The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I

Napoletano, Mauro; Norcini, Gabriele; Pellacini, Franco; Marchini, Francesco; Morazzoni, Gabriele; Ferlenga, Pierpaolo; Pradella, Lorenzo

doi:10.1016/s0960-894x(00)00449-2

Cited by 46 publications

(18 citation statements)

References 15 publications

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“…). These derivatives have been reported to possess antihypertensive , anticonvulsant , antidiabetic , antimicrobial , antitrypanosomal , anti‐inflammatory , and PDE4 inhibitory activities .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti‐Inflammatory and Anti‐Proliferative Agents

Hameed

Ovais

Yaseen

et al. 2016

Archiv der Pharmazie

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The chemistry of phthalazine derivatives has been of increasing interest since many of these compounds have found many chemotherapeutic applications. So this study aims to synthesize a library of phthalazine derivatives and to investigate their anti-inflammatory and anti-proliferative activities. Sixteen new phthalazinone derivatives (2a-p) were synthesized and tested for their in vitro antiproliferative and in vivo anti-inflammatory activities. All the synthesized compounds were identified and characterized by IR, (1) H NMR, (13) C NMR spectroscopy, and MS. Two compounds, 2b and 2i, showed significant anti-inflammatory activity comparable with that of the standard drug etoricoxib in the carrageenan-induced rat paw edema model at 3 and 5 h, respectively. Three compounds (2h, 2j, and 2g) showed moderate sensitivity toward the renal cancer cell line UO-31.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti‐Inflammatory and Anti‐Proliferative Agents

Hameed

Ovais

Yaseen

et al. 2016

Archiv der Pharmazie

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“…Some of phthalazinone derivatives were used in clinical medicine due to their antipyretic, analgesic, and tuberculostatic action , while others have broad spectra on the cardiovascular system including vasodilator action , antihypertensive effect , and inhibition of blood platelet aggregation . Phthalazinone phosphodiesterase 4 inhibitors are effective therapeutic agents for asthma, chronic obstructive monary, and atopic dermatitis . Phthalazinone derivatives have exhibited a broad spectrum of biological activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antiviral, and Antimicrobial Activity of N‐ and S‐Alkylated Phthalazine Derivatives

Moustafa

El‐Sayed

Haikal

et al. 2015

Journal of Heterocyclic Chem

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A series of N‐alkylphthalazinone were synthesized by the reaction of phthalazin‐1(2H)‐one derivatives 1a, 1b, 1c with alkylating agents namely, propargyl, allyl bromide, epichlorohydrin, 1,3‐dichloro‐2‐propanol, 4‐bromobutylacetate, and 1‐(bromomethoxy)ethyl acetate to give the corresponding N‐alkylphthalazinone 2a, 2b, 2c, 3a, 3b, 3c, 5a, 5b, 5c, 6a, 6b, 6c, 7a, 7b, 7c, and 9a, 9b, 9c. Alkylation of phthalazin‐1(2H)‐thione to give a series from S‐alkylphthalazine 12, 13, 14 and thioglycosides 15 and 17 was performed. Deprotection of compounds 7a, 7b, 7c, 9a, 9b, 9c, 15, and 17 resulted in the formation of the corresponding products 8a, 8b, 8c, 10a, 10b, 10c, 16, and 18. The structure of newly synthesized compounds was assigned by IR, 1H, 13C NMR, and elemental analysis. Some of these compounds were screened for antiviral and antimicrobial activity.

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“…[1][2][3] Phthalazine derivatives were reported to possess anticonvulsant, 4-6 cardiotonic, 7 antitumor, [8][9][10][11] antihypertensive, [12][13][14] antithrombotic, 15 antidiabetic, 16,17 antimicrobial, 18,19 anti-inflammatory, [20][21][22][23][24][25] cytotoxic, 26 vasorelexant 27 and vascular endothelial growth factor receptor II (VEGFR-2) inhibitory activities. 28 Therefore, a number of methods have been reported for the synthesis of phthalazine derivatives.…”

Section: Introductionmentioning

confidence: 99%

Novel Synthesis of Some Phthalazinone Derivatives

et al. 2011

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Dimethyl homophthalate condensed with isatin to give the unexpected five membered lactone 3 rather than the half ester 1 and the δ-lactone 2. Treatment of compound 3 with excess hydrazine hydrate afforded phthalazinone carbohydrazide 4 which represents a novel method for the synthesis of phthalazinone derivatives. The carbohydrazide 4 upon treatment with carbon disulphide afforded 1,3,4-oxadiazole derivative 5, which reacted with ethylchloroacetate to give the S-alkylated product 6. The structure of compound 3 compared with 2 was discussed using hyperchem professional (7) AM 1 calculations, X-ray single crystal structure and complete spectral data.

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The synthesis and biological evaluation of a novel series of phthalazine PDE4 inhibitors I

Cited by 46 publications

References 15 publications

Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti‐Inflammatory and Anti‐Proliferative Agents

Synthesis and Biological Evaluation of New Phthalazinone Derivatives as Anti‐Inflammatory and Anti‐Proliferative Agents

Synthesis, Antiviral, and Antimicrobial Activity of N‐ and S‐Alkylated Phthalazine Derivatives

Novel Synthesis of Some Phthalazinone Derivatives

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