Synthesis, biological, anti-inflammatory activities and quantum chemical calculation of some [4-(2, 4, 6-trimethylphenyl)-1(2H)-oxophthalazin-2yl] acetic acid hydrazide derivatives

Synthesis, biological, anti-inflammatory activities and quantum chemical calculation of some [4-(2, 4, 6-trimethylphenyl)-1(2H)-oxophthalazin-2yl] acetic acid hydrazide derivatives

WoS Article

The phthalazine carbohydrazide 2 was prepared and incorporated into the corresponding 1,2,4-triazole and carbamate derivatives. Phthalazine carboxylic acid hydrazide 2 was treated with isatine and cyclohexanone to give the corresponding hydrazone derivatives 16, 19 in good yields. Furthermore, a-amino acid derivative conjugated with 1-oxophthalazine moiety 35 was synthesized by the reaction of the corresponding aizde 28, via the azide-coupling method, with glycine methyl ester. The peptide ester 35 was converted into their orresponding amide 36 by treating with methanolic ammonia. Moreover, 35 was boiled with hydrazine hydrate to afford the corresponding hydrazide 37. Finally, the dipeptide 38 was prepared by coupling of 35 with L-alanine methyl ester. Some of these compounds were screened in vitro for their antimicrobial activity. The energy gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital has been calculated using the theoretical computations to reflect the chemical reactivity and kinetic stability of compounds.

The phthalazine carbohydrazide 2 was prepared and incorporated into the corresponding 1,2,4-triazole and carbamate derivatives. Phthalazine carboxylic acid hydrazide 2 was treated with isatine and cyclohexanone to give the corresponding hydrazone derivatives 16, 19 in good yields. Furthermore, a-amino acid derivative conjugated with 1-oxophthalazine moiety 35 was synthesized by the reaction of the corresponding aizde 28, via the azide-coupling method, with glycine methyl ester. The peptide ester 35 was converted into their orresponding amide 36 by treating with methanolic ammonia. Moreover, 35 was boiled with hydrazine hydrate to afford the corresponding hydrazide 37. Finally, the dipeptide 38 was prepared by coupling of 35 with L-alanine methyl ester. Some of these compounds were screened in vitro for their antimicrobial activity. The energy gap between the highest occupied molecular orbital and lowest unoccupied molecular orbital has been calculated using the theoretical computations to reflect the chemical reactivity and kinetic stability of compounds.

Synthesis, Phthalazine, Quantum calculation, Carbohydrazide, Biological, Anti-inflammatory activities

Synthesis, Phthalazine, Quantum calculation, Carbohydrazide, Biological, Anti-inflammatory activities

EL-SHAMY, I.; ABDEL-LATTIF, A.; AL MAHMOUD ALSHEIKH, A.; FOUDA, M.; ELDEYAB, S.; EL-HASHASH, M.; JANČÁŘ, J.

2016

15.02.2015

0143-7208

Dyes and Pigments

113

357

United Kingdom of Great Britain and Northern Ireland

357

371

15