scholarly journals Synthesis of (purin-6-yl)acetates and their transformations to 6-(2-hydroxyethyl)- and 6-(carbamoylmethyl)purines

2009 ◽  
Vol 74 (7-8) ◽  
pp. 1035-1059 ◽  
Author(s):  
Zbyněk Hasník ◽  
Radek Pohl ◽  
Blanka Klepetářová ◽  
Michal Hocek
Keyword(s):  
Antiviral Activity ◽  
Cross Coupling ◽  
Significant Activity ◽  
Coupling Reactions ◽  
Nucleophilic Substitutions ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Novel Approach ◽  
Reformatsky Reagent ◽  
Activity Screening

A novel approach to the synthesis of (purin-6-yl)acetates was developed based on Pd-catalyzed cross-coupling reactions of 6-chloropurines with a Reformatsky reagent. Their reduction with NaBH4 and treatment with MnO2 gave 6-(2-hydroxyethyl)purines, while reactions with amines in presence of NaCN afforded 6-(carbamoylmethyl)purines. Mesylation of the 6-(2-hydroxyethyl)purines followed by nucleophilic substitutions gave rise to several 6-(2-substituted ethyl)purines. This methodology was successfully applied to the synthesis of substituted purine bases and nucleosides for cytostatic and antiviral activity screening. None of the compounds exerted significant activity.

Copper-catalyzed synthesis of 2-aminophenyl benzothiazoles: a novel approach

2018 ◽  
Vol 16 (37) ◽  
pp. 8267-8272 ◽  
Author(s):  
S. N. Murthy Boddapati ◽  
Chandra Mohan Kurmarayuni ◽  
Baby Ramana Mutchu ◽  
Ramana Tamminana ◽  
Hari Babu Bollikolla
Keyword(s):  
Nucleophilic Substitution ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
Reaction Conditions ◽  
Moderate Reaction ◽  
Cross Coupling Reactions ◽  
Novel Approach

Substituted 2-aminophenyl benzothiazoles have been constructed from thiourea via copper-catalyzed desulfurization/nucleophilic substitution followed by domino intra- and intermolecular C–N cross-coupling reactions under moderate reaction conditions.

The synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) derivatives by diverse cross-coupling reactions

2011 ◽  
Vol 89 (4) ◽  
pp. 488-498 ◽  
Author(s):  
Ondřej Sedláček ◽  
Petra Břehová ◽  
Radek Pohl ◽  
Antonín Holý ◽  
Zlatko Janeba
Keyword(s):  
Antitumor Activity ◽  
Antiviral Activity ◽  
Parent Compound ◽  
Cross Coupling ◽  
Starting Material ◽  
Coupling Reactions ◽  
Systematic Screening ◽  
Cross Coupling Reactions

Diisopropyl 8-bromo-2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine was used as a starting material for the synthesis of the 8-C-substituted 2,6-diamino-9-[2-(phosphonomethoxy)ethyl]purine (PMEDAP) analogues. A systematic screening of diverse cross-coupling reactions was carried out. Stille, Suzuki–Miyaura, Negishi, and Sonogashira cross-couplings, as well as Pd-catalysed reactions with trialkylaluminiums, were employed for the introduction of various alkyl, alkenyl, alkynyl, aryl, and hetaryl substituents to the C-8 position of the 2,6-diaminopurine moiety. In contrast to the potent parent compound PMEDAP, which exhibits potent antiretroviral and antitumor activity, none of the sixteen newly synthesized 8-C-substituted analogues of PMEDAP showed any specific antiviral activity.

Cytostatic 6-Arylpurine Nucleosides V. Synthesis of 8-Substituted 6-Phenylpurine Ribonucleosides

2003 ◽  
Vol 68 (5) ◽  
pp. 837-848 ◽  
Author(s):  
Michal Hocek ◽  
Dana Hocková ◽  
Jan Štambaský
Keyword(s):  
Phenylboronic Acid ◽  
Cross Coupling ◽  
Cytostatic Activity ◽  
Coupling Reactions ◽  
Nucleophilic Substitutions ◽  
Cross Coupling Reactions

Regioselective Suzuki-Miyaura reaction of 8-bromo-6-iodo-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine with phenylboronic acid gave 8-bromo-6-phenylpurine derivative that was used for cross-coupling reactions (with PhB(OH)2, Me3Al, Et3Al, BnZnCl) or nucleophilic substitutions (with NaOH, NaOMe, NH3, NHMe2 or thiourea). A series of 8-X-substituted 6-phenyl-9-(β-D-ribofuranosyl)purines (X = Ph, Me, Et, Bn, OH, OMe, NH2, NMe2, SH) was prepared in this way directly or after deprotection. None of the title nucleosides exhibited any considerable cytostatic activity.

Synthesis of 6-Amino-, 6-Methyl- and 6-Aryl-2-(hydroxymethyl)purine Bases and Nucleosides

2006 ◽  
Vol 71 (6) ◽  
pp. 788-803 ◽  
Author(s):  
Peter Šilhár ◽  
Radek Pohl ◽  
Ivan Votruba ◽  
Blanka Klepetářová ◽  
Michal Hocek
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
Purine Derivatives ◽  
Purine Bases ◽  
Arylboronic Acids ◽  
Cross Coupling Reactions ◽  
Zinc Iodide

An efficient methodology of the synthesis of 6-substituted 2-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed. Regioselective Pd-catalyzed cross-coupling reactions of 6-chloro-2-iodopurines with [(benzoyloxy)methyl]zinc iodide gave 2-[(benzoyloxy)-methyl]-6-chloropurines that were converted to 2-(hydroxymethyl)adenines by reactions with ammonia and to 6-methyl- or 6-aryl-2-(hydroxymethyl)purines by cross-coupling reactions with trimethylaluminium or arylboronic acids followed by deprotection. The title 6-substituted 2-(hydroxymethyl)purine bases and nucleosides did not exhibit significant cytostatic or anti-HCV activity.

New developments in direct functionalization of C–H and N–H bonds of purine bases via metal catalyzed cross-coupling reactions

RSC Advances ◽  
2015 ◽  
Vol 5 (55) ◽  
pp. 44371-44389 ◽  
Author(s):  
Morteza Abdoli ◽  
Zohreh Mirjafary ◽  
Hamid Saeidian ◽  
Ali Kakanejadifard
Keyword(s):  
Cross Coupling ◽  
Coupling Reactions ◽  
New Developments ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Concise Overview ◽  
Direct Functionalization ◽  
The Cross ◽  
Metal Catalyzed

This review provides a concise overview on the cross-coupling reactions in direct functionalization of purine bases in recent years.

Synthesis of 2-Substituted 6-(Hydroxymethyl)purine Bases and Nucleosides

2005 ◽  
Vol 70 (10) ◽  
pp. 1669-1695 ◽  
Author(s):  
Peter Šilhár ◽  
Radek Pohl ◽  
Ivan Votruba ◽  
Michal Hocek
Keyword(s):  
Adenosine Deaminase ◽  
Cross Coupling ◽  
The Other ◽  
Coupling Reactions ◽  
Purine Derivatives ◽  
Cytostatic Effect ◽  
Purine Bases ◽  
Cross Coupling Reactions ◽  
Zinc Iodide

A facile and efficient methodology of the synthesis of 6-(hydroxymethyl)purine derivatives (bases and nucleosides) was developed based on Pd-catalyzed cross-coupling reactions of 6-halopurines or N-protected 2-amino-6-halopurines with (benzoyloxymethyl)zinc iodide followed by deprotection. Regioselective hydroxymethylations of 2,6-dihalopurines were also studied and used for the synthesis of 2-chloro-6-(hydroxymethyl)- or 2,6-bis(hydroxymethyl)purines. The 6-(hydroxymethyl)purine ribonucleoside 5f exerted high cytostatic effect and moderate inhibition of adenosine deaminase, while all the other derivatives were much less effective or entirely inactive.

Sign in / Sign up

Export Citation Format

Share Document