reaction with comparable yields.

  在无溶剂条件下，在Y（TFA）3的存在下，芳香醛与环状酮进行交叉醇醛缩合，以令人满意的产率得到相应的α，α'-双（取代的亚苄基）环烷酮。此外，可以方便地回收催化剂，并以相当的收率将其在反应中多次使用。