BASE-MODIFIED NUCLEOSIDES RELATED TO 2-CHLORO-2'-DEOXYADENOSINE

Autor(en): KAZIMIERCZUK, Z
VILPO, JA
SEELA, F
Stichwörter: 2-CHLORODEOXYADENOSINE; ADENOSINE-DEAMINASE; CELL-LINES; Chemistry; Chemistry, Multidisciplinary; DEOXYADENOSINE ANALOGS; DEOXYCYTIDINE KINASE; HUMAN-LYMPHOCYTES; LEUKEMIA; SODIUM-SALT GLYCOSYLATION; SUBSTRATE; TOXICITY
Erscheinungsdatum: 1992
Herausgeber: NEW SWISS CHEMICAL SOC
Journal: HELVETICA CHIMICA ACTA
Volumen: 75
Ausgabe: 7
Startseite: 2289
Seitenende: 2297
Zusammenfassung: 
Derivatives of 2-chloro-2'-deoxyadenosine (1a) containing secondary 6-NH2 groups (5a-c) or a 8-Br substituent (9) were synthesized. They were tested together with ring-modified congeners containing a pyrrolo[2,3-b]pyridine, pyrrolo[3,2-c]pyridine, or pyrazolo[3,4-d]pyrimidine ring system as inhibitors of various leukemic cell lines. Only the 8-Br derivatives 9 showed inhibitory activity, whereas the base-modified congeners were not active. Compound la was protonated at a pK(a) = 1.4(2'-deoxyadenosine at pK(a) = 3.8). Protonation occurred at N(7) and not at N(1) as observed for dA.
ISSN: 0018019X
DOI: 10.1002/hlca.19920750715

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