Microwave-assisted synthesis of some hybrid molecules containing penicillanic acid or cephalosporanic acid moieties and investigation of their biological activities

Basoglu, Serap; Ülker, Serdar; Karaoğlu, Şengül Alpay; Demirbaş, Neslihan

doi:10.1007/s00044-013-0898-4

Cited by 17 publications

(7 citation statements)

References 30 publications

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“…In addition, in one of our previous studies the discovery of some azole compounds as antiurease agents served to merge the azole groups, namely 1,3‐oxazol(idin)e and 1,3‐thiazol(idin)e, with the penicillanic acid skeleton. Another reason for choosing these azole groups for hybridization is that some hybrid compounds carrying 1,3‐oxazol(idin)e or 1,3‐thiazol(idin)e nucleus were obtained as antilipase agents in our laboratory .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some Heterofunctionalized Penicillanic Acid Derivatives and Investigation of Their Biological Activities

Demirci

Demırbas

Ülker

et al. 2013

Archiv der Pharmazie

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6-Substituted amino-penicillanic acid esters were synthesized starting with 6-apa. The compounds containing a 1,3-thiazole- or 1,3-thiazolidinone nucleus linked to the penicillanic acid skeleton via a hydrazino linkage were obtained from 6-apa. The treatment of carbonylamino and carbonothioylamino compounds with 4-chlorophenacyl bromide or ethyl bromoacetate gave 6-bis{4-[1,3-thiazol(idinone)amino]benzoyl}amino derivatives of 6-apa. Benzyl derivatives were synthesized in several steps, starting with 4-aminobenzoyl chloride. The treatment of 4-{[3-benzyl-4-oxo-1,3-thia(oxa)zolidin-2-ylidene]amino}benzoyl chlorides with 6-apa in ethanolic solution produced the 6-[bis(4-{[3-benzyl-4-oxo-1,3-thiazolidin-2-ylidene]amino}benzoyl)amino] derivative of penicillanic acid, while the reaction of the same intermediates in DMF gave the mono-substituted amino derivative of 6-apa. The synthesized compounds were screened for their biological activities, and some of them were found to possess good to moderate antimicrobial activity. Moreover, some of the compounds displayed antiurease, anti-β-lactamase, and/or antilipase activities.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Some Heterofunctionalized Penicillanic Acid Derivatives and Investigation of Their Biological Activities

Demirci

Demırbas

Ülker

et al. 2013

Archiv der Pharmazie

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“…Our research group has previously reported the synthesis of novel imine compounds, and most of these exhibited several biological activities including antimicrobial, antitumor, enzyme inhibition, and so on . As a part of our efforts aiming to obtain bioactive hybrid molecules, we performed the synthesis of arylidenehydrazides ( 5a , 5b , 5c , 5d , 5e ) via the condensation of compound 3 with suitable aldehydes.…”

Section: Resultsmentioning

confidence: 99%

Conventional and Microwave‐assisted Total Synthesis, Antioxidant Capacity, Biological Activity, and Molecular Docking Studies of New Hybrid Compounds

Demirci

Mermer

et al. 2016

Journal of Heterocyclic Chem

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Thiomorpholine was converted to the corresponding 1,3,4‐oxadiazole (4), arylidenehydrazide (5a, 5b, 5c, 5d, 5e), and 1,2,4‐triazole (7a and, 7b) derivatives via the formation of hydrazide (3). Compounds 4 and 7 were next converted to the corresponding Mannich bases containing piperidin, β‐lactam, fluoroquinolone, piperazine, or morpholine core. Conventional and microwave‐assisted methods were used for all syntheses. The effect of acid catalyst on Mannich reactions was also investigated. All the newly synthesized compounds were screened for their antimicrobial, antiglucosidase, antilipase, anti‐urease, and antioxidant activities. Most exhibited good–moderate antibacterial and/or antifungal activity. Docking of some of the synthesized compounds into the active sites of lipase, α‐glucosidase, and urease was carried out in order to predict the binding affinities and noncovalent interactions stabilizing the enzyme–ligand complexes. Docking results complemented well the experimental results on inhibitory effects of compounds. Higher binding affinities were observed for active compounds in contrary to inactive ones.

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“…Their applications in the treatment of inflammation, pain, migraine and asthma have also been reported. Some morpholine derivatives with antimicrobial activity have been synthesized in our laboratory …”

Section: Introductionmentioning

confidence: 99%

One‐pot, Four‐Component Green Synthesis, Carbonic Anhydrase II Inhibition and Docking Studies of 5‐Arylidenerhodanines

et al. 2018

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In the present study, a planning strategy for N‐substituted‐5‐arylidenerhodanines was developed by the condensation between 3‐morpholinopropan‐1‐amine, aldehyde, ethyl bromoacetate and carbon disulfide in the presence of trimethylamine in water via a one‐pot, sequential four component reaction at room temperature and additionally microwave and ultrasound irradiated techniques. The synthesis of arylidenerhodanine derivatives was performed through the optimized one pot strategy starting from commercially available materials in high yields and purity without troublesome work‐ups, after recrystallization from an appropriate solvent. Enzyme inhibition activity screening studies on CA II was also carried out. IC50 values of some of examined molecules could be determined and it was observed that they were nanomolar level except for 1r, and lower than that of reference molecule. The inhibition in the range of 8.6‐99.4% was seen in the presence of newly synthesized molecules at their reachable maximum concentration in the reaction mixtures. Among the examined molecules, 5a and 5p with the two lowest IC50 values were found to be the most potent inhibitors. In silico studies showed that all of the rhodanine derivatives have higher affinity than reference ligand against binding site, while none of the compounds have demonstrated any interaction with Zn2+ as with the classical sulfonamides.

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Microwave-assisted synthesis of some hybrid molecules containing penicillanic acid or cephalosporanic acid moieties and investigation of their biological activities

Cited by 17 publications

References 30 publications

Synthesis of Some Heterofunctionalized Penicillanic Acid Derivatives and Investigation of Their Biological Activities

Synthesis of Some Heterofunctionalized Penicillanic Acid Derivatives and Investigation of Their Biological Activities

Conventional and Microwave‐assisted Total Synthesis, Antioxidant Capacity, Biological Activity, and Molecular Docking Studies of New Hybrid Compounds

One‐pot, Four‐Component Green Synthesis, Carbonic Anhydrase II Inhibition and Docking Studies of 5‐Arylidenerhodanines

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