Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines
The purpose of the study was to synthesize potent antimicrobial and cytotoxic agents by condensing sulphanilamide with 1,2,3,4-tetrahydropyrimidines. A new series of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines was prepared by reacting N-[(4-aminophenyl) sulphonyl]-3-oxobutanamide wi...
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| Format: | Article |
| Language: | English |
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Taylor & Francis Group
2017-01-01
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| Series: | Journal of Taibah University for Science |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1658365515000187 |
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| author | Karthikeyan Elumalai Mohammed Ashraf Ali Sivaneswari Srinivasan Manogaran Elumalai Kalpana Eluri |
| author_facet | Karthikeyan Elumalai Mohammed Ashraf Ali Sivaneswari Srinivasan Manogaran Elumalai Kalpana Eluri |
| author_sort | Karthikeyan Elumalai |
| collection | DOAJ |
| description | The purpose of the study was to synthesize potent antimicrobial and cytotoxic agents by condensing sulphanilamide with 1,2,3,4-tetrahydropyrimidines. A new series of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines was prepared by reacting N-[(4-aminophenyl) sulphonyl]-3-oxobutanamide with urea/thiourea and aryl aldehyde in the presence of a catalytic amount of laboratory prepared chlorosulphonic acid as an efficient catalyst. The chemical structures of the synthesized compounds (7a-r) were confirmed by TLC, and the compounds were characterized by IR, 1H NMR, mass spectra and elemental analysis. The synthesized compounds were evaluated for antimicrobial activity against the Gram-positive bacteria Bacillus subtilis and the Gram-negative bacteria Escherichia coli and for cytotoxicity against Vero cells. These compounds exhibited weak, moderate, or high antimicrobial activities and cytotoxicity. In particular, compound 7p exhibited the best antimicrobial activity and cytotoxicity of all the 1,2,3,4-tetrahydropyrimidine derivatives with antimicrobial activity MIC values of 11.4 μM and 12.1 μM against B. subtilis and E. coli, respectively, and a cytotoxicity CTC50 value of 19.0 μM against Vero cells. The sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines generated here might prove interesting as potential antimicrobial cytotoxic agents. |
| first_indexed | 2024-12-24T13:02:45Z |
| format | Article |
| id | doaj.art-d16023d9f4624816aafccaceb7219e3d |
| institution | Directory Open Access Journal |
| issn | 1658-3655 |
| language | English |
| last_indexed | 2024-12-24T13:02:45Z |
| publishDate | 2017-01-01 |
| publisher | Taylor & Francis Group |
| record_format | Article |
| series | Journal of Taibah University for Science |
| spelling | doaj.art-d16023d9f4624816aafccaceb7219e3d2022-12-21T16:54:06ZengTaylor & Francis GroupJournal of Taibah University for Science1658-36552017-01-01111465610.1016/j.jtusci.2015.01.005Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidinesKarthikeyan Elumalai0Mohammed Ashraf Ali1Sivaneswari Srinivasan2Manogaran Elumalai3Kalpana Eluri4New Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan 301030, IndiaNew Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan 301030, IndiaCollege of Pharmacy, Sree Vidyanikethan Educational Institutions, Tirupati 517 102, IndiaFaculty of Pharmaceutical Sciences, UCSI University, Cheras, Kuala Lumpur 56000, MalaysiaFaculty of Pharmaceutical Sciences, UCSI University, Cheras, Kuala Lumpur 56000, MalaysiaThe purpose of the study was to synthesize potent antimicrobial and cytotoxic agents by condensing sulphanilamide with 1,2,3,4-tetrahydropyrimidines. A new series of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines was prepared by reacting N-[(4-aminophenyl) sulphonyl]-3-oxobutanamide with urea/thiourea and aryl aldehyde in the presence of a catalytic amount of laboratory prepared chlorosulphonic acid as an efficient catalyst. The chemical structures of the synthesized compounds (7a-r) were confirmed by TLC, and the compounds were characterized by IR, 1H NMR, mass spectra and elemental analysis. The synthesized compounds were evaluated for antimicrobial activity against the Gram-positive bacteria Bacillus subtilis and the Gram-negative bacteria Escherichia coli and for cytotoxicity against Vero cells. These compounds exhibited weak, moderate, or high antimicrobial activities and cytotoxicity. In particular, compound 7p exhibited the best antimicrobial activity and cytotoxicity of all the 1,2,3,4-tetrahydropyrimidine derivatives with antimicrobial activity MIC values of 11.4 μM and 12.1 μM against B. subtilis and E. coli, respectively, and a cytotoxicity CTC50 value of 19.0 μM against Vero cells. The sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines generated here might prove interesting as potential antimicrobial cytotoxic agents.http://www.sciencedirect.com/science/article/pii/S1658365515000187SulphanilamideTetrahydropyrimidinesB. subtilisE. coliAntimicrobialCytotoxicity |
| spellingShingle | Karthikeyan Elumalai Mohammed Ashraf Ali Sivaneswari Srinivasan Manogaran Elumalai Kalpana Eluri Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines Journal of Taibah University for Science Sulphanilamide Tetrahydropyrimidines B. subtilis E. coli Antimicrobial Cytotoxicity |
| title | Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines |
| title_full | Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines |
| title_fullStr | Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines |
| title_full_unstemmed | Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines |
| title_short | Antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1,2,3,4-tetrahydropyrimidines |
| title_sort | antimicrobial and in vitro cytotoxicity of novel sulphanilamide condensed 1 2 3 4 tetrahydropyrimidines |
| topic | Sulphanilamide Tetrahydropyrimidines B. subtilis E. coli Antimicrobial Cytotoxicity |
| url | http://www.sciencedirect.com/science/article/pii/S1658365515000187 |
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