Design and synthesis of spiro[indole-thiazolidine]spiro[indole-pyrans] as antimicrobial agents

Sakhuja, Rajeev; Panda, Siva S.; Khanna, Leena; Khurana, Shilpi; Jain, Subhash C.

doi:10.1016/j.bmcl.2011.06.121

Cited by 88 publications

(21 citation statements)

References 34 publications

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“…Sterile filter paper disks (6 mm diameter) were moistened with the test compound solution in DMSO of specific concentration 100 µg/disc and were carefully placed on the agar culture plates that had been previously inoculated separately with the microorganisms. The plates were incubated at 37°C, and the results were recorded for antibacterial activity after 14 h, and for antifungal activity after 30 h. Each experiment was carried out in triplicate, and the average diameter of inhibition zones of bacterial or fungal growth around the disks in mm were recorded by Himedia antibiotic zone scale .…”

Section: Methodsmentioning

confidence: 99%

An Organocatalyzed Efficient One‐pot Synthesis, Biological Evaluation, and Molecular Docking Studies of 4,4′‐(Arylmethylene)bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols)

Mahajan

Nikam

Khedkar

et al. 2016

Journal of Heterocyclic Chem

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The synthesis of 4,4′‐(arylmethylene)bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol) derivatives catalyzed by ʟ‐proline is a simple, versatile, and efficient method. In vitro antioxidant, anti‐inflammatory, and antimicrobial activities of compounds 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i, 4j were studied. Furthermore, to rationalize the observed anti‐inflammatory activity data, molecular docking study has been performed against COX‐2 enzyme which revealed a good binding affinity for these molecules and could provide an insight into the various bonded and non‐bonded interactions guiding their binding affinity.

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Section: Methodsmentioning

confidence: 99%

An Organocatalyzed Efficient One‐pot Synthesis, Biological Evaluation, and Molecular Docking Studies of 4,4′‐(Arylmethylene)bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols)

Mahajan

Nikam

Khedkar

et al. 2016

Journal of Heterocyclic Chem

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“…A literature survey reveals various reports on synthesis of spiro-indole thiazolidinones [47][48][49][50][51][52][53], but to the best of our knowledge there is no report on the synthesis of spiro compounds by incorporating acenapthaquinone and 4-thiazolidinone rings together. Hence, inspired by these findings and in continuation of our ongoing work to develop environmentally benign methodologies [54][55][56][57][58][59][60][61] for the synthesis of biologically useful heterocycles, we have investigated a threecomponent protocol for the synthesis of drug-like spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones from the multi-component reaction of acenapthaquinone, substituted anilines, and a-mercaptoacetic acid in good yield using thiamine hydrochloride as a green, inexpensive, and reusable catalyst in aqueous medium.…”

Section: Introductionmentioning

confidence: 97%

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

Singh

Ganaie

2016

Res Chem Intermed

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A water mediated and thiamine hydrochloride catalysed eco-compatible efficient method was developed for the synthesis of spiro[acenaphthylene-1,2 0 [1,3]-thiazolidine]-2,4 0 (1H)-diones via multi-component reaction of acenaphthylene-1,2-dione, substituted anilines, and a-mercaptocarboxylic acid at 80°C temperature. This transformation involves the formation of two C-N bonds and one C-S bond leading to the creation of a five-member ring in a one-pot operation. Easy availability and recovery of the catalyst, no toxic/organic solvents, and high yield of product make the protocol attractive, sustainable, and economic. Graphical AbstractO O NH 2 1 2 HS O OH 3 O N S O R 1 R 1 R R R 1 = H, CH 3

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“…Thus, continuing our awareness in green strategies and synthesis of biologically important heterocyclic compounds, we hereby compile the recent development in TM catalyzed synthesis of benzimidazoles from o ‐phenylenediamine, converging the latest trends of the past 5 years. This is because the development of competent clean synthetic methods is fast enough in making the older ones redundant.…”

Section: Introductionmentioning

confidence: 99%

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

Singhal

Khanna

Panda

et al. 2019

Journal of Heterocyclic Chem

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Benzimidazole is a heterocyclic moiety of immense importance as it acts as a primary “biolinker” in diverse synthetic routes to obtain bioactive compounds. Substituted benzimidazoles are known to possess a varied range of pharmacological applications, namely, anti‐cancer, anti‐diabetic, anti‐inflammatory, and antiviral like anti‐HIV and anti‐fungal. A number of reviews covering the important aspects of benzimidazoles such as pharmacological activities, SAR studies, and well‐known methods of synthesis have appeared in the literature. However, green synthetic methods particularly using transition metal (TM) catalysts and their nanoparticles, although being more viable and extensively applied by researchers in the present scenario, have not been exclusively and expansively reviewed. Besides this, the vital precursors required for knitting the skeleton of benzimidazole are mainly o‐aryldiamines. The conventional synthesis generally involved the condensation of these diamines with carbonyl/carboxylic acid derivatives either via high temperature heating or via adding strong acids, mostly resulting in poor yields or mixtures. However, recent trends are replacing these conditions by mild and green conditions through TM catalysts. Therefore, the current review emphasizes on the recent trends adopted in the synthesis of benzimidazoles using condensation reaction of o‐phenylenediamines and various aldehydes/ester/amide/alcohols with TM in a catalytic role in nanoform and under environmentally benign green conditions.

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Design and synthesis of spiro[indole-thiazolidine]spiro[indole-pyrans] as antimicrobial agents

Cited by 88 publications

References 34 publications

An Organocatalyzed Efficient One‐pot Synthesis, Biological Evaluation, and Molecular Docking Studies of 4,4′‐(Arylmethylene)bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols)

An Organocatalyzed Efficient One‐pot Synthesis, Biological Evaluation, and Molecular Docking Studies of 4,4′‐(Arylmethylene)bis‐(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ols)

An eco-compatible synthesis of novel spiro[acenaphthylene-1,2′[1,3]-thiazolidine]-2,4′(1H)-diones using thiamine hydrochloride as efficient catalyst in aqueous medium

Recent Trends in the Synthesis of Benzimidazoles From o‐Phenylenediamine via Nanoparticles and Green Strategies Using Transition Metal Catalysts

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