3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties
A convenient method for the synthesis of N3,N4-disubstituted 3,4-diaminopyrazolo[3,4-d]pyrimidines was developed using a three-component reaction of 3,5-diaminopyrazole-4-carbonitriles with primary amines and orthoesters. The preparation of 114 examples demonstrated the good scope of the reaction, w...
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Royal Society of Chemistry
2023
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| Online Access: | http://eprints.sunway.edu.my/2178/1/org%20biomol%20chem%202023%2021%203432.pdf http://eprints.sunway.edu.my/2178/ https://pubs.rsc.org/en/content/articlelanding/2023/ob/d3ob00350g |
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| author | Ng, Jia Hui Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_facet | Ng, Jia Hui Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V |
| author_sort | Ng, Jia Hui |
| building | Sunway Campus Library |
| collection | Institutional Repository |
| content_provider | Sunway University |
| content_source | Sunway Institutional Repository |
| continent | Asia |
| country | Malaysia |
| description | A convenient method for the synthesis of N3,N4-disubstituted 3,4-diaminopyrazolo[3,4-d]pyrimidines was developed using a three-component reaction of 3,5-diaminopyrazole-4-carbonitriles with primary amines and orthoesters. The preparation of 114 examples demonstrated the good scope of the reaction, which tolerated variations in the substrate structure and was particularly efficient under microwave irradiation. The short reaction time and chromatographyfree product isolation add practicality to this method. The anti-leukemic activity was assessed in vitro using K562 and Jurkat T cells, and the selectivity of the most active compounds was 3 evaluated using non-cancerous MRC5 cells. The most promising compound inhibited Jurkat T cells with a GI50 value of 0.5 µM and a selectivity index of 64. |
| format | Article |
| id | my.sunway.eprints.2178 |
| institution | Sunway University |
| language | en |
| publishDate | 2023 |
| publisher | Royal Society of Chemistry |
| record_format | eprints |
| spelling | my.sunway.eprints.21782023-04-26T23:41:15Z http://eprints.sunway.edu.my/2178/ 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties Ng, Jia Hui Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V QD Chemistry A convenient method for the synthesis of N3,N4-disubstituted 3,4-diaminopyrazolo[3,4-d]pyrimidines was developed using a three-component reaction of 3,5-diaminopyrazole-4-carbonitriles with primary amines and orthoesters. The preparation of 114 examples demonstrated the good scope of the reaction, which tolerated variations in the substrate structure and was particularly efficient under microwave irradiation. The short reaction time and chromatographyfree product isolation add practicality to this method. The anti-leukemic activity was assessed in vitro using K562 and Jurkat T cells, and the selectivity of the most active compounds was 3 evaluated using non-cancerous MRC5 cells. The most promising compound inhibited Jurkat T cells with a GI50 value of 0.5 µM and a selectivity index of 64. Royal Society of Chemistry 2023 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/2178/1/org%20biomol%20chem%202023%2021%203432.pdf Ng, Jia Hui and Lim, Felicia Phei Lin and Tiekink, Edward R. T. * and Dolzhenko, Anton V (2023) 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties. Organic & Biomolecular Chemistry, 21 (16). pp. 3432-3446. ISSN 1477-0539 (Submitted) https://pubs.rsc.org/en/content/articlelanding/2023/ob/d3ob00350g 10.1039/D3OB00350G |
| spellingShingle | QD Chemistry Ng, Jia Hui Lim, Felicia Phei Lin Tiekink, Edward R. T. * Dolzhenko, Anton V 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| title | 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| title_full | 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| title_fullStr | 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| title_full_unstemmed | 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| title_short | 3,4-Diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| title_sort | 3,4-diaminopyrazolo[3,4-d]pyrimidines: a new three-component microwave-assisted synthesis and anti-leukemic properties |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/2178/1/org%20biomol%20chem%202023%2021%203432.pdf http://eprints.sunway.edu.my/2178/ https://pubs.rsc.org/en/content/articlelanding/2023/ob/d3ob00350g |
| url_provider | http://eprints.sunway.edu.my/ |