9-[(Hydroxymethyl)phenyl]adenines: new aryladenine substrates of adenosine deaminase

Brakta, Mohamed; Murthy, Devangachinta; Ellis, L'Ouverture; Phadtare, Shashikant

doi:10.1016/s0960-894x(02)00192-0

Cited by 20 publications

(9 citation statements)

References 13 publications

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“…N ‐Arylnucleobases are very important compounds because of their significant pharmaceutical, biological, and chemical activities. Several arylnucleobases are agonists or antagonists for various receptors1 and enzymes 2. Other bioactivities reported include those against the rubella virus,3 and inhibition of rabbit skeletal muscle phosphorylase b 4…”

Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Cross‐Coupling Reactions of Nucleobases with Arylboronic Acids: An Efficient Access to N‐Arylnucleobases

Yue

Zheng

et al. 2005

Eur J Org Chem

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An efficient avenue for the direct N‐arylation of nucleobases with arylboronic acids that is catalyzed by simple copper salts was discovered. The N‐arylnucleobases were obtained in excellent yields at room temperature within 45 min when methanol and water were used as a mixed solvent. Under these conditions, the coupling reaction tolerates both electron‐donating and electron‐withdrawing substituents at the o‐, m‐, or p‐positions of phenylboronic acid and gives the corresponding coupling products in moderate to excellent yields. Experimental results show that this route is the most efficient, facile, and mild method for the synthesis of N‐arylnucleobases. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Methodsmentioning

confidence: 99%

Copper‐Catalyzed Cross‐Coupling Reactions of Nucleobases with Arylboronic Acids: An Efficient Access to N‐Arylnucleobases

Yue

Zheng

et al. 2005

Eur J Org Chem

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“…Cytotoxicity to noninfected cells is expressed as CC 50 . The evaluation of the first series of compounds (3,(8)(9)(10)(11)(12)(13)(14)(15) revealed that a chlorine or bromine atom was required at position 6 of the purine in order to get antiviral activity, as shown for compounds 3, 9, and 10. The nonsubstituted compound (12) or those with NHMe, OMe, or carbonyl at position 6 of the purine (compounds 13, 14, and 15, respectively) were antivirally inactive.…”

Section: Resultsmentioning

confidence: 99%

“…11 Later on, Brakta et al described the synthesis of the adenine derivative (Chart 1, X = NH 2 , Y = Z = H) as a substrate of adenosine deaminase. 12 More recently, Ueno et al prepared bis(hydroxymethyl)benzene residues directly connected to the nucleobases to construct a nucleic acid analogue. 13 The synthesis of these 9-arylpurines has been carried out following the classical method described by Greenberg in 1959 that involves reaction of 5-amino-4, 6-dihalopyrimidines with anilines followed by a ring closing reaction.…”

Section: Introductionmentioning

confidence: 99%

9-Arylpurines as a Novel Class of Enterovirus Inhibitors

et al. 2009

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Here we report on a novel class of enterovirus inhibitors that can be structurally described as 9-arylpurines. These compounds elicit activity against a variety of enteroviruses in the low microM range including Coxsackie virus A16, A21, A24, Coxsackie virus B3, and echovirus 9. Structure-activity relationship (SAR) studies indicate that a chlorine or bromine atom is required at position 6 of the purine ring for antiviral activity. The most selective compounds in this series inhibited Coxsackie virus B3 replication in a dose-dependent manner with EC(50) values around 5-8 microM. No toxicity on different cell lines was observed at concentrations up to 250 microM. Moreover, no cross-resistance to TBZE-029 and TTP-8307 CVB3 resistant strains was detected.

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“…[84][85][86][87] A few 9-[(hydroxyalkyl)phenyl]adenines 72-74 were synthesized and tested as substrates of ADA. 88 The time for quantitative enzymatic deamination of compounds 70-74 are shown in brackets in Figure 10. The results indicate that, in contrast to ortho-72 and meta-74 hydroxymethyl derivatives that were quantitatively deaminated in ten hours and six hours respectively, the ortho-hydroxyethyl 73 was not transformed, even after seven days ( Figure 10).…”

Section: Figurementioning

confidence: 99%

Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

Santaniello¹,

Ciuffreda²,

Alessandrini³

2005

Synthesis

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Adenosine deaminase (ADA) and adenylic acid deaminase (AMPDA) are enzymes that catalyze the hydrolytic deamination of various purine nucleosides. In light of recent reports, ADA and AMPDA may be considered as valuable biocatalysts in nucleoside chemistry. Here, they can find many synthetic applications in the transformation of purine nucleosides that are modified in the base or the ribose moiety. Their use can be extended to carbocyclonucleosides or acyclonucleosides as well.

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9-[(Hydroxymethyl)phenyl]adenines: new aryladenine substrates of adenosine deaminase

Cited by 20 publications

References 13 publications

Copper‐Catalyzed Cross‐Coupling Reactions of Nucleobases with Arylboronic Acids: An Efficient Access to N‐Arylnucleobases

Copper‐Catalyzed Cross‐Coupling Reactions of Nucleobases with Arylboronic Acids: An Efficient Access to N‐Arylnucleobases

9-Arylpurines as a Novel Class of Enterovirus Inhibitors

Synthesis of Modified Purine Nucleosides and Related Compounds Mediated by Adenosine Deaminase (ADA) and Adenylate Deaminase (AMPDA)

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