- Synthesis and Antimicrobial Activities of 1,2,4-Thiadiazolidin-3-thione Hydrochlorides
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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
- Mangte, Anvita D.,Nayak, Riddhi A.
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- Thiourea-containing arsenic sugar with anti-tumor activity and preparation method and application thereof
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The invention relates to the field of arsenic sugar, and in particular relates to thiourea-containing arsenic sugar with anti-tumor activity and a preparation method and application thereof. The thiourea-containing arsenic sugar is composed of two compounds: 1-(N-(4'-(1'', 3'', 2''-dithiaarsenic pentane-2-yl) phenyl)-thiourea)-2, 3, 4, 6-O-acetyl-beta-D-glucose and 1-(N-(4'-(1'', 3 '', 2''-dithiaarsenic hexane-2-yl) phenyl)-thiourea)-2, 3, 4, 6-O-acetyl-beta-D-glucose. The thiourea-containing arsenic sugar provided by the invention has the advantages of simple reaction operation and high yield. The thiourea-containing arsenic sugar with a specific three-dimensional configuration can be obtained, and the thiourea-containing arsenic sugar has good anti-tumor activity.
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Paragraph 0024; 0026; 0030; 0037-0038; 0045; 0052-0053
(2020/04/02)
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- Matrix metalloproteinase-12 inhibitors: synthesis, structure-activity relationships and intestinal absorption of novel sugar-based biphenylsulfonamide carboxylates
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MMP-12 is a validated target in pulmonary and cardiovascular diseases. The principal obstacles to clinical development of MMP-12 inhibitors are an inadequate selectivity for the target enzyme and a poor water solubility, with consequent poor oral bioavailability. We recently reported a new class of sugar-based arylsulfonamide carboxylates with a nanomolar activity for MMP-12, a good selectivity and an improved water solubility. In this study, we designed and synthesized new derivatives to characterize the structure-activity relationship (SAR) within this class of glycoconjugate inhibitors. All the new derivatives were tested on human recombinant MMP-12 and MMP-9 in order to evaluate their affinity and the selectivity for the target enzyme. Among them, the four most promising compounds were selected to assess their intestinal permeability using an ex vivo everted gut sac model. Given the high polarity and structural similarity to glucose, compound 3 was demonstrated to cross the intestinal membrane by using the facilitative GLUT2 transport.
- Cuffaro, Doretta,Camodeca, Caterina,D'Andrea, Felicia,Piragine, Eugenia,Testai, Lara,Calderone, Vincenzo,Orlandini, Elisabetta,Nuti, Elisa,Rossello, Armando
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p. 5804 - 5815
(2018/11/23)
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- Synthesis and schematic mechanism of 3-phenylamino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidines and Its De-acetylated Nucleoside
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A systematic synthesis of 3-phenylimino-4-phenyl-5-tetra-O-acetyl-β-D-glucopyranosylimino-1,2,4-dithiazolidine (acetylated glucopyranosylimino nucleoside) from glucose as starting material. The steps included acetylating glucose to glucose penta-acetate (II). Step 2 involves the bromination of glucose penta-acetate (II) to 2,3,4,6 tetra-O-acetyl-α-D-glucopyranosyl bromide (III). In step 3 compound (III) reacted with lead thiocyanate to give 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (IV). In the step 4 N-phenyl-3-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate (V) was prepared. In the last step on refluxing compound (V) with N-phenyl S-chloro isothiocarbamoyl chloride to yield acetylated glucopyranosyl nucleoside. Furthermore de-acetylating of acetylated glucopyranosyl nucleoside was carried out to obtain 3-phenylimino-4-phenyl-5-β-D-gluopyranosyl imino 1,2,4-dithiazolidine (de-acetylated glucopyranosylimino nucleoside). The synthesized acetylated glucopyranosylimino nucleoside and deacetylated glucopyranosylimono nucleoside were structurally confirmed by elemental analysis, ultraviolet spectral analysis, infrared spectroscopy, nuclear magnetic resonance spectroscopy and mass spectroscopy.
- Hardas, Aruna,Tayade, Priti
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p. 2310 - 2316
(2018/09/10)
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- Synthesis and evaluation of in?vivo antioxidant, in?vitro antibacterial, MRSA and antifungal activity of novel substituted isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones
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Some new isatin N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazones 4a-t with different substituents at 1-, 5- and 7-positions of isatin ring have been synthesized by reaction of N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide 2 with corresponding isatins 3a-t. Compounds 4a-t were evaluated in?vivo for antioxidant activity and in?vitro for anti-microorganism activities. The MIC values were found for Gram positive bacteria (MIC?=?1.56–6.25?μM), for Gram negative bacteria (MIC?=?12.5?μM), and for fungi Aspergillus niger (MIC?=?3.12–12.5?μM), Fusarium oxysporum (MIC?=?6.25–12.5?μM) and Saccharomyces cerevisiae (MIC?=?6.25–12.5?μM). Regarding the antioxidant activity, the SOD, GHS-Px and catalase activities of 4c-i and 4m-r were MIC?=?10.57–10.85, 0.27–0.93 and 345.45–399.75 unit/mg protein, respectively. Compounds 4e-h had MIC values of 0.78, 1.56, and 3.12?μM for three clinical MRSA isolates. Compound 4e showed the selective cytotoxic effects against some cancer (LU-1, HepG2, MCF7, P338, SW480, KB) cell lines and normal fibroblast cell line NIH/3T3.
- Thanh, Nguyen Dinh,Giang, Nguyen Thi Kim,Quyen, Tran Ha,Huong, Doan Thi,Toan, Vu Ngoc
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p. 532 - 543
(2016/08/12)
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- Synthesis and biological activity of novel N-glucosides containing substituted piperazine moiety
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A series of novel acetylated piperazine-containing N-glucosides and bis(N-glucoside) 8a-i were synthesized by the nucleophilic addition of acetylated glucopyranosyl isothiocyanate with various substituted piperazines in THF with high yields. Their novel deacetylated products 9a-i were also synthesized after Me-ONa/MeOH treatment. The preliminary bioassays for 18 novel title compounds showed that several compounds have significant fungicidal activity against Fusarium omysporum, Cercospora arachidicola and Phytophthora capsici at 50 μg/mL.
- Zhang, Li-Yuan,Wang, Bao-Lei,Zhan, Yi-Zhou,Hua, Xue-Wen,Liu, Ming,Zhang, Xiao,Song, Hai-Bin,Li, Zheng-Ming
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p. 343 - 351
(2016/04/04)
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- Synthesis of some new carbohydrate-containing thiouriedonaphtho-quinones
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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.
- Salameh, Bader A.,Al-Qawasmeh, Raed A.,Al-Jabari, Kumait,Voelter, Wolfgang
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p. 2929 - 2937
(2015/04/27)
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- Synthesis and Characterization of N -glucosylated 1,3,4-Thiadiazolidines
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A method is presented for the synthesis of 2-tetra-O-acetyl-β-d-glucopyranbreak; osylimino-5-(aryl)imino-1,3,4-thiadiazolidines by the interaction of substituted aryl thiosemicarbazide with peracetylated glucosyl isocyanodichloride to afford N-glucosylate
- Ulhe, Avinash G.,Chavan, Snehal A.,Berad, Baliram N.
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p. 170 - 177
(2015/05/20)
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- Thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate as reversible ON-OFF receptor for fluoride in acetonitrile
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A new thiourea linked peracetylated glucopyranosyl-anthraquinone conjugate (L) has been synthesized and characterized. The binding properties of L have been studied with nineteen different anions. The L exhibited selective chromogenic as well as fluorescent chemosensor property toward F- by a ～13-fold increase in the emission intensity upon binding with F -. The minimal detection limit for F- is 185 ± 5 ppb in acetonitrile. Interaction of F- led to a bathochromic shift of 80 nm in the absorption band. An INHIBIT logic gate has been proposed using the output obtained from the fluorescence studies. The structure of the species formed upon the interaction of F- with L has been established by DFT computations.
- Areti, Sivaiah,Khedkar, Jayshree K.,Chilukula, Ramakrishna,Rao, Chebrolu P.
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p. 5629 - 5634
(2013/09/23)
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- Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases
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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
- Moeker, Janina,Teruya, Kanae,Rossit, Sabine,Wilkinson, Brendan L.,Lopez, Marie,Bornaghi, Laurent F.,Innocenti, Alessio,Supuran, Claudiu T.,Poulsen, Sally-Ann
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scheme or table
p. 2392 - 2404
(2012/05/05)
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- Synthesis and antimicrobial activity of o- and p-hydroxybenzoic acid thiosemicarbazides
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The ortho- and para-hydroxybenzoic acid thiosemicarbazide derivatives which are potentially biologically active substances were obtained by the reaction of the corresponding hydrazides with various isothiocyanates. Their structures were determined using I
- Nurkenov,Satpaeva,Kulakov,Akhmetova,Zhaugasheva
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experimental part
p. 668 - 671
(2012/10/08)
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- Comparative study of microwave induced and conventional synthesis of acetylated sugar isothiocyanates and related thiocarbamides
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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.
- Yadgire, Atul V.,Korpe, Gajanan V.,Deshmukh, Shirish P.
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p. 1614 - 1619
(2012/05/05)
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- Synthesis of acetylated glycosyl-containing thiourea derivatives based on the alkaloids cytisine and anabasine and the molecular structure of N-cytisino-N′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiocarbamide
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Glycosylthiourea derivatives were synthesized from the alkaloids cytisine and anabasine and 1-deoxy-2,3,4,6tetra-O-acetyl-β-D- glucopyranosylisothiocyanate. The structures of the synthesized compounds were proved using PMR spectroscopy, mass spectrometry, and an x-ray crystal structure analysis.
- Kulakov,Nurkenov,Arinova,Turdybekov,Talipov,Ibragimov
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experimental part
p. 777 - 780
(2012/03/27)
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- Synthesis and antimicrobial studies of some bis-glycosyl isodithiobiurets
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Certain 2-S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl-5-tetra-Oacetyl-β-D- galactopyranosyl-2, 4- isodithiobiurets have been synthesized by the interaction of tetra-O-acetyl-β-D-galactopyranosyl isothiocyante and various S- tetra-O-benzoyl-D- glucopyranosyl-1-aryl isothiocarbamides. The newly synthesized compounds were screened for their antimicrobial activities.
- Mahalle, Prashant R.,Deshmukh, Shirish P.
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experimental part
p. 795 - 798
(2011/12/05)
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- The binding of β-d-glucopyranosyl-thiosemicarbazone derivatives to glycogen phosphorylase: A new class of inhibitors
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Glycogen phosphorylase (GP) is a promising target for the treatment of type 2 diabetes. In the process of structure based drug design for GP, a group of 15 aromatic aldehyde 4-(β-d-glucopyranosyl)thiosemicarbazones have been synthesized and evaluated as inhibitors of rabbit muscle glycogen phosphorylase b (GPb) by kinetic studies. These compounds are competitive inhibitors of GPb with respect to α-d-glucose-1-phosphate with IC50 values ranging from 5.7 to 524.3 μM. In order to elucidate the structural basis of their inhibition, the crystal structures of these compounds in complex with GPb at 1.95-2.23 resolution were determined. The complex structures reveal that the inhibitors are accommodated at the catalytic site with the glucopyranosyl moiety at approximately the same position as α-d-glucose and stabilize the T conformation of the 280s loop. The thiosemicarbazone part of the studied glucosyl thiosemicarbazones possess a moiety derived from substituted benzaldehydes with NO2, F, Cl, Br, OH, OMe, CF3, or Me at the ortho-, meta- or para-position of the aromatic ring as well as a moiety derived from 4-pyridinecarboxaldehyde. These fit tightly into the β-pocket, a side channel from the catalytic site with no access to the bulk solvent. The differences in their inhibitory potency can be interpreted in terms of variations in the interactions of the aldehyde-derived moiety with protein residues in the β-pocket. In addition, 14 out of the 15 studied inhibitors were found bound at the new allosteric site of the enzyme.
- Alexacou, Kyra-Melinda,Tenchiu, Alia-Cristina,Chrysina, Evangelia D.,Charavgi, Maria-Despoina,Kostas, Ioannis D.,Zographos, Spyros E.,Oikonomakos, Nikos G.,Leonidas, Demetres D.
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body text
p. 7911 - 7922
(2011/02/22)
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- Syntheses and evaluation of glucosyl aryl thiosemicarbazide and glucosyl thiosemicarbazone derivatives as antioxidant and anti-dyslipidemic agents
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A series of N-per-O-acetyl-glucosyl arylthiosemicarbazide and thiosemicarbazone derivatives have been synthesized and evaluated for their in vivo anti-dyslipidemic and in vitro antioxidant activities. Among 16 compounds tested, 3 compounds showed potent a
- Ghosh, Samir,Misra, Anup Kumar,Bhatia, Gitika,Khan,Khanna
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scheme or table
p. 386 - 389
(2011/02/28)
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- New N-galactosides: Synthesis of N-galactosylated thiocarbamides, benzothiazolyl thiocarbamides and thiocarbamates
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The title compounds were prepared by the condensation of tetra-O-acetyl-β-D-galactopyranosyl isothiocyanate with several amines, 2-aminobenzothiazole/substituted benzothiazoles and alcohols respectively. The structure of these new N-galactoside has been established on the basis of usual chemical transformations and IR, NMR and Mass spectral studies of some typical cases.
- Mahalle, Prashant R.,Korpe, Gajanan V.,Deshmukh, Shirish P.
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experimental part
p. 953 - 958
(2009/12/07)
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- Simple and efficient synthesis of novel glycosyl thiourea derivatives as potential antitumor agents
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The practical synthesis of pseudonucleosides incorporating thiourea derivative by coupling of monosaccharides (d-galactose, d-glucose and d-xylose) per-O-acetylated glycosyl isothiocyanates and different heterocyclic hydrazide derivatives is reported. The method involves the preparation of per-O-acetylated glycosyl isothiocyanates from per-O-acetylated sugars (two-step synthesis), which couple with heterocyclic hydrazides from amines to give thiourea-linked pseudonucleosides. All newly synthesized pseudonucleosides were assayed against human lung cancer-cell lines (PG) and human liver cancer-cell lines (BEL-7402) in vitro. The 2-(4-methoxybenzamide)-benzoimidazole-1-yl-acetyl pseudonucleosides showed moderate inhibition against these two cancer-cell lines with EC50 from 22.8 to 76.4 μM and from 54.9 to 82.4 μM, respectively. And the other compounds did not demonstrate any significant cytotoxicity even at concentrations up to 200 μM.
- Shusheng, Zhang,Tianrong, Zhan,Kun, Cheng,Youfeng, Xia,Bo, Yang
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experimental part
p. 2778 - 2783
(2009/04/11)
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- A novel, simple cyclocondensation reaction towards glycosyl triazines
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Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and 13C and 1H NMR (COSY, HMBC and HMQC). Georg Thieme Verlag.
- Kikelj, Vincent,Julienne, Karine,Janvier, Pascal,Meslin, Jean-Claude,Deniaud, David
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scheme or table
p. 3453 - 3460
(2009/05/26)
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- Synthesis of α- and β-glycosyl isothiocyanates via oxazoline intermediates
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(Chemical Equation Presented) A practical synthesis of acylated glycosyl isothiocyanates from sugar oxazolines, by reaction with thiophosgene, is reported. In the absence of any additive, the reaction is governed by the reverse anomeric effect, leading to
- Blanco, Jose L. Jimenez,Sylla, Balla,Mellet, Carmen Ortiz,Fernandez, Jose M. Garcia
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p. 4547 - 4550
(2008/02/05)
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- A simple method for the preparation of glycosyl isothiocyanates
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Glycosyl isothiocyanates became accessible from the corresponding peracetylated sugars in one step, by application of trimethylsilyl isothiocyanate and a Lewis acid in dichloromethane at room temperature. Georg Thieme Verlag Stuttgart.
- Kuehne, Marco,Gyoergydeak, Zoltan,Lindhorst, Thisbe K.
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p. 949 - 951
(2007/10/03)
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- Synthesis and interfacial properties of amphiphilic β-cyclodextrins and their substitution at the O-6 position with a mono bio-recognisable galactosyl antenna
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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.
- Salameh, Alain,Lazar, Adina N.,Coleman, Anthony W.,Parrot-Lopez, Hélène
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p. 8740 - 8745
(2007/10/03)
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- Anion complexation by glycocluster thioureamethyl cavitands: Novel ESI-MS-based methods for the determination of Ka values
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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.
- Oshovsky, Gennady V.,Verboom, Willem,Fokkens, Roel H.,Reinhoudt, David N.
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p. 2739 - 2748
(2007/10/03)
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- An Efficient Route to Pyrimidine Nucleoside Analogues by [4 + 2] Cycloaddition Reaction
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We report here an efficient synthesis for pyrimidine nucleoside analogues by [4 + 2] cycloaddition reaction. These compounds were obtained by convergent chemistry from glycosyl isothiocyanates 3a-f (pyranoses, furanoses, and dissaccharides) and diazadienium salt 5. In fact, diazapentadienium iodide 5 prepared from vinylthioamide 4 is an efficient intermediate in heterocyclic synthesis and reacts with isothiocyanates 3a-f affording β-D-uracil analogues 7a-f in good yields and with total regiocontrol. All compounds were fully characterized by IR, HRMS, and 13C and 1H NMR (COSY and HMQC).
- Pearson, Morwenna S. M.,Robin, Aelig,Bourgougnon, Nathalie,Meslin, Jean Claude,Deniaud, David
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p. 8583 - 8587
(2007/10/03)
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- Thiourea-linked upper rim calix[4]arene neoglycoconjugates: synthesis, conformations and binding properties.
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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.
- Sansone, Francesco,Chierici, Elisa,Casnati, Alessandro,Ungaro, Rocco
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p. 1802 - 1809
(2007/10/03)
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- Comparative X-ray single crystal study of acetylated-β-D-galactopyranosyls azide and isothiocyanate
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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.
- Selkti, Mohamed,Kassab, Rima,Parrot Lopez, Helene,Villain, Francoise,De Rango, Colette
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p. 1019 - 1032
(2007/10/03)
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- Syntheses of C- and N-nucleosides from 1-aza-2-azoniaallene and 1,3-diaza-2-azoniaallene salts
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C-Nucleosides are prepared by cycloaddition of 1-aza-2-azoniaallene salts 2 and 1,3-diaza-2-azoniaallene salts 5 to the triple bonds of a glycosylalkyne and of glycosyl cyanides. Thus, the glucosylalkyne 7 reacts with salts 5 to give the 4-glucosyl-1,2,3-
- Al-Masoudi, Najim,Hassan, Nasser A.,Al-Soud, Yaseen A.,Schmidt, Patrick,Gaafar, Alaa El-Din M.,Weng, Min,Marino, Stefano,Schoch, Annette,Amer, Atef,Jochims, Johannes C.
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p. 947 - 953
(2007/10/03)
-
- Synthesis of cyclodextrin derivatives carrying bio-recognisable saccharide antennae
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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.
- Kassab, Rima,Felix, Caroline,Parrot-Lopez, Helene,Bonaly, Roger
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p. 7555 - 7558
(2007/10/03)
-
- Solvent-free preparation of glycosyl isothiocyanates
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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%.
- Lindhorst,Kieburg
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p. 1228 - 1230
(2007/10/02)
-
- Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides
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Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.
- Pakulski, Zbigniew,Pierozynski, Donat,Zamojski, Aleksander
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p. 2975 - 2992
(2007/10/02)
-
- STRUCTURE AND REACTIVITY OF GLYCOSIDES. III. KINETICS AND MECHANISM OF THE ALKALINE HYDROLYSIS OF O-ARYL (2,3,4,6-TETRA-O-ACETYL-β-D-GLUCOPYRANOSYL)THIOCARBAMATES IN WATER-DIOXANE SOLUTIONS
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The kinetics were studied and the rate constants of hydrolysis were determined in water-dioxane alkaline solutions at 20 deg C and pH 10.87 of a number of O-aryl (tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamates substituted in the aromatic ring.Logarithms of the rate constants observed correlate with the pKa values of the corresponding phenols and with a set of Hammett constants.The temperature dependence of the rate constants of the hydrolysis of O-(4-propylphenyl) (tetra-O-acetyl-β-D-glucopyranosyl)thiocarbamate was determined, and its activation parameters were calculated.An intermediate formed in the hydrolysis of a glycosylthiocarbamate was identified as a glycosyl isothiocyanate on the basis of the electronic spectra and TLC.
- Petushkova, S. G.,Pavlov, A. E.,Sokolov, V. M.,Zakharov, V. I.,Lavrent'ev, A. N.
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p. 796 - 798
(2007/10/02)
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- SYNTHESIS AND SOME REACTIONS OF GLYCOSYL ISOTHIOCYANATES
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Peracetylglycosyl isothiocyanates were obtained by the nucleophilic substitution of glycosyl halides with potassium thiocyanate under the conditions of phase-transfer catalysis in the presence of quaternary ammonium salts.The reaction of glycosyl isothiocyanates with furfurylamine, benzylamine, and 1,2- and 1,3-amino alcohols gives the corresponding N-substituted glycosylthioureas.When treated with hydrazine hydrate, 1-isothiocyanato-1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose gives 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-thiosemicarbazide, which in reaction with 5-substituted furancarbaldehydes gives the corresponding acetylglycopyranosylthiosemicarbazones of these aldehydes.The products were also obtained with high yields by the reaction of glycosyl isothiocyanates with furfural and 5-nitrofurfural hydrazones.
- Tashpulatov, A. A.,Rakhmatullaev, I.,Afanas'ev, V. A.,Ismailov, N.
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p. 1707 - 1710
(2007/10/02)
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- New N-Glucosides. Syntheses of 1- and 5-glucosyl-2,4-isodithiobiurets
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Several 1-tetra-O-acetyl-β-D-glucopyranosyl-5-aryl/alkyl-2-S-benzyl-2,4-isodithiobiurets (4) and 1-aryl/(H)-5-tetra-O-acetyl-β-D-glucopyranosyl-2-S-benzyl-2,4-isodithiobiurets (7) have been prepared by the interaction of 1-tetra-O-acetyl-β-D-glucopyranosyl-2-S-benzyl isothiocarbamide with aryl/alkylisothiocyanates and 1-aryl-2-S-benzylisothiocarbamides with tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate, respectively.
- Deshmukh, S. P.,Berad, B. N.,Paranjpe, M. G.
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p. 315 - 316
(2007/10/02)
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