Synthesis and Properties of Purine Nucleosides and Nucleotides

Srivastava, Prem C.; Robins, Roland K.; Meyer, Rich B.

doi:10.1007/978-1-4613-0995-6_2

Cited by 28 publications

(28 citation statements)

References 589 publications

(235 reference statements)

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“…The reaction would obey a secondorder kinetics provided the concentrations of the reagents are maintained at appropriate stoichiometric levels [16]. To mimic the general conditions utilized for the deprotection of acetyl groups in nucleoside chemistry [1], the defluorination kinetic reactions were conducted with >100 molar excess of ammonia in methanol or 2-propanol. Under such conditions, the defluorination reaction would follow a pseudo-first-order kinetics.…”

Section: Defluorination Studiesmentioning

confidence: 99%

“…Yield: 5.2%, semi-solid. UV(CH 3 OH) l max = 242 and 276 nm; 1 Method B-Reaction solvent: CH 3 NO 2 . Yield: 5.7%.…”

Section: General Procedures [4]mentioning

confidence: 99%

“…Yield: 3.9%, colorless film. UV(CH 3 OH) l max = 262 and 280 nm (sh); 1 Method C-Reaction solvent: CHCl 3 (stabilized with 1% EtOH). Silica gel column chromatography eluent: CH 2 Cl 2 / CH 3 OH (98/2 followed by 95/5).…”

Section: General Procedures [4]mentioning

confidence: 99%

“…Purine nucleosides with C(8) substituents have been known to exhibit significant biological activities [1]. During the past 25 years, reports have appeared on the pharmacological properties of 8-chloro-and 8-bromopurine nucleosides [2].…”

Section: Introductionmentioning

confidence: 99%

“…Significant defluorination was observed when the protected 8-fluoropurine nucleosides were subjected to the standard deprotection conditions in basic media [1]. For example, deacetylation of N 2 -acetyl-2 0 ,3 0 ,5 0 -tri-O-acetyl-8-fluoroguanosine with methanolic ammonia yielded 8-fluoroguanosine (50%) along with a defluorinated derivative, namely 8-methoxyguanosine (50%) [4b].…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

Liu

Barrio

Satyamurthy

2006

Journal of Fluorine Chemistry

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Section: Defluorination Studiesmentioning

confidence: 99%

“…Yield: 5.2%, semi-solid. UV(CH 3 OH) l max = 242 and 276 nm; 1 Method B-Reaction solvent: CH 3 NO 2 . Yield: 5.7%.…”

Section: General Procedures [4]mentioning

confidence: 99%

Section: General Procedures [4]mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

Liu

Barrio

Satyamurthy

2006

Journal of Fluorine Chemistry

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Medicinal chemistry of the human adenosine A3 receptor

1998

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Partial agonists and antagonists were synthesized and evaluated biologically for extended pharmacologic characterization of the human adenosine A3 receptor. The affinities of all compounds were determined at the human adenosine A3 receptor stably transfected in HEK 293 cells and in rat brain membranes for the adenosine A1 and A2A receptors. The partial agonists were also evaluated for their ability to stimulate [35S]GTPγ[S] binding in Chinese hamster ovary cells expressing the human adenosine A3 receptor to determine their intrinsic activities. 5′‐(Alkylthio)‐substituted analogs of N6‐(3‐iodobenzyl)adenosine were synthesized in 47–60% overall yields. The compounds proved to be potent and selective partial agonists for the A3 receptor, displaying affinities in the nanomolar range. N6‐(3‐iodobenzyl)adenosine (2), 5′‐deoxy‐N6‐(3‐iodobenzyl)‐5′‐methyl‐thioadenosine (4), and 5′‐deoxy‐N6‐(3‐iodobenzyl)‐5′‐ethylthioadenosine (5) had highest affinities for the A3 receptor with Ki values ranging from 9–28 nM. Compound 6 (5′‐deoxy‐N6‐(3‐iodobenzyl)‐5′‐n‐propyl‐thioadenosine) had the highest (over 200‐fold) A3 receptor selectivity. Of all partial agonists, 2 and 4 had the highest intrinsic activities. Subsequently, a series of 3‐(2‐pyridinyl)isoquinoline derivatives was synthesized as potential antagonists for the human adenosine A3 receptor. A structure‐activity relationship was performed at the 1‐position of this series. This analysis indicated that a phenyl group, when coupled by a spacer allowing conjugation on position 1 of the isoquinoline ring, increased the adenosine A3 receptor affinity. Of all spacers tested, a carboxamide proved to be optimal. N‐[2‐(2‐pyridinyl)isoquinolin‐4‐yl]‐benzamide (9) had an affinity of 200 nM at the adenosine A3 receptor. Furthermore, the effects of mono‐ and disubstitution of the benzamide ring of 9 were investigated. This led to the A3‐selective compound 4‐methoxy‐N‐[2‐(2‐pyridinyl)quinazolin‐4‐yl]‐benzamide (18) with an affinity of 17 nM at the human adenosine A3 receptor. These partial agonists and antagonists may be useful tools in the pharmacologic characterization and the investigation of the physiologic function of this receptor. Drug Dev. Res. 45:182–189, 1998. © 1998 Wiley‐Liss, Inc.

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Enzymatic Synthesis of M₁G‐Deoxyribose

Schnetz-Boutaud

Chapeau

Marnett

2000

CP Nucleic Acid Chemistry

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Adducts formed between electrophiles and nucleic acid bases are believed to play a key role in chemically induced mutations and cancer. M(1)G-dR is an endogenous exocyclic DNA adduct formed by the reaction of the dicarbonyl compound malondialdehyde with a dG residue in DNA. It is an intermediate in the synthesis of a class of modified oligodeoxyribonucleotides that are used to study the mutagenicity and repair of M(1)G. This unit presents methods for synthesizing M(1)G-dR by enzymatic coupling.

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Synthesis and Properties of Purine Nucleosides and Nucleotides

Cited by 28 publications

References 589 publications

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

Medicinal chemistry of the human adenosine A3 receptor

Enzymatic Synthesis of M₁G‐Deoxyribose

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Synthesis and Properties of Purine Nucleosides and Nucleotides

Cited by 28 publications

References 589 publications

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

Kinetics and mechanism of the defluorination of 8-fluoropurine nucleosides in basic and acidic media

Medicinal chemistry of the human adenosine A3 receptor

Enzymatic Synthesis of M1G‐Deoxyribose

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Enzymatic Synthesis of M₁G‐Deoxyribose