2,5-bis(4-hydroxybenzylidene)-cyclopentanone | 27060-66-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,5-bis(4-hydroxybenzylidene)-cyclopentanone
• 英文别名: 2,5-bis(4-hydroxybenzylidene)cyclopentanone；BBCP；2,5-bis-(4-hydroxy-benzylidene)-cyclopentanone；2,5-Bis-(4-hydroxy-benzyliden)-cyclopentanon；2,5-Bis-<4-hydroxy-benzyliden>-cyclopentanon；Cyclopentanone, 2,5-bis[(4-hydroxyphenyl)methylene]-；2,5-bis[(4-hydroxyphenyl)methylidene]cyclopentan-1-one
• CAS: 27060-66-8
• 化学式: C₁₉H₁₆O₃
• mdl: MFCD00601653
• 分子量: 292.334
• InChiKey: YSEMBYWAAKOCKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2,5-bis(4-hydroxybenzylidene)-cyclopentanone 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成
  参考文献：
  名称：

  以吩噻嗪为表面单元的三唑桥接树枝状聚合物的合成和光物理研究

  摘要：

  描述了一些具有烯酮和 S-(-)-BINOL 核的新型 1, 2, 3-三唑桥接吩噻嗪树枝状聚合物的合成和光物理性质。

  DOI：

  10.3998/ark.5550190.p008.375
• 作为产物：
  描述：

  4-(四氢-吡喃-2-基氧基)-苯甲醛 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 2,5-bis(4-hydroxybenzylidene)-cyclopentanone
  参考文献：
  名称：

  Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway

  摘要：

  Osteosarcoma is a primary bone malignancy with aggressive metastatic potential and poor prognosis rates. In our earlier work we have investigated the therapeutic potential of curcumin as an anti-invasive agent in osteosarcoma by its ability to regulate the Wnt/beta-catenin signaling pathway. However, the clinical use of curcumin is limited owing to its low potency and poor pharmacokinetic profile. In this study, an attempt was made to achieve more potent Wnt inhibitory activity in osteosarcoma cells by carrying out synthetic chemical modifications of curcumin. We synthesized a total of five series consisting of 43 curcumin analogs and screened in HEK293T cells for inhibition of beta-catenin transcriptional activity. Six promising analogs, which were 6.5- to 60-fold more potent than curcumin in inhibiting Wnt activity, were further assessed for their anti-invasive activity and Wnt inhibitory mechanisms. Western blot analysis showed disruption of beta-catenin protein nuclear translocation following treatment with analogs 2f, 3c and 4f. Using transwell assays, we also found that these compounds were more potent than la (curcumin) in impeding the invasion of osteosarcoma cells, possibly through suppressing MMP-9 activity. Structure-activity-relationship studies revealed that Wnt inhibitory effects could be enhanced by shortening and restraining the flexibility of the 7-carbon linker moiety connecting the terminal aromatic rings of curcumin and substituting both rings with appropriate substituents. Our results demonstrate that the synthesized curcumin analogs are more potent Wnt inhibitors in osteosarcoma cell lines as compared to parental curcumin and are good lead compounds for further development. Future in vivo tests with these compounds will define their therapeutic potentials as promising drug candidates for clinical treatment of osteosarcoma. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.073

文献信息

• Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst
  作者：Li Q. Kang、Yue Q. Cai、Hao Wang、Li H. Li

  DOI：10.1007/s00706-013-1082-8

  日期：2014.2

  AbstractVarious 2,6-dibenzylidenecycloalkanones were readily prepared in a condensation reaction catalyzed by 2-hydroxyethylammonium acetate ionic liquid under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, lack of solvent, simplicity of performance, and low cost. Graphical abstract

  摘要在无溶剂条件下，由乙酸2-羟乙基铵离子液体催化的缩合反应中，很容易制得各种2,6-二亚苄基环烷酮。本方法的主要优点是产率高，反应时间短，溶剂少，性能简单和成本低。 图形概要
• 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。
• Green, rapid, and highly efficient syntheses of <i>α</i> , <i>α′</i> ‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones as potentially biologic compounds via solvent‐free microwave‐assisted Claisen–Schmidt condensation catalyzed by MoCl ₅
  作者：Reza Bakhshi、Behzad Zeynizadeh、Hossein Mousavi

  DOI：10.1002/jccs.201900081

  日期：2020.4

  A new, green, and highly efficient protocol for the expeditious preparation of some α,α′‐bis[(aryl or allyl)idene]cycloalkanones and 2‐[(aryl or allyl)idene]‐1‐indanones via a simple microwave‐assisted Claisen–Schmidt condensation reaction catalyzed by MoCl5 was successfully developed. Outstanding features of the current methodology include the use of solvent‐free conditions, simple operation, use of

  一种新的，绿色的，高效的方法，可通过简单的微波快速制备某些α，α'-双[（芳基或烯丙基）亚烷基]环烷酮和2 [[（芳基或烯丙基）亚烷基] -1-茚满酮MoCl 5催化的克莱森-施密特辅助缩合反应开发成功。当前方法的突出特点包括：使用无溶剂条件，操作简单，使用非常便宜和可用的催化剂，催化剂用量低，反应时间短，纯产物的收率高，无有害副产物，易于后处理以及微波辐射作为清洁能源的适用性。此外，成功进行了克级反应，证明了当前Claisen-Schmidt缩合反应的可扩展性。
• Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents
  作者：Nitesh Tamang、Gayathri Ramamoorthy、Mayank Joshi、Angshuman Roy Choudury、Siva Kumar B.、Nageswara Rao Golakoti、Mukesh Doble

  DOI：10.1007/s00044-020-02578-5

  日期：2020.9

  Cancer is often associated with chronic inflammation. In order to develop potential anticancer and anti-inflammatory agents a series of 26 diarylidenecyclopentanones (DACPs) Ia–Iv, II, III, and IV were synthesized. Five of the synthesized DACPs are novel (Ih, Ij, Ik, Is, and Iv), derivative Iv was characterized using single-crystal X-ray diffraction study. All the synthesized derivatives were tested

  癌症通常与慢性炎症有关。为了开发潜在的抗癌药和抗炎药，合成了26种二芳基亚环戊酮（DACP）Ia-Iv，II，III和IV。合成的DACP中有五个是新颖的（Ih，Ij，Ik，Is和Iv），使用单晶X射线衍射研究表征了衍生物Iv。测试所有合成的衍生物的抗炎和细胞毒性。复合是通过抑制PGE 2（前列腺素E 2）的产生，发现其具有最高的抗炎活性（93.67％）。观察到三个DACP s（Io，It和Iu）具有很高的细胞毒性，对HeLa的IC 50值分别为8.73±0.06 µM（Io），12.55±0.31 µM（It）和11.47±0.15 µM（Iu）细胞。使用这三个DACP进行了进一步的染色和细胞周期分析，以了解其作用机理。观察到G 0 / G 1相是细胞经历凋亡的最长相。
• The Syntheses of New Cyclopenta[d][1,3]thiazine Derivatives and Their Use as Antimicrobial Agents
  作者：M. S. A. El-Gaby、N. M. Saleh、J. A. Micky、Y. A. Ammar、H. S. A. Mohamed

  DOI：10.1080/10426500500366947

  日期：2006.6.1

  Cyclopentanone (1) was exploited as a starting material for the syntheses of hitherto unknown cyclopenta[d][1,3]thiazine derivatives.

  环戊酮 (1) 被用作合成迄今为止未知的环戊二烯 [d][1,3] 噻嗪衍生物的起始材料。