7051-86-7Relevant academic research and scientific papers
One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph3P/I2: simple route for carboacyclic nucleoside synthesis
Soltani Rad, Mohammad Navid,Soleimani, Faezeh
supporting information, p. 4947 - 4953 (2016/07/19)
A simple and efficient synthetic protocol for the one-pot N-alkylation of nucleobases and their related N-heterocycles via alcohols utilizing the combination of PPh3and I2is reported. In this protocol purine, pyrimidine and azole derivatives underwent the N-alkylation reaction with diverse primary alcohols using Ph3P/I2in the presence of Et3N-K2CO3in anhydrous DMF to give the N-alkyl adducts (carboacyclic nucleosides) in good yields (up to 90%). The influence of some parameters in this reaction including type of solvent, base, reagents and temperature was discussed. In addition, this protocol has proved the favorable selectivity towards primary hydroxyl versus secondary hydroxyl group in diols.
Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: A rapid route to access acyclic nucleosides
Rad, Mohammad Navid Soltani,Behrouz, Somayeh,Zarenezhad, Elham,Kaviani, Narjes
, p. 1603 - 1612 (2015/07/07)
Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-a
Structure-activity relationships of adenine and deazaadenine derivatives as ligands for adenine receptors, a new purinergic receptor family
Borrmann, Thomas,Abdelrahman, Aliaa,Volpini, Rosaria,Lambertucci, Catia,Alksnis, Edgars,Gorzalka, Simone,Knospe, Melanie,Schiedel, Anke C.,Cristalli, Gloria,Müller, Christa E.
supporting information; scheme or table, p. 5974 - 5989 (2010/03/24)
Adenine derivatives bearing substituents in the 2-, N6-, 7-, 8-, and/or 9-position and a series of deazapurines were synthesized and investigated in [3H]adenine binding studies at the adenine receptor in rat brain cortical membrane preparations (rAde1R). Steep structure-activity relationships were observed. Substitution in the 8-position (amino, dimethylamino, piperidinyl, piperazinyl) or in the 9-position (2-morpholinoethyl) with basic residues or introduction of polar substituents at the 6-amino function (hydroxy, amino, acetyl) represented the best modifications. Functional evaluation of selected adenine derivatives in adenylate cyclase assays at 1321N1 astrocytoma cells stably expressing the rAde1R showed that all compounds investigated were agonists or partial agonists. A subset of compounds was additionally investigated in binding studies at human embryonic kidney (HEK293) cells, which also express a high-affinity adenine binding site. Structure-affinity relationships at the human cell line were similar to those at the rAde1R, but not identical. In particular, N 6-acetyladenine (25, Ki rat: 2.85 μM; Ki human: 0.515 μM) and 8-aminoadenine (33, Ki rat: 6.51 μM; Ki human: 0.0341 μM) were much more potent at the human as compared to the rat binding site. The new AdeR ligands may serve as lead structures and contribute to the elucidation of the functions of the adenine receptor family. 2009 American Chemical Society.
One-pot synthesis of n-alkyl purine, pyrimidine and azole derivatives from alcohols using ph3p/ccl4: A rapid route to carboacyclic nucleoside synthesis
Rad, Mohammad Navid Soltani,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Asrari, Zeinab,Behrouz, Marzieh,Aminia, Zohreh
experimental part, p. 3067 - 3076 (2009/12/28)
A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n- butylammonium iodide (TBAI) in refluxing N,N-dimethylformamide, furnishes the corresponding N-alkyl derivatives in good yields. This methodology is highly efficient for various structurally diverse primary alcohols and also useful for N-alkylation of other N-heterocycles containing an acidic N-H bond.
One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: a rapid entry into carboacyclic nucleoside synthesis
Soltani Rad, Mohammad Navid,Khalafi-Nezhad, Ali,Behrouz, Somayeh,Faghihi, Mohammad?Ali,Zare, Abdolkarim,Parhami, Abolfath
, p. 1778 - 1785 (2008/09/18)
A convenient and efficient one-pot N-alkylation of nucleobases from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of purine or pyrimidine nucleobase, TsIm, K2CO3, and triethylamine in refluxing DMF regioselectively furnishes the corresponding N-alkyl nucleobases in good yields. This methodology is highly efficient for various structurally diverse primary alcohols.
9-(2-Aryloxyethyl) derivatives of adenine - A new class of non-nucleosidic antiviral agents
Petrov,Ozerov,Novikov,Pannecouque,Balzarini,De Clercq
, p. 1218 - 1226 (2007/10/03)
New 9-(aryloxyalkyl) derivatives of adenine have been prepared by alkylation of adenine with tosylates, bromides, and α-chloro ethers containing terminal aromatic fragments in anhydrous DMF in the presence of potassium carbonate. The compounds of the 9-(2-phenoxyethyl)adenine series appear to be highly reactive against cytomegaloviruses of mankind in vitro, while derivatives of 9-(2-benzyloxyethyl)adenine demonstrate anti-HIV-1 activity. Compounds with shorter or longer chains, and also compounds which do not have aromatic fragments at the ends of the chains, do not possess antiviral activity.
