Alkylation of 9-substituted guanine derivatives with α,ω-dihaloalkanes

2017 ◽  
Vol 28 (5) ◽  
pp. e21399 ◽  
Author(s):  
Grzegorz Framski ◽  
Tomasz Goslinski ◽  
Piotr Januszczyk ◽  
Bozenna Golankiewicz ◽  
Tomasz Ostrowski
Keyword(s):  
Guanine Derivatives

scholarly journals Synthesis, Oral Bioavailability and in vivo Activity of Acetal Derivatives of the Selective Antiherpesvirus Agent 9-(3-hydroxypropoxy) Guanine (BRL 44385)

1994 ◽  
Vol 5 (3) ◽  
pp. 147-154
Author(s):  
M. R. Harnden ◽  
R. J. Ashton ◽  
M. R. Boyd ◽  
L. J. Jennings ◽  
D. Sutton ◽  
...  
Keyword(s):  
Oral Administration ◽  
Oral Bioavailability ◽  
Oral Delivery ◽  
Ring Closure ◽  
Guanine Derivatives ◽  
Derivatives Of ◽  
Lesion Severity ◽  
Hsv 1

Acyclic acetal derivatives of the selective antiherpesvirus agent 9-(3-hydroxypropoxy) guanine (BRL44385) and of its 2-aminopurine congener (BRL46720) have been prepared and evaluated in mice for oral delivery of BRL 44385. Guanine derivatives (6 a-c) were prepared via Mitsunobu condensation of an alcohol with a 9-hydroxy-6-methoxypurine (Harnden and Wyatt, 1990). Synthesis of derivatives of 2-aminopurine (10 a-d) was achieved by hydrogenolysis of 9-alkoxy-6-chloropurines, which were obtained either by reaction of an alkoxyamine with 4,6-dichloro-2,5-diformamidopyrimidine and subsequent ring closure or by Mitsunobu condensation of an alcohol with a 6-chloro-9-hydroxypurine. Following oral administration, 2-amino-9-[3-(iso-propoxymethyl)propoxy]-purine (10b, BRL 55792) was very well absorbed and provided high and prolonged concentrations of BRL44385 in the blood. In a cutaneous HSV-1 infection in the ear pinna of mice, orally dosed BRL 55792 was at least 3-fold more potent than both BRL44385 and Acyclovir in reduction of lesion severity.

ChemInform Abstract: SYNTHESIS OF THIAZOLO(2,3-F)GUANINE DERIVATIVES

1975 ◽  
Vol 6 (29) ◽  
pp. no-no
Author(s):  
H. UNO ◽  
A. IRIE ◽  
K. HINO
Keyword(s):  
Guanine Derivatives

scholarly journals Guanine-vacancy–bearing G-quadruplexes responsive to guanine derivatives

2015 ◽  
Vol 112 (47) ◽  
pp. 14581-14586 ◽  
Author(s):  
Xin-min Li ◽  
Ke-wei Zheng ◽  
Jia-yu Zhang ◽  
Hong-he Liu ◽  
Yi-de He ◽  
...  
Keyword(s):  
Dimethyl Sulfate ◽  
Physiological Concentration ◽  
Unique Type ◽  
Cellular Processes ◽  
G Quadruplex ◽  
Guanine Derivatives ◽  
Guanine Base ◽  
Definition Of ◽  
Thermal Melting

G-quadruplex structures formed by guanine-rich nucleic acids are implicated in essential physiological and pathological processes and nanodevices. G-quadruplexes are normally composed of four Gn (n ≥ 3) tracts assembled into a core of multiple stacked G-quartet layers. By dimethyl sulfate footprinting, circular dichroism spectroscopy, thermal melting, and photo-cross-linking, here we describe a unique type of intramolecular G-quadruplex that forms with one G2 and three G3 tracts and bears a guanine vacancy (G-vacancy) in one of the G-quartet layers. The G-vacancy can be filled up by a guanine base from GTP or GMP to complete an intact G-quartet by Hoogsteen hydrogen bonding, resulting in significant G-quadruplex stabilization that can effectively alter DNA replication in vitro at physiological concentration of GTP and Mg2+. A bioinformatic survey shows motifs of such G-quadruplexes are evolutionally selected in genes with unique distribution pattern in both eukaryotic and prokaryotic organisms, implying such G-vacancy–bearing G-quadruplexes are present and play a role in gene regulation. Because guanine derivatives are natural metabolites in cells, the formation of such G-quadruplexes and guanine fill-in (G-fill-in) may grant an environment-responsive regulation in cellular processes. Our findings thus not only expand the sequence definition of G-quadruplex formation, but more importantly, reveal a structural and functional property not seen in the standard canonical G-quadruplexes.

Regioselective alkylation of guanine derivatives in the synthesis of peptide nucleic acid monomers

2015 ◽  
Vol 64 (5) ◽  
pp. 1100-1106 ◽  
Author(s):  
A. V. Dezhenkov ◽  
D. A. Cheshkov ◽  
I. A. Prokhorov ◽  
L. G. Dezhenkova ◽  
V. I. Shvets ◽  
...  
Keyword(s):  
Nucleic Acid ◽  
Peptide Nucleic Acid ◽  
Regioselective Alkylation ◽  
Guanine Derivatives

Lipophilicity of guanine derivatives

1989 ◽  
Vol 57 (3) ◽  
pp. 229-234 ◽  
Author(s):  
A. Kristl ◽  
A. Mrhar ◽  
F. Kozjek ◽  
J. Kobe
Keyword(s):  
Guanine Derivatives

Guanine derivatives modulate extracellular matrix proteins organization and improve neuron-astrocyte co-culture

2007 ◽  
Vol 85 (9) ◽  
pp. 1943-1951 ◽  
Author(s):  
Helena Decker ◽  
Sheila S. Francisco ◽  
Cláudia B.N. Mendes-de-Aguiar ◽  
Luciana F. Romão ◽  
Carina R. Boeck ◽  
...  
Keyword(s):  
Extracellular Matrix ◽  
Extracellular Matrix Proteins ◽  
Matrix Proteins ◽  
Guanine Derivatives
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