121959-10-2Relevant academic research and scientific papers
Anion complexation by glycocluster thioureamethyl cavitands: Novel ESI-MS-based methods for the determination of Ka values
Oshovsky, Gennady V.,Verboom, Willem,Fokkens, Roel H.,Reinhoudt, David N.
, p. 2739 - 2748 (2004)
A series of saccharide-thiourea functionalized cavitands was prepared in good yields (72-86 %) by reaction of a tetrakis(aminomethyl) cavitand with the thiocyanate derivatives of acetylated glucose, galactose, and cellobiose. The anion complexation behavior of the acetylated and deacetylated glycocluster thioureamethyl cavitands was studied with electrospray ionization mass spectrometry (ESI-MS) in acetonitrile and in a 1:1 acetonitrile/water mixture, respectively. All compounds show a preference for Cl-. A linear relationship was found between the square root of the intensity and the concentration of the formed host-guest complex. Based on this relationship, novel methods have been developed to determine Ka values, by means of direct titration and competition experiments.
Synthesis and interfacial properties of amphiphilic β-cyclodextrins and their substitution at the O-6 position with a mono bio-recognisable galactosyl antenna
Salameh, Alain,Lazar, Adina N.,Coleman, Anthony W.,Parrot-Lopez, Hélène
, p. 8740 - 8745 (2005)
The synthesis of a mono-galactosylated amphiphilic β-cyclodextrin, in five steps from mono-6-azido-6-deoxy-β-cyclodextrin, via coupling to a N-β-d-galactopyranosylamino-antenna is described. Both characterization by electrospray mass spectrometry and NMR show the presence of only the mono-substituted product. The Langmuir isotherms of the final product and intermediates are described.
Comparative X-ray single crystal study of acetylated-β-D-galactopyranosyls azide and isothiocyanate
Selkti, Mohamed,Kassab, Rima,Parrot Lopez, Helene,Villain, Francoise,De Rango, Colette
, p. 1019 - 1032 (1999)
The structures of two peracetylated β-D-galactopyranosides substituted at the anomeric C atom with either an isothiocyanate or an azide group, have been determined by single crystal X-ray diffraction analysis. The two compounds show very similar molecular conformation, except for the substituent groups at the anomeric C atom and for the acetyl groups of the O6 atoms. They crystallize in different infinite chain-type structures. While the isothiocyanate group extends in a large intermolecular space, the azide group is placed in a more crowded environment.
Synthesis of cyclodextrin derivatives carrying bio-recognisable saccharide antennae
Kassab, Rima,Felix, Caroline,Parrot-Lopez, Helene,Bonaly, Roger
, p. 7555 - 7558 (1997)
The use of coupling saccharide antenna onto cyclodextrins allows mobility for the biologically active galactose head group, and allows die recognition process by the lectin (KbCWL). This paper reports a chemical synthesis of β-CD derivatives using spacer arms 3, 4, 5, 6 and 9 carbon atoms. Preliminary results suggested that recognition is strongly dependent on the length of the spacer chain between the cyclodextrin and the sugar head group.
Solvent-free preparation of glycosyl isothiocyanates
Lindhorst,Kieburg
, p. 1228 - 1230 (1995)
By a novel solvent-free procedure, peracetylated glycosyl bromides are reacted with potassium thiocyanate in the melt to give the corresponding glycosyl isothiocyanates. The method is applicable to several glycosyl bromides tested, including classical hexoses and pentoses, deoxy sugars and even disaccharides. No glycosyl thiocyanates are obtained. In general, the glycosyl isothiocyanates are formed stereoselectively having 1,2-trans configuration in yields between 41-74%.
Thiourea-linked upper rim calix[4]arene neoglycoconjugates: synthesis, conformations and binding properties.
Sansone, Francesco,Chierici, Elisa,Casnati, Alessandro,Ungaro, Rocco
, p. 1802 - 1809 (2003)
The thiourea group has been exploited to link two or four carbohydrate units at the upper rim of tetrapropoxycalix[4]arene derivatives in the cone conformation. Two synthetic methodologies were used, the first one consisting of the condensation of di- and tetraminocalix[4]arenes with the isothiocyanate of monosaccharides in dry CH2Cl2 at room temperature and the second one exploiting the condensation of an aminolactoside with a calixarene isothiocyanate. The first method allows the glycoconjugates to be obtained in 75-80% overall yields. The disfunctionalized derivatives exist in a closed flattened cone conformation in CDCl3 and CD3OD due to the formation of intramolecular hydrogen bonds involving the thiourea groups which are broken in DMSO-d6 to give an open flattened cone conformation. The thiourea groups act not only as linkers but also as binding units for anionic substrates as evidenced by solution 1H NMR and ESI-MS experiments. Turbidimetric analysis indicates that the tetraglucoside and tetragalactoside clusters give specific interactions with Concanavalin A (Con A) and peanut lectin (PNA), respectively. Both features show that the neoglycoconjugates could also be used as site specific molecular delivery systems.
Synthesis of some new carbohydrate-containing thiouriedonaphtho-quinones
Salameh, Bader A.,Al-Qawasmeh, Raed A.,Al-Jabari, Kumait,Voelter, Wolfgang
, p. 2929 - 2937 (2015)
Abstract New alkyl, aryl, and glycosylthiouriedo derivatives of 2,3-diamino-1,4-naphthoquinone were synthesized via the reaction of isothiocyanates with 2,3-diamino-1,4-naphthoquinone. The new compounds were fully characterized through their physicochemical properties.
Synthesis and Antimicrobial Activities of 1,2,4-Thiadiazolidin-3-thione Hydrochlorides
Mangte, Anvita D.,Nayak, Riddhi A.
, p. 77 - 83 (2022/03/27)
Synthesis of N-glucosyl/lactosyl/maltosyl-1,2,4-thiadizolidin-3-thione hydrochlorides by the reaction of N-phenyl-S-chloroisothiocarbamoyl chloride and N-glucosyl/lactosyl/maltosyl thiocarbamides is reported. The simple isolation method with good yields under mild condition is applicable for the present protocol. All the newly synthesized thiadiazolidin-3-thiones exhibit moderate to good antimicrobial activities against a variety of pathogen
Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases
Moeker, Janina,Teruya, Kanae,Rossit, Sabine,Wilkinson, Brendan L.,Lopez, Marie,Bornaghi, Laurent F.,Innocenti, Alessio,Supuran, Claudiu T.,Poulsen, Sally-Ann
scheme or table, p. 2392 - 2404 (2012/05/05)
A library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were inve
Comparative study of microwave induced and conventional synthesis of acetylated sugar isothiocyanates and related thiocarbamides
Yadgire, Atul V.,Korpe, Gajanan V.,Deshmukh, Shirish P.
experimental part, p. 1614 - 1619 (2012/05/05)
The synthesis of several acetylated sugar isothiocyanates have been carried out under microwave irradiation in excellent yields of products by using related bromides and lead thiocyanate in sodium dried xylene. Several acetylated sugar thiocarbamides have been synthesized by the interaction of respective acetylated sugar isothiocyanates with appropriate aryl amines under microwave irradiation. Copyright E-Journal of Chemistry 2004-2011.
