Ultrasonication-ionic liquid synergy for the synthesis of new potent anti-tuberculosis 1,2,4-triazol-1-yl-pyrazole based spirooxindolopyrrolizidines

Pogaku, Vinay; Krishna, Vagolu Siva; Sriram, Dharmarajan; Rangan, Krishnan; Basavoju, Srinivas

doi:10.1016/j.bmcl.2019.04.026

Cited by 50 publications

(30 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The in vitro cytotoxicity of the synthesized compounds was assessed by 3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide (MTT) assay against growth inhibition of RAW 264.7 cells at 50 μg/mL concentration . The values were calculated for percentage inhibition that enables us to achieve the cytotoxicity data of the test compounds.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Doğan

Buran

Gündüz

et al. 2019

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

The discovery of new antimicrobial agents is extremely needed to overcome multidrug-resistant bacterial and tuberculosis infections. In the present study, eight novel substituted urea derivatives (10a-10h) containing disulfide bond were designed, synthesized and screened for their in vitro antimicrobial activities on standard strains of Gram-positive and Gram-negative bacteria as well as on Mycobacterium tuberculosis. According to the obtained results, antibacterial effects of the compounds were found to be considerably better than their antimycobacterial activities along with their weak cytotoxic effects. Molecular docking studies were performed to gain insights into the antibacterial activity mechanism of the synthesized compounds. The interactions and the orientation of compound 10a (1,1'-((disulfanediylbis(methylene))bis(2,1-phenylene))bis(3-phenylurea)) were found to be highly similar to the original ligand within the binding pocket E. faecalis β-ketoacyl acyl carrier protein synthase III (FabH). Finally, a theoretical study was established to predict the physicochemical properties of the compounds. Scheme 1. Synthetic scheme for the preparation of the key compound, 2,2'-[disulfanediylbis(methylene)]dibenzoic acid (5).

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Doğan

Buran

Gündüz

et al. 2019

Chemistry & Biodiversity

Self Cite

View full text Add to dashboard Cite

show abstract

“…39 ) were synthesized and evaluated for their anti-TB potential against Mtb H 37 Rv by Pogaku et al. [ 171 ]. Among all, most active compound 192a was 2 folds more potent (MIC: 0.78 μg/mL) than the standard drug ethambutol and compounds 192b-g were equally potent to ethambutol (MIC: 1.56 μg/mL).…”

Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

216

View full text Add to dashboard Cite

The present review aims to summarize the pharmacological profile of 1,2,4-triazole, one of the emerging privileged scaffold, as antifungal, antibacterial, anticancer, anticonvulsant, antituberculosis, antiviral, antiparasitic, analgesic and anti-inflammatory agents, etc. along with structure-activity relationship. The comprehensive compilation of work carried out in the last decade on 1,2,4-triazole nucleus will provide inevitable scope for researchers for the advancement of novel potential drug candidates having better efficacy and selectivity.

show abstract

“…This methodology proved to be efficient, as short reaction times were required and good yields were obtained. Furthermore, the ionic liquid could be reused without significant loss of activity [20] …”

Section: Spirooxindole Derivativesmentioning

confidence: 99%

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Brandão

Marques

Carreiro

et al. 2021

The Chemical Record

View full text Add to dashboard Cite

Multicomponent reactions (MCRs) are a valuable tool in diversity‐oriented synthesis. Its application to privileged structures is gaining relevance in the fields of organic and medicinal chemistry. Isatin, due to its unique reactivity, can undergo different MCRs, affording multiple interesting scaffolds, namely oxindole‐derivatives (including spirooxindoles, bis‐oxindoles and 3,3‐disubstituted oxindoles) and even, under certain conditions, ring‐opening reactions occur that leads to other heterocyclic compounds. Over the past few years, new methodologies have been described for the application of this important and easily available starting material in MCRs. In this review, we explore these novelties, displaying them according to the structure of the final products obtained.

show abstract

Ultrasonication-ionic liquid synergy for the synthesis of new potent anti-tuberculosis 1,2,4-triazol-1-yl-pyrazole based spirooxindolopyrrolizidines

Cited by 50 publications

References 38 publications

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

An insight on medicinal attributes of 1,2,4-triazoles

Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity

Contact Info

Product

Resources

About