Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach
An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N...
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| Format: | Article |
| Language: | English |
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Elsevier
2019-10-01
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| Series: | Heliyon |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2405844019362759 |
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| author | Mohd. Shahnawaz Khan Ranu Agrawal Mohd Ubaidullah Md. Imtaiyaz Hassan Nazia Tarannum |
| author_facet | Mohd. Shahnawaz Khan Ranu Agrawal Mohd Ubaidullah Md. Imtaiyaz Hassan Nazia Tarannum |
| author_sort | Mohd. Shahnawaz Khan |
| collection | DOAJ |
| description | An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N-(substituted)phenyl malonic acid in the presence of a base catalyst, piperidine. All reported compounds were assessed for their antimicrobial activities which clearly suggested their therapeutic implications to address antimicrobial pathogenesis. The synthesized coumarin compounds were examined for their antimicrobial activity against 7 fungal strains and 2 bacterial strains at concentration 125–1000 μg/mL. In particular, the compounds 4 and 5 showed lower minimum inhibitory concentration value (125 μg/mL) against maximum microbial strains. Further, docking of all the synthesized compounds was performed with the enzymes lanosterol 14α-demethylase and glucosamine-6-phosphate synthase and a significant binding affinity was observed which supports in vivo antimicrobial study. In addition, the thermal analysis revealed good thermal stability of compounds up to 250 °C. The compounds showed abroad absorption spectrum between 280-550 nm establishing them to be good UV absorbers. |
| first_indexed | 2024-12-23T10:23:35Z |
| format | Article |
| id | doaj.art-ff386a1e4da44bb9a10f78d2980b0e76 |
| institution | Directory Open Access Journal |
| issn | 2405-8440 |
| language | English |
| last_indexed | 2024-12-23T10:23:35Z |
| publishDate | 2019-10-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Heliyon |
| spelling | doaj.art-ff386a1e4da44bb9a10f78d2980b0e762022-12-21T17:50:37ZengElsevierHeliyon2405-84402019-10-01510e02615Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approachMohd. Shahnawaz Khan0Ranu Agrawal1Mohd Ubaidullah2Md. Imtaiyaz Hassan3Nazia Tarannum4Department of Chemistry, JKLakshmipat University, Rajasthan, Jaipur 302026, India; Corresponding author.Department of Chemistry, Chaudhary Charan Singh University, Meerut 250005, Uttar Pradesh, IndiaDepartment of Chemistry, College of Science, King Saud University, Riyadh 11451, Saudi ArabiaCentre for Interdisciplinary Science, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, IndiaDepartment of Chemistry, Chaudhary Charan Singh University, Meerut 250005, Uttar Pradesh, India; Corresponding author.An ecofriendly itinerary for the synthesis of newly substituted chromene-3-carboxamide derivatives was undertaken to avoid impurities, usage of toxic solvents, toxic catalyst, and having improved quantitative yields. The green synthesis involves the condensation of substituted salicylaldehyde with N-(substituted)phenyl malonic acid in the presence of a base catalyst, piperidine. All reported compounds were assessed for their antimicrobial activities which clearly suggested their therapeutic implications to address antimicrobial pathogenesis. The synthesized coumarin compounds were examined for their antimicrobial activity against 7 fungal strains and 2 bacterial strains at concentration 125–1000 μg/mL. In particular, the compounds 4 and 5 showed lower minimum inhibitory concentration value (125 μg/mL) against maximum microbial strains. Further, docking of all the synthesized compounds was performed with the enzymes lanosterol 14α-demethylase and glucosamine-6-phosphate synthase and a significant binding affinity was observed which supports in vivo antimicrobial study. In addition, the thermal analysis revealed good thermal stability of compounds up to 250 °C. The compounds showed abroad absorption spectrum between 280-550 nm establishing them to be good UV absorbers.http://www.sciencedirect.com/science/article/pii/S2405844019362759Organic chemistryPharmaceutical chemistryGreen synthesisSubstituted coumarin derivativesMolecular dockingAntimicrobial activity |
| spellingShingle | Mohd. Shahnawaz Khan Ranu Agrawal Mohd Ubaidullah Md. Imtaiyaz Hassan Nazia Tarannum Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach Heliyon Organic chemistry Pharmaceutical chemistry Green synthesis Substituted coumarin derivatives Molecular docking Antimicrobial activity |
| title | Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach |
| title_full | Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach |
| title_fullStr | Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach |
| title_full_unstemmed | Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach |
| title_short | Design, synthesis and validation of anti-microbial coumarin derivatives: An efficient green approach |
| title_sort | design synthesis and validation of anti microbial coumarin derivatives an efficient green approach |
| topic | Organic chemistry Pharmaceutical chemistry Green synthesis Substituted coumarin derivatives Molecular docking Antimicrobial activity |
| url | http://www.sciencedirect.com/science/article/pii/S2405844019362759 |
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