A facile and convenient synthesis of novel imidazo[1,2-b] isoxazoles and their Mannich bases as potential biodynamic agents

Rajanarendar, E.; Thirupathaiah, Kammari; Ramakrishna, Seeram; Nagaraju, D.

doi:10.1016/j.cclet.2015.07.024

Cited by 5 publications

(4 citation statements)

References 18 publications

(10 reference statements)

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“…[28,29] 4.1. methoxybenzaldehyde (0.01 mol), were refluxed in glacial acetic acid for 7-9 h. The precipitate was filtered and crystallized from acetic acid. [26,27] Ethyl 106-107°C, as reported. [30] 4.1.5 | Synthesis of ethyl 4-[(4-oxothiazolidin-2ylidene)amino]benzoate (5) To a solution of ethyl 4-(2-chloroacetamido)benzoate (4) (0.01 mol) in ethanol (30 ml), ammonium thiocyanate (0.015 mol) was added.…”

Section: Adme and Drug-likeness Predictionmentioning

confidence: 60%

“…Equimolar amounts of ethyl 4‐aminobenzaote ( 1 ), 2‐(benzo[ d ]thiazol‐2‐yl)acetonitrile ( 2 ), and appropriate aldehydes, namely, furaldehyde, benzaldehyde, 4‐chloro benzaldehyde, 4‐fluoro benzaldehyde, and 4‐methoxybenzaldehyde (0.01 mol), were refluxed in glacial acetic acid for 7–9 h. The precipitate was filtered and crystallized from acetic acid. [ 26,27 ]…”

Section: Methodsmentioning

confidence: 99%

“…In Scheme 1, the arylidene derivatives 3a-e were synthesized via refluxing benzocaine 1 with benzothiazole acetonitrile 2 and appropriate aromatic aldehydes in glacial acetic acid. [26,27] The synthon 2 was prepared via the cyclization reaction of O-aminothiophenol and malononitrile according to the reported procedure. [28,29] On the other hand, chloroacetamide benzoate derivative 4 was obtained in a good yield from benzocaine 1 by treatment with chloroacetyl chloride using acetic acid as a solvent stirred in a warm water bath for 15 min according to the reported procedure.…”

Section: Chemistrymentioning

confidence: 99%

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Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Elzahabi

Nossier

Mousa

et al. 2022

Archiv der Pharmazie

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The need for new chemotherapeutics to overcome development of resistance merits research to discover new agents. Benzocaine derivatives are essential compounds in medicinal chemistry due to their various biological activities including antibacterial and anticancer activities. Therefore, this study focuses on the synthesis of new benzocaine derivatives 3a–e, 6, 7a and 7b, 8, 10–14, and 16a–d and their in vitro evaluation as antibacterial agents against gram +ve and –ve strains and as anticancer agents against HepG‐2, HCT‐116, and MCF‐7 human cancer cell lines. The obtained results demonstrated that thiazolidines 6 and 7b showed higher antibacterial and anticancer activity in comparison with the reference drugs. In addition, 6 and 7b showed high potency as inhibitors toward their biological targets, that is DNA gyrase and human topoisomerase IIα, as compared to the reference standard drugs novobiocin and etoposide, respectively. Molecular docking demonstrated that both compounds could identify the active site of their target enzymes and develop effective binding interactions. Absorption, distribution, metabolism and elimination (ADME) and drug‐likeness predictions of both compounds showed that they both have good ADME profiles and no structural alerts that might cause toxicity. Based on this, 6 and 7b could serve as lead compounds for the design of more potent antibacterial and anticancer agents.

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Section: Adme and Drug-likeness Predictionmentioning

confidence: 60%

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 1 more Smart Citation

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Elzahabi

Nossier

Mousa

et al. 2022

Archiv der Pharmazie

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“…The synthesis of compounds 10a and 10b was carried out by the treatment of NaOH in water under reflux condition, thereby introducing 1,2,4-triazole nucleus to piperazine skeleton. It is well known that bioactive compounds can be more effective if two or more biologically active heterocyclic systems are introduced to their structures as a single molecular framework [28][29][30] (Scheme 2). It is also known that 1,2,4-triazol-3-(thi)ol derivatives can be found in Scheme 1 Synthesis of compounds 2, 3, 4a-c, 5a, and 5b mercapto-thioxo (or enol-keto) tautomeric forms.…”

Section: Synthesis and Characterizationmentioning

confidence: 99%

Newly synthesized piperazine derivatives as tyrosinase inhibitors: in vitro and in silico studies

et al. 2022

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In this study, a series of new organic compounds with piperazine as a fundamental skeleton was synthesized and evaluated for their tyrosinase inhibitory potentials by in vitro and in silico studies. The in vitro studies have shown that compounds 10a and 10b bearing 1,2,4, triazole nucleus could be considered potent tyrosinase inhibitors with IC 50 values of 31.2 ± 0.7 and 30.7 ± 0.2 µM, respectively. 10b (K i = 9.54 µM, mixed type inhibition) with the lowest IC 50 value among derivatives was selected to determine kinetic constants and inhibition types. Furthermore, molecular docking analysis was performed for all compounds and it was observed that 4b, 5a, 4c, and 10b showed promising inhibitory effect on tyrosinase activity. Based on docking results, ADME predictions and in vitro studies, 10b might be considered suitable oral drug candidates for further studies.

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Synthesis of hydrazine containing piperazine or benzimidazole derivatives and their potential as α-amylase inhibitors by molecular docking, inhibition kinetics and in vitro cytotoxicity activity studies

et al. 2021

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A facile and convenient synthesis of novel imidazo[1,2-b] isoxazoles and their Mannich bases as potential biodynamic agents

Cited by 5 publications

References 18 publications

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Antibacterial and anticancer profiling of new benzocaine derivatives: Design, synthesis, and molecular mechanism of action

Newly synthesized piperazine derivatives as tyrosinase inhibitors: in vitro and in silico studies

Synthesis of hydrazine containing piperazine or benzimidazole derivatives and their potential as α-amylase inhibitors by molecular docking, inhibition kinetics and in vitro cytotoxicity activity studies

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