Medicinal Chemistry of Ureido Derivatives as Anti-Infectives

Batra, Sanjay; Tusi, Zehra; Madapa, Sudharshan

doi:10.2174/187152106776359048

Cited by 22 publications

(12 citation statements)

References 1 publication

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“…In addition, the compound 5 K was also showed good activity with IC 50 = 98.7 and 76.9 μg/mL on HCT‐116, and MIA‐PaCa2 cell lines respectively. Some of the important pharmacological activities ascribed to ureides are anti‐infectives, antitumor, anticancer and the various metabolic disorders include diabetes and hyperlipidemia . In a recent report by Pratap et al ., N,N′‐disubstituted thiourea molecules and their copper complexes showed moderate to potent cytotoxic properties against cervical carcinoma (2008 and C 13 ) and ovarian carcinoma (A2780, A2780/CP and IGROV‐1) cell lines.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Anticancer and Antimicrobial Activity Studies of Novel Isomeric 2,4‐Disubstituted Ureide Derivatives of Pyrimidinopiperidines

et al. 2019

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A series of isomeric ureide derivatives of novel 2,4-disubstituted pyrimidinopiperidines were synthesized starting from 2,4dichloropyrimidine. All the final products were purified on silica and characterized by spectral analysis. Both the 2,4-disubstituted pyrimidinopiperidines were analyzed for their in vitro anticancer activity on the cell lines HCT116, MIA-PaCa2 and MDA-MB 231 by using MTT cell proliferation assay. Further, the antimicrobial studies were carried out against different bacterial and fungal strains by employing cup plate method. These compounds were showed significant anticancer activity on tested three cancer cell lines and exhibited potent antimicrobial activity in tested strains of bacteria and fungi. Results and Discussion Chemistry Synthesis of ureide derivatives of 2-aryl-4-(-4-amino piperidinyl) pyrimidines (5 a-l):The reaction of 2,4-dichloro-pyrimidine (1) with tert-butylpiperidin-4-ylcarbamate in presence of diisopropylethylamine in dichloromethane at room temperature afforded the 4-substituted 2-chloropyrimidine derivative 2 a with 62% yield (Scheme 1) after purifying by column Scheme 1. Reagents and conditions: i) tert-butyl-piperidin-4yl-carbamate, DIPEA, THF, rt, 4 h; ii) R = a-d, Pd 2 (dba) 3 , X-Phos, DIPEA, rt, 18 h; iii) TFA, DCM, rt, 10 min; iv) R 1 = e-g, DIPEA, reflux, 10 min. EntryAmino piperidine derivative (4 A-4D) Isocyanate (e-g) Urea derivative (5 A-5 L) Yield (%) 6 95 7 92 8 91 9 95 10 92

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Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Anticancer and Antimicrobial Activity Studies of Novel Isomeric 2,4‐Disubstituted Ureide Derivatives of Pyrimidinopiperidines

et al. 2019

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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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“…Some of the important pharmacological properties assigned to ureides [5] include antibacterial and antitumor activity [6] and the activity with respect to various metabolic disorders such as diabetes and hyperlipidemia. They are also of biological interest as antimycobacterial [7] and antitrypanosomal agents [8], and as inhibitors of HIV protease [9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and in vitro antimicrobial evaluation of new glycosyl imidothiocarbamates

Dandale

Deshmukh

2011

Pharm Chem J

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A series of new glycosyl imidothiocabamates were synthesized and charaterized and their antimicrobial properties were evaluated. These compounds were synthesized by the condensation of per-O-acetyl lactosyl isocyanate with N-aryl-S-benzyl isothiourea and per-O-benzoyl glucosyl aryl isothiourea and characterised using the IR, 1 H NMR, and mass spectroscopy and elemental analysis. The synthesized compounds were screened for their in vitro antimicrobial activity against bacteria (S. aureus, E. coli, P. vulgaris, P. aeruginosa) and fungi (A. niger, Penicillium). Some of these compounds exhibited moderate to good activity, whereas some were inactive.

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Medicinal Chemistry of Ureido Derivatives as Anti-Infectives

Cited by 22 publications

References 1 publication

Synthesis, Characterization, Anticancer and Antimicrobial Activity Studies of Novel Isomeric 2,4‐Disubstituted Ureide Derivatives of Pyrimidinopiperidines

Synthesis, Characterization, Anticancer and Antimicrobial Activity Studies of Novel Isomeric 2,4‐Disubstituted Ureide Derivatives of Pyrimidinopiperidines

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

Synthesis, characterization and in vitro antimicrobial evaluation of new glycosyl imidothiocarbamates

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