Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells
A new series of N-sec/tert-butyl 2-arylbenzimidazole derivatives was synthesised in 85–96% yields within 2–3.5 min by condensing ethyl 3-amino-4-butylamino benzoate with various substituted metabisulfite adducts of benzaldehyde under focused microwave irradiation. The benzimidazole analogues were ch...
| Main Authors: | , , , , , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
Informa UK, Ltd.
2013
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| Online Access: | http://irep.iium.edu.my/29457/4/JEnxInhibition.pdf |
| _version_ | 1796877926991396864 |
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| author | Abdul Rahim, Aisyah Saad Muhamad Salhimi, Salizawati Natarajan, Arumugam Lim, Chung Pin Ng, Shy Yee Muttiah, Nithya Niranjini Wong , Boon Keat Abd Hamid, Shafida Osman, Hasnah Mat, Ishak |
| author_facet | Abdul Rahim, Aisyah Saad Muhamad Salhimi, Salizawati Natarajan, Arumugam Lim, Chung Pin Ng, Shy Yee Muttiah, Nithya Niranjini Wong , Boon Keat Abd Hamid, Shafida Osman, Hasnah Mat, Ishak |
| author_sort | Abdul Rahim, Aisyah Saad |
| collection | IIUM |
| description | A new series of N-sec/tert-butyl 2-arylbenzimidazole derivatives was synthesised in 85–96% yields within 2–3.5 min by condensing ethyl 3-amino-4-butylamino benzoate with various substituted metabisulfite adducts of benzaldehyde under focused microwave irradiation. The benzimidazole analogues were characterised using 1H NMR, 13C NMR, high resolution MS and melting points. Evaluation of antiproliferative activity of the benzimidazole analogues against MCF-7 and MDA-MB-231 revealed several compounds with unexpected selective inhibitions of MDA-MB-231 in micromolar range. All analogues were found inactive towards MCF-7. The most potent inhibition against MDA-MB-231 human breast cancer cell line came from the unsubstituted 2-phenylbenzimidazole 10a.
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| first_indexed | 2024-03-05T23:14:13Z |
| format | Article |
| id | oai:generic.eprints.org:29457 |
| institution | International Islamic University Malaysia |
| language | English |
| last_indexed | 2024-03-05T23:14:13Z |
| publishDate | 2013 |
| publisher | Informa UK, Ltd. |
| record_format | dspace |
| spelling | oai:generic.eprints.org:294572014-11-28T07:14:17Z http://irep.iium.edu.my/29457/ Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells Abdul Rahim, Aisyah Saad Muhamad Salhimi, Salizawati Natarajan, Arumugam Lim, Chung Pin Ng, Shy Yee Muttiah, Nithya Niranjini Wong , Boon Keat Abd Hamid, Shafida Osman, Hasnah Mat, Ishak QD Chemistry RS Pharmacy and materia medica A new series of N-sec/tert-butyl 2-arylbenzimidazole derivatives was synthesised in 85–96% yields within 2–3.5 min by condensing ethyl 3-amino-4-butylamino benzoate with various substituted metabisulfite adducts of benzaldehyde under focused microwave irradiation. The benzimidazole analogues were characterised using 1H NMR, 13C NMR, high resolution MS and melting points. Evaluation of antiproliferative activity of the benzimidazole analogues against MCF-7 and MDA-MB-231 revealed several compounds with unexpected selective inhibitions of MDA-MB-231 in micromolar range. All analogues were found inactive towards MCF-7. The most potent inhibition against MDA-MB-231 human breast cancer cell line came from the unsubstituted 2-phenylbenzimidazole 10a. Informa UK, Ltd. 2013-12 Article PeerReviewed application/pdf en http://irep.iium.edu.my/29457/4/JEnxInhibition.pdf Abdul Rahim, Aisyah Saad and Muhamad Salhimi, Salizawati and Natarajan, Arumugam and Lim, Chung Pin and Ng, Shy Yee and Muttiah, Nithya Niranjini and Wong , Boon Keat and Abd Hamid, Shafida and Osman, Hasnah and Mat, Ishak (2013) Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells. Journal of Enzyme Inhibition and Medicinal Chemistry, 28 (6). pp. 1255-1260. ISSN 1475-6374 (O), 1475-6366 (P) http://informahealthcare.com/doi/abs/10.3109/14756366.2012.729828 10.3109/14756366.2012.729828 |
| spellingShingle | QD Chemistry RS Pharmacy and materia medica Abdul Rahim, Aisyah Saad Muhamad Salhimi, Salizawati Natarajan, Arumugam Lim, Chung Pin Ng, Shy Yee Muttiah, Nithya Niranjini Wong , Boon Keat Abd Hamid, Shafida Osman, Hasnah Mat, Ishak Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells |
| title | Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells |
| title_full | Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells |
| title_fullStr | Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells |
| title_full_unstemmed | Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells |
| title_short | Microwave-assisted synthesis of sec/tert-butyl 2-arylbenzimidazoles and their unexpected antiproliferative activity towards ER negative breast cancer cells |
| title_sort | microwave assisted synthesis of sec tert butyl 2 arylbenzimidazoles and their unexpected antiproliferative activity towards er negative breast cancer cells |
| topic | QD Chemistry RS Pharmacy and materia medica |
| url | http://irep.iium.edu.my/29457/4/JEnxInhibition.pdf |
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