27060-66-8Relevant articles and documents
Green, rapid, and highly efficient syntheses of α,α′-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 MoCl5
Bakhshi, Reza,Zeynizadeh, Behzad,Mousavi, Hossein
, p. 623 - 637 (2019/08/26)
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 a very inexpensive and available catalyst, low catalyst loading, short reaction times, high yields of the pure products, no harmful by-products, easy workup, and also the applicability of microwave irradiation as a clean source of energy. Furthermore, a gram-scale reaction was successfully conducted, proving the scalability of this current Claisen–Schmidt condensation reaction.
Diarylidenecyclopentanone derivatives as potent anti-inflammatory and anticancer agents
Tamang, Nitesh,Ramamoorthy, Gayathri,Joshi, Mayank,Choudury, Angshuman Roy,B, Siva Kumar,Golakoti, Nageswara Rao,Doble, Mukesh
, p. 1579 - 1589 (2020/07/02)
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 for their anti-inflammatory as well as cytotoxicity properties. Compound Is is found to have the highest anti-inflammatory activity (93.67%) by inhibiting PGE2 (prostaglandin E2) production. Three of the DACPs (Io, It, and Iu) were observed to have high cytotoxicity with IC50 value of 8.73 ± 0.06 μM (Io), 12.55 ± 0.31 μM (It), and 11.47 ± 0.15 μM (Iu) against HeLa cells. Further staining and cell cycle analysis was done using these three DACPs to understand their mechanism of action. The G0/G1 phase was observed to be the longest one through which the cells undergo apoptosis.
Synthesis and anti-tumor activity of EF24 analogues as IKKβ inhibitors
Jin, Rong,Chen, Qiuxiang,Yao, Song,Bai, Encheng,Fu, Weitao,Wang, Ledan,Wang, Jiabing,Du, Xiaojing,Wei, Tao,Xu, Haineng,Jiang, Chengxi,Qiu, Peihong,Wu, Jianzhang,Li, Wulan,Liang, Guang
, p. 218 - 228 (2018/01/26)
EF24 is an IKKβ inhibitor (IC50: 72 μM) containing various anti-tumor activities. In this study, a series of EF24 analogs targeting IKKβ were designed and synthesized. Several IKKβ inhibitors with better activities than EF24 were screened out and B3 showed best IKKβ inhibitory (IC50: 6.6 μM). Molecular docking and dynamic simulation experiments further confirmed this inhibitory effect. B3 obviously suppressed the viability of Hela229, A549, SGC-7901 and MGC-803 cells. Then, in SGC-7901 and MGC-803 cells, B3 blocked the NF-κB signal pathway by inhibiting IKKβ phosphorylation, and followed arrested the cell cycle at G2/M phase by suppressing the Cyclin B1 and Cdc2 p34 expression, induced the cell apoptosis by down-regulating Bcl-2 protein and up-regulating cleaved-caspase3. Moreover, B3 significantly reduced tumor growth and suppressed the IKKβ-NF-κB signal pathway in SGC-7901 xenograft model. In total, this study present a potential IKKβ inhibitor as anti-tumor precursor.
Sulfonated PEG-intercalated montmorillonite [(Mt/PEG)-SO3H] as efficient and ecofriendly nanocatalyst for synthesis of α,α′-bis(substituted benzylidene)cycloalkanones
Dalil Heirati, Seyedeh Zahra,Shirini, Farhad,Fallah Shojaei, Abdollah
, p. 6167 - 6186 (2017/10/05)
(Montmorillonite/PEG)-SO3H nanocomposite was successfully prepared for the first time and introduced as a solid acid nanocatalyst. Initially, polyethylene glycol (PEG) polymeric chains were intercalated into interlayer spaces of montmorillonite. The resulting Mt/PEG nanocomposite with good mechanical and thermal stability was chosen as a useful clay mineral/polymer support for further modification with chlorosulfonic acid. Structural characterization of (Mt/PEG)-SO3H was carried out using X-ray diffraction (XRD) analysis, Brunauer–Emmett–Teller (BET) measurements, Barrett–Joyner–Halenda (BJH) analysis, scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and Fourier-transform infrared (FT-IR) spectroscopy. The results showed that PEG chains were intercalated into the clay mineral layers and that the Mt/PEG nanocomposite was successfully sulfonated. (Mt/PEG)-SO3H nanocomposite exhibited high specific surface area and good stability up to around 150?°C, showing excellent potential for application as a recyclable nanocatalyst. (Mt/PEG)-SO3H was used as an efficient and ecofriendly solid acid nanocatalyst for preparation of α,α′-bis(substituted benzylidene)cycloalkanones under solvent-free conditions, leading to many interesting findings. The excellent conversion values confirm that the catalyst has strong and sufficient acidic sites, which are responsible for its catalytic performance. The reaction under mild conditions (room temperature) with excellent yield, catalyst recyclability (up to ten times), and simple work-up procedure represent useful advantages of (Mt/PEG)-SO3H for catalysis. Moreover, the reaction could be scaled up to 10 and 15?mmol scales.
Solvent-free catalytic preparation of 2,6-dibenzylidenecycloalkanones using 2-hydroxyethylammonium acetate ionic liquid as catalyst
Kang, Li Q.,Cai, Yue Q.,Wang, Hao,Li, Li H.
, p. 337 - 340 (2014/03/21)
Various 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: [Figure not available: see fulltext.]
Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway
Leow, Pay-Chin,Bahety, Priti,Boon, Choon Pei,Lee, Chong Yew,Tan, Kheng Lin,Yang, Tianming,Ee, Pui-Lai Rachel
, p. 67 - 80 (2014/01/06)
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/β-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 β-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 β-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 1a (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.
Design and synthesis of dimethylaminomethyl-substituted curcumin derivatives/analogues: Potent antitumor and antioxidant activity, improved stability and aqueous solubility compared with curcumin
Fang, Xubin,Fang, Lei,Gou, Shaohua,Cheng, Lin
supporting information, p. 1297 - 1301 (2013/03/28)
A series of dimethylaminomethyl-substituted curcumin derivatives/analogues were designed and synthesized. All compounds effectively inhibited HepG2, SGC-7901, A549 and HCT-116 tumor cell lines proliferation in MTT assay. Particularly, compounds 2a and 3d showed much better activity than curcumin against all of the four tumor cell lines. Antioxidant test revealed that these compounds had higher free radical scavenging activity than curcumin towards both DPPH and galvinoxyl radicals. Furthermore, the aqueous solubility and stability of the target compounds were also significantly improved compared with curcumin.
A convenient synthesis of α,α'-bis(substituted benzylidene)cycloalkanones Catalyzed by Y(TFA) 3
Luo, Genxiang,Wang, Runxia,Liu, Chunsheng
experimental part, p. 554 - 556 (2012/06/30)
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. Copyright Taylor & Francis Group, LLC.
Synthesis and evaluation of DPPH and anti-inflammatory activities of 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives
Lam, Kok Wai,Tham, Chau Ling,Liew, Choi Yi,Syahida, Ahmad,Rahman, Mohd. Basyaruddin Abdul,Israf, Daud A.,Lajis, Nordin H.
experimental part, p. 333 - 344 (2012/08/28)
A series of thirty three 2,6-bisbenzylidenecyclohexanone and pyrazoline derivatives were synthesized and evaluated for inhibitory activities on IFN-γ/LPS-activated RAW 264.7 cells and DPPH radical scavenging activity. Compounds 8, 9, and 11a demonstrated significant NO inhibitory activity as compared to L-NAME and curcumin with IC50 values of 6.68 ± 0.16, 6.09 ± 0.46, and 6.84 ± 0.12 μM, respectively. Apparently the suppression upon NO secretion was not due to cell death since the active compounds did not reduce the cell viability in close proximity to the IC 50 of NO inhibition. Overall, incorporation of pyrazoline ring as part of the linker chain improved cell viability compared to the 2,6-bisbenzylidenecyclohexanone derivatives. Meanwhile, compound 11 (IC 50 = 13.27 ± 1.78 μM) bearing ortho hydroxyls on the aromatic rings recorded the highest radical scavenging activity as compared with quercetin (IC50 = 21.46 ± 0.85 μM). Springer Science+Business Media, LLC 2010.
Synthesis, crystal structure and anti-inflammatory properties of curcumin analogues
Liang, Guang,Yang, Shulin,Zhou, Huiping,Shao, Lili,Huang, Kexin,Xiao, Jian,Huang, Zhifeng,Li, Xiaokun
experimental part, p. 915 - 919 (2009/09/08)
Curcuminoids have been reported to possess multifunctional bioactivities, especially the ability to inhibit proinflammatory induction. Since it has been suggested that the seven-carbon β-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-α 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.
