Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach
In the present study we designed and synthesized 26 coumarin clubbed chalcone hybrids (1–13 and 14–26) in good yields (54.32–74.25%) and further tested for their antimicrobial and antioxidant activities considering the potential bioactivities of these two pharmacophores. All Spectroscopic techniques...
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| Format: | Article |
| Language: | English |
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Elsevier
2021-06-01
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535221001696 |
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| author | Sathish Kumar Konidala Vijay Kotra Ravi Chandra Sekhara Reddy Danduga Phani Kumar Kola Richie R. Bhandare Afzal B. Shaik |
| author_facet | Sathish Kumar Konidala Vijay Kotra Ravi Chandra Sekhara Reddy Danduga Phani Kumar Kola Richie R. Bhandare Afzal B. Shaik |
| author_sort | Sathish Kumar Konidala |
| collection | DOAJ |
| description | In the present study we designed and synthesized 26 coumarin clubbed chalcone hybrids (1–13 and 14–26) in good yields (54.32–74.25%) and further tested for their antimicrobial and antioxidant activities considering the potential bioactivities of these two pharmacophores. All Spectroscopic techniques including FT-IR, 1H NMR, 13C NMR and mass were used to characterize the compounds. The antimicrobial and antioxidant activities of these compounds were performed by agar well diffusion method and DPPH free radical assay respectively. The compounds elicited considerable antimicrobial and potential antioxidant activities. Bioactivity data designated that the compounds 1 and 7 with no and 4-Cl substitution on the phenyl ring of coumarin clubbed chalcones with 3,4-dihydropyrimidine-2-one displayed antibacterial activity with minimum inhibitory concentration (MIC) value of 10 µM and 17 µM against Staphylococcus aureus and MIC value of 8 µM and 13 µM against Escherichia coli and antifungal activity with MIC value of 10 µM and 11 µM against Aspergillus niger respectively. On the other hand, coumarin clubbed chalcones with 3,4-dihydropyrimidine-2(1H)-thione scaffold (14–26) exhibited potential antioxidant activity. Among them, compounds 22 containing electron releasing 2-OH substituent was the most active with 77.92% scavenging activity, followed by 14 and 26 (75.22% and 71.32%). The promising leads evolved through this investigation are important for the future development of novel and potential antioxidant compounds. |
| first_indexed | 2024-12-20T08:27:57Z |
| format | Article |
| id | doaj.art-bf48a16846fa49aea8674e8fce47deb4 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-12-20T08:27:57Z |
| publishDate | 2021-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-bf48a16846fa49aea8674e8fce47deb42022-12-21T19:46:47ZengElsevierArabian Journal of Chemistry1878-53522021-06-01146103154Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approachSathish Kumar Konidala0Vijay Kotra1Ravi Chandra Sekhara Reddy Danduga2Phani Kumar Kola3Richie R. Bhandare4Afzal B. Shaik5University College of Pharmaceutical Sciences, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, A.P. 522510, India; Department of Pharmaceutical Sciences, Vignan’s Foundation for Science, Technology, and Research, Guntur, Andhra Pradesh, IndiaFaculty of Pharmacy, Quest International University Perak (QIUP), MalaysiaUniversity College of Pharmaceutical Sciences, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, A.P. 522510, IndiaUniversity College of Pharmaceutical Sciences, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, A.P. 522510, India; Corresponding authors at: University College of Pharmaceutical Sciences, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, A.P. 522510, India (P.K. Kola); Department of Pharmaceutical Sciences, Vignan’s Foundation for Science, Technology, and Research, Guntur, Andhra Pradesh, India and Department of Pharmaceutical Sciences, College of Pharmacy & Health Sciences, Ajman University, PO Box 346, Ajman, United Arab Emirates (R.R. Bhandare); Department of Pharmaceutical Chemistry, Vignan Pharmacy College, Jawaharlal Nehru Technological University, Vadlamudi 522213, Andhra Pradesh, India (A.B. Shaik).Department of Pharmaceutical Sciences, College of Pharmacy & Health Sciences, Ajman University, PO Box 346, Ajman, United Arab Emirates; Center of Medical and Bio-allied Health Research, Ajman University, Ajman, United Arab Emirates; Corresponding authors at: University College of Pharmaceutical Sciences, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, A.P. 522510, India (P.K. Kola); Department of Pharmaceutical Sciences, Vignan’s Foundation for Science, Technology, and Research, Guntur, Andhra Pradesh, India and Department of Pharmaceutical Sciences, College of Pharmacy & Health Sciences, Ajman University, PO Box 346, Ajman, United Arab Emirates (R.R. Bhandare); Department of Pharmaceutical Chemistry, Vignan Pharmacy College, Jawaharlal Nehru Technological University, Vadlamudi 522213, Andhra Pradesh, India (A.B. Shaik).Department of Pharmaceutical Chemistry, Vignan Pharmacy College, Jawaharlal Nehru Technological University, Vadlamudi 522213, Andhra Pradesh, India; Corresponding authors at: University College of Pharmaceutical Sciences, Acharya Nagarjuna University, Nagarjuna Nagar, Guntur, A.P. 522510, India (P.K. Kola); Department of Pharmaceutical Sciences, Vignan’s Foundation for Science, Technology, and Research, Guntur, Andhra Pradesh, India and Department of Pharmaceutical Sciences, College of Pharmacy & Health Sciences, Ajman University, PO Box 346, Ajman, United Arab Emirates (R.R. Bhandare); Department of Pharmaceutical Chemistry, Vignan Pharmacy College, Jawaharlal Nehru Technological University, Vadlamudi 522213, Andhra Pradesh, India (A.B. Shaik).In the present study we designed and synthesized 26 coumarin clubbed chalcone hybrids (1–13 and 14–26) in good yields (54.32–74.25%) and further tested for their antimicrobial and antioxidant activities considering the potential bioactivities of these two pharmacophores. All Spectroscopic techniques including FT-IR, 1H NMR, 13C NMR and mass were used to characterize the compounds. The antimicrobial and antioxidant activities of these compounds were performed by agar well diffusion method and DPPH free radical assay respectively. The compounds elicited considerable antimicrobial and potential antioxidant activities. Bioactivity data designated that the compounds 1 and 7 with no and 4-Cl substitution on the phenyl ring of coumarin clubbed chalcones with 3,4-dihydropyrimidine-2-one displayed antibacterial activity with minimum inhibitory concentration (MIC) value of 10 µM and 17 µM against Staphylococcus aureus and MIC value of 8 µM and 13 µM against Escherichia coli and antifungal activity with MIC value of 10 µM and 11 µM against Aspergillus niger respectively. On the other hand, coumarin clubbed chalcones with 3,4-dihydropyrimidine-2(1H)-thione scaffold (14–26) exhibited potential antioxidant activity. Among them, compounds 22 containing electron releasing 2-OH substituent was the most active with 77.92% scavenging activity, followed by 14 and 26 (75.22% and 71.32%). The promising leads evolved through this investigation are important for the future development of novel and potential antioxidant compounds.http://www.sciencedirect.com/science/article/pii/S1878535221001696CoumarinChalconeCoumarin clubbed chalconeHybridsAntimicrobialAntioxidant |
| spellingShingle | Sathish Kumar Konidala Vijay Kotra Ravi Chandra Sekhara Reddy Danduga Phani Kumar Kola Richie R. Bhandare Afzal B. Shaik Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach Arabian Journal of Chemistry Coumarin Chalcone Coumarin clubbed chalcone Hybrids Antimicrobial Antioxidant |
| title | Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach |
| title_full | Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach |
| title_fullStr | Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach |
| title_full_unstemmed | Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach |
| title_short | Design, multistep synthesis and in-vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach |
| title_sort | design multistep synthesis and in vitro antimicrobial and antioxidant screening of coumarin clubbed chalcone hybrids through molecular hybridization approach |
| topic | Coumarin Chalcone Coumarin clubbed chalcone Hybrids Antimicrobial Antioxidant |
| url | http://www.sciencedirect.com/science/article/pii/S1878535221001696 |
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