Synthesis and Pharmacological Activity of 1‐Hydroxy‐, 1‐Amino‐ and 1‐Hydrazino‐2,3‐dihydro‐1H‐pyrazolo[1,2‐a]pyridazine‐5,8‐diones and ‐2,3‐dihydro‐1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐diones.

Al-Assar, Fatema; Зеленин, K. Н.; Lesiovskaya, E. E.; Bezhan, I. P.; Chakchir, B. A.

doi:10.1002/chin.200316162

Cited by 12 publications

(10 citation statements)

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“…[75] were reported as anti-inflammatory, analgesic, antihypoxic and antipyretic agents [4]. Furthermore, treatment of the adduct 81 with MnO 2 and O 2 afforded phthalazine derivatives 83 and 84 (Scheme 19).…”

Section: Fromcis-diolmentioning

confidence: 99%

“…Lebsack et al [75] synthesized [1,2,4] triazolo [3,4-a]phthalazine derivative 118 as follows: (Scheme 33).…”

Section: [124] Triazolophthalazinesmentioning

confidence: 99%

“…Among a large variety of nitrogen-containing heterocyclic compounds, heterocyclic containing hydrazine has received considerable attention because of their pharmacological properties and clinical applications [1][2][3][4][5][6]. Phthalazine derivatives were reported to possess anticonvulsant [7][8][9][10], cardiotonic [11], antitumor [12][13][14][15][16], antihypertensive [17][18][19], antithrombotic [20], a ntidiabetic [21,22], antimicrobial [23,24], antitry-panosomal [25], anti-inflammatory [26][27][28][29][30][31][32], cytotoxic [14], vasorelexant [19] and vascular endothelial growth factor receptor 11(VEGFR-2) inhibitory [33].…”

Section: Introductionmentioning

confidence: 99%

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Recent Developments in Chemistry of Phthalazines

El-Azm¹,

Mahmoud²,

Hekal³

2014

Organic Chem Curr Res

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El-Azm et al., Organic Chem Curr Res 2015, 4:1 http://dx.Hydrazines with 2-acyl benzoic acids: Kirill et al. [31] reported the cyclization of 2-nitro-5-chloro phenylhydrazine27 with acyl benzoic acids 28 yielded 2-(2-nitro-5-chlorobenzene)-4-substituted phthalazin-1-ones 29 (Scheme 7).Lukacs and Simig [61] adopted a novel method for the synthesis of phthalazine derivatives 32 via the reaction of benzophenones30 with chromium (VI) oxide in a mixture of acetic anhydride and sulphuric acid followed by cyclization of the products with hydrazine hydrate in refluxing ethanol (Scheme 8).Hydrazine with 1,2-diester:The dimethylphthalate derivative 33 reacted with hydrazine to yield the desired phthalhydrazide34 which undergo chlorination with phosphorus oxychloride to give 35. Subsequent treatment with sodium methoxide afforded the methoxychloride 36 [62] (Scheme 9). Hydrazines with Phthalides: Chloroformylation of 3-methoxy benzoic acid 37 and subsequently radical bromination of 38 produced 39 in good yield. Treatment with triphenyl phosphine gave 40 and wittig olefination with 3,5-dichloro-4-pyridine carboxaldehyde 41 afforded the phthalide 42. Hydrazine cyclization of 42 resulted phthalazine derivative 43 [42] (Scheme 10). Cockcroft et al. [12] synthesized the phthalazinone derivative 47 according the following (Scheme 11). AbstractThis review highlights the methods used for the synthesis of phthalazine derivatives and fused phthalazinones. Their reactivity and synthetic importance were investigated. Phthalazine derivatives can be used as building blocks for heterocycles as well as fused heterocyclic compounds. Scheme 1: Synthesis of phthalazinone derivatives 2 and 5 Scheme 2: Synthesis of phthalazinone derivatives 7-9. Reagents and conditions: (a) CHCl 3 , reflux, 5 h, 51%; (b) hydrazinehydrate, EtOH, addition at rt and then reflux, 90˚C, 2 h, 71%; (c) MeI, KOBu t , DMF, 30 min, 80%; (d) LiOH, THF:MeOH:water (1:1:1), rt, 8-10 h, 81%. Scheme 3: Synthesis of phthalazin(2H)-1-one 11, 12 Scheme 4: Synthesis of 2-[1-(4-oxo-3,4-dihydrophthalazin-1-yl)alkyl]-1Hisoindole-1,3-(2H)-diones Scheme 5: Synthesis of 1,4-disubstituted phthalazinylpiperazine derivatives 21 Scheme 6: One-pot Synthesis of thiadiazinyl-phthalazine-1,4-diones 24 and 26 Scheme 7: Synthesis of 4-substituted phthalazin-1-ones 29. Scheme 8: Synthesis of phthalazine derivatives 32 Scheme 9: Hydrazinolysis of dimethylphthalate derivative 33 Citation: El-Azm FSMA, Mahmoud MR, Hekal MH (2015) Recent Developments in Chemistry of Phthalazines. Organic Chem Curr Res 1:132. Scheme 23: Synthesis of 1H-pyrazolo [1,2-b] phthalazin-5,10-dione derivatives 92 Scheme 24: A plausible mechanism for the synthesis of 1H-pyrazolo[1,2-b] phthalazine-5,10-diones 95 Scheme 25: Synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives 97. Scheme 28: Synthesis of 1-{[(1H-1,2,3-triazol-4-yl)methoxy]phenyl}-1Hpyrazolo[1,2-b] phthalazine-5,10-dione derivatives 104 Scheme 30: Synthesis of 2H-indazolo[1,2-b] phthalazine-triones 107 Scheme 29: Synthesis of 2H-indazolo[2,1-b]pht...

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Section: Fromcis-diolmentioning

confidence: 99%

“…Lebsack et al [75] synthesized [1,2,4] triazolo [3,4-a]phthalazine derivative 118 as follows: (Scheme 33).…”

Section: [124] Triazolophthalazinesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Recent Developments in Chemistry of Phthalazines

El-Azm¹,

Mahmoud²,

Hekal³

2014

Organic Chem Curr Res

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“…Nitrogen-containing heterocyclic compound, especially heterocycles containing bridgehead hydrazine, has attracted (immense or considerable) attention because of their pharmaceutical and biological properties. For example, 1H-pyrazolo[1,2-b]phthalazine-5,10-diones were reported as the anti-inflammatory, analgesic, anti-hypoxic, anti-pyretic agents [3].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of magnetically recoverable 1-(copperferritesiloxypropyl)-3-methylimidazolium heteropolytungstate ionic liquid as a new nanocatalyst for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones

Saadati-Moshtaghin

Zonoz

2017

J Nanostruct Chem

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A novel, efficient and magnetically recoverable nanomaterial consisting of heteropoly acid supported on ionic liquid-modified copper ferrite nanoparticle was prepared and performed as a heterogeneous catalyst in the fast and convenient synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-dione derivatives under mild and solvent-free conditions. The synthesized nanomaterial was characterized with FT-IR, XRD, FESEM, TEM, ICP and VSM. Furthermore, the obtained nanomaterial displayed striking reusability in the titled catalytic reaction. Compared with the various previously reported catalysts, the newly synthesized nanocatalyst is found to be most efficient with regard to operation simplicity, reaction time, yield and ease of catalyst separation.

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“…[1][2][3] The diverse biological activities of various functional derivatives of 4-substituted alkyl-1-(2H) phthalazinones are well known. Some of the phthalazinone derivatives have found application in clinical medicine due to their pronounced antihypertensive properties, 4) cardiotonic, 5,6) anticonvulsant, 7,8) antidiabetic, 9,10) antithrombotic, 11) antimicrobial, 12,13) vasorelexant, 14) antipyretic, analgesic, antitumor, [15][16][17][18] and cytotoxic, 19) while others have shown interesting vasodilator, 20) vascular endothelial growth factor receptor (VEGFR) II inhibitory activities, 21) and tuberculostatic activity allergic rhinitis.…”

mentioning

confidence: 99%

Design and Synthesis of New Phthalazinone Derivatives Containing Benzyl Moiety with Anticipated Antitumor Activity

Marzouk

Shaker

Hafiz

et al. 2016

Biological & Pharmaceutical Bulletin

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The acetohydrazide derivative reacted with carbon electrophiles such as acid chlorides, acetylacetone, ethyl acetoacetate and aromatic aldehydes to give some interesting heterocyclic compounds. The hydrazide derivative reacted with acetophenone which in turn underwent Vielsmeier-Haack reaction. Also, the phthalazinethione has been synthesized and its behavior towards hydrazine hydrate, oxidizing agent and ethyl chloroacetate has been investigated. The newly synthesized compounds were characterized by spectroscopic data. The antimicrobial, the cytotoxic, and the antioxidant activities of some of the synthesized products were evaluated. Some of the tested compounds showed very strong cytotoxic activity with respect to the standard.

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Synthesis and Pharmacological Activity of 1‐Hydroxy‐, 1‐Amino‐ and 1‐Hydrazino‐2,3‐dihydro‐1H‐pyrazolo[1,2‐a]pyridazine‐5,8‐diones and ‐2,3‐dihydro‐1H‐pyrazolo[1,2‐b]phthalazine‐5,10‐diones.

Cited by 12 publications

References 0 publications

Recent Developments in Chemistry of Phthalazines

Recent Developments in Chemistry of Phthalazines

Synthesis and characterization of magnetically recoverable 1-(copperferritesiloxypropyl)-3-methylimidazolium heteropolytungstate ionic liquid as a new nanocatalyst for the preparation of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones

Design and Synthesis of New Phthalazinone Derivatives Containing Benzyl Moiety with Anticipated Antitumor Activity

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