The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole/ 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones

Rollas, Sevım

doi:10.12991/201216410

Cited by 6 publications

(2 citation statements)

References 49 publications

(56 reference statements)

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“…[36,37] The conversion of 10 into oxadiazolyl derivative 11 occurred under reflux with acetic anhydride. [38,39] Compound 12 was achieved in good yield by refluxing compound 10 with hydroxylamine HCl in acetic acid in the presence of fused sodium acetate to enhance cyclization of the hydrazone moiety in affording oxadiazole derivative. Moreover, compound 13 was afforded upon refluxing compound 10 with morpholine in ethanol using reported procedures.…”

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: Chemistrymentioning

confidence: 99%

“…180-183°C. IR (KBr) (cm Compound 10 (0.01 mol) was refluxed in acetic anhydride (10 ml) for 1 h. [38,39] After cooling, the reaction mixture was poured into ice water; the precipitate was washed with water and crystallized from ethanol to yield a white powder (60%), m.p. 260-264°C.…”

Section: Synthesis Of 4-aminobenzohydrazide (9)mentioning

confidence: 99%

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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Synthesis, Biological Evaluation andin SilicoStudies of 3‐Hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide Derivatives

Kamboj

Thakral

Kumar

et al. 2023

Chemistry & Biodiversity

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In the present study, a series of 3‐hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide derivatives were synthesized, characterized and evaluated for theirin vitroactivity, i. e., antimicrobial, antioxidant and anti‐inflammatory. The target compounds were synthesized by condensation reaction of 3‐hydroxy‐2‐naphthoic acid hydrazide with substituted benzaldehydes which were subjected to cyclization reaction with thioglycolic acid and ZnCl2 to get target compounds. The synthesized 3‐hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide derivatives were examined for their antimicrobial activity and 3‐hydroxy‐N‐(4‐oxo‐2‐(3,4,5‐trimethoxyphenyl)thiazolidin‐3‐yl)‐2‐naphthamide (S20) exhibited the highest antimicrobial potential. The N′‐(2,3‐dichlorobenzylidene)‐3‐hydroxy‐2‐naphthohydrazide (S5) displayed good antifungal potential against Rhizopus oryzae, whereas N′‐(2,3‐dichlorobenzylidene)‐3‐hydroxy‐2‐naphthohydrazide (S20) showed the highest antioxidant potential and N‐(2‐(2,6‐dichlorophenyl)‐4‐oxothiazolidin‐3‐yl)‐3‐hydroxy‐2‐naphthamide (S16) displayed the highest anti‐inflammatory activity. The results of molecular docking studies revealed that existence of hydrogen bonding and hydrophobic interactions with their respective proteins. In silico ADMET studies were carried out by Molinspiration, Pre‐ADMET and OSIRIS property explorer to predict the pharmacokinetic behaviour of synthesized 3‐hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide derivatives.

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ChemInform Abstract: The Synthesis and Biological Activities of 3‐Acyl‐2,3‐dihydro‐1,3,4‐oxadiazole/3‐Acyl‐1,3,4‐oxadiazoline Derivatives Obtained from Hydrazide‐hydrazones

Rollas

Karakuş

2013

ChemInform

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The synthesis and biological activities of 3-acyl- 2,3-dihydro-1,3,4-oxadiazole/ 3-acyl-1,3,4-oxadiazoline derivatives obtained from hydrazide-hydrazones

Cited by 6 publications

References 49 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

Synthesis, Biological Evaluation andin SilicoStudies of 3‐Hydroxy‐N‐(2‐(substituted phenyl)‐4‐oxothiazolidin‐3‐yl)‐2‐napthamide Derivatives

ChemInform Abstract: The Synthesis and Biological Activities of 3‐Acyl‐2,3‐dihydro‐1,3,4‐oxadiazole/3‐Acyl‐1,3,4‐oxadiazoline Derivatives Obtained from Hydrazide‐hydrazones

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