Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions
Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English English |
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Multidisciplinary Digital Publishing Institute
2013
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| Online Access: | http://psasir.upm.edu.my/id/eprint/30099/ http://psasir.upm.edu.my/id/eprint/30099/1/Synthesis%20of%20new%20cytotoxic%20aminoanthraquinone%20derivatives%20via%20nucleophilic%20substitution%20reactions.pdf |
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| author | Mohd Nor, Siti Mariam Md. Sukari, Mohd. Aspollah Syed Abd. Azziz, Saripah Salbiah Wong, Chee Fah Alimon, Hasimah Juhan, Siti Fadilah |
| author_facet | Mohd Nor, Siti Mariam Md. Sukari, Mohd. Aspollah Syed Abd. Azziz, Saripah Salbiah Wong, Chee Fah Alimon, Hasimah Juhan, Siti Fadilah |
| author_sort | Mohd Nor, Siti Mariam |
| building | UPM Institutional Repository |
| collection | Online Access |
| description | Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5a–d. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1–13.0 µg/mL). |
| first_indexed | 2025-11-15T09:05:00Z |
| format | Article |
| id | upm-30099 |
| institution | Universiti Putra Malaysia |
| institution_category | Local University |
| language | English English |
| last_indexed | 2025-11-15T09:05:00Z |
| publishDate | 2013 |
| publisher | Multidisciplinary Digital Publishing Institute |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | upm-300992015-10-09T00:39:37Z http://psasir.upm.edu.my/id/eprint/30099/ Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions Mohd Nor, Siti Mariam Md. Sukari, Mohd. Aspollah Syed Abd. Azziz, Saripah Salbiah Wong, Chee Fah Alimon, Hasimah Juhan, Siti Fadilah Aminoanthraquinones were successfully synthesized via two reaction steps. 1,4-Dihydroxyanthraquinone (1) was first subjected to methylation, reduction and acylation to give an excellent yield of anthracene-1,4-dione (3), 1,4-dimethoxyanthracene-9,10-dione (5) and 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl diacetate (7). Treatment of 1, 3, 5 and 7 with BuNH2 in the presence of PhI(OAc)2 as catalyst produced seven aminoanthraquinone derivatives 1a, b, 3a, and 5a–d. Amination of 3 and 5 afforded three new aminoanthraquinones, namely 2-(butylamino)anthracene-1,4-dione (3a), 2-(butylamino)anthracene-9,10-dione (5a) and 2,3-(dibutylamino)anthracene-9,10-dione (5b). All newly synthesised aminoanthraquinones were examined for their cytotoxic activity against MCF-7 (estrogen receptor positive human breast) and Hep-G2 (human hepatocellular liver carcinoma) cancer cells using MTT assay. Aminoanthraquinones 3a, 5a and 5b exhibited strong cytotoxicity towards both cancer cell lines (IC50 1.1–13.0 µg/mL). Multidisciplinary Digital Publishing Institute 2013 Article PeerReviewed application/pdf en http://psasir.upm.edu.my/id/eprint/30099/1/Synthesis%20of%20new%20cytotoxic%20aminoanthraquinone%20derivatives%20via%20nucleophilic%20substitution%20reactions.pdf Mohd Nor, Siti Mariam and Md. Sukari, Mohd. Aspollah and Syed Abd. Azziz, Saripah Salbiah and Wong, Chee Fah and Alimon, Hasimah and Juhan, Siti Fadilah (2013) Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions. Molecules, 18 (7). pp. 8046-8062. ISSN 1431-5157; ESSN: 1420-3049 http://www.mdpi.com/1420-3049/18/7 10.3390/molecules18078046 English |
| spellingShingle | Mohd Nor, Siti Mariam Md. Sukari, Mohd. Aspollah Syed Abd. Azziz, Saripah Salbiah Wong, Chee Fah Alimon, Hasimah Juhan, Siti Fadilah Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| title | Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| title_full | Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| title_fullStr | Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| title_full_unstemmed | Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| title_short | Synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| title_sort | synthesis of new cytotoxic aminoanthraquinone derivatives via nucleophilic substitution reactions |
| url | http://psasir.upm.edu.my/id/eprint/30099/ http://psasir.upm.edu.my/id/eprint/30099/ http://psasir.upm.edu.my/id/eprint/30099/ http://psasir.upm.edu.my/id/eprint/30099/1/Synthesis%20of%20new%20cytotoxic%20aminoanthraquinone%20derivatives%20via%20nucleophilic%20substitution%20reactions.pdf |