29581-48-4Relevant academic research and scientific papers
Highly Diastereoselective Route to α-Glucosidase Inhibitors, Neosalacinol and Neoponkoranol
Tanabe, Genzoh,Matsuda, Youya,Oka, Misato,Kunikata, Yousuke,Tsutsui, Nozomi,Xie, Weija,Balakishan, Gorre,Amer, Mumen F. A.,Marumoto, Shinsuke,Muraoka, Osamu
, p. 3407 - 3415 (2016)
A facile and highly diastereoselective route to potent natural α-glucosidase inhibitors, i.e., neosalacinol (4) and neoponkoranol (6), isolated from the traditional Ayurvedic medicine "Salacia" was developed by intramolecular cyclization of appropriately substituted sulfides (9 and 12).
Synthesis of Triazole-Containing Furanosyl Nucleoside Analogues and Their Phosphate, Phosphoramidate or Phoshonate Derivatives as Potential Sugar Diphosphate or Nucleotide Mimetics
Concei??o Oliveira, M.,Costa, Paulo J.,Fortuna, Andreia,Piedade, M. Fátima M.,Xavier, Nuno M.
, p. 1676 - 1691 (2020/09/02)
The synthesis of stable and potentially bioactive xylofuranosyl nucleoside analogues and potential sugar diphosphate or nucleotide mimetics comprising a 1,2,3-triazole moiety is reported. 3′-O-Methyl-branched N-benzyltriazole isonucleosides were accessed
Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands
Mishra, Nidhi,Singh, Anoop S.,Agrahari, Anand K.,Singh, Sumit K.,Singh, Mala,Tiwari, Vinod K.
, p. 389 - 399 (2019/05/06)
Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.
Titanocene dihalides and ferrocenes bearing a pendant α-d- xylofuranos-5-yl or α-d-ribofuranos-5-yl moiety. synthesis, characterization, and cytotoxic activity
Hodik, Tomas,Lamac, Martin,Cervenkova St'Astna, Lucie,Karban, Jindrich,Koubkova, Lucie,Hrstka, Roman,Cisarova, Ivana,Pinkas, Jiri
, p. 2059 - 2070 (2014/05/20)
Titanocene dichlorides of general formula [(η5-C 5H5)(η5-C5H4R) TiCl2] (where R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl-α- d-xylofuranos-5-yl (Xylf) (8a); R = 5-deoxy-1,2-di-O-isopropylidene-3-O-benzyl- α-d-ribofuranos-5-yl (Ribf) (8b)) and [(η5-C 5H4R)2TiCl2] (R = Xylf (9a); R = Ribf (9b)) were prepared by reaction of the corresponding lithium cyclopentadienides 7a,b with an equimolar amount of [(η5-C 5H5)TiCl3] or a 0.5 mol amount of [TiCl 4(THF)2]. Titanocene difluorides of the general formula [(η5-C5H4R1)(η5- C5H4R2)TiF2] (R1 = H and R2 = Ribf (10); R1 = R2 = Xylf (11a); R 1 = R2 = Ribf (11b)) were obtained by fluorination of the corresponding titanocene dichlorides 8b and 9 with the fluorinating agent {2-(CH2NMe2)C6H4-κC,N}(n-Bu) 2SnF in high yields. Alternatively, complexes 11 were prepared in a straightforward way by direct reaction of [TiF4(THF)2] with 2 equiv of the corresponding lithium cyclopentadienide 7a,b. Ferrocene complexes [(η5-C5H4R)2Fe] (R = Xylf (12a); R = Ribf (12b)) were synthesized by metathesis of 2 equiv of lithium cyclopentadienide 7a,b and 1 equiv of anhydrous FeCl2. Deprotection of the benzyl group in ferrocenes 12 proceeded cleanly by a catalytic hydrogenation on Pd/C and afforded the ferrocene diols [(η5- C5H4R)2Fe] (R = 5-deoxy-1,2-di-O- isopropylidene-α-d-xylofuranos-5-yl (Xylf-OH) (14a); R = 5-deoxy-1,2-di-O-isopropylidene-α-d-ribofuranos-5-yl (Ribf-OH) (14b)). A scaled up benzyl deprotection with Et3SiH as a hydrogen source led to the replacement of only one benzyl group, which gave the ferrocene alcohol [(η5-C5H4R1)(η5- C5H4R2)Fe] (R1 = Xylf and R 2 = Xylf-OH (13)). The prepared complexes were characterized by elemental analysis, melting point determination, NMR, IR, and ESI-MS, and the molecular structure of 9b was determined by X-ray diffraction analysis. The cytotoxic activity of complexes 8-14 against A2780 and A2780cis cancer cells was evaluated by MTT tests. Titanocene difluorides 10 and 11 and ferrocene diol 14a showed cytotoxicity against A2780 cells in the medium to low micromolar range, while the most active species, 11b, displayed about 40% higher cytotoxicity against A2780cis in comparison to a cisplatin standard.
Click chemistry inspired highly facile synthesis of triazolyl ethisterone glycoconjugates
Kumar, Dhananjay,Mishra, Kunj B.,Mishra, Bhuwan B.,Mondal, Saheli,Tiwari, Vinod K.
supporting information, p. 71 - 79 (2014/01/17)
Numerous deoxy-azido sugars 3 were prepared by the reaction of tosyl/bromo sugars with NaN3 in dry DMF under heating condition. The 1,3-dipolar cycloaddition of deoxy-azido sugars 3 with ethisterone 4 to afford regioselective triazole-linked ethisterone glycoconjugates 5 was investigated in the presence of CuI and DIPEA in dichloromethane or CuSO4· 5H2O and sodium ascorbate in aqueous medium. All the developed compounds were characterized by spectroscopic analysis (IR, 1H & 13C NMR, and MS spectra). Structure of triazolyl ethisterone glycoconjugate 5a has been further confirmed by its Single Crystal X-ray analysis.
First stereoselective total synthesis of stagonolide G
Srihari,Kumaraswamy,Bhunia, Dinesh C.,Yadav
scheme or table, p. 2903 - 2905 (2010/06/14)
First stereoselective total synthesis of nonenolide stagonolide G involving a convergent strategy is described. The key reactions include Keck allylation and Grubbs ring closing metathesis reaction.
Total synthesis of pachastrissamine (jaspine B) enantiomers from d-glucose
Ramana,Giri, Awadut G.,Suryawanshi, Sharad B.,Gonnade, Rajesh G.
, p. 265 - 268 (2007/10/03)
Synthesis of both enantiomers of pachastrissamine is described from a common chiral template. The stereoselective construction of the central tetrahydrofuran units was based on the pseudodesymmetrization of a pentodialdo-1,4-furanose derivative taking adv
Stereoselective synthesis of cytotoxic anhydrophytosphingosine pachastrissamine (Jaspine B) from D-xylose
Du, Yuguo,Liu, Jun,Linhardt, Robert J.
, p. 1251 - 1253 (2007/10/03)
The first naturally occurring anhydrophytosphingosine, pachastrissamine (jaspine B), a marine compound cytotoxic toward P388, A549, HT29, and MEL28 cell lines at IC50 = 0.01 μg/mL level, has been stereoselectively synthesized from D-xylose in 1
Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity
Muraoka, Osamu,Yoshikai, Kazuya,Takahashi, Hideo,Minematsu, Toshie,Lu, Guangxin,Tanabe, Genzoh,Wang, Tao,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 500 - 509 (2007/10/03)
Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring α-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-d- arabinitol (3), with cyclic sulfates (8, 9, and 10), and their α-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the α-glucosidase inhibitory activity. A practical synthetic route to 3 starting from d-xylose is also described.
1-Aza-sugars from D-Glucose. Preparation of 1-Deoxy-5-dehydroxymethyl-Nojirimycin, its analogues and evaluation of glycosidase inhibitory activity
Patil, Nitin T.,John, Sheeja,Sabharwal, Sushma G.,Dhavale, Dilip D.
, p. 2155 - 2160 (2007/10/03)
D-Glucose derived pentodialdoses 11a-c on reduction followed by tosylation, azide displacement, hydrogenation and protection with -Cbz group gave N-Cbz protected compounds 14a-c, respectively, which on removal of 1,2-acetonide functionality and hydrogenat
