- In vitro antioxidant activity and scavenging effects of some synthesized 4-Aminochalcones
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A new series of substituted 4'-aminochalcones were synthesized by Claisen-Schmidt condensation of 4-aminoacetophenone with various substituted aromatic/heteroaromatic aldehydes. The antioxidant activity for all these compounds were studied on various reac
- Prasad, Y.Rajendra,Rani, V. Jhansi,Rao, A. Srinivasa
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- Design and synthesis of new coumarin–chalcone/NO hybrids of potential biological activity
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Abstract: This study aims at investigating a synthesis approach based on molecular hybridization strategy through grafting an nitric oxide-releasing moiety, oxime, to coumarin–chalcone hybrids. In vitro anti-proliferative activity of some of the prepared compounds showed moderate activity (growth inhibition values = 45.85, 40.86, 39.25 for compound 8a against leukemia, Central Nervous system and breast cancer cells, respectively). Also, IC50 = 9.62 and 14.40 for compounds 8h and 8f, respectively against breast Michigan Cancer Foundation-7 cell lines. The antibacterial screening results suggest a possible role for nitric oxide in enhancement of the antibacterial activity where nitric oxide is not the only factor but other factors like physicochemical properties should be investigated for their potential role on the activity.
- El-Sherief, Hany A.,Abuo-Rahma, Gamal El-Din A.,Shoman, Mai E.,Beshr, Eman A.,Abdel-baky, Rehab M.
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- Novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids: Synthesis, physicochemical properties, anticancer and topoisomerase i and II inhibitory activity
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A group of novel N-4-piperazinyl-ciprofloxacin-chalcone hybrids was prepared. One-dose anticancer test results indicated that compounds 3a and 3g exhibited the highest ability to inhibit the proliferation of different cancer cell lines. Compound 3a exhibited a broad-spectrum of anti-tumor activity without pronounced selectivity while compound 3g revealed high selectivity toward the leukemia subpanel with selectivity ratio of 6.71 at GI50 level. Moreover, compounds 3e and 3j have shown remarkable topo II inhibitory activity compared to etoposide at 100 μM and 20 μM concentrations. Compounds 3e and 3j exhibited comparably potent topo I inhibitory activity at 20 μM concentration compared to camptothecin. Compounds 3e and 3j exhibited strong topo II inhibitory activities compared to topo I at 20 μM concentration. Studying of the solubility and partition coefficient revealed higher lipophilicity of the hybrids 3a-j compared to the parent ciprofloxacin.
- Abdel-Aziz, Mohamed,Park, So-Eun,Abuo-Rahma, Gamal El-Din A.A.,Sayed, Mohamed A.,Kwon, Youngjoo
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- Design, synthesis and molecular modelling studies of some pyrazole derivatives as carbonic anhydrase inhibitors
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In this study, newly synthesised compounds 6, 8, 10 and other compounds (1–5, 7 and 9) and their inhibitory properties against the human isoforms hCA I and hCA II were reported for the first time. Compounds 1–10 showed effective inhibition profiles with KI values in the range of 5.13–16.9 nM for hCA I and of 11.77–67.39 nM against hCA II, respectively. Molecular docking studies were also performed with Glide XP to get insight into the inhibitory activity and to evaluate the binding modes of the synthesised compounds to hCA I and II. More rigorous binding energy calculations using MM-GBSA protocol which agreed well with observed activities were then performed to improve the docking scores. Results of in silico calculations showed that all compounds obey drug likeness properties. The new compounds reported here might be promising lead compounds for the development of new potent inhibitors as alternatives to classical hCA inhibitors.
- Dizdaroglu, Yazg?,Albay, Canan,Arslan, Tayfun,Ece, Abdulilah,Turkoglu, Emir A.,Efe, Asiye,Senturk, Murat,Supuran, Claudiu T.,Ekinci, Deniz
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- Design, synthesis, and anticancer activity studies of novel quinoline-chalcone derivatives
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The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 μM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents.
- Guan, Yong-Feng,Li, Wen,Li, Yin-Ru,Liu, Wen-Bo,Liu, Xiu-Juan,Song, Jian,Tian, Xin-Yi,Yu, Guang-Xi,Yuan, Xin-Ying,Zhang, Sai-Yang,Zhang, Yan-Bing
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- Chalcones bearing a 3,4,5-trimethoxyphenyl motif are capable of selectively inhibiting oncogenic K-Ras signaling
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Ras proteins are small GTPases which regulate cellular proliferation, differentiation, and apoptosis. Constitutively active mutant Ras are expressed in ~15–20% human cancers, and K-Ras mutations account for ~85% of all Ras mutations. Despite the significa
- Cho, Kwang-jin,Fourman, Cody,Ketcha, Daniel M.,Kinstedt, Christine,Kovar, Sarah E.,Morris, Christopher,Williams, Brandon
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supporting information
(2020/04/15)
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- Synthesis and biological evaluation of amino chalcone derivatives as antiproliferative agents
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Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity of amino chalcone derivatives was studied in vitro and 5-Fu as a control group. Some of the compounds showed moderate to good activity against three human cancer cells (MGC-803, HCT-116 and MCF-7 cells) and compound 13e displayed the best antiproliferative activity against MGC-803 cells, HCT-116 cells and MCF-7 cells with IC50 values of 1.52 μM (MGC-803), 1.83 μM (HCT-116) and 2.54 μM (MCF-7), respectively which was more potent than the positive control (5-Fu). Further mechanism studies were explored. The results of cell colony formatting assay suggested compound 10e inhibited the colony formation of MGC-803 cells. DAPI fluorescent staining and flow cytometry assay showed compound 13e induced MGC-803 cells apoptosis. Western blotting experiment indicated compound 13e induced cell apoptosis via the extrinsic/intrinsic apoptosis pathway in MGC-803 cells. Therefore, compound 13e might be a valuable lead compound as antiproliferative agents and amino chalcone derivatives worth further effort to improve amino chalcone derivatives’ potency.
- Gu, Yu-Fan,Hu, Yang-Yang,Jin, Min-Jie,Li, Hong-Li,Li, Qian-Yu,Li, Qing-Rong,Li, Yin-Ru,Lu, Chao-Fan,Mu, Zhao-Yang,Pang, Xiao-Jing,Song, Jian,Wang, Sheng-Hui,Zhang, Sai-Yang,Zhang, Yan-Bing,Zhu, Ting
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- Discovery of novel chalcone-dithiocarbamates as ROS-mediated apoptosis inducers by inhibiting catalase
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Novel chalcone-dithiocarbamate hybrids were designed, synthesized and evaluated for antiproliferative activity against selected cancer cell lines (MGC803, MCF7, and PC3). Among these analogues, (E)-2-oxo-2-((4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)am
- Fu, Dong-Jun,Li, Jia-Huan,Yang, Jia-Jia,Li, Ping,Zhang, Yan-Bing,Liu, Simeng,Li, Zhong-Rui,Zhang, Sai-Yang
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p. 375 - 385
(2019/02/15)
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- Discovery of novel AHLs as potent antiproliferative agents
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Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog 11e induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner.
- Ren, Jing-Li,Zhang, Xu-Yao,Yu, Bin,Wang, Xi-Xin,Shao, Kun-Peng,Zhu, Xiao-Ge,Liu, Hong-Min
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p. 321 - 329
(2015/03/04)
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- Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents
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A new series of chalcone-coumarin derivatives (9-19) linked by the 1,2,3-triazole ring were synthesized through the azide/alkyne dipolar cycloaddition. Hybrid molecules were evaluated for their cytotoxic activity against four cancer cell lines (e.g., HuCC
- Pingaew, Ratchanok,Saekee, Amporn,Mandi, Prasit,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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- Synthesis, biological evaluation and molecular docking of novel chalcone-coumarin hybrids as anticancer and antimalarial agents
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A new series of chalcone-coumarin derivatives (9-19) linked by the 1,2,3-triazole ring were synthesized through the azide/alkyne dipolar cycloaddition. Hybrid molecules were evaluated for their cytotoxic activity against four cancer cell lines (e.g., HuCC
- Pingaew, Ratchanok,Saekee, Amporn,Mandi, Prasit,Nantasenamat, Chanin,Prachayasittikul, Supaluk,Ruchirawat, Somsak,Prachayasittikul, Virapong
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- Hybrid α-bromoacryloylamido chalcones. Design, synthesis and biological evaluation
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Research into the anti-tumor properties of chalcones has received significant attention over the last few years Two novel large series of α-bromoacryloylamido chalcones 1a-m and 2a-k containing a pair of Michael acceptors in their structures, corresponding to the α-bromoacryloyl moiety and the α,β-unsaturated ketone system of the chalcone framework, were synthesized and evaluated for antiproliferative activity against five cancer cell lines. Such hybrid derivatives demonstrated significantly increased anti-tumor activity compared with the corresponding amino chalcones. The most promising lead molecules were 1k, 1m and 2j, which had the highest activity toward the five cell lines. Flow cytometry with K562 cells showed that the most active compounds resulted in a large proportion of the cells entering in the apoptotic sub-G0-G1 peak. Moreover, compound 1k induced apoptosis through the mitochondrial pathway and activated caspase-3.
- Romagnoli, Romeo,Baraldi, Pier Giovanni,Carrion, Maria Dora,Cruz-Lopez, Olga,Cara, Carlota Lopez,Balzarini, Jan,Hamel, Ernest,Canella, Alessandro,Fabbri, Enrica,Gambari, Roberto,Basso, Giuseppe,Viola, Giampietro
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supporting information; experimental part
p. 2022 - 2028
(2009/11/30)
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- Carbonic anhydrase inhibitors. Part 36*. Inhibition of isozymes I and II with Schiff bases derived from chalkones and aromatic/heterocyclic sulfonamides
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A series of 27 Schiff bases was prepared by reaction of chalkones with sulfanilamide and 5-amino-1,3,4-thiadiazole-2-sulfonamide. The new compounds were characterized by analysis and standard physico-chemical methods. They possess good inhibitory properties towards isozymes I and II of carbonic anhydrase. Structure-activity effects in this series of inhibitors are also discussed.
- Supuran,Popescu,Ilisiu,Costandache,Banciu
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p. 439 - 447
(2007/10/03)
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