THE SYNTHESIS AND EVALUATION OF NEW CARBOCYCLIC PYRROLO[2,3-d]PYRIMIDINE NUCLEOSIDE ANALOGS
- Title
- THE SYNTHESIS AND EVALUATION OF NEW CARBOCYCLIC PYRROLO[2,3-d]PYRIMIDINE NUCLEOSIDE ANALOGS
- Author
- 이학준
- Keywords
- TOYOCAMYCIN; ANTIBIOTICS; ANTIVIRAL AGENT CARBOVIR; HUMAN CYTOMEGALOVIRUS; EFFICIENT SYNTHESIS; TUBERCIDIN; PYRIMIDINES; SANGIVAMYCIN; CYTOTOXICITY; PI-ALLYLPALLADIUM COMPLEXES
- Issue Date
- 2014-07
- Publisher
- Elsevier BV
- Citation
- Heterocycles, v. 89, NO. 7, Page. 1606-1619
- 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.
- URI
- https://www.heterocycles.jp/newlibrary/libraries/abst/23922https://repository.hanyang.ac.kr/handle/20.500.11754/183971
- ISSN
- 0385-5414;1881-0942
- DOI
- 10.3987/COM-14-12999
- Appears in Collections:
- COLLEGE OF SCIENCE AND CONVERGENCE TECHNOLOGY[E](과학기술융합대학) > CHEMICAL AND MOLECULAR ENGINEERING(화학분자공학과) > Articles
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