The Experts below are selected from a list of 270 Experts worldwide ranked by ideXlab platform
Marvin J. Miller - One of the best experts on this subject based on the ideXlab platform.
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cyclopropanation of nitroso diels alder cycloadducts and application to the synthesis of a 2 3 methano Carbocyclic Nucleoside
ChemInform, 2010Co-Authors: Marvin J. MillerAbstract:Abstract Treatment of nitroso Diels–Alder cycloadducts 1 with diazomethane in the presence of palladium acetate gives synthetically useful exo -6-oxa-7-azatricyclo[3.2.1.0 2,4 ]octane derivatives 7 in good to excellent yield. Using this methodology, a conformationally restricted 2′,3′-methano Carbocyclic Nucleoside was efficiently synthesized from nitroso cycloadduct 1a in seven steps.
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Substrate-Dependent Dihydroxylation of Substituted Cyclopentenes: Toward the Syntheses of Carbocyclic Sinefungin and Noraristeromycin
The Journal of organic chemistry, 2006Co-Authors: May Xiao-wu Jiang, Bohan Jin, Jennifer L. Gage, Alain Priour, Gordon Savela, Marvin J. MillerAbstract:Carbocyclic Nucleosides are of considerable interest for the development of new therapeutic agents. A key reaction in the preparation of many such Nucleoside analogues is dihydroxylation of appropriately substituted cyclopentenes. Although often considered a routine reaction, in this paper, we report the dramatic influence of substituents on the facial selectivity of dihydroxylations. The substituted cyclopentene substrates are derived from acylnitroso cycloaddition reactions of cyclopentadiene, followed by N-O reduction and efficient enzymatic resolution. The results are directly utilized in a very efficient asymmetric synthesis of an antiviral Carbocyclic Nucleoside, noraristeromycin 5. Extensions toward the synthesis of Carbocyclic sinefungin 7 document the importance of realizing the substituent dependence of the dihydroxylation reaction.
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rapid syntheses of either enantiomer of important Carbocyclic Nucleoside precursors
Tetrahedron Letters, 2000Co-Authors: Brock T Shireman, Marvin J. MillerAbstract:Abstract The syntheses of both enantiomers of aminocyclopentanetriol 1, a versatile Carbocyclic Nucleoside precursor, is reported utilizing an amino acid-derived acylnitroso Diels–Alder cycloaddition. The sequence is practical and proceeds in an overall yield of 36% from the d -alanine-derived hydroxamic acid.
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efficient functionalization of acylnitroso cycloadducts application to the syntheses of Carbocyclic Nucleoside precursors
Tetrahedron Letters, 1996Co-Authors: D Zhang, A Ghosh, Carsten Suling, Marvin J. MillerAbstract:Abstract 1,4- cis -disubstituted cyclopentene precursors of Carbocyclic nucleotides were readily prepared utilizing acylnitroso hetero Diels-Alder reactions and Pd(0)-catalyzed alkylation reactions as the key steps. The chemistry was explored in both racemic and asymmetric fashion. The hydroxymethyl components of the Carbocyclic Nucleoside precursors were obtained from nitromethyl groups under oxidative Nef conditions and may be further elaborated into a variety of compounds of potential biological interest.
Kamal H Bouhadir - One of the best experts on this subject based on the ideXlab platform.
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novel Carbocyclic Nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ros dependent mechanism in the diabetic milieu ii acylhydrazone functionalized pyrimidines
Bioorganic & Medicinal Chemistry Letters, 2016Co-Authors: Kamal H Bouhadir, Ali Koubeissi, Fatima A Mohsen, Mira Diab Elharakeh, Rouba Cheaib, Joan Younes, Georges Azzi, Assaad A EidAbstract:We report herein the synthesis of a novel series of Carbocyclic acylhydrazone derivatives of uracil, thymine and cytosine from the corresponding nucleic bases and their biological activity to treat diabetic nephropathy. Intriguingly, five derivatives significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro. The anti-oxidative effects displayed by these molecules suggest that their activity might involve a ROS-dependent mechanism.
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novel Carbocyclic Nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ros dependent mechanism in the diabetic milieu
Bioorganic & Medicinal Chemistry Letters, 2013Co-Authors: Assaad A Eid, Ali Koubeissi, Ribal Boumjahed, Nadine Al Khalil, Manal Farah, Rita Maalouf, Niveen Nasser, Kamal H BouhadirAbstract:The synthesis of a series of novel 3,4-cis- and 3,4-trans-substituted Carbocyclic Nucleoside analogs from protected uracil and thymine is described. The key reaction in the followed synthetic protocols utilized the Mitsunobu reaction to couple 3,4-substituted cyclopentanols to (3)N-benzoyl uracil or (3)N-benzoyl thymine. These molecules were evaluated with regard to their ability to treat diabetic nephropathy. Our results show that two analogs significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro and, more interestingly, exhibited an anti-oxidative effect suggesting that the activity may be mediated through ROS-dependent mechanism.
Assaad A Eid - One of the best experts on this subject based on the ideXlab platform.
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novel Carbocyclic Nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ros dependent mechanism in the diabetic milieu ii acylhydrazone functionalized pyrimidines
Bioorganic & Medicinal Chemistry Letters, 2016Co-Authors: Kamal H Bouhadir, Ali Koubeissi, Fatima A Mohsen, Mira Diab Elharakeh, Rouba Cheaib, Joan Younes, Georges Azzi, Assaad A EidAbstract:We report herein the synthesis of a novel series of Carbocyclic acylhydrazone derivatives of uracil, thymine and cytosine from the corresponding nucleic bases and their biological activity to treat diabetic nephropathy. Intriguingly, five derivatives significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro. The anti-oxidative effects displayed by these molecules suggest that their activity might involve a ROS-dependent mechanism.
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novel Carbocyclic Nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ros dependent mechanism in the diabetic milieu
Bioorganic & Medicinal Chemistry Letters, 2013Co-Authors: Assaad A Eid, Ali Koubeissi, Ribal Boumjahed, Nadine Al Khalil, Manal Farah, Rita Maalouf, Niveen Nasser, Kamal H BouhadirAbstract:The synthesis of a series of novel 3,4-cis- and 3,4-trans-substituted Carbocyclic Nucleoside analogs from protected uracil and thymine is described. The key reaction in the followed synthetic protocols utilized the Mitsunobu reaction to couple 3,4-substituted cyclopentanols to (3)N-benzoyl uracil or (3)N-benzoyl thymine. These molecules were evaluated with regard to their ability to treat diabetic nephropathy. Our results show that two analogs significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro and, more interestingly, exhibited an anti-oxidative effect suggesting that the activity may be mediated through ROS-dependent mechanism.
Ali Koubeissi - One of the best experts on this subject based on the ideXlab platform.
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novel Carbocyclic Nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ros dependent mechanism in the diabetic milieu ii acylhydrazone functionalized pyrimidines
Bioorganic & Medicinal Chemistry Letters, 2016Co-Authors: Kamal H Bouhadir, Ali Koubeissi, Fatima A Mohsen, Mira Diab Elharakeh, Rouba Cheaib, Joan Younes, Georges Azzi, Assaad A EidAbstract:We report herein the synthesis of a novel series of Carbocyclic acylhydrazone derivatives of uracil, thymine and cytosine from the corresponding nucleic bases and their biological activity to treat diabetic nephropathy. Intriguingly, five derivatives significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro. The anti-oxidative effects displayed by these molecules suggest that their activity might involve a ROS-dependent mechanism.
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novel Carbocyclic Nucleoside analogs suppress glomerular mesangial cells proliferation and matrix protein accumulation through ros dependent mechanism in the diabetic milieu
Bioorganic & Medicinal Chemistry Letters, 2013Co-Authors: Assaad A Eid, Ali Koubeissi, Ribal Boumjahed, Nadine Al Khalil, Manal Farah, Rita Maalouf, Niveen Nasser, Kamal H BouhadirAbstract:The synthesis of a series of novel 3,4-cis- and 3,4-trans-substituted Carbocyclic Nucleoside analogs from protected uracil and thymine is described. The key reaction in the followed synthetic protocols utilized the Mitsunobu reaction to couple 3,4-substituted cyclopentanols to (3)N-benzoyl uracil or (3)N-benzoyl thymine. These molecules were evaluated with regard to their ability to treat diabetic nephropathy. Our results show that two analogs significantly reduced high-glucose induced glomerular mesangial cells proliferation and matrix protein accumulation in vitro and, more interestingly, exhibited an anti-oxidative effect suggesting that the activity may be mediated through ROS-dependent mechanism.
Chris Meier - One of the best experts on this subject based on the ideXlab platform.
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synthesis of enantiomerically pure 1 2 cis dideoxy dideoxydi dehydro ribo and deoxy Carbocyclic Nucleoside analogues
Synthesis, 2018Co-Authors: Simon Weising, Johan Neyts, Patrick Dekiert, Dominique Schols, Chris MeierAbstract:We describe a short and stereospecific synthesis of different series of 1′,2′-cis-disubstituted Carbocyclic Nucleoside analogues. All-natural nucleobases or their precursors are coupled in a microwave-assisted Mitsunobu-type reaction with enantiomerically pure (1R,2S)-2-(benzyloxymethyl)cyclopent-3-enol. By modifying the cyclopentene scaffold, our synthetic strategy gives access to a series of 1′,2′-cis-disubstituted Carbocyclic Nucleoside analogues of the dideoxy (dd), dideoxydidehydro (d4) or the ribo series. The ribo series is synthesized in a more convenient way compared to a previous route. The deoxy series of 1′,2′-cis-disubstituted Carbocyclic Nucleoside analogues is prepared following an earlier reported approach. This synthesis involves the microwave-assisted coupling of (1R,2S,3S)-3-(benzyloxy)-2-[(benzyloxy)methyl]cyclopentan-1-ol with the appropriate nucleobases.