SYNTHESIS OF 3-AMINO-2,3-DIDEOXY-D-lyxo-HEXOSE

1965 ◽  
Vol 43 (11) ◽  
pp. 3074-3079 ◽  
Author(s):  
Hans H. Baer ◽  
Frank Kienzle
Keyword(s):  
Aspartic Acid ◽  
Catalytic Hydrogenation ◽  
Title Compound ◽  
Amine Hydrochloride ◽  
Derivatives Of ◽  
Potential Use

Catalytic hydrogenation of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-threo-hexo-pyranos-2-enide (I) afforded methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-lyxo-hexo-pyranoside (II). Acid debenzylidenation and further hydrogenation gave in turn methyl 2,3-dideoxy-3-nitro-β-D-lyxo-hexopyranoside (III) and the corresponding amine hydrochloride (IV). Several crystalline derivatives of IV were prepared, and the configuration at C-3 was proved by degradation of the N-benzoate (VII) to N-benzoyl-D-aspartic acid. The title compound (V) was obtained as a chromatographically homogeneous sirup.Some methyl 3-deoxy-3-nitro-β-L-hexopyranosides were prepared for potential use as starting materials in analogous syntheses in the L-series.

scholarly journals Biguanide-Based Synthesis of 1,3,5-Triazine Derivatives with Anticancer Activity and 1,3,5-Triazine Incorporated Calcium Citrate Nanoparticles

Molecules ◽  
2021 ◽  
Vol 26 (4) ◽  
pp. 1028
Author(s):  
Monnaya Chalermnon ◽  
Sarocha Cherdchom ◽  
Amornpun Sereemaspun ◽  
Rojrit Rojanathanes ◽  
Tanatorn Khotavivattana
Keyword(s):  
Anticancer Activity ◽  
Cell Lines ◽  
Anticancer Agent ◽  
Drug Loading ◽  
Calcium Citrate ◽  
Colorectal Cancer Cell Lines ◽  
Triazine Derivatives ◽  
Further Development ◽  
Derivatives Of ◽  
Potential Use

Twelve derivatives of biguanide-derived 1,3,5-triazines, a promising class of anticancer agent, were synthesised and evaluated for their anticancer activity against two colorectal cancer cell lines—HCT116 and SW620. 2c and 3c which are the derivatives containing o-hydroxyphenyl substituents exhibited the highest activity with IC50 against both cell lines in the range of 20–27 µM, which is comparable to the IC50 of cisplatin reference. Moreover, the potential use of the calcium citrate nanoparticles (CaCit NPs) as a platform for drug delivery system was studied on a selected 1,3,5-triazine derivative 2a. Condition optimisation revealed that the source of citrate ions and reaction time significantly influence the morphology, size and %drug loading of the particles. With the optimised conditions, “CaCit-2a NPs” were successfully synthesised with the size of 148 ± 23 nm and %drug loading of up to 16.3%. Furthermore, it was found that the release of 2a from the synthesised CaCit-2a NPs is pH-responsive, and 2a could be control released under the acidic cancer environment. The knowledge from this study is perceptive for further development of the 1,3,5-triazine-based anticancer drugs and provide the platform for the incorporation of other drugs in the CaCit NPs in the future.

Selective catalytic hydrogenation of unsaturated derivatives of nitrobenzene in alcoholic media

1999 ◽  
Vol 144 (1) ◽  
pp. 199-206 ◽  
Author(s):  
E. Lamy-Pitara ◽  
B. N'Zemba ◽  
J. Barbier ◽  
F. Barbot ◽  
L. Miginiac
Keyword(s):  
Catalytic Hydrogenation ◽  
Derivatives Of

Synthesis of 5'-O-phosphonomethyl derivatives of pyrimidine 2'-deoxynucleosides

1990 ◽  
Vol 55 (10) ◽  
pp. 2521-2536 ◽  
Author(s):  
Marcela Krečmerová ◽  
Hubert Hřebabecký ◽  
Antonín Holý
Keyword(s):  
Sodium Salt ◽  
Catalytic Hydrogenation ◽  
Bond Cleavage ◽  
Diethyl Ester ◽  
Derivatives Of

Reaction of sodium salt of 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxyuridine (X) and 3-N,3'-O-bis(benzyloxymethyl)-2'-deoxythymidine (XI) with diethyl p-toluenesulfonyloxymethanephosphonate in dimethylformamide afforded diesters of the respective 5'-O-phosphonomethyl derivatives XII and XVII. Diethyl esters of 5'-O-phosphonomethyl-2'-deoxynucleosides XV and XIX, obtained after hydrogenolytic removal of the benzyloxymethyl groups, were converted into free 2'-deoxy-5'-O-phosphonomethyluridine (XVI) and a mixture of anomeric 1-(2-deoxy-5-O-phosphonomethyl-β-D-erythro-pentofuranosyl)thymines (XXIIIa, XXIIIb), respectively. Analogously, 2'-deoxy-5'-O-phosphonomethylcytidine (XXXIV) was prepared from 4-N-benzoyl-2'-deoxy-3'-O-(tetrahydro-2H-pyran-2-yl) cytidine (XXX) via diethyl ester of 2'-deoxy-5'-O-phosphonomethylcytidine (XXXIII). This compound reacted with bromotrimethylsilane to give compound XXXIV without anomerization and nucleoside bond cleavage. Condensation of the protected nucleosides X and XI with dibenzyl p-toluenesulfonyloxymethanephosphonate afforded dibenzyl esters of the corresponding 5'-O-phosphonomethyl derivatives XIII and XVIII. The free 5'-O-phosphonomethyl derivatives XVI and XXIIIa were obtained from XIII and XVIII by catalytic hydrogenation.

Inhibition of thrombin by derivatives of the dipeptide aspartic acid-amidinophenylalanine

Peptides ◽  
1994 ◽  
pp. 643-645 ◽  
Author(s):  
W. Stüber ◽  
R. Koschinsky ◽  
C. Kolar ◽  
M. Reers ◽  
G. Dickneite ◽  
...  
Keyword(s):  
Aspartic Acid ◽  
Derivatives Of ◽  
Inhibition Of Thrombin

scholarly journals Synthesis of L-2-(N-Pteroylamino )-3-(N -phosphonoacetyl)aminopropanoic Acid as an Analogue of the Putative Phosphorylated Intermediate in the γ-Glutamation of Folic Acid by Folylpolyglutamate Synthetase

Pteridines ◽  
1999 ◽  
Vol 10 (1) ◽  
pp. 39-46 ◽  
Author(s):  
Ronald Forsch ◽  
Henry Bader ◽  
Andre Rosowsky
Keyword(s):  
Folic Acid ◽  
Glutamic Acid ◽  
Aspartic Acid ◽  
Catalytic Hydrogenation ◽  
Spatial Orientation ◽  
Sequential Treatment ◽  
Folylpolyglutamate Synthetase ◽  
Phosphonate Esters ◽  
Catalytic Addition

L-2-(N-Pteroyl)amino-3-(N-phosphonoacetyl)aminopropanoic acid was synthesized as an analogue of the putative y-phosphorylated intermediate in the enzyme-catalyzed γ-glutamation of folic acid by folylpolyglutamate synthetase (FPGS). N-(Benzyloxycarbonyl)-L-aspartic acid was converted in four steps to methyl L-2-(N-benzyloxycarbonyl)amino-3-aminopropanoate, and the latter was allowed to react with p-nitrophenyl dimethoxyphosphonoacetate to obtain methyl L-2-(N-benzyloxycarbonylamino)- 3-(N-dimethoxyphosphonoacetyl)aminopropanoate. After catalytic hydrogenation, the resulting amine was coupled to N10-formylpteroic acid via the mixed carboxylic-carbonic anhydride method, and the three ester groups were removed by sequential treatment with Me3SiBr in DMF and NaOH in DMSO. When the last step was performed only with NaOH/DMSO, one of the phosphonate esters remained intact, giving L-2-(N -pteroyl )amino-3 -(N -monOInethoxyphosphonoacetyl )aminopropanoic acid. Also synthesized as a potential FPGS inhibitor was Nα-(4-amino-4-deoxy-N10-methylpteroyl)-Nε-phosphonoacetyl- L-Iysine. The ability of these phosphonoacetyl derivatives to inhibit catalytic addition of L-glutamic acid to folic acid proved to be very low, suggesting that replacement of the CH2C(=O)OP(=O)(OH)2 moiety by NHC(=O)CH2P(=O)(OH)2 may place the terminal phosphonyl group in an unfavorable spatial orientation for binding to the enzyme.

The synthesis of D-angolosamine

1977 ◽  
Vol 55 (6) ◽  
pp. 1100-1103 ◽  
Author(s):  
Hans H. Baer ◽  
Fawzy F. Z. Georges
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Title Compound ◽  
Amino Glycoside ◽  
Starting Point ◽  
Simplified Procedure

The synthesis of 2,3,6-trideoxy-3-dimethylamino-D-arabino-hexose hydrochloride (10) (D-angolosamine, a constituent of the antibiotic, angolamycin) is described. First, a simplified procedure for the preparation of methyl 6-deoxy-α-D-glucopyranoside from methyl α-D-glucopyranoside is recorded. The deoxy derivative served as the starting point for sequential preparation of methyl 3,6-dideoxy-3-nitro-α-D-glucopyranoside (1), its 2,4-diacetate (2), its 4-monoacetate (3), its 2-O-mesyl-4-acetate (4), its 2-mesylate (5), and methyl 2,3,6-trideoxy-3-nitro-α-D-erythro-hex-2-enopyranoside (6) essentially according to procedures previously established (in part, in the L-series). Treatment of 5 or 6 with sodium borohydride produced methyl 2,3,6-trideoxy-3-nitro-α-D-arabino-hexopyranoside (7). Catalytic hydrogenation of 7 gave the corresponding 3-amino glycoside hydrochloride (8) which was hydrolyzed to furnish 3-amino-2,3,6-trideoxy-D-arabino-hexose hydrochloride (9) (D-acosamine, the enantiomer of a component of the antibiotic, actinoidin). N,N-Dimethylation of 8 followed by hydrolysis afforded the crystalline title compound (10).

A New Approach to 3′-Amino-3′-deoxynucleosides. Synthesis of 9-(3-Amino-3-deoxy-α-L-ribofuranosyl)adenine

1971 ◽  
Vol 49 (4) ◽  
pp. 568-573 ◽  
Author(s):  
Hans H. Baer ◽  
Monika Bayer
Keyword(s):  
Catalytic Hydrogenation ◽  
Title Compound ◽  
Condensation Product ◽  
Periodate Oxidation ◽  
Borohydride Reduction ◽  
New Approach

Methyl 2,3,4-tri-O-acetyl-6-deoxy-6-nitro-α-D-glucopyranoside (1) was acetolyzed to give 1,2,3,4-tetra-O-acetyl-6-deoxy-6-nitro-α-D-glucopyranose (2). Compound 2 (or alternatively, 6-deoxy-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose 4) was converted into 2,3,4-tri-O-acetyl-6-deoxy-6-nitro-α- D-glucopyranosyl bromide (3) which was condensed with chloromercuri 6-benzamidopurine. De-O-acetylation of the condensation product 5 afforded 6-benzamido-9-(6-deoxy-6-nitro-β-D-glucopyranosyl)purine (6) which could be hydrogenated to the corresponding 6′-amino nucleoside 7. Periodate oxidation of 6 followed by internal Henry cyclization and borohydride reduction gave 6-benzamido-9-(3-deoxy-3-nitro-α-L-ribofuranosyl)purine (10) which upon catalytic hydrogenation and subsequent de-N-benzoylation produced the title compound, 12. The sensitivity of certain nitro intermediates towards alkali is commented upon.

scholarly journals Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

2017 ◽  
Vol 13 ◽  
pp. 579-588 ◽  
Author(s):  
Jan Szabo ◽  
Julian Greiner ◽  
Gerhard Maas
Keyword(s):  
Crystal Structure ◽  
Carboxylic Acid ◽  
Nitrogen Atom ◽  
Catalytic Hydrogenation ◽  
Acid Chlorides ◽  
Reaction Conditions ◽  
Derivatives Of ◽  
Guanidinium Salts ◽  
Triazolium Salts

Depending on the reaction conditions, N,N’,N’’-tris(benzylamino)guanidinium salts can react with carboxylic acid chlorides to form either symmetrical N,N’,N’’-tris(N-acyl-N-benzylamido)guanidines 6 or mesoionic 4-amino-1,2,4-triazolium-3-hydrazinides 7. The latter were converted into 1,2,4-triazolium salts by protonation or methylation at the hydrazinide nitrogen atom. Neutral 1,2,4-triazoles 10 were obtained by catalytic hydrogenation of an N-benzyl derivative. Crystal structure analyses of a 4-benzylamino-1,2,4-triazolium-3-hydrazinide and of two derived 1,2,4-triazolium salts are presented.

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