New 2-Alkynyl Derivatives of the Acyclic Nucleoside 9-(2,3-Dihydroxypropyl)adenine and Their 6-Guanidinopurine Counterparts as Potential Effectors of Adenosine Receptors

2003 ◽  
Vol 68 (11) ◽  
pp. 2201-2218 ◽  
Author(s):  
Michal Česnek ◽  
Antonín Holý ◽  
Milena Masojídková
Keyword(s):  
Adenosine Receptors ◽  
Sonogashira Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

A series of the new 2-alkynyl derivatives of the acyclic nucleoside 9-(2,3-dihydroxypropyl)- adenine and their 6-guanidinopurine analogues were prepared by the Sonogashira coupling. The effect of the prepared compounds on A1 and A2A receptors was examined.

scholarly journals Facile synthesis of 1-alkoxy-1H-benzo- and 7-azabenzotriazoles from peptide coupling agents, mechanistic studies, and synthetic applications

2014 ◽  
Vol 10 ◽  
pp. 1919-1932 ◽  
Author(s):  
Mahesh K Lakshman ◽  
Manish K Singh ◽  
Mukesh Kumar ◽  
Raghu Ram Chamala ◽  
Vijayender R Yedulla ◽  
...  
Keyword(s):  
Amide Bond ◽  
Coupling Agents ◽  
Cyclic Ketones ◽  
Substitution Reactions ◽  
Facile Synthesis ◽  
Reaction Conditions ◽  
Peptide Coupling ◽  
Acyclic Nucleoside ◽  
Derivatives Of

(1H-Benzo[d][1,2,3]triazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP), 1H-benzo[d][1,2,3]triazol-1-yl 4-methylbenzenesulfonate (Bt-OTs), and 3H-[1,2,3]triazolo[4,5-b]pyridine-3-yl 4-methylbenzenesulfonate (At-OTs) are classically utilized in peptide synthesis for amide-bond formation. However, a previously undescribed reaction of these compounds with alcohols in the presence of a base, leads to 1-alkoxy-1H-benzo- (Bt-OR) and 7-azabenzotriazoles (At-OR). Although BOP undergoes reactions with alcohols to furnish 1-alkoxy-1H-benzotriazoles, Bt-OTs proved to be superior. Both, primary and secondary alcohols undergo reaction under generally mild reaction conditions. Correspondingly, 1-alkoxy-1H-7-azabenzotriazoles were synthesized from At-OTs. Mechanistically, there are three pathways by which these peptide-coupling agents can react with alcohols. From 31P{1H}, [18O]-labeling, and other chemical experiments, phosphonium and tosylate derivatives of alcohols seem to be intermediates. These then react with BtO− and AtO− produced in situ. In order to demonstrate broader utility, this novel reaction has been used to prepare a series of acyclic nucleoside-like compounds. Because BtO− is a nucleofuge, several Bt-OCH2Ar substrates have been evaluated in nucleophilic substitution reactions. Finally, the possible formation of Pd π–allyl complexes by departure of BtO− has been queried. Thus, alpha-allylation of three cyclic ketones was evaluated with 1-(cinnamyloxy)-1H-benzo[d][1,2,3]triazole, via in situ formation of pyrrolidine enamines and Pd catalysis.

Bifunctional Acyclic Nucleoside Phosphonates. 1. Symmetrical 1,3-Bis[(phosphonomethoxy)propan-2-yl] Derivatives of Purines and Pyrimidines

2006 ◽  
Vol 71 (4) ◽  
pp. 543-566 ◽  
Author(s):  
Silvie Vrbovská ◽  
Antonín Holý ◽  
Radek Pohl ◽  
Milena Masojídková
Keyword(s):  
Biological Activity ◽  
Cytostatic Activity ◽  
Secondary Alcohols ◽  
Phosphonic Acids ◽  
Acyclic Nucleoside Phosphonates ◽  
Pyrimidine Bases ◽  
Acyclic Nucleoside ◽  
Derivatives Of ◽  
Purines And Pyrimidines ◽  
General Method

We report here a general method for the synthesis of new symmetrical bis-phosphonates of acyclic nucleosides. 1,3-Bis[(diisopropoxyphosphoryl)methoxy] derivatives of purine and pyrimidine bases were prepared by their reaction with 1,3-bis[(diisopropoxyphosphoryl)-methoxy]propan-2-yl tosylate. Cytosine, uracil and thymine provided regiospecificallyN1-isomers. This alkylation regiospecificity applies to several other tosylates of primary and secondary alcohols as well. 6-Chloropurine and 2-amino-6-chloropurine were alkylated in N9position. Resulting bis-phosphonates were converted to the respective free phosphonic acids and tested for antiviral and cytostatic activity. Despite the fact that no biological activity was found so far, the outcome of this work can serve as a useful tool in synthesis of novel groups of acyclic nucleoside phosphonates (ANPs).

Effects of amino and ammonio derivatives of adenosine on smooth muscle preparations and mouse neuroblastoma adenylate cyclase

1985 ◽  
Vol 63 (1) ◽  
pp. 58-61 ◽  
Author(s):  
H. P. Baer ◽  
M. Morr
Keyword(s):  
Smooth Muscle ◽  
Adenylate Cyclase ◽  
Adenosine Receptors ◽  
Smooth Muscles ◽  
Mouse Neuroblastoma ◽  
Derivatives Of ◽  
Stimulation Of

Several amino- and ammonio-substituted derivatives of adenosine were tested as effectors of adenosine receptors in different smooth muscle preparations and mouse neuroblastoma adenylate cyclase. The compounds did not affect adenosine receptors in smooth muscles. N6-[3-(trimethylammonio)propyl]adenosine was a weak stimulator of adenylate cyclase, and 3′-amino-3′-deoxyadenosine and 3′-rnonomethylamino-3′-deoxyadenosine antagonized the stimulation of adenylate cyclase by 2-chloroadenosine.

scholarly journals Electrophilic derivatives of purines as irreversible inhibitors of A1 adenosine receptors

1989 ◽  
Vol 32 (5) ◽  
pp. 1043-1051 ◽  
Author(s):  
Kenneth A. Jacobson ◽  
Suzanne Barone ◽  
Udai Kammula ◽  
Gary L. Stiles
Keyword(s):  
Adenosine Receptors ◽  
Irreversible Inhibitors ◽  
A1 Adenosine Receptors ◽  
Derivatives Of

scholarly journals Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

2012 ◽  
Vol 8 ◽  
pp. 522-527 ◽  
Author(s):  
Supriya Dey ◽  
Narayanaswamy Jayaraman
Keyword(s):  
Suzuki Reaction ◽  
Ring Expansion ◽  
Protecting Groups ◽  
Coupling Reactions ◽  
Sonogashira Coupling ◽  
Alkyl Aryl ◽  
Organometallic Reactions ◽  
Bond Forming ◽  
Derivatives Of ◽  
Cyclopropane Derivatives

This paper deals with the synthesis of 2-deoxy-2-C-alkyl/aryl septanosides. A range of such septanoside derivatives was synthesized by using a common bromo-oxepine intermediate, involving C–C bond forming organometallic reactions. Unsaturated, seven-membered septanoside vinyl bromides or bromo-oxepines, obtained through a ring expansion methodology of the cyclopropane derivatives of oxyglycals, displayed a good reactivity towards several acceptor moieties in C–C bond forming Heck, Suzuki and Sonogashira coupling reactions, thus affording 2-deoxy-2-C-alkyl/aryl septanosides. Whereas Heck and Sonogashira coupling reactions afforded 2-deoxy-2-C-alkenyl and -alkynyl derivatives, respectively, the Suzuki reaction afforded 2-deoxy-2-C-aryl septanosides. Deprotection and reduction of the 2-deoxy-2-alkenyl derivative afforded the corresponding 2-deoxy-2-C-alkyl septanoside free of protecting groups. The present study illustrates the reactivity of bromo-oxepine in the synthesis of hitherto unknown septanosides, branching out at C-2, through C–C bond formation with alkyl and aryl substituents.

2-Alkynyl derivatives of adenosine and adenosine-5'-N-ethyluronamide as selective agonists at A2 adenosine receptors

1992 ◽  
Vol 35 (13) ◽  
pp. 2363-2368 ◽  
Author(s):  
Gloria Cristalli ◽  
Alessandra Eleuteri ◽  
Sauro Vittori ◽  
Rosaria Volpini ◽  
Martin J. Lohse ◽  
...  
Keyword(s):  
Adenosine Receptors ◽  
Selective Agonists ◽  
Derivatives Of ◽  
A2 Adenosine Receptors
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