19132-98-0Relevant academic research and scientific papers
Photophysical study and biological applications of synthetic chalcone-based fluorescent dyes
Aryamueang, Sirimongkon,Chansaenpak, Kantapat,Kamkaew, Anyanee,Lai, Rung-Yi,Ngivprom, Utumporn,Nootem, Jukkrit,Wangngae, Sirilak
supporting information, (2021/06/02)
A chalcone series (3a–f) with electron push–pull effect was synthesized via a one-pot Claisen–Schmidt reaction with a simple purification step. The compounds exhibited strong emission, peaking around 512–567 nm with mega-stokes shift (?λ = 93–139 nm) in p
Synthesis, characterization and structure–activity relationship of non-linear optical response of chalcone derivatives with in silico insights
Rai, Prashant,Chettri, Prajal,Kar, Swayamsiddha,Nagar, Malhar Anupam,Srivastava, Shailesh,Golakoti, Nageswara Rao
supporting information, p. 2603 - 2615 (2021/02/01)
Fifteen chalcone derivatives having D–A–D, D–A–A and A–A–D architectures have been synthesized by Claisen–Schmidt condensation reaction and characterized by UV–Vis, IR, 1H-NMR, 13C-NMR and Mass spectrometry. In order to unambiguously establish the structure–activity relationship for the non-linear optical activity of these compounds, for the first time to our knowledge, we use the femtosecond degenerate four wave mixing (DFWM) technique to quantify and compare the third-order non-linear optical (NLO) activity of all the 15 compounds, under identical conditions. The second harmonics generation (SHG) efficiencies for all the compounds have also been evaluated using the Kurtz-Perry powder method. Among the compounds that we have synthesized here, the ones with A–A–D architecture show the highest NLO activity. Our results show that the NLO activity of a compound with A–A–D architecture can be further enhanced by incorporating a substituent with strong electron withdrawing ability on ring A and strong electron donating substituent on ring B. The results of the in silico studies that we have carried out correlate well with our experimental findings. The compounds (E)-3-(4-(dimethylamino)phenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-N(CH3)2–4′-NO2) and (E)-3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-en-1-one with the compound code (4-MeO-4′-NO2) show the highest NLO activity among the compounds we have reported here. Graphical abstract: [Figure not available: see fulltext.]
Pyrazoline analogs as potential anticancer agents and their apoptosis, molecular docking, MD simulation, DNA binding and antioxidant studies
Rana, Manish,Arif, Rizwan,Khan, Faez Iqbal,Maurya, Vikas,Singh, Raja,Faizan, Md Imam,Yasmeen, Shama,Dar, Sajad Hussain,Alam, Raquib,Sahu, Ankita,Ahmad, Tanveer,Rahisuddin
, (2021/02/12)
N-formyl pyrazoline derivatives (3a–3l) were designed and synthesized via Michael addition reaction through cyclization of chalcones with hydrazine hydrate in presence of formic acid. The structural elucidation of N-formyl pyrazoline derivatives was carri
Design and synthesis of novel pyrazoles, pyrazolines, and pyridines from chalcone derivatives with evaluation of their in vitro anticancer activity against T-47D and UACC-257 cell lines
Mangouda, Mangoud M.,Hussein, Mohamed Z.,El-Bordany, Eman A.
, p. 5203 - 5218 (2021/01/18)
Novel series of pyrazoline carbothioamides, acetyl pyrazoles, pyridine-3-carbonitrile, pyridine-2-carbonitriles, and nicotinonitriles were synthesized. The structures of the newly synthesized compounds were established based on their spectral data, elemen
Silica-supported heterogeneous catalysts-mediated synthesis of chalcones as potent urease inhibitors: in vitro and molecular docking studies
Sultan, Aeysha,Shajahan, Shanavas,Ahamad, Tansir,Alshehri, Saad M.,Sajjad, Noreen,Mehr-un-Nisa,Rehman, Mian Habib Ur,Torun, Lokman,Khalid, Muhammad,Acevedo, Roberto
, p. 123 - 133 (2020/01/11)
Abstract: We herein report a facile and high yielding protocol for silica-supported heterogeneous catalysts-mediated synthesis of chalcones. A comparison of results of our synthesis with conventional synthetic protocols is also being offered to assess the efficiency of the prepared catalysts. Biological evaluation of the newly synthesized compounds as urease inhibitors was performed. Most of the compounds were found to have potent urease inhibition activity. The chalcone 3-(3-hydroxyphenyl)-1-phenylpropenone was found to be the most potent with percentage inhibition 86.17 ± 0.89 and half maximal inhibitory concentration (IC50) value 11.51 ± 0.03 μM. The molecular docking study emphasized that the same congeners 3-(furan-2-yl)-1-(4-hydroxyphenyl)propenone, 3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)propanone, and 3-[4-(dimethylamino)phenyl]-1-(p-tolyl)propenone showed very good inhibitory potential against urease and show a higher docking scores 5718, 5940, 5596 and an ACE of ? 246.66, ? 244.79, and ? 243.06 kJ/mol, respectively than the control ligand. Graphic abstract: [Figure not available: see fulltext.].
Synthesis, molecular docking and α-glucosidase inhibitory activity study of 2,4,6-triaryl pyrimidine derivatives
Abdollahi, Mohammad,Amini, Mohsen,Bule, Mohammed Hussen,Esfandyari, Roghaieh,Faramarzi, Mohammad Ali,Tafesse, Tadesse Bekele
, p. 1216 - 1226 (2020/10/06)
Background: α-Glucosidase inhibitors hinder the carbohydrate digestion and play an important role in the treatment of diabetes mellitus. α-glucosidase inhibitors available on the market are acarbose, miglitol, and voglibose. However, the use of acarbose is diminishing due to related side effects like diarrhea, bloating and abdominal distension. Objectives: This study aimed to synthesize 2,4,6-triaryl pyrimidines derivatives, screen their α-glucosidase inhibitory activity, perform kinetic and molecular docking studies. Methods: A series of 2,4,6-triaryl pyrimidine derivatives were synthesized and their α-glucosidase inhibitory activity was screened in vitro. Pyrimidine derivatives 4a-m were synthesized via a two-step reaction with a yield between 49 and 93%. The structure of the synthesized compounds was confirmed by different spectroscopic techniques (IR, NMR and MS). The in vitro α-glucosidase inhibition activities of the synthesized compounds 4a-m was also evaluated against Saccharomyces cerevisiae α-glucosidase. Results and Discussion: The majority of synthesized compounds had α-glucosidase inhibitory activity. Particularly compounds 4b and 4g were the most active compounds with an IC50 value of 125.2± 7.2 and 139.8 ± 8.1 μM respectively. The kinetic study performed for the most active compound 4b revealed that the compound was a competitive inhibitor of Saccharomyces cerevisiae α-glucosidase with Ki of 122 μM. The molecular docking study also revealed that the two compounds have important binding interactions with the enzyme active site. Conclusion: 2,4,6-triarylpyrimidine derivative 4a-m were synthesized and screened for α-glucosidase inhibitory activity. Most of the synthesized compounds possess α-glucosidase inhibitory activity, and compound 4b demonstrated the most significant inhibitory action as compared to acarbose.
Design, Synthesis, and Docking Study of Pyrimidine–Triazine Hybrids for GABA Estimation in Animal Epilepsy Models
Sahu, Meeta,Siddiqui, Nadeem,Naim, Mohd. Javed,Alam, Ozair,Yar, Mohammad Shahar,Sharma, Vidushi,Wakode, Sharad
, (2017/09/05)
A series of new pyrimidine–triazine hybrids (4a–t) was designed and synthesized, from which potent anticonvulsant agents were identified. Most of the compounds exhibited promising anticonvulsant activity against the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) tests, along with minimal motor impairment with higher safety compared to the standard drugs, phenytoin and carbamazepine. In the series, 5-(4-(4-fluorophenyl)-6-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4o) and 5-(6-(4-hydroxy-3-methoxyphenyl)-4-(4-hydroxyphenyl)-2-thioxo-5,6-dihydropyrimidin-1(2H)-yl)-1,2-dihydro-1,2,4-triazin-3(6H)-one (4s) emerged as most potent anticonvulsant agents with median doses of 22.54 and 29.40 mg/kg (MES ED50), 285.02 and 293.42 mg/kg (scPTZ ED50), and 389.11 and 412.16 mg/kg (TD50), respectively. Docking studies were also performed for all synthesized compounds to get insight into the binding pattern toward the GABAA receptor as a possible mechanism of their anticonvulsant action, and in silico ADME studies were carried out to predict the safety and stability of the molecules. The increased GABA level in the experimental animals in the neurochemical estimation assay confirmed their GABAergic modulating activity. The most potent compounds were also evaluated for their neurotoxic and hepatotoxic effects. Fortunately, they did not show any sign of neurotoxicity or hepatotoxicity, suggesting that they have a broad spectrum of anticonvulsant activity with a large safety margin. Together, this research suggested that 4o and 4s may serve as leads in the discovery and development of new anticonvulsant drugs.
A colorimetric and fluorescent pH probe for imaging in E. coli cells
Chao, Jianbin,Song, Kailun,Wang, Huijuan,Li, Zhiqing,Zhang, Yongbin,Yin, Caixia,Huo, Fangjun,Wang, Juanjuan,Zhang, Ting
, p. 964 - 970 (2017/01/13)
A colorimetric and fluorescent pH probe 1-(4-methylphenyl)-3-(4-dimethylaminophenyl) acrylketone (MDAK) was facilely prepared. The probe exhibited strong pH-dependent behavior and responded linearly and rapidly to minor pH fluctuations within the range of
Rational design, synthesis and in vitro evaluation of allylidene hydrazinecarboximidamide derivatives as BACE-1 inhibitors
Jain, Priti,Wadhwa, Pankaj K.,Rohilla, Shilpa,Jadhav, Hemant R.
supporting information, p. 33 - 37 (2015/12/18)
BACE-1 (β-secretase) is considered to be one of the promising targets for treatment of Alzheimer's disease as it catalyzes the rate limiting step of Aβ-42 production. Herein, we report a novel class of allylidene hydrazinecarboximidamide derivatives as moderately potent BACE-1 inhibitors, having aminoguanidine substitution on allyl linker with two aromatic groups on either side. A library of derivatives was designed based on the docking studies, synthesized and evaluated for BACE-1 inhibition in vitro. The designed ligands displayed interactions with the catalytic aspartate dyad through guanidinium functionality. Further, the aromatic rings placed on either side of the linker occupied S1 and S3 active site regions contributing to the activity. These ligands were also predicted to follow Lipinski rule and cross blood brain barrier. Compound 2.21, having high docking score, was found to be most active with IC50 of 6.423 μM indicating good correlation with docking prediction.
Characterization of the Fluorescence Properties of 4-Dialkylaminochalcones and Investigation of the Cytotoxic Mechanism of Chalcones
Zhou, Bo,Jiang, Peixin,Lu, Junxuan,Xing, Chengguo
, p. 539 - 552 (2016/08/26)
Understanding the mechanisms responsible for the various biological activities of chalcones, particularly the direct cellular targets, presents an unmet challenge. Here, we prepared a series of fluorescent chalcone derivatives as chemical probes for their
