1,2,3-Triazolo-Bridged Click Coupling of Pinane-Based Azidodiol Enantiomers with Pyrimidine- and Purine-Based Building Blocks Synthesis, Antiproliferative, and Antimicrobial Evaluation /
Key intermediate azidodiols were synthesized according to literature from commercially available (+)- and (−)-α-pinene in a four-step sequence, including epoxidation with mCPBA, allylic rearrangement, a second epoxidation and, finally, a regioselective azidolysis of the resulting epoxide by sodium a...
Elmentve itt :
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| Dokumentumtípus: | Cikk |
| Megjelent: |
2025
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| Sorozat: | INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
26 No. 23 |
| Tárgyszavak: | |
| doi: | 10.3390/ijms262311705 |
| mtmt: | 36470378 |
| Online Access: | http://publicatio.bibl.u-szeged.hu/38454 |
| Tartalmi kivonat: | Key intermediate azidodiols were synthesized according to literature from commercially available (+)- and (−)-α-pinene in a four-step sequence, including epoxidation with mCPBA, allylic rearrangement, a second epoxidation and, finally, a regioselective azidolysis of the resulting epoxide by sodium azide, yielding the enantiomerically pure azidodiols. The pyrimidine-based alkyne building blocks were prepared from dichloropyrimidines following our method reported previously, while the purine-containing alkyne analogues were synthesized in a procedure of two or three steps. Click reactions were carried out in the presence of Cu(OAc)2 and sodium ascorbate. The obtained pinane-coupled 2,4-diaminopyrimidines were screened for antiproliferative activity by MTT assay on HeLa, MD231, SiHa, MCF-7, and A2780 human cancer cell lines compared with fibroblast cells (NIH/3T3), on Gram-positive and Gram-negative pathogenic bacteria, and two yeasts, and the SAR was explained in detail. The prepared compounds showed moderate antiproliferative activity. While the starting azidodiols (+)-2 and (−)-2 exhibited excellent and selective antibacterial activities against S. aureus with a moderate antimycotic effect on C. krusei, only the (−)-enantiomer was active against P. aeruginosa. In a similar manner, most pyrimidine and purine derivatives also expressed moderate antimycotic effect against C. krusei. One of the purine-based derivatives (−)-30 possessed remarkable and selective antibacterial effect against P. aeruginosa. |
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| Terjedelem/Fizikai jellemzők: | 19 |
| ISSN: | 1661-6596 |