A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one
A novel synthesis of the anticancer drug gefitinib (Iressa) through novel alternative pathway has been successfully carried out. The synthesis was performed using 6,7-dimethoxy-3H-quinazolin-4-one as the starting material through four reaction stages: Chlorination, nucleophilic aromatic substitution...
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| Format: | Article |
| Language: | en |
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Penerbit Universiti Kebangsaan Malaysia
2025
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| Online Access: | http://journalarticle.ukm.my/25630/1/SE%207.pdf http://journalarticle.ukm.my/25630/ https://www.ukm.my/jsm/english_journals/vol54num4_2025/contentsVol54num4_2025.html |
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| _version_ | 1838231917635305472 |
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| author | Santoso, Prio Danova, Ade Hermawati, Elvira Natalia, Dessy Alni, Anita |
| author_facet | Santoso, Prio Danova, Ade Hermawati, Elvira Natalia, Dessy Alni, Anita |
| author_sort | Santoso, Prio |
| building | Tun Sri Lanang Library |
| collection | Institutional Repository |
| content_provider | Universiti Kebangsaan Malaysia |
| content_source | UKM Journal Article Repository |
| continent | Asia |
| country | Malaysia |
| description | A novel synthesis of the anticancer drug gefitinib (Iressa) through novel alternative pathway has been successfully carried out. The synthesis was performed using 6,7-dimethoxy-3H-quinazolin-4-one as the starting material through four reaction stages: Chlorination, nucleophilic aromatic substitution, demethylation, and Williamson etherification to produce gefitinib. The chlorination of 6,7-dimethoxy-3H-quinazolin-4-one as the first key step in this synthesis followed by aromatic substitution were effective to produce the target product with high yield (98% for two steps). In addition, synthesis of gefitinib from this precursor omits the necessity for functional group protection and deprotection. Purification was carried out using crystallization and radial chromatography. The structural analysis of the resulting compound was performed using FTIR, 1H-NMR, 13C-NMR, and mass spectrometry. The purity of the resulting compounds was measured using HPLC and melting point measurements (195-197 °C). The overall yield obtained through this pathway was 21%. |
| format | Article |
| id | my-ukm.journal.25630 |
| institution | Universiti Kebangsaan Malaysia |
| language | en |
| publishDate | 2025 |
| publisher | Penerbit Universiti Kebangsaan Malaysia |
| record_format | eprints |
| spelling | my-ukm.journal.256302025-07-16T05:25:26Z http://journalarticle.ukm.my/25630/ A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one Santoso, Prio Danova, Ade Hermawati, Elvira Natalia, Dessy Alni, Anita A novel synthesis of the anticancer drug gefitinib (Iressa) through novel alternative pathway has been successfully carried out. The synthesis was performed using 6,7-dimethoxy-3H-quinazolin-4-one as the starting material through four reaction stages: Chlorination, nucleophilic aromatic substitution, demethylation, and Williamson etherification to produce gefitinib. The chlorination of 6,7-dimethoxy-3H-quinazolin-4-one as the first key step in this synthesis followed by aromatic substitution were effective to produce the target product with high yield (98% for two steps). In addition, synthesis of gefitinib from this precursor omits the necessity for functional group protection and deprotection. Purification was carried out using crystallization and radial chromatography. The structural analysis of the resulting compound was performed using FTIR, 1H-NMR, 13C-NMR, and mass spectrometry. The purity of the resulting compounds was measured using HPLC and melting point measurements (195-197 °C). The overall yield obtained through this pathway was 21%. Penerbit Universiti Kebangsaan Malaysia 2025 Article PeerReviewed application/pdf en http://journalarticle.ukm.my/25630/1/SE%207.pdf Santoso, Prio and Danova, Ade and Hermawati, Elvira and Natalia, Dessy and Alni, Anita (2025) A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one. Sains Malaysiana, 54 (4). pp. 1053-1062. ISSN 0126-6039 https://www.ukm.my/jsm/english_journals/vol54num4_2025/contentsVol54num4_2025.html |
| spellingShingle | Santoso, Prio Danova, Ade Hermawati, Elvira Natalia, Dessy Alni, Anita A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one |
| title | A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one |
| title_full | A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one |
| title_fullStr | A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one |
| title_full_unstemmed | A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one |
| title_short | A novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3H-quinazolin-4-one |
| title_sort | novel synthesis of anti-cancer drug gefitinib from 6,7-dimethoxy-3h-quinazolin-4-one |
| url | http://journalarticle.ukm.my/25630/1/SE%207.pdf http://journalarticle.ukm.my/25630/ https://www.ukm.my/jsm/english_journals/vol54num4_2025/contentsVol54num4_2025.html |
| url_provider | http://journalarticle.ukm.my/ |