Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties
Pyrimidines, sulphonamides and carboxamides have shown a large number of pharmacological properties against different types of diseases including helminthiasis. Seventeen new pyrimidine derivatives bearing sulphonamide and carboxamide were synthesized and investigated for their in vitro anthelmintic...
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| Format: | Article |
| Language: | English |
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Serbian Chemical Society
2018-01-01
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| Series: | Journal of the Serbian Chemical Society |
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| Online Access: | http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391700109U.pdf |
| _version_ | 1818065078214197248 |
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| author | Ugwu David I. Okoro Uchechukwu C. Mishra Narendra K. |
| author_facet | Ugwu David I. Okoro Uchechukwu C. Mishra Narendra K. |
| author_sort | Ugwu David I. |
| collection | DOAJ |
| description | Pyrimidines, sulphonamides and carboxamides have shown a large number of pharmacological properties against different types of diseases including helminthiasis. Seventeen new pyrimidine derivatives bearing sulphonamide and carboxamide were synthesized and investigated for their in vitro anthelmintic properties. Substituted benzenesulphonyl chlorides 15a–c were treated with various amino acids (16a–h) to obtain benzenesulphonamide derivatives 17a–l. Compounds 17a–f were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives 19a–f. Further reactions of compounds 19a–f and 17g–l with 4- or 2-aminopyrimidine (20) using boric acid as a catalyst gave the required sulphonamide carboxamide derivatives 21a–q in excellent yields. The compounds were isolated in their analytical grade and characterized using FTIR, 1H-NMR, 13C-NMR and HRMS. The in vitro anthelmintic studies showed that all the synthesized compounds possessed anthelmintic property. Compounds 21a–c, e, g, m and p showed mean paralyzing times of 15, 19, 14, 18, 19, 19 and 18 min, respectively, at 100 mg mL-1 compared to 10 min for albendazole. Compounds 21a–c, g and m had mean death times of 18, 24, 16, 20 and 25 min, respectively, at 100 mg mL-1 compared to 13 min for albendazole. |
| first_indexed | 2024-12-10T14:46:10Z |
| format | Article |
| id | doaj.art-cd0fa9648f644cdd8f720085cd7cd919 |
| institution | Directory Open Access Journal |
| issn | 0352-5139 1820-7421 |
| language | English |
| last_indexed | 2024-12-10T14:46:10Z |
| publishDate | 2018-01-01 |
| publisher | Serbian Chemical Society |
| record_format | Article |
| series | Journal of the Serbian Chemical Society |
| spelling | doaj.art-cd0fa9648f644cdd8f720085cd7cd9192022-12-22T01:44:33ZengSerbian Chemical SocietyJournal of the Serbian Chemical Society0352-51391820-74212018-01-0183440140910.2298/JSC170127109U0352-51391700109USynthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moietiesUgwu David I.0Okoro Uchechukwu C.1Mishra Narendra K.2University of Nigeria, Department of Pure and Industrial Chemistry, Nsukka, Nigeria + Indian Institute of Technology, Department of Chemistry, Kanpur, IndiaUniversity of Nigeria, Department of Pure and Industrial Chemistry, Nsukka, NigeriaIndian Institute of Technology, Department of Chemistry, Kanpur, IndiaPyrimidines, sulphonamides and carboxamides have shown a large number of pharmacological properties against different types of diseases including helminthiasis. Seventeen new pyrimidine derivatives bearing sulphonamide and carboxamide were synthesized and investigated for their in vitro anthelmintic properties. Substituted benzenesulphonyl chlorides 15a–c were treated with various amino acids (16a–h) to obtain benzenesulphonamide derivatives 17a–l. Compounds 17a–f were subsequently treated with benzoyl chloride to obtain the N-benzoylated derivatives 19a–f. Further reactions of compounds 19a–f and 17g–l with 4- or 2-aminopyrimidine (20) using boric acid as a catalyst gave the required sulphonamide carboxamide derivatives 21a–q in excellent yields. The compounds were isolated in their analytical grade and characterized using FTIR, 1H-NMR, 13C-NMR and HRMS. The in vitro anthelmintic studies showed that all the synthesized compounds possessed anthelmintic property. Compounds 21a–c, e, g, m and p showed mean paralyzing times of 15, 19, 14, 18, 19, 19 and 18 min, respectively, at 100 mg mL-1 compared to 10 min for albendazole. Compounds 21a–c, g and m had mean death times of 18, 24, 16, 20 and 25 min, respectively, at 100 mg mL-1 compared to 13 min for albendazole.http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391700109U.pdfcatalysisanthelminticssynthesiscarboxamidessulphonamides |
| spellingShingle | Ugwu David I. Okoro Uchechukwu C. Mishra Narendra K. Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties Journal of the Serbian Chemical Society catalysis anthelmintics synthesis carboxamides sulphonamides |
| title | Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties |
| title_full | Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties |
| title_fullStr | Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties |
| title_full_unstemmed | Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties |
| title_short | Synthesis, characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties |
| title_sort | synthesis characterization and anthelmintic activity evaluation of pyrimidine derivatives bearing carboxamide and sulphonamide moieties |
| topic | catalysis anthelmintics synthesis carboxamides sulphonamides |
| url | http://www.doiserbia.nb.rs/img/doi/0352-5139/2018/0352-51391700109U.pdf |
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