- Synthesis and Antimicrobial and Antioxidant Activities of Sulfonamide Derivatives Containing Tetrazole and Oxadiazole Rings
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In the present work, we synthesized new sulfonamide derivatives with 1,3,4-oxadiazole moiety and tetrazole ring. The synthesized derivatives of sulfonamides were characterized through Fourier transform infrared, 13C-APT-NMR, 1H-NMR, and high-resolution liquid chromatography–mass spectrometry. The biological activities of resulting compound were also investigated and observed that the compounds reveal strong antimicrobial activity over some important bacterial strains including Bacillus subtilis ATCC 6633, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 13883, and Staphylococcus aureus ATCC 29213. The in vitro antifungal properties of synthesized compounds were also a target using Candida albicans NRRL Y-477 and Saccharomyces cerevisiae fungal strains. We have provided a useful guideline for future studies about the effect of the chemical structures of sulfonamide compounds on the biological activities. Among the target compounds, 7b, 7c, 7d, and 7e demonstrated surprisingly high antimicrobial activities than did others.
- ?zkan, Hamdi,Demirci, Bayram
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- Synthesis of aminotetrazolyl esters from cyanogen azide with amino esters
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Several α-amino esters (and their hydrochloride salts) were treated with cyanogen azide at ambient temperature in a mixture of water and acetonitrile to form chiral 5-aminotetrazole derivatives in good yields (47-69 %). The cyanogen azide was prepared from cyanogen bromide and sodium azide. Other functionalized α-amino esters (cysteine, arginine, histidine, and serine) were formed in only trace amounts and were difficult to purify by column chromatography. All 5-aminotetrazoles (i.e., 1-8) were characterized by IR spectroscopy, 1H, 13C, and 15N NMR spectroscopy, and elemental analysis. The structures of 3-7 were obtained by single-crystal X-ray structure analysis. 5-Aminotetrazolyl esters were prepared by a reaction between cyanogen azide and an amino ester to give 1-substituted aminotetrazoles in good yields. Compounds were fully characterized, and the structures of 3-7 were supported by single-crystal X-ray structure analysis. Heats of formation for all compounds were calculated by the Gaussian 03 program and differential scanning calorimetry. Copyright
- Joo, Young-Hyuk,Cho, Soo Gyeong,Goh, Eun Mee,Parrish, Damon A.,Shreeve, Jean'Ne M.
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p. 688 - 692
(2013/03/14)
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- Energetic salts based on nitroiminotetrazole-containing acetic acid
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2-(5-Nitroiminotetrazol-1-yl)acetic acid (4) was synthesized from 100% nitric acid and ethyl 2-(5-aminotetrazol-1-yl)acetate (2), which was easily obtained by reaction of ethyl aminoacetate hydrochloride, sodium hydroxide, and cyanogen azide. Compound 4 was also formed with 100% nitric acid and 2-(5-aminotetrazol-1-yl)acetic acid which was prepared from sodium 5-aminotetrazolate and 2-chloroacetic acid. New energetic materials comprised of nitroiminotetrazolate salts with nitroiminotetrazolate and carboxylate anions have been characterized spectroscopically as well as with single crystal X-ray diffraction and elemental analyses. In addition, the heats of formation (ΔHf), and detonation pressures (P) and velocities (D) were calculated. All compounds were insensitive (>40 J) for impact with BAM Fallhammer. The Royal Society of Chemistry 2012.
- Joo, Young-Hyuk,Gao, Haixiang,Parrish, Damon A.,Cho, Soo Gyeong,Goh, Eun Mee,Shreeve, Jean'Ne M.
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p. 6123 - 6130
(2012/06/29)
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