Synthesis, cytotoxicity and in vitro antibacterial screening of novel hydrazones bearing thienopyridine moiety as potent COX-2 inhibitors

Sanad, Sherif M. H.; Mekky, Ahmed E. M.

doi:10.1007/s13738-020-01987-y

Cited by 31 publications

(12 citation statements)

References 48 publications

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“…[36] 2-Thioxopyridine-3-carbonitriles 6(7) were prepared according to literature procedures. [42][43][44] 4.1 | Preparation of nicotinonitriles 9(10) A mixture of 2-thioxopyridine-3-carbonitriles 6(7) (5 mmol) in ethanol (20 mL) containing KOH (5 mmol) was stirred at rt for 10 minutes. To the mixture, a solution of benzyl chloride derivative 8 (5 mmol) in 10 mL of ethanol was added and the stirring was continued for 2 hours.…”

Section: Methodsmentioning

confidence: 99%

“…Therefore, each of acetophenones 2 was reacted with benzaldehyde 1a or anisaldehyde 1b in ethanolic potassium hydroxide solution under stirring at room temperature (rt) for 3 hours to afford a series of α,β-unsaturated carbonyl derivatives 3(4). [37][38][39][40][41] Each of the latter derivatives were cyclocondensed with 2-cyanothioacetamide 5 in ethanol in the presence of piperidine at reflux for 5 hours afforded the key intermediates 2-thioxopyridine-3-carbonitriles 6(7) [42][43][44] (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and in vitro study of new coumarin derivatives linked to nicotinonitrile moieties as potential acetylcholinesterase inhibitors

Mekky

Sanad

2020

Journal of Heterocyclic Chem

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The appropriate pyridine-2(1H)-thiones were reacted with an equivalent amount of 5-(chloromethyl)-2-hydroxybenzaldehyde in ethanol in the presence of potassium hydroxide to give the corresponding 2-hydroxybenzaldehyde derivatives in excellent yields. The latter derivatives were taken as key synthons for the preparation of the target hybrids. Therefore, 2-hydroxybenzaldehydes were reacted with benzoylglycine in acetic anhydride in the presence of fused sodium acetate at 100 C for 6 hours to afford a new series of nicotinonitrile-coumarin hybrids. The in vitro acetylcholinesterase inhibitory activities were estimated for the new coumarins. The results were expressed as the inhibition percentage of the tested hybrids at concentration of 25 nM, compared to donepezil as a reference (inhibition percentage of 70.5). Coumarin hybrids linked to 6-(4-nitrophenyl) or 6-(4-chlorophenyl)-4-phenylnicotinonitrile exhibited more effective inhibitory activities than donepezil with inhibition percentages of 94.1 and 72.3, respectively. The new coumarins were tested for their free radical-scavenging capabilities against DPPH. Furthermore, some new coumarins were tested for in vitro cytotoxic activity against each MCF-10A, MCF-7, Caco2, and HEPG2. The new hybrids showed cytotoxicity in micromolar range (IC 50 of 3.5-13.9 μM) against all tested cell lines. These results clearly demonstrated that the hybrids being tested are not cytotoxic at the concentration required to inhibit acetylcholinesterase effectively.

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Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Synthesis and in vitro study of new coumarin derivatives linked to nicotinonitrile moieties as potential acetylcholinesterase inhibitors

Mekky

Sanad

2020

Journal of Heterocyclic Chem

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“…27. 97 A series of fused-ring derivatives incorporating a thienopyridine moiety were reported by Sanad et al 98 to be COX-2 inhibitors with significant antibacterial activity (Fig. 26).…”

Section: Rsc Medicinal Chemistry Reviewmentioning

confidence: 99%

Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors

et al. 2022

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“…Several studies have shown that thienopyridine-fused pyrimidines linked to a thiophene unit have significant bioactivity, including antimicrobial and cytotoxic activity. [43][44][45] Motivated by the aforementioned findings and in context with our attempts to develop facile synthetic routes to prepare potential bioactive hybrids, [46][47][48][49] we report an efficient one-pot method for the preparation of a new series of pyrazolo [3,4b]pyridine-fused mono-and bis(pyrimidines) linked to a thiophene unit as potential cytotoxic agents. SwissADME program was used to calculate the physicochemical properties and drug-likeness of new pyrimidines.…”

Section: Introductionmentioning

confidence: 99%

3‐Aminopyrazolo[3,4‐b]pyridine: Effective Precursor for Barium Hydroxide‐Mediated Three Components Synthesis of New Mono‐ and Bis(pyrimidines) with Potential Cytotoxic Activity

Sanad

Mekky

2021

Chemistry & Biodiversity

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In this study, an efficient one-pot procedure for preparing a new series of pyrazolo [3,4-b]pyridine-fused pyrimidines was described. The target hybrids were developed through a three-component reaction of 3-amino-1H-pyrazolo [3,4-b]pyridine, benzaldehydes, and acetophenones (molar ratio 1 : 1 : 1). The best conditions for the previous reaction were 2.5 equivalents of barium hydroxide in DMF at 150 °C for 6 h. New bis(pyrimidines) were synthesized in high yields using a similar one-pot reaction protocol with some modifications. Thus, two equivalents of each of the appropriate acetophenones and 3-aminopyrazolopyridine were reacted with one equivalent of the appropriate bis(aldehydes). The reaction was carried out at 150 °C for 8 h using 4.5 equivalents of barium hydroxide in DMF. Repeating the previous reaction with the appropriate bis(acetyl) derivatives and benzaldehydes resulted in good yields of the target bis(pyrimidines). The in vitro cytotoxic activity of new pyrimidines against the MCF-7, HEPG2, and Caco2 cell lines was evaluated using the reference doxorubicin (IC 50 values of 4.34 -6.97 μM). Hybrid 6h had the best activity against Caco2 and MCF-7 cell lines, IC 50 values of 12.62 and 14.50 μM, respectively. The IC 50 values for hybrids 6c, 6e, and 6f against MCF-7 and Caco2 cell lines were 23.99 -41.69 and 33.14 -43.33 μM, respectively. Furthermore, hybrid 6e displayed IC 50 value of 20.06 μM HEPG2 cell lines, while the hybrids 6c, 6f and 6h exhibited IC 50 values ranging between 26.29 -50.51 μM. Furthermore, hybrid 6e had an IC 50 value of 20.06 μM for the HEPG2 cell lines, whereas hybrids 6c, 6f, and 6h had IC 50 values ranging from 26.29 to 50.51 μM.

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Synthesis, cytotoxicity and in vitro antibacterial screening of novel hydrazones bearing thienopyridine moiety as potent COX-2 inhibitors

Cited by 31 publications

References 48 publications

Synthesis and in vitro study of new coumarin derivatives linked to nicotinonitrile moieties as potential acetylcholinesterase inhibitors

Synthesis and in vitro study of new coumarin derivatives linked to nicotinonitrile moieties as potential acetylcholinesterase inhibitors

Non-steroidal anti-inflammatory drugs: recent advances in the use of synthetic COX-2 inhibitors

3‐Aminopyrazolo[3,4‐b]pyridine: Effective Precursor for Barium Hydroxide‐Mediated Three Components Synthesis of New Mono‐ and Bis(pyrimidines) with Potential Cytotoxic Activity

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