4005-46-3Relevant academic research and scientific papers
Total synthesis of a novel isoprostane IPF(2α)-I and its identification in biological fluids
Adiyaman, Mustafa,Lawson, John A.,Hwang, Seong-Woo,Khanapure, Subhash P.,FitzGerald, Garret A.,Rokach, Joshua
, p. 4849 - 4852 (1996)
The first tokai synthesis of IPF(2α)-I 25 is described using D-glucose as starting material. This novel isoprostane has been used to establish its presence in human urine.
Total synthesis of verbalactone: an efficient, carbohydrate-based approach
Salunke, Ganesh B.,Shivakumar,Gurjar, Mukund K.
, p. 2048 - 2049 (2009)
A carbohydrate-based strategy for the total synthesis of verbalactone has been described. (3R,5R)-3,5-dihydroxydecanoic acid was dimerised under Yamaguchi conditions to provide verbalactone in an overall yield of 17% starting from 3-deoxy-1,2:5,6-di-O-iso
Novel oxolane derivative DMTD mitigates high glucose-induced erythrocyte apoptosis by regulating oxidative stress
Jagadish, Swamy,Hemshekhar, Mahadevappa,NaveenKumar, Somanathapura K.,Sharath Kumar, Kothanahally S.,Sundaram, Mahalingam S.,Basappa,Girish, Kesturu S.,Rangappa, Kanchugarakoppal S.
, p. 167 - 179 (2017)
Chronic hyperglycemia is one of the characteristic conditions associated with Diabetes Mellitus (DM), which often exerts deleterious effects on erythrocyte morphology and hemodynamic properties leading to anemia and diabetes-associated vascular complications. High glucose-induced over production of reactive oxygen species (ROS) can alter the blood cell metabolism and biochemical functions subsequently causing eryptosis (red blood cell death), yet another complication of concern in DM. Therefore, blocking high glucose-induced oxidative damage and subsequent eryptosis is of high importance in the better management of DM and associated vascular complications. In this study, we synthesized an oxolane derivative 1-(2,2-dimethyltetrahydrofuro[2,3][1,3]dioxol-5-yl)ethane-1,2-diol (DMTD), and demonstrated its efficacy to mitigate hyperglycemia-induced ROS generation and subsequent eryptosis. We showed that DMTD effectively inhibits high glucose-induced ROS generation, intracellular calcium levels, phosphaditylserine (PS) scrambling, calpain and band 3 activation, LDH leakage, protein glycation and lipid peroxidation, meanwhile enhances the antioxidant indices, osmotic fragility and Na+/K+-ATPase activity in erythrocytes. DMTD dose dependently decreased the glycated hemoglobin level and enhances the glucose utilization by erythrocytes in vitro. Further, DMTD alleviated the increase in ROS production, intracellular Ca2 + level and PS externalization in the erythrocytes of human diabetic subjects and enhanced the Na+/K+-ATPase activity. Taken together, the synthesized oxolane derivative DMTD could be a novel synthetic inhibitor of high glucose-induced oxidative stress and eryptosis. Considering the present results DMTD could be a potential therapeutic to treat DM and associated complications and open new avenues in developing synthetic therapeutic targeting of DM-associated complications.
Synthesis and antiviral evaluation of novel conformationally locked nucleosides and masked 5′-phosphate derivatives thereof
Bryld, Torsten,Sorensen, Marianne H.,Nielsen, Poul,Koch, Troels,Nielsen, Claus,Wengel, Jesper
, p. 1655 - 1662 (2002)
As part of a programme towards evaluating the potential of conformationally locked 3′-deoxy- and 3′-azido-3′-deoxy-nucleoside derivatives as prodrugs of potential 5′-O-triphosphorylated anti-HIV drugs, novel nucleoside derivatives with locked N-type (nort
TLR7 AGONISTS
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, (2021/05/28)
The present invention relates to TLR7 agonists according to Formula I and their use in the treatment of diseases such as cancer and infectious disease.
Synthesis, characterization, and reactivity of complex tricyclic oxonium ions, proposed intermediates in natural product biosynthesis
Sam Chan, Hau Sun,Nguyen, Q. Nhu N.,Paton, Robert S.,Burton, Jonathan W.
, p. 15951 - 15962 (2019/10/16)
Reactive intermediates frequently play significant roles in the biosynthesis of numerous classes of natural products although the direct observation of these biosynthetically relevant species is rare. We present here direct evidence for the existence of c
PROCESS FOR THE PREPARATION OF 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-d]PYRIMIDINE-2,7-DIONE COMPOUNDS
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, (2018/07/31)
The present invention relates to a process for synthesizing a compound of formula (I), R1 is H or C1-6alkyl; R2 is H or hydroxy; or pharmaceutically acceptable salt or diastereomer thereof, which is useful for prophylaxis
An antiviral medicament for the method for the preparation of entecavir
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Paragraph 0062-0069, (2016/10/17)
The invention relates to a preparation method of an antiviral drug Entecavir. Taking D-glucose and acetone as starting materials, the method has advantages of easy operation, high yield, easy separation and purification, wide source of raw materials and low cost. The selectivity and stereospecificity are controlled at the beginning of a reaction to effectively inhibit the production of chiral isomer. The purification method of product is simple with high yield. A key intermediate of the reaction is 4- methylol-5- methylene cyclopentane-1,3-diol, of which 4- methylol is selectively protected by trityl chloride, and the intermediate combines with 2-amino-6-chloropurine by mitsunobu. Because of the steric hinderance effect, the protecting group can effectively protect target group and the operation is easy to carry out while removing the protecting group.
Synthesis of (2S,4S)-4-hydroxyproline from D-glucose
Mereyala, Hari Babu,Pathuri, Gopal,Nagarapu, Lingaiah
experimental part, p. 1278 - 1287 (2012/04/17)
Diacetone-D-glucose 1 gives 3-O-methylxanthate 2 on reaction with NaH=Me I. Reductive deoxygenation of compound 2 by Bu3SnH gives the corresponding 3-deoxy glucose derivative 3 and on acid-catalyzed regioselective deprotection of C-5,6-acetonide gives the diol 4. The diol on oxidative cleavage with NaIO4 gives the aldehyde 5, which on further condensation with benzylamine followed by reduction with NaBH4 gives the amine 7. Z-Protection of the amine followed by methanolysis gives methyl furanoside 9. Reaction of 9 with methanesulfonyl chloride=Et3N gives the corresponding C-3-O-mesylate derivative 10. Catalytic hydrogenation of compound 10 (Pd=C=H2=MeOH 3 kg) gives bicyclic oxaazo compound 11, due to deprotection of the N-benzyl- and Z-protecting groups and intramolecular nucleophilic displacement of the C-2-O-mesylate by the C-5 amine in a one-pot reaction. Z-Protection of the amine 11 followed by acid-catalyzed hydrolysis gives acetal 13. Reduction of acetal by use of NaBH4 gives Z-prolinol 14. Selective oxidation of diol 14 by (2,2,6,6-tetramethylpiperidin-1-yl)-oxyl (TEMPO)=[(bis)(acetoxy)iodo]-benzene (BAIB) and NaClO2=NaH 2PO4, followed by Z-deprotection, gives the title compound I in 3.5% overall yield from D-glucose. Copyright Taylor & Francis Group, LLC.
Synthesis of locked pyranosyl nucleic acid (LpNA)
Bomholt, Niels,Jorgensen, Per T.,Pedersen, Erik B.
, p. 7376 - 7378 (2012/02/15)
A new locked pyranosyl nucleoside was synthesized by phenylsulfinyl- assisted chemistry. The novel building block was inserted into oligonucleotides and provides new insight on conformational restricted pyranosyl nucleosides on duplex formation
