- Synthesis and antioxidant capacity of novel stable 5-tellurofuranose derivatives
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Novel stable tellurium-containing carbohydrate derivatives are prepared from hexitols and pentitols through a double nucleophilic substitution with NaHTe in PEG-400. These tellurosugars react at very high rates with two-electron oxidants, including hypochlorous and peroxynitrous acid, formed at sites of inflammation, and show considerable promise as protective agents against oxidative damage.
- Borges, Elton L.,Ignasiak, Marta T.,Velichenko, Yuliia,Perin, Gelson,Hutton, Craig A.,Davies, Michael J.,Schiesser, Carl H.
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- Synthesis of zwitterionic selenonium and sulfonium sulfates from D-mannose as potential glycosidase inhibitors
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Four chain-extended analogues of the naturally occurring glycosidase inhibitor salacinol were synthesized for structure-activity studies with different glycosidase enzymes. The syntheses involved the reaction of isopropylidene-protected 1,4-thio- and 1,4-
- Liu, Hui,Pinto, B. Mario
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Read Online
- Discovery and Structure-Activity Relationships of Novel Template, Truncated 1′-Homologated Adenosine Derivatives as Pure Dual PPARγ/δModulators
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Following our report that A3 adenosine receptor (AR) antagonist 1 exhibited a polypharmacological profile as a dual modulator of peroxisome proliferator-activated receptor (PPAR)γ/δ, we discovered a new template, 1′-homologated adenosine analogues 4a-4t, as dual PPARγ/δmodulators without AR binding. Removal of binding affinity to A3AR was achieved by 1′-homologation, and PPARγ/δdual modulation was derived from the structural similarity between the target nucleosides and PPAR modulator drug, rosiglitazone. All the final nucleosides were devoid of AR-binding affinity and exhibited high binding affinities to PPARγ/δbut lacked PPARα binding. 2-Cl derivatives exhibited dual receptor-binding affinity to PPARγ/δ, which was absent for the corresponding 2-H derivatives. 2-Propynyl substitution prevented PPARδ-binding affinity but preserved PPARγaffinity, indicating that the C2 position defines a pharmacophore for selective PPARγligand designs. PPARγ/δdual modulators functioning as both PPARγpartial agonists and PPARδantagonists promoted adiponectin production, suggesting their therapeutic potential against hypoadiponectinemia-associated cancer and metabolic diseases.
- An, Seungchan,Kim, Gyudong,Kim, Hyun Jin,Ahn, Sungjin,Kim, Hyun Young,Ko, Hyejin,Hyun, Young Eum,Nguyen, Mai,Jeong, Juri,Liu, Zijing,Han, Jinhe,Choi, Hongseok,Yu, Jinha,Kim, Ji Won,Lee, Hyuk Woo,Jacobson, Kenneth A.,Cho, Won Jea,Kim, Young-Mi,Kang, Keon Wook,Noh, Minsoo,Jeong, Lak Shin
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p. 16012 - 16027
(2021/01/09)
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- Correlation study between A3 adenosine receptor binding affinity and anti-renal interstitial fibrosis activity of truncated adenosine derivatives
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Truncated 4′-thionucleosides 1–4 and 4′-oxonucleosides 5–8 as potent and selective A3AR antagonists were synthesized from d-mannose and d-erythronic acid γ-lactone, respectively. These nucleosides were evaluated for their anti-fibrotic renoprot
- Yu, Jinha,Kim, Gyudong,Jarhad, Dnyandev B.,Lee, Hyuk Woo,Lee, Jiyoun,Park, Chong Woo,Ha, Hunjoo,Jeong, Lak Shin
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p. 773 - 779
(2018/10/09)
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- Proline-based hydroxamates targeting the zinc-dependent deacetylase LpxC: Synthesis, antibacterial properties, and docking studies
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The Zn2+-dependent deacetylase LpxC is an essential enzyme in Gram-negative bacteria, which has been validated as antibacterial drug target. Herein we report the chiral-pool synthesis of novel D- and L-proline-derived 3,4-dihydroxypyrrolidine hydroxamates and compare their antibacterial and LpxC inhibitory activities with the ones of 4-monosubstituted and 3,4-unsubstituted proline derivatives. With potent antibacterial activities against several Gram-negative pathogens, the L-proline-based tertiary amine 41g ((S)-N-hydroxy-1-(4-{[4-(morpholinomethyl)phenyl]ethynyl}benzyl)pyrrolidine-2-carboxamide) was found to be the most active antibacterial compound within the investigated series, also showing some selectivity toward EcLpxC (Ki = 1.4 μM) over several human MMPs.
- Kalinin, Dmitrii V.,Agoglitta, Oriana,Van de Vyver, Hélène,Melesina, Jelena,Wagner, Stefan,Riemann, Burkhard,Sch?fers, Michael,Sippl, Wolfgang,L?ffler, Bettina,Holl, Ralph
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p. 1997 - 2018
(2019/04/08)
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- A sulfur-containing thick mixed four ring aza sugar derivative and its preparation method
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The invention discloses a sulfur-containing thick and mixed tetracyclic azasugar derivative, which has a general chemical formula as shown in figure I. A preparation method of the sulfur-containing thick and mixed tetracyclic azasugar derivative comprises
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- Polypharmacology of N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide (IB-MECA) and Related A3 Adenosine Receptor Ligands: Peroxisome Proliferator Activated Receptor (PPAR) γ Partial Agonist and PPARδ Antagonist Activity Suggests Their
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A3 adenosine receptor (AR) ligands including A3 AR agonist, N6-(3-iodobenzyl)adenosine-5′-N-methyluronamide (1a, IB-MECA) were examined for adiponectin production in human bone marrow mesenchymal stem cells (hBM-MSCs). In
- Yu, Jinha,Ahn, Seyeon,Kim, Hee Jin,Lee, Moonyoung,Ahn, Sungjin,Kim, Jungmin,Jin, Sun Hee,Lee, Eunyoung,Kim, Gyudong,Cheong, Jae Hoon,Jacobson, Kenneth A.,Jeong, Lak Shin,Noh, Minsoo
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p. 7459 - 7475
(2017/09/23)
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- Preventing protein oxidation with sugars: Scavenging of hypohalous acids by 5-selenopyranose and 4-selenofuranose derivatives
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Heme peroxidases including myeloperoxidase (MPO) are released at sites of inflammation by activated leukocytes. MPO generates hypohalous acids (HOX, X = Cl, Br, SCN) from H2O2; these oxidants are bactericidal and are key components o
- Storkey, Corin,Pattison, David I.,White, Jonathan M.,Schiesser, Carl H.,Davies, Michael J.
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p. 2589 - 2599
(2013/01/15)
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- SELENO-COMPOUNDS AND THERAPEUTIC USES THEREOF
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The present invention relates to compounds and compositions useful as antioxidants and in particular to selenium containing compounds of formula (I): wherein n is 1, 2, or 3; m is 2, 3, 4, or 5; and each R] is independently -(optionally substituted C 1 -C3 alkylene) p-OH, where p is 0 or 1, or a salt thereof. The invention also relates to the use of these seleno-compounds in the treatment of diseases or conditions associated with increased levels of oxidants produced by myeloperoxidase (MPO), such as for instance, atherosclerosis.
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Page/Page column 60-61
(2012/05/19)
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- Design, synthesis, and binding of homologated truncated 4′-thioadenosine derivatives at the human A3 adenosine receptors
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We synthesized homologated truncated 4′-thioadenosine analogues 3 in which a methylene (CH2) group was inserted in place of the glycosidic bond of a potent and selective A3 adenosine receptor antagonist 2. The analogues were designed
- Lee, Hyuk Woo,Kim, Hea Ok,Choi, Won Jun,Choi, Sun,Lee, Jin Hee,Park, Seul-Gi,Yoo, Lena,Jacobson, Kenneth A.,Jeong, Lak Shin
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scheme or table
p. 7015 - 7021
(2010/10/21)
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- ADENOSINE DERIVATIVES, METHOD FOR THE SYNTHESIS THEREOF, AND THE PHARMACEUTICAL COMPOSITIONS FOR THE PREVENTION AND TREATMENT OF THE INFLAMMATORY DISEASES CONTAINING THE SAME AS AN ACTIVE INGREDIENT
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Disclosed are adenosine derivatives, methods for the synthesis thereof, and pharmaceutical compositions for the prevention and treatment of inflammatory diseases, comprising the same as an active ingredient. The adenosine derivatives have high binding aff
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Page/Page column 30-31
(2008/12/08)
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- SYNTHESIS OF THE MANNOSIDASE INHIBITORS SWAINSONINE AND 1,4-DIDEOXY-1,4-IMINO-D-MANNITOL AND OF THE RING CONTRACTED SWAINSONINES, (1S, 2R, 7R, 7aR)-1,2,7-TRIHYDROXYPYRROLIZIDINE AND (1S, 2R, 7S, 7aR)-1,2,7-TRIHYDROXYPYRROLIZIDINE.
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4,5-Anhydro-1-azido-1-deoxy-2,3-O-isopropylidene-D-talitol is a divergent intermediate for the efficient and practical syntheses of 1,4-dideoxy-1,4-imino-D-mannitol, swainsonine and of the ring contracted swainsonines, (1S, 2R, 7R, 7aR)-1,2,7-trihydroxypyrrolizidine and (1S, 2R, 7S, 7aR)-1,2,7-trihydroxypyrrolizidine.The effect on glycosidases of the ring contracted swainsonines is reported.
- Carpenter, Neil M.,Fleet, George W. J.,Bello, Isabelle Cenci di,Winchester, Bryan,Fellows, Linda E.,Nash, Robert J.
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p. 7261 - 7264
(2007/10/02)
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- SYNTHESIS FROM D-MANNOSE OF 1,4-DIDEOXY-1,4-IMINO-L-RIBITOL AND OF THE α-MANNOSIDASE INHIBITOR 1,4-DIDEOXY-1,4-IMINO-D-TALITOL
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The syntheses of 1,4-dideoxy-1,4-imino-L-ribitol and of 1,4-dideoxy-1,4-imino-D-talitol from D-mannose are described. 1,4-Dideoxy-1,4-imino-D-talitol is a specific and competitive inhibitor of human liver α-mannosidase in vitro and also blocks the lysosomal catabolism of asparigine-linked glycans of glycoproteins in vivo.
- Fleet, George W. J.,Son, Jong Chan,Green, Donovan St. C.,Bello, Isabelle Cenci di,Winchester, Bryan
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p. 2649 - 2656
(2007/10/02)
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