Heterocycles p. 1606 - 1619 (2014)
Update date:2022-08-11
Topics:
Lee, Jongbok
Seo, Hyewon
Yoon, Sangeun
Choi, Kowoon
Lee, Chul-Hoon
Rheea, Hakjune
New carbocyclic pyrrolo[2,3-d]pyrimidine nucleoside analogs were synthesized with the key intermediate, 4-amino-6-bromo-5-cyanopyrrolo[2,3- d]pyrimidine (2), by SN2 reaction. One of the products, 4-amino-6-bromo-1- cyclopentyl-1H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (9), showed significant anti-proliferative activity to the human ovarian cancer PA-1 cells (IC50: 3.9 μM). Based on the biological effects and the functional group characteristics of the compound 9, other carbocyclic nucleoside analogs related to the compound 9 were synthesized with key intermediate 2 by a Pd(0)-catalyzed coupling reaction. As expected, syn-4-amino-6-bromo-7-[4-(methoxymethyl)-2- cyclopenten-1-yl]- 7H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (15) showed very similar antiproliferative activity (IC50: 2.6 μM) when compared to compound 9.
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