Search for new pharmacophores for antimalarial activity. Part I: Synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides

Madapa, Sudharshan; Tusi, Zehra; Sridhar, D.; Kumar, Ashok; Siddiqi, Mohammad Imran; Srivastava, Kumkum; Rizvi, Amber; Tripathi, Renu; Puri, Sunil K.; Keshava, G.B. Shiva; Shukla, Pragya; Batra, Sanjay

doi:10.1016/j.bmc.2008.11.021

Cited by 43 publications

(10 citation statements)

References 24 publications

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“…A mixture of 3 (218.21 mg, 1 m m ) and 3‐fluoroaniline ( 4a , 1 m m ) was heated and stirred at reflux in acetic acid (10 mL) for 1 h. The yellow precipitate that formed was filtered hot, washed with hot acetic acid, diethyl ether, and dried to give the desired nitroquinazoline 5a as light yellow solid (180 mg, rate 63.2%). m.p: 230.7–232.6 °C (227–229 °C, lit …”

Section: Methodsmentioning

confidence: 99%

“…By the procedure described above for 5a using 3 (218.21 mg, 1 m m ) and 3‐chloroaniline ( 4b , 127.57 mg, 1 m m ) to give 233 mg (77.7%) of yellow powder. m.p: 276.0–279.0 °C (278–281 °C, lit …”

Section: Methodsmentioning

confidence: 99%

“…Chromatography on silica gel eluting with a mixture of ethyl acetate/petroleum ether gave the expected product with 52.2% yield (66.3 mg). m.p: 128.2–129.5 °C (122–124 °C, lit …”

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis, and Biological Evaluation of Novel Quinazoline Derivatives as Anti‐inflammatory Agents against Lipopolysaccharide‐induced Acute Lung Injury in Rats

Zhang

Dong

et al. 2014

Chem Biol Drug Des

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Quinazoline has been reported to exhibit multiple bioactivities. The aim of this study was to discover new quinazoline derivatives with preventive effect on lipopolysaccharide-induced acute lung injury via anti-inflammatory actions. Thirty-three 4-amino quinazolin derivatives were synthesized and screened for anti-inflammatory activities in lipopolysaccharide-induced macrophages. The most potent four compounds, 6h, 6m, 6p, and 6q, were shown dose-dependent inhibition against lipopolysaccharide-induced TNF-α and IL-6 release. Then, the preliminary structure-activity relationship and quantitative structure-activity relationship analyses were conducted. To further determine the effects of quinazolines on acute lung injury treatment, lipopolysaccharide-induced acute lung injury model was employed. Male Sprague Dawley rats were pretreated with 6m or 6q before instillation of lipopolysaccharide. The results showed that 6m and 6q, especially 6q, obviously alleviated lung histopathological changes, inflammatory cells infiltration, and cytokines mRNA expression initiated by lipopolysaccharide. Taken together, this work suggests that 6m and 6q suppressed the lipopolysaccharide-induced acute lung injury through inhibition of the inflammatory response in vivo and in vitro, indicating that quinazolines might serve as potential agents for the treatment of acute lung injury and deserve the continuing drug development and research.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Design, Synthesis, and Biological Evaluation of Novel Quinazoline Derivatives as Anti‐inflammatory Agents against Lipopolysaccharide‐induced Acute Lung Injury in Rats

Zhang

Dong

et al. 2014

Chem Biol Drug Des

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“…reported that the synthesis of ureido-4-quinolinamides, 22 showed antimalarial activity at MIC 0.25 mg/mL against chloroquine-sensitive Plasmodium falciparum strain [22]. Several 7-chloroquinolinyl thioureas, 23, 24 have been synthesized by Mahajan et al that possess excellent antimalarial properties [23].…”

Section: Biological Activity 31 Antimalarialmentioning

confidence: 99%

Quinoline Heterocycles: Synthesis and Bioactivity

Rajesh¹

2020

Heterocycles - Synthesis and Biological Activities

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Among heterocyclic compounds, quinoline is a privileged scaffold that appears as an important construction motif for the development of new drugs. Quinoline nucleus is endowed with a variety of therapeutic activities, and new quinolone derivatives are known to be biologically active compounds possessing several pharmacological activities. Many new therapeutic agents have been developed by using quinoline nucleus. Hence, quinoline and its derivatives form an important class of heterocyclic compounds for the new drug development. Numerous synthetic routes have been developed for the synthesis of quinoline and its derivatives due to its wide range of biological and pharmacological activities. The article covers the synthesis as well as biological activities of quinoline derivatives such as antimalarial, anticancer, antibacterial, anthelmintic, antiviral, antifungal, antiinflammatory, analgesic, cardiovascular, central nervous system, hypoglycemic, and miscellaneous activities.

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“…In this work, based on previous structure activity relationships (SARs) of sorafenib and its analogs we retained the diarylurea functionality as the key pharmacophore and focused our main modification on replacement of pyridyl carboxamid group of sorafenib with quinoxalindione moiety in order to investigate the impact of increasing rigidity at the end of this backbone on the biological activities of the resulting compounds. Since antibacterial activities of quinoxalindione and diaryl urea derivatives have been reported separately, we were interested in investigating the antimicrobial activities of these new hybrid compounds with both pharmacophore moieties in a single scaffold( 14 15 16 17 18 19 ).…”

Section: Introductionmentioning

confidence: 99%

Biological evaluation, docking and molecular dynamic simulation of some novel diaryl urea derivatives bearing quinoxalindione moiety

et al. 2017

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In this study a series of diarylurea derivatives containing quinoxalindione group were biologically evaluated for their cytotoxic activities using MTT assay against MCF-7 and HepG2 cell lines. Antibacterial activities of these compounds were also evaluated by Microplate Alamar Blue Assay (MABA) against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-positive (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungus (Candida albicans) strain. Furthermore, molecular docking was carried out to study the binding pattern of the compounds to the active site of B-RAF kinase (PDB code: 1UWH). Molecular dynamics simulation was performed on the best ligand (16e) to investigate the ligand binding dynamics in the physiological environment. Cytotoxic evaluation revealed the most prominent cytotoxicity for 6 compounds with IC50 values of 10-18 μM against two mentioned cell lines. None of the synthesized compounds showed significant antimicrobial activity. The obtained results of the molecular docking study showed that all compounds fitted in the binding site of enzyme with binding energy range of -11.22 to -12.69 kcal/mol vs sorafenib binding energy -11.74 kcal/mol as the lead compound. Molecular dynamic simulation indicated that the binding of ligand (16e) was stable in the active site of B-RAF during the simulation.

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Search for new pharmacophores for antimalarial activity. Part I: Synthesis and antimalarial activity of new 2-methyl-6-ureido-4-quinolinamides

Cited by 43 publications

References 24 publications

Design, Synthesis, and Biological Evaluation of Novel Quinazoline Derivatives as Anti‐inflammatory Agents against Lipopolysaccharide‐induced Acute Lung Injury in Rats

Design, Synthesis, and Biological Evaluation of Novel Quinazoline Derivatives as Anti‐inflammatory Agents against Lipopolysaccharide‐induced Acute Lung Injury in Rats

Quinoline Heterocycles: Synthesis and Bioactivity

Biological evaluation, docking and molecular dynamic simulation of some novel diaryl urea derivatives bearing quinoxalindione moiety

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