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THE SYNTHESIS AND EVALUATION OF NEW CARBOCYCLIC PYRROLO[2,3-d]PYRIMIDINE NUCLEOSIDE ANALOGS
- Issue Date
- Jul-2014
- Publisher
- Elsevier BV
- Keywords
- TOYOCAMYCIN; ANTIBIOTICS; ANTIVIRAL AGENT CARBOVIR; HUMAN CYTOMEGALOVIRUS; EFFICIENT SYNTHESIS; TUBERCIDIN; PYRIMIDINES; SANGIVAMYCIN; CYTOTOXICITY; PI-ALLYLPALLADIUM COMPLEXES
- Citation
- Heterocycles, v.89, no.7, pp 1606 - 1619
- Pages
- 14
- Indexed
- SCI
SCIE
SCOPUS
- Journal Title
- Heterocycles
- Volume
- 89
- Number
- 7
- Start Page
- 1606
- End Page
- 1619
- ISSN
- 0385-5414
1881-0942
- Abstract
- New carbocyclic pyrrolo[2,3-d]pyrimidine nucleoside analogs were synthesized with the key intermediate, 4-amino-6-bromo-5-cyanopyrrolo[2,3-c]pyrimidine (2), by S(N)2 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 mu M). 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]-17H-pyrrolo[2,3-d]pyrimidine-5-carboxamide (15) showed very similar antiproliferative activity (IC50: 2.6 mu M) when compared to compound 9.
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Related Researcher
- Rhee, Hak june
- COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY (DEPARTMENT OF CHEMICAL AND MOLECULAR ENGINEERING)