71198-75-9Relevant academic research and scientific papers
Novel 1,2,4-triazine-quinoline hybrids: The privileged scaffolds as potent multi-target inhibitors of LPS-induced inflammatory response via dual COX-2 and 15-LOX inhibition
Ghanim, Amany M.,Rezq, Samar,Ibrahim, Tarek S.,Romero, Damian G.,Kothayer, Hend
, (2021/04/23)
Based on the observed pharmacophoric structural features for the reported dual COX/15-LOX inhibitors and inspired by the abundance of COX/LOX inhibitory activities reported for the 1,2,4-triazine and quinoline scaffolds, we designed and synthesized novel 1,2,4-triazine-quinoline hybrids (8a-n). The synthesized hybrids were evaluated in vitro as dual COXs/15-LOX inhibitors. The new triazine-quinoline hybrids (8a-n) exhibited potent COX-2 inhibitory profiles (IC50 = 0.047–0.32 μM, SI ～ 20.6–265.9) compared to celecoxib (IC50 = 0.045 μM, SI ～ 326). Moreover, they revealed potent inhibitory activities against 15-LOX enzyme compared to reference quercetin (IC50 = 1.81–3.60 vs. 3.34 μM). Hybrid 8e was the most potent and selective dual COX-2/15-LOX inhibitor (COX-2 IC50 = 0.047 μM, SI = 265.9, 15-LOX IC50 = 1.81 μM). These hybrids were further challenged by their ability to inhibit NO, ROS, TNF-α, IL-6 inflammatory mediators, and 15-LOX product, 15-HETE, production in LPS-activated RAW 264.7 macrophages cells. Compound 8e was the most potent hybrid in reducing ROS and 15-HETE levels showing IC50 values of 1.02 μM (11-fold more potent than that of celecoxib, IC50 = 11.75 μM) and 0.17 μM (about 43 times more potent than celecoxib, IC50 = 7.46 μM), respectively. Hybrid 8h exhibited an outstanding TNF-α inhibition with IC50 value of 0.40 μM which was about 25 times more potent than that of celecoxib and diclofenac (IC50 = 10.69 and 10.27 μM, respectively). Docking study of the synthesized hybrids into the active sites of COX-2 and 15-LOX enzymes ensures their favored binding affinity. To our knowledge, herein we reported the first 1,2,4-triazine-quinoline hybrids as dual COX/15-LOX inhibitors.
Design, Synthesis, and Antimicrobial Activity of Novel Fluorine-Containing Imidazolones
Desai,Wadekar,Mehta,Pandit
, p. 976 - 985 (2021/08/09)
Abstract: A simple synthetic protocol have been developed for the preparation of novelN-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N′-phenylthiourea derivatives by the reaction of4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones with N
Pharmaceutical composition and method of treating cancer
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Page/Page column 47, (2020/12/07)
Cytotoxic compounds containing a phenyl core, amide link(s), an imidazolinone or a propenamide moiety. Also described are pharmaceutical compositions incorporating the cytotoxic compounds and methods for treating cancer. These compounds are cytotoxic against breast, prostate, and leukemia cancer cell lines via dual inhibition of Src kinases and tubulin.
Benzothiazol clubbed imidazol-4-ones as anti-fungal, anti-tubercular and anti-HIV-1 agents: Their synthesis and molecular docking study
Patel, Navin B.,Shaikh, Asif R.,Patel, Vatsal M.,Lara-Ramirez, Edgar E.,Rivera, Gildardo
, p. 382 - 391 (2019/06/18)
Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).
Synthesis, biological evaluation and docking studies of N-(2-benzamido feruloyl) aryl hydrazone analogues
Soujanya,Rajitha,Umamaheswari,Sudheer Kumar
, p. 875 - 886 (2018/07/03)
Background: Nowadays inflammation recognized as the underlying basis of number of diseases but still NSAIDS are the first drugs of choice having several side effects. In addition to that, oxidative stress also triggers the inflammation. This creates an in
Synthesis of Erlenmeyer-Pl?chl azlactones promoted by 5-Sulfosalicylic acid
Kiyani, Hamzeh,Aslanpour, Shiva
, p. 1314 - 1321 (2017/07/18)
5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was eas
A Facile and Efficient Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones and Their Antimicrobial Evaluation against Selected Human and Phytopathogens
Voosala, Christopher,Kilaru, Padma Suhasini,Dasari, Uday Kumar
, p. 909 - 916 (2016/11/23)
A simple and convenient method has been developed for the synthesis of a series of 2-(4-substituted phenyl)-4-(substituted arylidene)-1,3-oxazol-5-ones (5a–j) via reactions of hippuric acid with differently substituted aromatic aldehydes (4a–j) in sodium acetate, potassium acetate, calcium acetate, and ammonium acetate, respectively, which were tested for their efficiency as catalysts in both conventional and microwave-assisted synthetic methods in presence of 4 ? zeolites. The title compounds were evaluated for their antimicrobial properties against selected human pathogens (bacterial and fungal) and phytopathogens (fungal) and were compared with standard drugs. The results of the study are reported.
Synthesis of Erlenmeyer azlactones using arylsulphonyl chloride as cyclocondensing agent
Goswami, Limi,Tripathy, Pradeep K.
, p. 281 - 282 (2019/01/21)
A fast and facile procedure for one flask synthesis of (Z)-2-substituted-4- arylmethylene-2-oxazolin-5-ones (3) which are popularly known as Erlenmeyer azlactones, is being reported starting from N-acylglycines (1) and different aromatic aldehydes using arylsulphonyl chloride as cyclocondensing agent in the presence of triethyl amine base and dry benzene. The reaction time is reduced to minute under milder conditions alongwith higher yields of the products.
[Et3NH][HSO4]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones
Parveen, Mehtab,Ahmad, Faheem,Malla, Ali Mohammed,Azaz, Shaista,Silva, Manuela Ramos,Silva, P. S. Pereira
, p. 52330 - 52346 (2015/06/25)
A facile, green and stereoselective approach for the synthesis of azlactones/oxazolones 3(a-q) has been developed. The protocol involves reaction of hippuric acid and substituted heterocyclic/aromatic aldehydes in ionic liquid [Et3NH][HSO4] to yield the desired 4-arylidene-2-phenyl-5(4H)-oxazolones in excellent yields (94-97%) with a high degree of purity. The remarkable feature of this pathway is that the ionic liquid eliminates the use of toxic and expensive acetic anhydride and is endowed with catalytic and medium engineering ability. This eco-friendly approach improved synthetic efficiency (94-97% yield), minimizing the production of chemical waste without using highly toxic reagents for the synthesis and more notably, it promoted the selectivity for Z-azlactones/oxazolones. Density functional theory (DFT) calculations revealed that the Z-isomer of compound 3a is stabilised by 2.32 kcal mol-1 more than the E-isomer. This synthetic scheme possesses diverse applicability and is compatible to a range of functional groups (electron donating/electron withdrawing).
Efficient synthesis of 5(4H)-imidazolones and IN VITRO antifungal activity studies against selected phytopathogens
Voosala, Christopher,Yellajyosula, Lakshmi Narasimha Murthy,Uppuleti, Viplava Prasad,Kilaru, Padma Suhasini
, p. 2873 - 2876 (2014/06/09)
A series of five new 1-(substituted phenyl)-2-phenyl-4-(substituted benzylidine)imidazole-5-one derivatives (or) 5(4H)-imidazolones I have been synthesized adopting SiO2, Al2O3-90 and Y-faujasite (Y-H type) zeolite as cata
