Synthesis and Anticancer Activities of Novel 1,4-Disubstituted Phthalazines

Abstract

A series of novel 1-anilino-4-(arylsulfanylmethyl)phthalazines were designed and synthesized. The structures of all the compounds were confirmed by IR, 1 H-NMR, elemental analysis and MS. The analogues 1-(3-chloro-4-fluoroanilino)-4-(3,4-difluorophenylthio-methyl)phthalazine (12) and 1-(4-fluoro-3-trifluoromethylanilino)-4-(3,4-difluorophenyl-thiomethyl)phthalazine (13) showed higher activity than a cisplatin control when tested in vitro against two different cancer cell lines using the microculture tetrazolium method (MTT) method.

Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives: assessment of their antimicrobial, antituberculosis and antioxidant activity

“…Among a large variety of N-containing heterocyclic compounds, those containing an hydrazine moiety as a ''fusion site'' have received considerable attention because of their pharmacological properties and clinical applications [12]. Moreover, fused phthalazines were found to possess multiple biological activities, such as antimicrobial [13], anticonvulsant [14], antifungal [15], anticancer [16] and anti-inflammatory activities [17]. Nevertheless, the development of new synthetic methods for the efficient preparation of heterocycles containing a phthalazine ring fragment is an interesting challenge.…”

An Efficient Three Component Synthesis of 1H-Indazolo[2, 1-b]phthalazine-triones Catalyzed by Orthophosphoric Acid in Water-Phenol System

“…Amongst, nitrogen heterocyclic containing a phthalazine moiety was reported to possess anticonvulsant 10 , cardiotonic 11 , vasorelaxant 12 antimicrobial 13 , anti-inflammatory 14 , antifungal 15 and anticancer 16,17 activities. Newly, three-RESEARCH ARTICLE component reactions of dimedone (5,5- 23 , N-halo sulphonamides 24 , silica supported poly phosphoric acid 25 , 26 Mg(HSO 4 ) 2 , phosphor sulfonic acids 27 , nano silica sulphuric acid 28 , sulfonated polyethylene glycol 29 and boron sulfonic acid 30 .…”

Sulfonic Acid Functionalized Nanoporous Silica (Sba-Pr-So3h) as an Efficient Catalyst for the One-Pot Synthesis of 2h-Indazolo[1,2-B]phthalazine-Triones

“…12 Among a large variety of N-containing heterocyclic compounds, heterocycles containing hydrazine moiety as 'fusion site' have received considerable attention due to their pharmacological properties and clinical applications. 13 Moreover, fused phthalazine derivatives were found to possess multiple biological activities such as anticonvulsant, 14 cardiotonic, 15 vasorelaxant, 16 antifungal, 17 and anticancer 18 activities. Many methods are available for the synthesis of phthalazine derivatives, [19][20][21][22] however, some of these methods suffered from several drawbacks such as hazardous organic solvents, high cost, long reaction times, excess amounts of acids, and harsh reaction conditions with non-recyclable catalysts.…”