Synthesis and Antibacterial Activity Studies of 8,9‐Dihydro [7h] Benzo 1,2,4‐Oxadiazoles and its Coumarin Derivatives

Srinivas, B.; Suryachandram, Jettiboina; Devi, Yerraguntla Katyayani; Rao, Koya Prabhakara

doi:10.1002/jhet.2960

Cited by 13 publications

(10 citation statements)

References 21 publications

(13 reference statements)

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“…The coumarin–oxadiazole hybrids showed weak‐to‐moderate antibacterial activity; for example, hybrids 32 (MIC: 31.2 to >125 µg/ml) were far less potent than ciprofloxacin (MIC: 0.5 µg/ml) against S. aureus and E. coli . [ 77,78 ] The coumarin–oxadiazoline hybrids 33 (MIC: 7.8–250 µg/ml) displayed moderate‐to‐excellent activity against S. aureus , B. subtilis , P. aeruginosa , and E. coli , and the introduction of methoxy into phenyl ring (R position) was favorable to the activity. [ 79 ] Compound 33 (MIC: 7.8–15.6 µg/ml) was found to be most active against the tested strains, warranting further investigations.…”

Section: Coumarin–isoxazole/oxadiazole Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

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Infections caused by Gram-positive and -negative bacteria are one of the foremost causes of morbidity and mortality globally. Antibiotics are the mainstay of therapy for bacterial infections, but the emergence and wide spread of drug-resistant pathogens have already become a huge issue for public healthcare systems. The coumarin moiety, which is ubiquitous in nature, could bind to the B subunit of DNA gyrase in bacteria and inhibit DNA supercoiling by blocking the ATPase activity; hence, coumarin derivatives possess potential antibacterial activity. Several coumarin-containing hybrids such as coumermycin A1, clorobiocin, and novobiocin have already been used in clinical practice for the treatment of various bacterial infections; thus, it is conceivable that hybridization of the coumarin moiety with other antibacterial pharmacophores may provide opportunities for the development of novel antibiotics. This review outlines the advances in coumarin-containing hybrids with antibacterial potential in the recent 5 years and the structure-activity relationships are also discussed. K E Y W O R D S antibacterial, coumarin, hybrid compounds, structure-activity relationships

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Section: Coumarin–isoxazole/oxadiazole Hybridsmentioning

confidence: 99%

Coumarin‐containing hybrids and their antibacterial activities

Feng

Zhang

Yang

et al. 2020

Archiv der Pharmazie

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“…Besides, one of the major research area for our group is to design and synthesize a new heterocyclic scaffold containing compounds for novel biological activity and material applications. 8 , 19 − 26 …”

Section: Introductionmentioning

confidence: 99%

Design and Synthesis of “Chloropicolinate Amides and Urea Derivatives” as Novel Inhibitors for Mycobacterium tuberculosis

et al. 2021

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A series of 30 novel diamino phenyl chloropicolinate fettered carboxamides, urea, and thiourea derivatives were synthesized by coupling of methyl 4-amino-6-(2-aminophenyl)-3-chloropyridine-2-carboxylate with different acid chlorides, urea, and thiourea moieties, respectively. All of these compounds were characterized by 1H and 13C nuclear magnetic resonance spectroscopy, CHN analysis, and high-resolution mass spectra for confirmation of the structures. Two compounds were also characterized by single-crystal X-ray diffraction analysis to confirm the structures obtained by spectral analysis. All these 30 compounds were tested for their in vitro antimycobacterial activity using the microplate alamar blue assay method against Mycobacterium tuberculosis. Five compounds have shown good minimum inhibitory concentration (MIC) values with low cytotoxicity when compared with the reference drugs. Moreover, some of the compounds have high MIC values compared with isoniazid, rifampicin, and so forth and also had shown good reign in the spread of bacteria by the nutrient starvation model. These antimycobacterial activity results have shown a good correlation with molecular docking model analysis with the inhibitors MurB by exhibiting strong interactions. Some of these compounds could be promising candidates against M. tuberculosis for future preclinical agent drug development.

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“…Coumarins (known as benzopyran-2-ones) are a family of lactones and they are the most abundant secondary metabolite. They show important biological activities such as antibacterial (6,7), antifungal (8,9), anti-tubercular (10,11), antitumor (12), antioxidant (13), and anti-HIV (14). Also, coumarins are used as food additive and cosmetics industry (15).…”

Section: Introductionmentioning

confidence: 99%

Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

Yılmaz¹,

Faiz

2018

Journal of the Turkish Chemical Society Section A: Chemistry

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In this work, 15 different coumarin hydrazides were successfully synthesized and screened for their antioxidant and antilipase activities. To do this, firstly, salicylaldehyde derivatives and Meldrum's Acid were reacted in absolute ethanol with catalytic amount of pyridine to obtain coumarin-3-carboxylic acid derivatives (1a-e). Then, these compounds were treated with 1H-benzotriazole in dichloromethane by using thionyl chloride to synthesize benzotriazole derivatives (2a-e). Then, compounds 2a-e were reacted with three commercial hydrazides (nicotinic hydrazide, benzhydrazide,and phenyl acetichydrazide) in ethanol by using microwave irradiation and conventional heating procedures to obtain final products (3-5a-e). Finally, these compounds were tested for their anti-oxidant and anti-lipase activities. The structure of newly synthesized compounds was identified by IR, 1 H NMR, 13 C NMR, and elemental analysis data.

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Synthesis and Antibacterial Activity Studies of 8,9‐Dihydro [7h] Benzo 1,2,4‐Oxadiazoles and its Coumarin Derivatives

Cited by 13 publications

References 21 publications

Coumarin‐containing hybrids and their antibacterial activities

Coumarin‐containing hybrids and their antibacterial activities

Design and Synthesis of “Chloropicolinate Amides and Urea Derivatives” as Novel Inhibitors for Mycobacterium tuberculosis

Microwave-Assisted Synthesis and Biological Evaluation of Some Coumarin Hydrazides

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