5336-08-3Relevant academic research and scientific papers
Design and synthesis of 2,6-disubstituted-4′-selenoadenosine- 5′-N,N-dimethyluronamide derivatives as human A3 adenosine receptor antagonists
Choi, Hongseok,Jacobson, Kenneth A.,Yu, Jinha,Jeong, Lak Shin
, (2021/05/03)
A new series of 4′-selenoadenosine-5′-N,N-dimethyluronamide derivatives as highly potent and selective human A3 adenosine receptor (hA3AR) antagonists, is described. The highly selective A3AR agonists, 4′-selenoadenosine-5′-N-methyluronamides were successfully converted into selective antagonists by adding a second N-methyl group to the 5′-uronamide position. All the syn-thesized compounds showed medium to high binding affinity at the hA3AR. Among the synthe-sized compounds, 2-H-N6-3-iodobenzylamine derivative 9f exhibited the highest binding affinity at hA3AR. (Ki = 22.7 nM). The 2-H analogues generally showed better binding affinity than the 2-Cl analogues. The cAMP functional assay with 2-Cl-N6-3-iodobenzylamine derivative 9l demonstrated hA3AR antagonist activity. A molecular modelling study suggests an important role of the hydrogen of 5′-uronamide as an essential hydrogen bonding donor for hA3AR activation.
Novel synthesis method for synthesizing remdesivir
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Paragraph 0073-0076, (2021/08/14)
The invention discloses a novel synthesis method for synthesizing remdesivir. According to the synthesis method disclosed by the invention, D-ribose is taken as a raw material and is subjected to a series of reactions such as oxidation, cyclohexanone protection, silanization protection, substitution, substitution, deprotection, coupling, deprotection and the like to synthesize the remdesivir. The post-treatment operation is optimized, and the method has the advantages of being short in reaction time, high in yield, low in cost, suitable for industrial production and the like. The structure of the remdesivir provided by the invention is shown in the specification.
Stereoselective Palladium-Catalyzed Arylation of Exo-Glycals with Aryl Iodides
Bolshan, Yuri,Ghanty, Supriya,Regier, Jeffery
supporting information, (2022/01/12)
A novel methodology for the arylation of exo-glycals has been developed. A range of exo-glycals underwent reactions with aryl iodides in the presence of a palladium catalyst. The transformation proceeded in a stereoselective manner to afford Z-isomers. Th
High-Yielding Diastereoselective syn-Dihydroxylation of Protected HBO: An Access to D-(+)-Ribono-1,4-lactone and 5-O-Protected Analogues
Moreaux, Maxime,Bonneau, Guillaume,Peru, Aurélien,Brunissen, Fanny,Janvier, Marine,Haudrechy, Arnaud,Allais, Florent
supporting information, p. 1600 - 1604 (2019/01/14)
A diastereoselective chemoenzymatic synthetic pathway to D-(+)-ribono-1,4-lactone, a versatile chiral sugar derivative widely used for the synthesis of various natural products, has been designed from cellulose-based levoglucosenone (LGO). This route involves a sustainable Baeyer-Villiger oxidation of LGO to produce enantiopure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) that is further functionalized with various protecting groups to provide 5-O-protected γ-hydroxymethyl-α,β-butenolides. The latter then undergo a diastereoselective and high-yielding syn-dihydroxylation of the α,β-unsaturated lactone moiety followed by a deprotection step to give D-(+)-ribono-1,4-lactone. Through this 4-step synthetic route from LGO, D-(+)-ribono-1,4-lactone is obtained with d.r. varying from 82:18 to 97:3 and in overall yields between 32 and 41 % depending on the protecting group used. Moreover, valuable synthetic intermediates 5-O-tert-butyldimethylsilyl-, 5-O-tert-butyldiphenylsilyl- as well as 5-O-benzyl-ribono-1,4-lactones are obtained in 3 steps from LGO in 58, 61 and 40 %, respectively.
Antioxidant composition comprising marliolide derivatives
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Paragraph 0039-0045, (2019/11/23)
The present invention relates to a marliolide derivative and an antioxidant composition containing the same as an active component, wherein the marliolide derivative increases the expression of a transcription factor Nrf2 that regulates the expression of an antioxidant-related protein without cytotoxicity, thereby increasing the expression of HO-1 and NQO1, which are antioxidant-related proteins. In addition, since the marliolide derivative is confirmed to inhibit the oxidation of DNA and lipids induced by TPA that induces oxidative stress, a composition containing the marliolide derivative can be provided as the antioxidant composition.(AA) Compound 1 (10 andmu;M)COPYRIGHT KIPO 2019
Highly (Z)-Diastereoselective Synthesis of Trifluoromethylated exo-Glycals via Photoredox and Copper Catalysis
Frédéric, Christophe J.-M.,Cornil, Jér?me,Vandamme, Mathilde,Dumitrescu, Lidia,Tikad, Abdellatif,Robiette, Rapha?l,Vincent, Stéphane P.
supporting information, p. 6769 - 6773 (2018/10/24)
Highly (Z)-diastereoselective approaches for the synthesis of trifluoromethylated exo-glycals by copper and photoredox catalysis are described. These complementary reactions are applicable to a wide range of methylene exo-glycals generated from the corresponding pyranoses and furanoses and give trifluoromethylated compounds under mild conditions in moderate to good yields. DFT calculations have allowed a rationalization of the observed (Z)-stereoselectivity.
Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar
Ishii, Kazuki,Saito-Tarashima, Noriko,Ota, Masashi,Yamamoto, Seigi,Okamoto, Yasuko,Tanaka, Yoshiyuki,Minakawa, Noriaki
supporting information, p. 6589 - 6594 (2016/09/23)
The synthesis of a variety of chemically modified oligonucleotides requires the development of a practical synthetic method for its building block, i.e., nucleoside analogs. The one-pot Pummerer-like reaction using hypervalent iodine in combination with 6-chloropurine and an ‘armed’ 4-selenosugar bearing an electron-donating group at the 2-position gave the desired 4′-seleno-6-chloropurine derivative in higher yield as compared to the previous method using a ‘disarmed’ 4-selenosugar bearing an electron-withdrawing group at the 2-position. In addition, the use of 2,6-dichloropurine as a nucleobase transformable into guanine skeleton enabled an effective Pummerer-like reaction followed by isomerization to the desired N9 isomer under the acidic conditions. This Pummerer-like reaction between chlorinated purine bases and an ‘armed’ 4-selenosugar is advantageous because it affords 4′-selenopurine nucleosides in one-pot without the need for isolation of the unstable selenoxide derivative.
Molecular sieves mediated green per-O-acetylation of carbohydrate templates and lipase catalyzed regioselective alcoholysis of 2,3,5-Tri-O-acetyl-D-ribonolactone
Cardozo, Herbert M.,Ribeiro, Thaís F.,Sá, Marcus M.,Sebr?o, Damianni,Nascimento, Maria G.,Silveira, Gustavo P.
, p. 755 - 764 (2015/04/14)
The per-O-acetylation of D-ribono-1,4-lactone and representative carbohydrates through the combination of acetic anhydride and molecular sieves under solvent-free conditions is demonstrated. The use of 13X/KCl molecular sieves as the heterogeneous catalyst was found to be more efficient than the excess of pyridine normally employed in the conventional method, giving high yields of the expected peracetylated product after 3 h at 25 °C or 1 h at 50 °C. The transformation can be carried out in gram scale and in an open flask. Additionally, the catalyst is readily separated from the reaction medium and can be reutilized without significant loss of activity. This green procedure for acetylation was extended to D-ribonolactone derivatives and natural carbohydrates. To demonstrate the synthetic utility of the method, 2,3,5-tri-O-acetyl-D-ribonolactone was selected as the substrate for the regioselective alcoholysis of acetyl group catalyzed by Candida antarctica lipase B in EtOH to selectively produce 2,3-di-O-acetyl-D-ribonolactone in gram scale.
Convenient syntheses of orthogonally protected aminocyclopentitols from aldopentoses
Ko?ak, Urban,Hrast, Martina,Knez, Damijan,Mara?, Nenad,?rnugelj, Martin,Gobec, Stanislav
supporting information, p. 529 - 531 (2015/03/03)
Orthogonally protected aminocyclopentitols were synthesized from commercially available aldopentoses using a convenient three-step procedure that does not require protection of the free anomeric hydroxyl group of the starting carbohydrate. The synthesized compounds are important building blocks with potential use in medicinal chemistry and drug discovery.
A general and enantioselective approach to pentoses: A rapid synthesis of PSI-6130, the nucleoside core of sofosbuvir
Peifer, Manuel,Berger, Rapha?lle,Shurtleff, Valerie W.,Conrad, Jay C.,Macmillan, David W. C.
supporting information, p. 5900 - 5903 (2014/05/20)
An efficient route towards biologically relevant pentose derivatives is described. The de novo synthetic strategy features an enantioselective α-oxidation reaction enabled by a chiral amine in conjunction with copper(II) catalysis. A subsequent Mukaiyama aldol coupling allows for the incorporation of a wide array of modular two-carbon fragments. Lactone intermediates accessed via this route provide a useful platform for elaboration, as demonstrated by the preparation of a variety of C-nucleosides and fluorinated pentoses. Finally, this work has facilitated expedient syntheses of pharmaceutically active compounds currently in clinical use.
