Synthesis of new Schiff bases bearing 1,2,4-triazole, thiazolidine and chloroazetidine moieties and their pharmacological evaluation

Kandile, Nadia G.; Mohamed, Mohamed Bakr; Ismaeel, Hind M.

doi:10.1080/14756366.2016.1238365

Cited by 34 publications

(23 citation statements)

References 32 publications

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“…synthesized two bis‐spiro‐β‐lactams 17 containing two oxindole moieties, from the reaction carried out in refluxing DMF of chloroacetyl chloride ( 11 ) with bis‐Schiff bases 16 , the latter obtained from the condensation of the corresponding 4,4′‐diamino‐1,1′‐biphenyl and isatin derivatives (Scheme 4). [18] The target products were obtained in moderate yields (52–67%).…”

Section: Spiro‐β‐lactamsmentioning

confidence: 99%

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Alves

Soares

et al. 2021

Adv Synth Catal

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Spirocyclic molecules are widely recognized for their complex three-dimensional features and structural rigidity. Among this class of molecules, the spiro-lactams subclass stands out, being extensively explored due to its bioactivity and utility in a variety of scientific fields such as drug design and organic synthesis. Given the recognition of spirocyclic lactams' broad potential, several efforts have been engaged on the pursuit of new synthetic strategies towards these molecules. The present review gathers advances on the synthesis of both spiroβ-lactams (spiroazetidin-2-ones) and spiro-δ-lactams (spiropiperidon-2-ones) reported since 2015. The work is divided into two distinct parts, each one dedicated to one of these types of spiro-lactam, with the approach used for building the spirocyclic system being extensively discussed, according to the meth-

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Section: Spiro‐β‐lactamsmentioning

confidence: 99%

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Alves

Soares

et al. 2021

Adv Synth Catal

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“…[3] Besides, these compounds are versatile synthetic intermediates to develop a variety of heterocycles. [4] The 2-azetidinone (β-lactam) is the common structural unit present in a variety of βlactam antibiotics including penicillin, cephalosporin, carbapenem, monobactams [5] and have been widely used as chemotherapeutic agents to treat microbial infections. Amongst azoles, imidazole component has attracted much attention because of its potentiality to generate new chemotherapeutic agents.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Molecular Properties Prediction and Antimicrobial Activity of Imidazolyl Schiff Bases, Triazoles and Azetidinones

Rekha

Ummadi

Padmaja

et al. 2019

Chemistry & Biodiversity

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Benzylidenehydrazinyl imidazoles (3) are prepared from 2‐hydrazinyl imidazoles (2) on treatment with hydrazine. The imine functionality in 3 is utilized to develop 5′‐aryl‐N‐(4‐aryl‐1H‐imidazol‐2‐yl)‐1H‐1,2,3‐triazol‐1‐amines (5) by 1,3‐dipolar cycloaddition of diazomethane followed by aromatization with I2 in DMSO. Compounds 3 are also explored to prepare 4′‐aryl‐1‐(4‐aryl‐1H‐imidazol‐2‐ylamino)‐3‐chloroazetidin‐2‐ones (6) on treatment with chloroacetyl chloride. The Molinspiration calculations predicted that 3, 5 and 6 have molecular hydrophobicity, conformational flexibility, good intestinal absorption and bioactivity scores. The chloro, bromo and nitro substituted imidazolyl azetidinones (6c, 6d, 6f) and nitro substituted imidazolyl triazole (5f) exhibited excellent antibacterial activity on B. subtilis, whereas chloro and nitro substituted imidazolyl triazoles (5c, 5f) showed prominent antifungal activity on A. niger.

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“…The reaction volume was concentrated and kept at 7–8 °C for 24 h for the precipitation of Schiff bases. The synthesized Schiff bases were purified by recrystallization and column chromatography using ethyl acetate: methanol (70:30) on silica gel 100–200 mesh size [27, 40].…”

Section: Methodsmentioning

confidence: 99%

Indole hybridized diazenyl derivatives: synthesis, antimicrobial activity, cytotoxicity evaluation and docking studies

2019

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Background In search of effective antimicrobial and cytotoxic agents, a series of indole hybridized diazenyl derivatives ( DS-1 to DS-21 ) was efficiently prepared by condensation of diazotized p -aminoacetophenone with indole or nitroindole followed by reaction with different aromatic/heteroaromatic amines of biological significance. The synthesized derivatives were characterized by various spectroscopic techniques. Methodology The antimicrobial evaluation of DS-1 to DS-23 was done by tube dilution method against various pathogenic bacterial and fungal strains. The active antimicrobial derivatives were further evaluated for cytotoxicity against human lung carcinoma cell line (HCT-116), breast cancer cell line (MDAMB231), leukemic cancer cell line (K562), and normal cell line (HEK293) by MTT assay using doxorubicin as the standard drug. The test derivatives were additionally docked for the B-subunit of enzyme DNA gyrase from E. coli at the ATPase binding site to study the molecular interactions using Schrodinger maestro v11.5 software. Results and discussion Most of the synthesized derivatives have shown high activity against Gram-negative bacteria particularly E. coli and K. pneumonia with MIC ranging from 1.95 to 7.81 μg/ml. The derivatives have demonstrated very less activity against tested Gram positive bacterial and fungal strains. The derivatives DS-14 and DS-20 have been found to active against breast cancer cell line and human colon carcinoma cell line having IC 50 in the range of 19–65 µg/ml. All the derivatives were found to less potent against leukemic cancer cell line. The synthesized derivatives have revealed their safety by exhibiting very less cytotoxicity against the normal cell line (HEK-293) with IC 50 > 100 µg/ml. Most of the active derivatives have shown good docking scores in comparison to the standard drugs against DNA gyrase from E. coli . Further ADME predictions by Qikprop module of the Schrodinger confirmed these molecules have drug like properties. Conclusion The derivatives DS-14 and DS-20 have shown potential against Gram-negative bacteria and breast cancer cell line and can be used as a lead for rational drug designing of the antimicrobial and cytotoxic agents. .

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Synthesis of new Schiff bases bearing 1,2,4-triazole, thiazolidine and chloroazetidine moieties and their pharmacological evaluation

Cited by 34 publications

References 32 publications

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Recent Advances in the Synthesis of Spiro‐β‐Lactams and Spiro‐δ‐Lactams

Synthesis, Molecular Properties Prediction and Antimicrobial Activity of Imidazolyl Schiff Bases, Triazoles and Azetidinones

Indole hybridized diazenyl derivatives: synthesis, antimicrobial activity, cytotoxicity evaluation and docking studies

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