Supplementary Material to Design, synthesis and antibacterial activity of new phthalazinedione derivatives

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Design, synthesis and antibacterial activity of new phthalazinedione derivatives

Dibenzobarallene (1) was utilized as the key intermediate for the synthesis of some new 2-substituted 1,4-dioxo-3,4,4a,5,10,10a-hexahydro-1H-5,10-[1’,2’]-benzenobenzo[g]phthalazine: 2, 5a–d, 8a–c and 10. Condensation of 2 with benzaldehyde or anisaldehyde gave the corresponding acrylonitrile derivatives 3a and b, respectively. Thiophene derivatives 4a and b were obtained via the Gewald reaction of 2 with cyclohexanone or cyclopentanone, respectively. Treatment of 5d with acetyl chloride or p-toluenesulfonyl chloride afforded the corresponding esters 6 and 7, respectively. Cyclization of 8a–c with formalin afforded the corresponding triazine derivatives 9a–c. Ring opening of 10 with sodium hydroxide gave the corresponding triazole derivative 11, which when alkylated with pentyl bromide afforded the pentylthio derivative 12. Representative compounds of the synthesized products were established and evaluated as antibacterial agents

Synthesis and antibacterial activity of some new 3-hydroxy-2-naphthoic acid hydrazide derivatives for dyeing polyester fabrics

Dibenzobarallene was used as a key intermediate for the synthesis of 2-(3-hydroxy-2-naphthoyl)-3,4,4a,5,10,10a-hexahydro-1H-5,10-benzenobenzo[g]phthalazine-1,4-dione (2). The previous compound was coupled with the appropriate diazonium chloride to give the corresponding 4-arylazo-2-naphthol derivatives 3a–l. Also, nitration, nitrosation and bromination of compound 2 afforded the corresponding nitro, nitroso and bromo derivatives 4–6, respectively. The synthesized compounds were established and evaluated as antibacterial agents. The results showed clearly that compounds 2, 3a, 3c, 3d, 3g, 3i, 4, 5 and 6 exhibited interesting high activities compared with reference drugs. Also, these compounds were applied to polyester as disperse dyes in which their color measurement and fastness properties were evaluated

Synthesis and antitumor evaluation of thiophene based azo dyes incorporating pyrazolone moiety

A series of thiophene incorporating pyrazolone moieties 5a–f and 6a–c were synthesized via diazo coupling of diazonium salt of 3-substituted-2-amino-4,5,6,7-tetrahydrobenzo[b]thiophenes 1a–c with 3-methyl-1H-pyrazol-5(4H)-one, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one or 3-amino-1H-pyrazol-5(4H)-one, respectively. Newly synthesized dyes were applied to polyester fabric as disperse dyes in which their color measurements and fastness properties were evaluated. These dyes showed generally red to blue shifted color with high extinction coefficient in comparison with aniline-based azo dyes. The antitumor activity of the synthesized dyes was evaluated. The results showed clearly that most of them exhibited good activity and compounds 5c and 5d exhibited moderate activity