* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference:
[1] European Journal of Medicinal Chemistry, 2017, vol. 136, p. 63 - 73
2
[ 127-73-1 ]
[ 127-79-7 ]
Reference:
[1] Yakugaku Zasshi, 1949, vol. 69, p. 27,29[2] Chem.Abstr., 1950, p. 3453
[3] Journal of the American Chemical Society, 1942, vol. 64, p. 2340
[4] Patent: CH230863, 1938, ,
[5] Journal of the American Chemical Society, 1941, vol. 63, p. 3028
[6] Journal of the American Chemical Society, 1940, vol. 62, p. 2002,2003[7] Journal of the American Chemical Society, 1942, vol. 64, p. 567,568
[8] Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 627,666,667
[9] Yakugaku Zasshi, 1949, vol. 69, p. 417[10] Chem.Abstr., 1950, p. 1924
[11] J.Chin.chem.Soc., 1947, vol. 15, p. 138,145
[12] Journal of the Chemical Society, 1945, p. 689,691
[13] Patent: CH233768, 1944, ,
[14] Patent: US2407966, 1940, ,
3
[ 108-52-1 ]
[ 127-79-7 ]
Reference:
[1] Journal of the American Chemical Society, 1942, vol. 64, p. 2340
[2] Patent: CH230863, 1938, ,
[3] Journal of the American Chemical Society, 1941, vol. 63, p. 3028
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 2002,2003[5] Journal of the American Chemical Society, 1942, vol. 64, p. 567,568
[6] Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 627,666,667
[7] J.Chin.chem.Soc., 1947, vol. 15, p. 138,145
4
[ 121-60-8 ]
[ 127-79-7 ]
Reference:
[1] Journal of the American Chemical Society, 1942, vol. 64, p. 2340
[2] Patent: CH230863, 1938, ,
[3] Journal of the American Chemical Society, 1941, vol. 63, p. 3028
[4] Journal of the American Chemical Society, 1940, vol. 62, p. 2002,2003[5] Journal of the American Chemical Society, 1942, vol. 64, p. 567,568
[6] Recueil des Travaux Chimiques des Pays-Bas, 1942, vol. 61, p. 627,666,667
[7] J.Chin.chem.Soc., 1947, vol. 15, p. 138,145
8-(5-{4-Hydroxy-3-[4-(4-methyl-pyrimidin-2-ylsulfamoyl)-phenylazo]-phenyl}-[1,3,4]oxadiazol-2-ylmethoxy)-quinoline-5-sulfonic acid dimethylamide[ No CAS ]
4-azido-N-(4-methylpyrimidin-2-yl)benzenesulfonamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
76%
General procedure: Each 4-aminobenzenesulfonamide (3.0 mmol) was added in asolution of concentrated sulfuric acid (0.5 mL) and H2O (3.0 mL)and then cooled to 0 C in an ice bath. A solution of NaNO2 (3.0mmol) in water (2.1 mL) was added dropwise to the reaction andleft stirring for 10 min. After a color change to a yellowish toneand appearance of foam in the medium, solid urea (150 mg) wasadded followed by NaN3 solution (9.0 mmol, 1.5 eq) in H2O (3.2mL) dropwise. Finally, after stirring for few minutes each reactionwas filtered through Buchner funnel and washed subsequentlywith 5% NaHCO3 and H2O. Each obtained product was dried underreduced pressure and analyzed by TLC, being verified at increasedretention factors (Rf) if compared to the corresponding startingmaterials. Compounds 8-14 were obtained in corresponding yieldsof 38% (8), 45% (9), 91% (10), 52% (11), 42,5% (12), 40% (13) and 76%(14). 1H NMR and IR [2100 cm1 (N3)] (2100 cm1) analysis of 8-14 were in accordance with the literature.28
74%
With sodium azide; tert.-butylnitrite; In 1,4-dioxane; water; at 55℃; for 0.333333h;Microwave irradiation;
General procedure: Sodium azide (78 mg, 1.20 mmol, 3 equiv.) wasintroduced in a microwave flask equipped with a stirringbar and solubilized with water (150 muL). To this solution,the remaining reagents were added in the following order: solvent reaction (1 mL), 4-aminobenzenesulfonamide (16-22) (0.4 mmol, 1 equiv.) and tert-butyl nitrite(t-BuONO). The mixture was stirred and heated undermicrowave radiation at 150 W. The reaction was followedby TLC and after completion, the reaction mixture waspartitioned between hexane and EtOAc. The aqueousphase was extracted with EtOAc (3 times), and the organicphase was dried over Na2SO4, filtered and concentrated.The product was obtained after flash chromatographyon a Biotage Horizon, using 12 mm flash cartridge,flow 8 mL min-1; hexane/EtOAc; gradient 0-40% and40%-40% (v/v).
Benzoic acid 2-{5-carboxymethyl-3-[4-(4-methyl-pyrimidin-2-ylsulfamoyl)-phenyl]-4-oxo-2-phenyl-thiazolidin-2-yl}-4-chloro-6-nitro-phenyl ester[ No CAS ]
General procedure: alpha-CD/beta-CD (0.9728/1.135g) was dissolved in 40ml distilled water at 50C in a water bath. SMRZ (0.264g) in 10ml methanol was slowly added to the CD solution with continuous agitation. The molar ratio of SMRZ to CDs was 1:1. The vessel covered with aluminum foil and stirred continuously for 24h. Then the final solution was refrigerated overnight at 5C. The precipitated SMRZ/CDs complexes were recovered by filtration and washed with small amount of methanol and water to remove uncomplexed drug and CDs, respectively. This precipitate was dried in vacuum at room temperature for two days and stored in an airtight bottle. This powder samples were further analyzed by using FT-IR,1H NMR, DSC, XRD and SEM methods.
General procedure: 5.0 ml of 0.5M hydrochloric acid solution was placed into a 25ml volumetric flask. Then a sample of solution containing 0.4-14.0mugml-1 of sulphanilamide in final volume was added.Next 5.0 ml of 1.25x10-2M sodium nitrite solution was added into the flask. Obtained solution was stirred and cooled on an ice bath(~0 C) for 10 min. Then 1.0 ml of 1.25x10-3M Tropaeolin O solution was added into the flask. Obtained mixture was neutralized by adding of 2.5 ml of 1M sodium hydroxide solution and the pH value was adjusted to pH= 10.5 and distilled water was added to the full volume of 25ml. Then the solution was mixed thoroughly and the absorbance measurements (at room temperature ~20 C) were carried out against all corresponding reagents blank solution at 595nm in 1.0cm cuvettes. Sulphanilamide concentration was calculated using the methods of calibration curve and single-point standardization.
General procedure: The compounds were prepared through condensation reaction between 0.001 mol tetrafluorophthalic anhydride and 0.001 mol sulfonamides in 5 mL acetic acid under reflux at 120 C for 3-4 h. Then 20 mL distilled water was added into the reaction media. The compounds were filtered and recrystallized in ethanol.
The complexes were synthesized according to the procedure describedby Bult et al. [26], mixing 0.8 mmol of sulfonamide (SIGMA)in water and adding NaOH 1 M until total dissolution was achieved(pH = 9-10). To the resulting solution, 0.4 mmol of CoSO4 7H2O(Baker) dissolved in 20 mL of water were added dropwise.
General procedure: The title compounds were synthesized in a general procedure by the condensation of indole-3-carboxaldehyde with sulfanilamide, sulfadiazine, sulfamerazine, sulfamethoxazole, sulfamethoxypyridazine,sulfapyridine and sulfacetamide sodium, respectively, in ethanol (1:1). The synthesis of Schiff bases were performed in accordance with reaction Scheme 1. The reaction mixture was refluxed for half to three hours and allowed to cool, filtered and the products recrystallized by appropriate solvent. The purity of the products and composition of the reaction mixture were monitored by thin layer chromatography using chloroform:ethanol (9:1) or ethyl acetate:benzene (3:7). The structures of synthesized Schiff bases with related sulfa drugs are shown in Table 1. Also, the observed physical properties of title compounds are given in Table 2.
With triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 200℃; for 0.166667h;Microwave irradiation;
General procedure: 1-Adamantyl isocyanate (177 mg, 1.0 mmol), 4-aminosulfonamide (1.2 mmol) and triethylamine (502 muL, 3.6 mmol) were dissolved in a 1:1 mixture of THF/DMF (5 mL) in a microwave safe tube and stirred at 200 C for 10 min. The solvents were removed under reduced pressure and the crude residue was purified by reverse-phase flash column chromatography using a 0.1% formic acid in water to 0.1% formic acid in acetonitrile gradient.
General procedure: Aliquots of sulfonamide derivative solutions (sulfanilamide, sulfamethoxazole,sulfamethiazole, sulfathiazole, sulfacetamide,Ssulfamerazine, sulfadiazine, sulfadimethoxine) ranging from 0.1-1.0 mL (10 mug mL-1) were transferred into each of the series of10 mL flasks, 1 mL of sodium (1% w/v) and 1 mL of 1 M hydrochloricacid were added with swirling at room temperature. After 5 min,1 mL of sulfamic acid (2% w/v) and 1 mL of <strong>[1465-25-4]N-(1-naphthyl)ethylenediamine dihydrochloride</strong> (1% w/v) were added withswirling. The volumes were adjusted to the mark with distilledwater, and then the solutions were mixed thoroughly. The absorbanceof the light pink colored solutions was measured at 536 nmagainst the reagent blank. Fig. 2 shows a picture of a gradient of concentrationsof the pink colored solutions tested.