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Literature DB >> 24312722

Carbocyclic 5'-nor "reverse" fleximers. Design, synthesis, and preliminary biological activity.

Sarah C Zimmermann¹, Joshua M Sadler, Graciela Andrei, Robert Snoeck, Jan Balzarini, Katherine L Seley-Radtke.

Abstract

A series of 5'-nor carbocyclic "reverse" flexible nucleosides or "fleximers" have been designed wherein the nucleobase scaffold resembles a "split" purine as well as a substituted pyrimidine. This modification was employed to explore recognition by both purine and pyrimidine metabolizing enzymes. The synthesis of the carbocyclic fleximers and the results of their preliminary biological screening are described herein.

Entities: CellLine Chemical Disease Gene Species

Year: 2011 PMID： 24312722 PMCID： PMC3849035 DOI： 10.1039/C1MD00094B

Source DB: PubMed Journal: Medchemcomm ISSN： 2040-2503 Impact factor: 3.597

15 in total

1. DNA chain termination activity and inhibition of human immunodeficiency virus reverse transcriptase by carbocyclic 2',3'-didehydro-2',3'-dideoxyguanosine triphosphate.

Authors: D C Orr; H T Figueiredo; C L Mo; C R Penn; J M Cameron
Journal: J Biol Chem Date: 1992-02-25 Impact factor: 5.157

2. Simple fluorescent pyrimidine analogues detect the presence of DNA abasic sites.

Authors: Nicholas J Greco; Yitzhak Tor
Journal: J Am Chem Soc Date: 2005-08-10 Impact factor: 15.419

3. Substrate discrimination by the human GTP fucose pyrophosphorylase.

Authors: Stephen Quirk; Katherine L Seley
Journal: Biochemistry Date: 2005-08-16 Impact factor: 3.162

4. "Fleximers". Design and synthesis of a new class of novel shape-modified nucleosides(1).

Authors: Katherine L Seley; Liang Zhang; Asmerom Hagos; Stephen Quirk
Journal: J Org Chem Date: 2002-05-17 Impact factor: 4.354

5. S-adenosylhomocysteine hydrolase inhibitors interfere with the replication of human immunodeficiency virus type 1 through inhibition of the LTR transactivation.

Authors: D Daelemans; J A Esté; M Witvrouw; C Pannecouque; H Jonckheere; S Aquaro; C F Perno; E De Clercq; A M Vandamme
Journal: Mol Pharmacol Date: 1997-12 Impact factor: 4.436

6. Understanding the binding of 5-substituted 2'-deoxyuridine substrates to thymidine kinase of herpes simplex virus type-1.

Authors: H De Winter; P Herdewijn
Journal: J Med Chem Date: 1996-11-22 Impact factor: 7.446

7. Structures of HIV-1 RT-DNA complexes before and after incorporation of the anti-AIDS drug tenofovir.

Authors: Steve Tuske; Stefan G Sarafianos; Arthur D Clark; Jianping Ding; Lisa K Naeger; Kirsten L White; Michael D Miller; Craig S Gibbs; Paul L Boyer; Patrick Clark; Gang Wang; Barbara L Gaffney; Roger A Jones; Donald M Jerina; Stephen H Hughes; Eddy Arnold
Journal: Nat Struct Mol Biol Date: 2004-04-25 Impact factor: 15.369

8. Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside.

Authors: Katherine L Seley; Stephen Quirk; Samer Salim; Liang Zhang; Asmerom Hagos
Journal: Bioorg Med Chem Lett Date: 2003-06-16 Impact factor: 2.823

9. High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: strategic flexibility explains potency against resistance mutations.

Authors: Kalyan Das; Joseph D Bauman; Arthur D Clark; Yulia V Frenkel; Paul J Lewi; Aaron J Shatkin; Stephen H Hughes; Eddy Arnold
Journal: Proc Natl Acad Sci U S A Date: 2008-01-29 Impact factor: 11.205

10. Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine.

Authors: Pamela Russ; Pierre Schelling; Leonardo Scapozza; Gerd Folkers; Erik De Clercq; Victor E Marquez
Journal: J Med Chem Date: 2003-11-06 Impact factor: 7.446

7 in total

Carbocyclic 5'-nor "reverse" fleximers. Design, synthesis, and preliminary biological activity.

1. DNA chain termination activity and inhibition of human immunodeficiency virus reverse transcriptase by carbocyclic 2',3'-didehydro-2',3'-dideoxyguanosine triphosphate.

2. Simple fluorescent pyrimidine analogues detect the presence of DNA abasic sites.

3. Substrate discrimination by the human GTP fucose pyrophosphorylase.

4. "Fleximers". Design and synthesis of a new class of novel shape-modified nucleosides(1).

5. S-adenosylhomocysteine hydrolase inhibitors interfere with the replication of human immunodeficiency virus type 1 through inhibition of the LTR transactivation.

6. Understanding the binding of 5-substituted 2'-deoxyuridine substrates to thymidine kinase of herpes simplex virus type-1.

7. Structures of HIV-1 RT-DNA complexes before and after incorporation of the anti-AIDS drug tenofovir.

8. Unexpected inhibition of S-adenosyl-L-homocysteine hydrolase by a guanosine nucleoside.

9. High-resolution structures of HIV-1 reverse transcriptase/TMC278 complexes: strategic flexibility explains potency against resistance mutations.

10. Synthesis and biological evaluation of 5-substituted derivatives of the potent antiherpes agent (north)-methanocarbathymine.

1. Nucleoside Analogs with Fleximer Nucleobase.

2. "Reverse" carbocyclic fleximers: synthesis of a new class of adenosine deaminase inhibitors.

3. Syntheses of isoxazoline-carbocyclic nucleosides and their antiviral evaluation: a standard protocol.

Review 4. Flexibility-Not just for yoga anymore!

5. Design and synthesis of a series of truncated neplanocin fleximers.

6. Synthesis of distal and proximal fleximer base analogues and evaluation in the nucleocapsid protein of HIV-1.

7. Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity.