- Simple and convenient synthesis method of N9-alkylate nucleoside analogs on purine framework
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The invention discloses a simple and convenient synthesis method of N9-alkylate nucleoside analogs on a purine framework. The method comprises the following steps that 2,6-site substituted purine derivatives and excessive alkyl ether are added into a reactor; next, non-metallic catalysts and oxidizing agents are added; oxidization coupling reaction is performed under the heating and stirring conditions; thin layer chromatography is used for tracking the reaction; after the reaction is completed, the materials are cooled to the room temperature; vacuum concentration is performed to remove solvents; column chromatography purification is performed; the N9-alkylate nucleoside analogs on the purine framework are obtained. The synthesis method provided by the invention has the advantages that the raw materials are cheap and can be easily obtained; the reaction conditions are mild; the reaction steps are few; the operation is simple; the problems of easy poisoning by metal catalysts, compatibility difficulty of active groups and many reaction sites in the purine derivatization reaction in the prior art are solved; the N9-alkylate nucleoside analogs on the purine framework can be efficiently synthesized.
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Paragraph 0063; 0064; 0065; 0066; 0067; 0068
(2018/03/26)
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- C-H amination of purine derivatives via radical oxidative coupling
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An oxidative coupling reaction between purines and alkyl ethers/benzyl compounds was developed to synthesize a series of N9 alkylated purine derivatives using n-Bu4NI as a catalyst and t-BuOOH as an oxidant. This protocol uses commercially available, inexpensive catalysts and oxidants and has a wide range of substrates with a simple operation.
- Luo, Zheng,Jiang, Ziyang,Jiang, Wei,Lin, Dongen
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p. 3710 - 3718
(2018/04/14)
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- N6,9-Disubstituted Adenines: Potent, Selective Antagonists at the A1 Adenosine Receptor
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N6-Substituted 9-methyladenines are potent antagonists of the activation of A1 adenosine receptors.The present study assessed the effect of N6 and N-9-substituents on the binding of adenines to the A1 and A2 receptors, respectively, of rat brain cortex and striatum and also on the antagonism of the A2 receptor mediated stimulation of the adenylate cyclase of PC12 cells by N-ethyladenosine-5'-uronamide.The potency ranking of 9-substituted adenines varied directly with the hydrophobicity of the substituent: cyclopentyl > phenyl > tetrahydrofuryl > ethyl > methyl > 2-hydroxyethyl.The 9-substituted adenines showed little selectivity for either receptor and the R enantiomer of N6-(1-phenyl-2-propyl)-9-methyladenine was only 4-fold more potent than the S enantiomer at the A1 receptor.An N6-cyclopentyl substituent increased potency at the A1 receptor and decreased potency at the A2 receptor, resulting in selectivity for the A1 receptor of up to 39-fold.The N6-cyclopentyl group completely overshadowed the effect of the hydrophobicity of the 9-substituent.A 2-chloro substituent did not alter the potency of an N6-substituted 9-methyladenine.
- Thompson, Robert D.,Secunda, Sherrie,Daly, John W.,Olsson, Ray A.
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p. 2877 - 2882
(2007/10/02)
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- FACILE SYNTHESIS OF TETRAHYDRO-2-FURYLATED PYRIMIDINES AND PURINES USING A NEW CATALYST OF CESIUM CHLORIDE
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1-(Tetrahydro-2-furyl)pyrimidine and 9-(tetrahydro-2-furyl)purine derivatives were successfully synthesized in good yields by the reactions of trimethylsilylated pyrimidine and purine bases with 2-acetoxytetrahydrofuran using a new catalyst of cesium chloride in acetonitrile under mild conditions.
- Lee, Chun Ho,Kim, Joong Young,Kim, Wan Joo,Kim, Yong Hae
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p. 211 - 214
(2007/10/02)
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- Nucleic Acid Derived Allenols: Unusual Analogues of Nucleosides with Antiretroviral Activity
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Racemic 1,2-butadien-4-ols substituted with a nucleic acid base were prepared by a base-catalyzed isomerization of the corresponding 2-butynols.With basic heterocycles such as adenine, cytosine, 5-methylcytosine, or N-guanine, the respective allenes were obtained without difficulty, but with guanine, side reactions were observed.Reaction of 2-butynols in stronger base (1 M NaOH) gave cyclized products-oxacyclopentenes 8a-c. (+/-)-Adenallene (3a) and (+/-)-cytallene (3c) are strong inhibitors of replication of human immunodeficiency virus(HIV) in vitro. (+/-)-Adenallene (3a) and butyne 6a are substrates for adenosine deaminase.Racemic 3a was deaminated quantitatively to (+/-)-hypoxallene (3h), indicating a low stereoselectivity as contrasted with the natural substrate-adenosine.When the deamination was stopped ad ca. 50percent conversion, (-)-adenallene (3a) and (+)-hypoxallene (3h) were obtained.Antiretroviral and adenosine deaminase substrate activities are discussed in terms of the similarity of several steric and stereoelectronic features of allenic derivatives of nucleic bases with those of the corresponding nucleosides or 2',3'-dideoxyribonuclesides.
- Phadtare, Shashikant,Zemlicka, Jiri
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p. 5925 - 5931
(2007/10/02)
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