2,5-Disubstituted 1,3,4-oxadiazole derivatives of chromeno[4,3-<i>b</i>]pyridine: synthesis and study of antimicrobial potency

Jadhav, Ghanshyam R.; Deshmukh, Dattatray G.; Medhane, Vijay; Gaikwad, V. B.; Bholay, Avinash D.

doi:10.1515/hc-2015-0215

Cited by 25 publications

(10 citation statements)

References 37 publications

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“…The ligands of each of Q7 and Q8 possess either the benzothiazole moiety or the p -chloro substituent. Enhanced antimicrobial activity of compounds containing either benzothiazole moiety or the chlorine substituent in the para-position is in accordance with the literature report [ 55 , 56 ] making them targets for drug design. In addition, both Q7 and Q8 have the perchlorate anion.…”

Section: Resultssupporting

confidence: 90%

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

et al. 2021

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A series of fifteen silver (I) quinoline complexes Q1–Q15 have been synthesized and studied for their biological activities. Q1–Q15 were synthesized from the reactions of quinolinyl Schiff base derivatives L1–L5 (obtained by condensing 2-quinolinecarboxaldehyde with various aniline derivatives) with AgNO3, AgClO4 and AgCF3SO3. Q1–Q15 were characterized by various spectroscopic techniques and the structures of [Ag(L1)2]NO3Q1, [Ag(L1)2]ClO4Q6, [Ag(L2)2]ClO4Q7, [Ag(L2)2]CF3SO3Q12 and [Ag(L4)2]CF3SO3Q14 were unequivocally determined by single crystal X-ray diffraction analysis. In vitro antimicrobial tests against Gram-positive and Gram-negative bacteria revealed the influence of structure and anion on the complexes′ moderate to excellent antibacterial activity. In vitro antioxidant activities of the complexes showed their good radical scavenging activity in ferric reducing antioxidant power (FRAP). Complexes with the fluorine substituent or the thiophene or benzothiazole moieties are more potent with IC50 between 0.95 and 2.22 mg/mL than the standard used, ascorbic acid (2.68 mg/mL). The compounds showed a strong binding affinity with calf thymus-DNA via an intercalation mode and protein through a static quenching mechanism. Cytotoxicity activity was examined against three carcinoma cell lines (HELA, MDA-MB231, and SHSY5Y). [Ag(L2)2]ClO4Q7 with a benzothiazole moiety and [Ag(L4)2]ClO4Q9 with a methyl substituent had excellent cytotoxicity against HELA cells.

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Section: Resultssupporting

confidence: 90%

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

et al. 2021

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“…Griseofulvin used as reference substance displayed similar activity (MIC = 3 µg/ml, ZOI = 16.8 mm) ( Fig. 32) (Jadhav et al 2016). Ghaisas and Patel (2018) synthesized novel series of 1-(2-(3-phenoxyphenyl)-5-((substitutedaminoaryl)methyl)-1,3,4-oxadiazol-3(2H)-yl)ethanone and evaluated their activity against: C. albicans (MTCC 227), A. niger (MTCC 282) and A. clavatus (MTCC 1323).…”

Section: Antifungal Activitymentioning

confidence: 81%

“…Its activity, as authors suggest, may be connected with the substitution of chlorine atom at para position of phenyl ring (Fig. 17) (Jadhav et al 2016). Lole et al (2016) synthesized novel 1,3,4-oxadiazole derivatives and evaluated their antibacterial activity against E. coli and S. aureus.…”

Section: Antibacterial Activitymentioning

confidence: 99%

“…Authors also suggested that the presence of furan ring increases the antifungal activity of synthesized derivatives (Zorzi et al 2014). Novel 2,5-disubstituted 1,3,4-oxadiazoline derivatives of chromen[4,3-b]pyridine were synthesized by Jadhav et al (2016) and tested for antifungal activity against two species of fungi: C. albicans (MTCC 277) and A. niger (MCIM 545). One of the obtained derivatives with 4-NO 2 -phenyl substituent 103 showed interesting activity (MIC = 5 µg/ml, ZOI = 14.4 mm).…”

Section: Antifungal Activitymentioning

confidence: 99%

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Antimicrobial and antiprotozoal activity of 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines: a review

2019

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In the last 20 years there has been a significant increase in interest in the structure of oxadiazole derivatives, especially 3-acetyl-1,3,4-oxadiazolines. It is known that these derivatives possess: antibacterial, antifungal, antitubercular, antiprotozoal, anticancer and anti-inflammatory activity. Therefore, many medicinal chemists choose 3-acetyl-1,3,4oxadiazoline scaffold for the synthesis of new potentially active substances with a better effectiveness and less toxicity. This article is a literature review since 2000 presenting new derivatives with proven antimicrobial and antiprotozoal activity, containing in its structure a 3-acetyl-1,3,4-oxadiazoline system.

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“…The 3-acetyl-1,3,4-oxadiazolines are usually obtained as a result of the cyclization reaction of the corresponding hydrazones in an acetic anhydride medium [ 12 , 30 , 42 , 43 , 44 , 45 ].…”

Section: Introductionmentioning

confidence: 99%

Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines: Synthesis and Biological Activity

et al. 2020

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The aim of our study was the two-stage synthesis of 1,3,4-oxadiazole derivatives. The first step was the synthesis of hydrazide–hydrazones from 3-methyl-4-nitrobenzhydrazide and the corresponding substituted aromatic aldehydes. Then, the synthesized hydrazide–hydrazones were cyclized with acetic anhydride to obtain new 3-acetyl-2,3-disubstituted-1,3,4-oxadiazolines. All of obtained compounds were tested in in vitro assays to establish their potential antimicrobial activity and cytotoxicity. Our results indicated that few of the newly synthesized compounds had some antimicrobial activity, mainly compounds 20 and 37 towards all used reference bacterial strains (except Klebsiella pneumoniae, Proteus mirabilis, and Pseudomonas aeruginosa) and fungi. These substances showed a strong or powerful bactericidal effect, especially against Staphylococcus spp. belonging to Gram-positive bacteria. Compound 37 was active against Staphylococcus epidermidis at minimal inhibitory concentration (MIC) = 0.48 µg/mL and was characterized by low cytotoxicity. This compound possessed quinolin-4-yl substituent in the second position of 1,3,4-oxadiazole ring and 3-methyl-4-nitrophenyl in position 5. High effectiveness and safety of these derivatives make them promising candidates as antimicrobial agents. Whereas the compound 20 with the 5-iodofurane substituent in position 2 of the 1,3,4-oxadiazole ring showed the greatest activity against S. epidermidis at MIC = 1.95 µg/mL.

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2,5-Disubstituted 1,3,4-oxadiazole derivatives of chromeno[4,3-b]pyridine: synthesis and study of antimicrobial potency

Abstract: A convenient synthesis of 1,3,4-oxadiazole containing derivatives of chromeno[4,3-

Cited by 25 publications

References 37 publications

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

Quinoline Functionalized Schiff Base Silver (I) Complexes: Interactions with Biomolecules and In Vitro Cytotoxicity, Antioxidant and Antimicrobial Activities

Antimicrobial and antiprotozoal activity of 3-acetyl-2,5-disubstituted-1,3,4-oxadiazolines: a review

Novel 3-Acetyl-2,5-disubstituted-1,3,4-oxadiazolines: Synthesis and Biological Activity

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