New tetrazolic azo dyes linked to (thio)barbiturate and electron-rich aromatics as potential antimicrobial agents

Abstract

A series of new tetrazolic azo dyes based on (thio)barbiturate and electron-rich aromatics were synthesized in excellent yield. The electron-donor and tetrazole ring moieties were linked by a p -phenylazo bridge and the structural characterizations were achieved by FT IR, 1 H and 13 C NMR, and UV-visible spectrometry. The antibacterial activity of the synthesized compounds was tested against gram-positive and gram-negative bacterial strains, namely Acinetobacter calcoaceticus (ATCC23055), Escherichia coli (ATCC2592), Pseudomonas aeruginosa (ATCC27853), and Staphylococcus aureus (ATCC25923). As a result, potential antimicrobial effects were seen for some of the synthesized compounds.

A comprehensive spectroscopic, solvatochromic and photochemical analysis of 5-hydroxyquinoline and 8-hydroxyquinoline mono-azo dyes

“…General tautomerization for azo dyes 4a-i ( A ), and 5a-i ( B ). shift in the 1 H NMR spectra of these compounds deshields up to δ 14 ppm which confirms the coupling from the OH vicinal position [63] . In the present work, the absence of the highly deshielded proton (around 14 ppm) confirms that no intramolecular H-bonds are present, which was expected if the reaction had occurred in the OH vicinal position (7-position for 8HQ dyes and 6-position for 5HQ dyes) ( Scheme 1 ).…”

“…Some organic azo dyes derived from β-naphthol and its derivatives show an intramolecular H-bond between OH group and azo nitrogen ( Fig. 2 ) [63] . The corresponding proton chemical Scheme 1.…”

One‐pot, fast cyclopropanation reaction of indandione with various aldehydes in the presence of cyanogen bromide and trimethylamine

“…The structures of salts 4a'-4b' are shown in Figure 1. According to our previous reported mechanisms for the formation of the salts 10 [3] and 11, [19][20][21][22][23][24][25] a representative proposed reaction mechanism for the formation of salt 4a' is shown in Scheme 3. The salt of 7a' was formed in the presence of Et 3 N and in the absence of BrCN (path b).…”

“…The teflon-faced screw cap tube prevents the evaporation of cyanogen bromide. A cream color F I G U R E 1 Formula structure of salts 4a 0 , 4b 0 (this work), 10, [3] and 11 [14,[19][20][21][22][23][24][25] S C H E M E 2 Proposed reaction mechanism for the formation of full-substituted cyclopropanes S C H E M E 3 Proposed mechanism for the formation of 4a 0 3.1.5 | Synthesis of 3 0 -(4-nitrophenyl)-dispiro [indan-2,1 0 -cyclopropane-2 0 ,2 00 -indan]-1,1 00 ,3,3 00tetrone (3d) 3.1.11 | Synthesis of 3 0 -(4-methoxyphenyl)dispiro[indan-2,1 0 -cyclopropane-2 0 ,2 00 -indan]-1,1 00 ,3,3 00 -tetrone (3j)…”

4‐Methyl morpholinium bis‐(thio)barbiturates: Synthesis, structure, anticancer evaluation, and CoMFA study

“…[ 26 ] There are a lot of researches on a variety of organic compounds including eight‐membered intramolecular H ‐bond. [ 27–35 ] This type of interaction in bis‐(thio)barbiturates based on triethylamine has been recently investigated in our lab. [ 36 ]…”