Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity
The paper describes the facile synthesis of new N-cyclopropyl-1-methyl-1H-indole-2-carboxamide derivatives bearing substituted 2-amino pyrimidine moiety at position-3 of the indole ring. All the intermediate and title compounds were characterized adeptly by 1H NMR, 13C NMR, ESI–MS and elemental anal...
| Main Authors: | , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2017-11-01
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| Series: | Journal of Saudi Chemical Society |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S1319610315001131 |
| _version_ | 1819153341381345280 |
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| author | Nikhila Gokhale Udayakumar Dalimba Manjunatha Kumsi |
| author_facet | Nikhila Gokhale Udayakumar Dalimba Manjunatha Kumsi |
| author_sort | Nikhila Gokhale |
| collection | DOAJ |
| description | The paper describes the facile synthesis of new N-cyclopropyl-1-methyl-1H-indole-2-carboxamide derivatives bearing substituted 2-amino pyrimidine moiety at position-3 of the indole ring. All the intermediate and title compounds were characterized adeptly by 1H NMR, 13C NMR, ESI–MS and elemental analyses. These compounds were evaluated for their in vitro anticancer activity against HeLa, HepG2 and MCF-7 cells. Three among 22 molecules, showed more than 70% growth inhibition against all three tested cancer cells. The nature of the substituent group on the pyrimidine ring (R2) affected significantly the anti-proliferative activity of the molecules. The anti-microbial evaluation of the title molecules revealed the significance of fluoro/chloro groups (R2) in enhancing their inhibition activity. Eight molecules which contain fluoro/chloro groups showed potent anti-microbial activity. In addition, the active molecules displayed negligible toxicity to benign Vero cells. |
| first_indexed | 2024-12-22T15:03:39Z |
| format | Article |
| id | doaj.art-4a05e952450f47b0b35c5a2883b9fe9b |
| institution | Directory Open Access Journal |
| issn | 1319-6103 |
| language | English |
| last_indexed | 2024-12-22T15:03:39Z |
| publishDate | 2017-11-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Journal of Saudi Chemical Society |
| spelling | doaj.art-4a05e952450f47b0b35c5a2883b9fe9b2022-12-21T18:22:02ZengElsevierJournal of Saudi Chemical Society1319-61032017-11-0121776177510.1016/j.jscs.2015.09.003Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activityNikhila Gokhale0Udayakumar Dalimba1Manjunatha Kumsi2Organic Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasanagar, Mangalore 575025, Karnataka, IndiaOrganic Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka, Surathkal, Srinivasanagar, Mangalore 575025, Karnataka, IndiaDepartment of Chemistry, Nagarjuna College of Engineering and Technology, Devanahalli, Bangalore 562110, Karnataka, IndiaThe paper describes the facile synthesis of new N-cyclopropyl-1-methyl-1H-indole-2-carboxamide derivatives bearing substituted 2-amino pyrimidine moiety at position-3 of the indole ring. All the intermediate and title compounds were characterized adeptly by 1H NMR, 13C NMR, ESI–MS and elemental analyses. These compounds were evaluated for their in vitro anticancer activity against HeLa, HepG2 and MCF-7 cells. Three among 22 molecules, showed more than 70% growth inhibition against all three tested cancer cells. The nature of the substituent group on the pyrimidine ring (R2) affected significantly the anti-proliferative activity of the molecules. The anti-microbial evaluation of the title molecules revealed the significance of fluoro/chloro groups (R2) in enhancing their inhibition activity. Eight molecules which contain fluoro/chloro groups showed potent anti-microbial activity. In addition, the active molecules displayed negligible toxicity to benign Vero cells.http://www.sciencedirect.com/science/article/pii/S1319610315001131IndolePyrimidineHATUClaisen–Schmidt condensationAnticancer activityAntimicrobial studies |
| spellingShingle | Nikhila Gokhale Udayakumar Dalimba Manjunatha Kumsi Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity Journal of Saudi Chemical Society Indole Pyrimidine HATU Claisen–Schmidt condensation Anticancer activity Antimicrobial studies |
| title | Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity |
| title_full | Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity |
| title_fullStr | Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity |
| title_full_unstemmed | Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity |
| title_short | Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity |
| title_sort | facile synthesis of indole pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity |
| topic | Indole Pyrimidine HATU Claisen–Schmidt condensation Anticancer activity Antimicrobial studies |
| url | http://www.sciencedirect.com/science/article/pii/S1319610315001131 |
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