The effects of a new phthalazine derivative mdl 899 on human lymphocyte functions. The invention relates to the use of phthalazine derivatives as inhibitors of the enzyme polyadpribosepolymerase or parp ec 2. Phthalazine derivative an overview sciencedirect topics. Utilization of nontoxic and inexpensive catalyst, improved yields in short reaction times, wide substrate scope and easy purification of products are. Imidazolecontaining phthalazine derivatives inhibit fesod. Interaction of 9 with ambident anions was also studied. Phthalazine derivatives containing imidazole rings behave as. The synthesis of 1hpyrazolo1,2bphthalazine5,10dione derivatives via the threecomponent coupling of aldehydes, malononitrile or ethyl cyanoacetate, and phthalhydrazide has been. Pdf pharmacological activities of various phthalazine. Recent advances in the synthesis of biologically active. As a part of a medicinal chemistry approach to hiv1 protease inhibitors, the resulting products 30 were further alkylated with benzyl bromide in 90% yields. A highly flexible green synthesis of 1hpyrazolo1,2bphthalazine5,10dione derivatives with cui nanoparticles as catalyst under solventfree conditions. Although quinoxaline itself is mainly of academic interest, quinoxaline. This improved greener synthetic methodology provides a simple and straightforward onepot approach to the synthesis of a variety of heterocycles.
The synthesis of 1 h indazolo1,2 b phthalazine1,6,11 h trione derivatives, using onepot threecomponent condensation reaction of 3nitrophthalic anhydride, hydrazine monohydrate, dimedone, and aromatic aldehydes in the presence of zrono 3 2. Phthalazine1,4diones, chalcones, pyrazolines, cytotoxic activity, vegf2. Short reaction time, simple operation, and high yields are the advantages of. Nanostructured cuo was successfully utilized for the synthesis of 1hpyrazolo1,2b phthalazine 5,10dione derivatives via onepot multicomponent reaction among phthalhydrazide, malononitrile and aromatic aldehydes under solvent free conditions. In vitro, most of the synthesized derivatives were screened for their. Solvent free synthesis of phthalazine 21hcarboxamide derivatives using k10 clay under microwave irradiation authors. Pyridazine and phthalazine derivatives with potential antimicrobial activity.
In this research, certain phthalazine scaffolds were designed and synthesized. Efficient synthesis of selected phthalazine derivatives. Compounds 2 and 4 highly inhibited the antioxidant parasite enzyme fesod, and molecular modeling. Synthesis of novel series of phthalazine derivatives as. Synthesis and reactions of phthalazine derivatives. Newer agents are more selective inhibitors of the cgmpinhibited phosphor diesterase pde and casn be exemplified by phthalazine derivatives like my5445 b, figure 1 25. Young taek han, college of pharmacy, dankook university, cheonan, 31116, korea jongwha jung, college of pharmacy, research institute of pharmaceutical sciences, kyungpook national university, daegu 41566, korea namjung kim. Treatment of 5d with acetic anhydride and ptoluenesulfonyl. It is a mancude organic heterobicyclic parent, a member of phthalazines, an azaarene and an orthofused heteroarene. Utilization of nontoxic and inexpensive catalyst, improved yields in short reaction times, wide substrate scope and easy. Synthesis of novel series of phthalazine derivatives as potential antitumor. Facile and solvent free synthesis of 2hindazolo2,1b phthalazine 1,6,11trione derivatives ali alinasab amiri, shahrzad javanshir,a zahra dolatkhah and mohammad g. Cuo nanoparticles as a reusable catalyst for the synthesis.
Phthalazine derivatives as phosphodiesterase 4 inhibitors. Phthalazine derivatives are obtained in high yields and from a broad scope readily accessible orthoalkynylsulfonohydrazone precursors. Synthesis of novel phthalazine derivatives as pharmacological. Representative examples of anticonvulsant phthalazine compounds are shown in figure 1. In vitro leishmanicidal activity of imidazole or pyrazole. The chemical structure of this compound is shown in figure 2312. Reusable silica supported poly phosphoric acid catalyzed. Design, synthesis and antibacterial activity of new. Preparation of 4benzyl2substituted phthalazin1one derivatives 28 is reported. Aqueous nheterocyclization of primary amines and hydrazines.
To evaluate the in vitro leishmanicidal activity of imidazolebased 14 and pyrazolebased 56 benzogphthalazine derivatives against leishmania infantum and leishmania braziliensis. Phthalazine derivatives and salts thereof free patents online. Design and facile synthesis of 6 benzo thiophen3yl3. Pdf a highly flexible green synthesis of 1hpyrazolo1,2b. Young taek han, jongwha jung and namjung kim affiliation. Pdf the effects of a new phthalazine derivative mdl 899.
Jan 21, 2020 this method is found to accelerate significantly reaction rate and improved yields of isoxazolidine, isoxazoline derivatives. Dec 24, 2002 phthalazine derivatives phosphodiesterase 4 inhibitors. Pdf in this research, certain phthalazine scaffolds were designed and synthesized. All compounds tested showed selectivity indexes higher than that of the reference drug glucantime for the three leishmania. The synthesis of nitrogencontaining heterocycles from alkyl dihalides ditosylates and primary amines and hydrazines via a simple and efficient cyclocondensation in an alkaline aqueous medium that occurs under microwave irradiation is described. A series of new phthalazine derivatives 14 containing imidazole rings were prepared.
Pharmacological action and sar of phthalazine derivatives. A novel series of phthalazine derivatives bearing isoindol1,3dione moiety were synthesized by treating 244chlorophthalazine1ylphenyl1hisoindole1,32hdione 3 with various chemical reagents. In addition to the base, a peak at z 178 corresponding to anthracene was also m observed. Recent advances in the synthesis of biologically active cinnoline, phthalazine and quinoxaline derivatives volume. Method for treating a patient having precancerous lesion with 4phenylphthalazine derivatives. Onepot synthesis of 1hpyrazolo1,2bphthalazine5,10dione. Pthalazine derivatives have been exhibited pharmacological activities like antitumor, parp1 inhibitors, antimicrobial, antivirus. Several phthalazine derivatives were synthesized by the onepot threecomponent condensation in good to high yields in the presence of diatomiteso3h as a solid acid catalyst. It is isomeric with other naphthyridines including quinoxaline, cinnoline and quinazoline. Synthesis and antimicrobial evaluation of some annelated.
Unsaturated 1,1dioxo derivatives 30 were accessed in c. Antioxidants are molecules, natural, or synthetic, capable to interact with free. Zopolrestat c, figure 1 is a phthalazinone derivative that has been in clinical. Synthesis, modeling and anticonvulsant activity of some. Efficient synthesis of selected phthalazine derivatives article pdf available in heterocyclic communications 183. Phthalazine derivatives phosphodiesterase 4 inhibitors. Hydralazine is one of a series of phthalazine derivatives that have been shown to reduce blood pressure and is the only agent of this series available in the united states. Lithiumbromide exchange was carried out by adding 1. Onepot synthesis of 1hpyrazolo1,2bphthalazine5,10dione derivatives under solventfree conditions supporting information ramin ghorbanivaghei, samira noori, zahra toghraeisemiromi, zahra salimi department of organic chemistry, faculty of chemistry, buali sina university 65174, hamedan, iran. Phthalazine derivatives are biological potential compounds having diverse biological activities. We report the synthesis of various phthalazines via a new cascade reaction, initiated by visible light photocatalysis, involving a radical hydroamination reaction followed by a radical smiles rearrangement. Phthalazine, also called benzoorthodiazine or benzopyridazine, is a heterocyclic organic compound with the molecular formula c 8 h 6 n 2. Solventfree synthesis of 2hindazolo2,1b phthalazine. Pdf new phthalazine and pyradazino4,5gphthalazine derivatives.
Nanoorganocatalyzed onepot fourcomponent reactions for the synthesis of phthalazinetrionedione derivatives have been devised for the first time from easily accessible starting materials under solventfree conditions. Various pthalazine derivatives have been synthesized and tested for their diverse biological activities. Several series of 1,2dihydrophthalazine derivatives were prepared andproved to possess anticonvulsant activity via antagonism of ampa competitive manner. A robust, facile, and solventfree route for the threecomponent synthesis of 2 h indazolo2,1 b phthalazinetriones in the presence of a catalytic amount of p toluene sulfonic acid utilizing grinding has been developed. A highly flexible green synthesis of 1hpyrazolo1,2b phthalazine 5,10dione derivatives with cui nanoparticles as catalyst under solvent free conditions. An efficient onepot fourcomponent synthesis of 1 h. It is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. This methodology showed very good substrate scope and.
Cufe2o4 and zrp o catalysts for the onepot synthesis of. In the presence of et 3 n, a series of phthalazine derivatives were conveniently prepared in high yield by the reaction of ortho. Sno2 nanoparticles as an efficient heterogeneous catalyst. Aug 01, 2016 therefore, we describe here the behavior of novel phenylsulfonohydrazone moieties in an unprecedented photoinduced reaction cascade. Benzazine derivatives phosphodiesterase 4 inhibitors. New pyrrolo2,1a phthalazine derivatives by onepot threecomponent synthesis. Recent advances in the synthesis of biologically active cinnoline, phthalazine and quinoxaline derivatives authors. The phthalazine derivative azelastine a, figure 1 is an antihistamine used in the treatment of allergic rhinitis. This phthalazine derivative is effective in the management of essential or. Pdf new pyrrolo2,1aphthalazine derivatives by onepot. Abstract phthalazine derivatives attached to amino acid derivatives were synthesized with high yields. Design, synthesis and in vitro antitumor activity of novel.
Condensation of 4benzyl1chlorophthalazine 9 with a series of different nucleophiles gave 4benzylphthalazin1ylamino derivatives 10 and 16 and 4amino2n4benzylphthalazin1ylhydrazino6arylpyrimidine5carbonitriles 14a,b. The monoalkylamino substituted derivatives 2 and 4 were more active in vitro against t. College of pharmacy, dankook university, cheonan, 31116, college of pharmacy, research institute of pharmaceutical sciences, kyungpook national university, daegu 41566, college of. This methodology showed very good substrate scope and high degree of tolerance for a variety o. Then, a series n14 of phthalazine sulfonamides were synthesized by the reaction phthalazine sulfonyl chloride and various amines under solventfree conditions. Pharmacological activities of various phthalazine and phthalazinone derivatives. Synthesis of some more heterocyclic compounds containing 4. Onepot synthesis of 1hpyrazolo1,2b phthalazine 5,10dione derivatives under solvent free conditions supporting information ramin ghorbanivaghei, samira noori, zahra toghraeisemiromi, zahra salimi department of organic chemistry, faculty of chemistry, buali sina university 65174, hamedan, iran. Cuo nanoparticles as a reusable catalyst for the synthesis of. Pdf a highly flexible green synthesis of 1hpyrazolo1,2. A comparative study with the corresponding solvent.
Our approach to phthalazine derivatives is outlined in scheme 1. Pdf some new phthalazine and pyridazino4, 5gphthalazine derivatives have been prepared through. Pdf design, synthesis and antioxidant evaluation of. The present invention relates to the use of phthalazine derivatives as inhibitors of the enzyme polyadpribose polymerase or parp ec 2.
Pdf design, synthesis and antioxidant evaluation of certain new. Journal of chemistry hindawi publishing corporation. These phthalazine derivatives also exhibit, in particular, a. The synthesis of 1hpyrazolo1,2b phthalazine 5,10dione derivatives via the threecomponent coupling of aldehydes, malononitrile or ethyl cyanoacetate, and phthalhydrazide has been reported using mcrs in the presence of. The in vitro leishmanicidal activity of a series of imidazolecontaining phthalazine derivatives 1 4 was tested on leishmania infantum, leishmania braziliensis and leishmania donovani parasites, and their cytotoxicity on j7742 macrophage cells was also measured. The starting bromoacetal derivatives 2ad were either known or readily prepared using standard methodology remy et al. Solventfree synthesis of phthalazine21hcarboxamide. Using the create set and random method option in qsar project of sybylx 2. In view of the aforementioned facts, it seemed most interesting to study the chemical behavior of 1chloro42,4,6. Nanoferrite supported glutathione as a reusable nano. Antiradical activity of novel phenolic products du.
The tested derivatives improved significantly serum levels of glucose, lipid profile and free fatty acids. Pdf pharmacological activities of various phthalazine and. The starting bromoacetal derivatives 2ad were either known or readily. Pdf efficient synthesis of selected phthalazine derivatives. Nanoorganocatalyzed onepot fourcomponent reactions for the synthesis of phthalazine trionedione derivatives have been devised for the first time from easily accessible starting materials under solvent free conditions. New phthalazine and pyradazino4,5gphthalazine derivatives article pdf available in heterocycles 207 january 1983 with 105 reads how we measure reads. Department of chemistry, payame noor university, po box 193953697 tehran, iran. A quinoxaline, also called a benzopyrazine, in organic chemistry, is a heterocyclic compound containing a ring complex made up of a benzene ring and a pyrazine ring. Synthesis, characterization and in vitro antibacterial. Dekamin heterocyclic chemistry research laboratory,department of chemistry. Imidazolecontaining phthalazine derivatives inhibit fe.
Chemical and process engineering research issn 22247467 paper issn 222509 online vol. This method is found to accelerate significantly reaction rate and improved yields of isoxazolidine, isoxazoline derivatives. The newly synthesized compounds were characterized on the basis of their spectral 1 h nmr, c nmr, ms, ir analyses. The most important advantages of this procedure are its. Phthalazine derivatives containing imidazole rings behave. Hyperidzation with pharmacophoric moieties possessing antioxidant activity including glycine hydrazides and derivatives 10, 11 and 12, amide derivatives 19, hydrazone. A series of 44bromophenyl phthalazine and phthalazinone analogs connected through 2propanol spacer to nsubstituted piperazine residue were tested for their effect on. Then, a series n14 of phthalazine sulfonamides were synthesized by the reaction phthalazine sulfonyl chloride and various amines under solvent free conditions. Then, the prepared nanomaterial was used as a simple, costeffective, and reusable heterogeneous catalyst for the synthesis of 2hindazolo2,1b phthalazine 1,6,11htrione derivatives by a one. Synthesis and biological screening of 4benzyl2hphthalazine. A set of 28 phthalazine derivatives reported as epidermal growth factor receptor were taken from literature for this study amin et al. We have studied the catalytic ability of copperii acetate monohydrate as a mild, environmentally benign, natural and economical catalyst for the multicomponent efficient synthesis of biologically active spiro4hpyran derivatives and 1hpyrazolo1,2bphthalazine5,10dione derivatives with excellent yields and short reaction times. Some commercially used phthalazine derivatives and structure of pthalazine figure2 structure of 1, 2, 4 tri azole 1,2,4triazoles are very interesting targets for medicinal and pharmaceutical applications.
Recent developments in chemistry of phthalazines longdom. A new efficient domino approach for the synthesis of. Methods the in vitro activity of compounds 1 6 was assayed on extracellular promastigote and axenic amastigote forms, and on intracellular amastigote. Phthalazine is an azaarene that is the 2,3diaza analogue of naphthalene. Nanostructured cuo was successfully utilized for the synthesis of 1hpyrazolo1,2bphthalazine5,10dione derivatives via onepot multicomponent reaction among phthalhydrazide, malononitrile and aromatic aldehydes under solventfree conditions. It is a colorless oil that melts just above room temperature. Supplementary information 1 so3hfunctionalized mesoporous silica materials as solid acid catalyst for facile and solventfree synthesis of 2hindazolo2,1bphthalazine1,6,11 trione derivatives ali alinasab amiri, shahrzad javanshir,a zahra dolatkhah and mohammad g.
Solventfree synthesis of phthalazine21hcarboxamide derivatives using k10 clay under microwave irradiation volume. A new pathway for phthalazine derivatives via metal. Qsar and molecular docking of phthalazine derivatives as. Page 59 reusable silica supported poly phosphoric acid catalyzed three component synthesis of 2hindazolo2,1bphthalazinetrione derivatives hamid reza shaterian, asghar hosseinian, and majid ghashang department of chemistry, faculty of sciences, university of sistan and baluchestan po box 985674, zahedan, iran email. New phthalazine and pyradazino4,5g phthalazine derivatives article pdf available in heterocycles 207 january 1983 with 105 reads how we measure reads.
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