Synthesis of novel phthalazine derivatives as pharmacological activities

Abstract

Phthalazine derivatives attached to amino acid derivatives were synthesized with high yields. The reaction of phthalazine derivatives with different phthalyl and tosylamino acids such as glycine, alanine, phenylalanine, valine, serine, and threonine in the presence of N,N-dicyclo hexylcarbodiimide (DCC) as a dehydrating agent reagent yielded high yields of the afforded compounds.Phthalylamino acids derivatives were obtained by deprotection of phthalazine derivatives, with the latter heating with hydrazine hydrate. The chemical structures of all phthalazine derivatives were affirmed by elemental analysis and spectral data (IR, MS, 1 HNMR, and 13 C NMR). Screening out and estimation of the synthesized derivatives for their cytotoxic and antioxidant activity were done, and most of them showed powerful activity in comparison with standard drugs.We got all chemical reagents from Sigma-Aldrich. Solvents were purchased from El-Nasr Chemicals in analytical grade. Also, we did thin-layer chromatography (TLC) on all products by using silica gel polyester sheets (Kieselgel 60 F254, 0.20 mm, Merck). All melting points are in degree centigrade (uncorrected). We recorded IR spectra (KBr) at the Microanalytical Center (Faculty of S C H E M E 1 Synthesis of phthalazinone derivative 2 S C H E M E 2 Synthesis of phthalazines derivative (4,5) WASFY ET AL.

Synthesis, Reactions, and Antimicrobial Evaluation of 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide derivatives

“…Phthalic anhydride reacted with alkyl glycinate (methyl or ethyl) to afford alkyl 2-(1,3dioxoisoindolin-2-yl)acetate (methyl or ethyl) in a good yield which reacted with hydrazine hydrate to afford 2-(1,3-dioxoisoindolin-2-yl)acetohydrazide ( 1) in an excellent yield (Scheme 1). Data analyses are in accordance with previously reported results [29][30][31][32].…”

Microwave‐Assisted Synthesis of Phthalazinone Derivatives with Biological Activity and In Silico Antiproliferative Studies

“…Phthalazinone derivatives exhibit several biological activities such as cytotoxic, antioxidant activities, [3][4][5][6][7][8] and acetylcholinesterase inhibitor. [9] Therefore, some phthalazinone derivatives have shown interesting pharmacological properties such as antimicrobial, [10][11][12][13][14][15][16][17] anti-inflammatory activities, analgesic, [4,12,18] anticonvulsant agents, and antithrombotic antiplatelet agents, [12,19] antihistaminic, [20] virus inhibitors, [5,12,21] antidepressant, androgen receptor, [22] VEGFR-2 inhibitors, [23] antileishmanial activity, [24] cardiotonic antitumor activity, [19,25] and metabolic enzymes inhibition. [26] Furthermore, using microwave (MW) in the synthesis of heterocyclic compounds has been prevalent for almost 20 years, mainly because of the convenience of temperature control, as it is far faster and better in results than conventional techniques.…”

Facile and Efficient Nitration of 4‐Aryl‐1(2H)‐Phthalazinone Derivatives Using Different Catalysts

“…[47] To the best of our knowledge, there have been no reports on nitration of 4-Aryl-1(2H)-phthalazinone derivatives. 4-Substituted phenyl-1(2H)-phthalazinones attracted our attention due to its fame in constructions of various compounds with highly interesting clinical applications and pharmacological properties, such as antibacterial, antifungal, anti-inflammatory anticonvulsant, [48] antitumor [49] and treatment of Hepatitis B virus. [50] Therefore, more convenient and efficient strategies nitrating 4-substitutedphenyl-1(2H)-phthalazininones are still in demand.…”