23313-03-3Relevant articles and documents
Synthesis of glycosylated aminothiol from D-glucose as promising anti-tubercular agent
Singh, Archana,Prasad, Virendra,Rajkhowa, Sanchayita,Tripathi, Vishwa D.,Tiwari, Vinod K.
, p. 213 - 225 (2020/03/18)
A facile method for a series of novel glycosylated β-aminothiols by employing TBAB/NEt3-catalyzed ring opening of thiirane ring of D-glucose-derived 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose with different primary and secondary amines including aliphatic, aromatic, heterocyclic, and glycosyl amine has been devised. Diamines on the other hand for thiirane ring opening of anhydroglucose derivative led to the formation of respective bis-glycosylated N1,Nn-diaminothiols in good yield. The method is straight forward, economical, high-yielding and easy to scale up. One of the glycosylated aminothiol contains both the hydrophilic carbohydrate moiety and hydrophobic hexadecyl residue, thus can serve a promising candidate to exhibit surface-active properties. The resulted glycosylated β-aminothiols may serve as an interesting scaffold to develop mechanism-based novel chemotherapeutic agents.
Gram-level total synthesis method of sulfur onium salt type natural product neoponkoranol extracted from salacia plants
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Paragraph 0037; 0038; 0039; 0040, (2019/02/19)
The invention belongs to the field of chemical synthesis and particularly relates to a gram-level total synthesis method of a sulfur onium salt type natural product neoponkoranol with hypoglycemic activity extracted from salacia plants. According to the m
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.
Synthesis of Structurally Diverse Substituted Aziridinyl Glycoconjugates via Base-Mediated One-Pot Post-Ugi Cyclization
Sangwan, Rekha,Dubey, Atul,Prajapati, Gurudayal,Ampapathi, Ravi Sankar,Mandal, Pintu Kumar
supporting information, p. 2859 - 2862 (2019/04/25)
The base-promoted intramolecular cyclization of Ugi-azide adduct has been demonstrated for the synthesis of highly substituted aziridinyl glycoconjugates in one pot. The reactions are scalable and efficient and have an operationally simple broad substrate
Stereoselective Total Synthesis of Unnatural (+)-Anisomycin
Ajay, Sama,Saidhareddy, Puli,Shaw, Arun K.
, p. 1191 - 1196 (2016/05/11)
Stereoselective total synthesis of unnatural (+)-anisomycin from d-glucose has been achieved with an overall yield of 23%. The key synthetic features are regioselective opening of an epoxide, azidation of the resulting alcohol, and finally one-pot hydroge
Metal free synthesis of morpholine fused [5,1-c] triazolyl glycoconjugates via glycosyl azido alcohols
Mishra, Kunj B.,Shashi, Somesh,Tiwari, Vinod K.
, p. 86840 - 86848 (2015/11/03)
A series of diverse glycosyl 1,2-azido alcohols, obtained from readily available carbohydrates, were converted to structurally varied rare and novel sugar derived morpholine fused [5,1-c]-triazoles via a one-pot strategy. After incorporating a propargyl functionality at the hydroxyl group of the sugar derived 1,2-azido alcohols, the resulting in situ generated azido-alkyne affords numerous C- and O-glycosyl bicyclic ring systems with medicinal value via a metal free cycloaddition reaction. The structures of all the developed molecules have been elucidated using 1H NMR, 13C NMR, IR and MS spectroscopy.
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.
Structure-activity relationships of β-hydroxyphosphonate nucleoside analogues as cytosolic 5′-nucleotidase II potential inhibitors: Synthesis, in vitro evaluation and molecular modeling studies
Meurillon, Ma?a,Marton, Zsuzsanna,Hospital, Audrey,Jordheim, Lars Petter,Béjaud, Jér?me,Lionne, Corinne,Dumontet, Charles,Périgaud, Christian,Chaloin, Laurent,Peyrottes, Suzanne
, p. 18 - 37 (2014/03/21)
The cytosolic 5′-nucleotidase II (cN-II) has been proposed as an attractive molecular target for the development of novel drugs circumventing resistance to cytotoxic nucleoside analogues currently used for treating leukemia and other malignant hemopathies
The Synthesis of L-aminosugar and the studies of L-pyranoses on the ring III of pyranmycins.
Wang, Jinhua,Li, Jie,Tuttle, David,Takemoto, Jon Y,Chang, Cheng-Wei Tom
, p. 3997 - 4000 (2007/10/03)
The synthesis of a novel class of aminoglycoside, pyranmycin, and a convenient method for the preparation of 6-amino-L-idopyranosides were reported. One of the members in the reported pyranmycin families, TC010, has prominent activity against Escherichia
Synthesis of peracetylated chacotriose
Morillo, Marielba,Lequart, Vincent,Grand, Eric,Goethals, Gerard,Usubillaga, Alfredo,Villa, Pierre,Martin, Patrick
, p. 281 - 287 (2007/10/03)
Steroidal glycoalkaloids of many Solanum species have recognized biological activities, especially those containing the glycosyl moiety α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 4)]-D-glucopyranose (chacotriose) whose peracetate is here synthe
