Synthesis, Bioevaluation and Structural Study of Substituted Phthalazin-1(2H)-ones Acting as Antifungal Agents

Derita, Marcos Gabriel; Olmo, Esther del; Barboza, Bianca; García-Cadenas, Ana Esther; López-Pérez, Jose Luis; Andújar, Sebastián Antonio; Enriz, Ricardo D.; Zacchino, Susana; Feliciano, Arturo San

doi:10.3390/molecules18033479

Cited by 14 publications

(13 citation statements)

References 24 publications

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“…Among the different nitrogen containing heterocycles, phthalazines play an important role in medicinal chemistry and subsequently have emerged as a pharmacophore. The phthalazine structural motifs have attracted a great deal of interest because of their ready accessibility, diverse chemical reactivity, and wide gamut of biological activities like antibacterial, antifungal, antitumor, anti‐inflammatory, and anticonvulsant activities. In organic synthesis, N ‐protected amino acids are essential key precursors and have been used in many areas, for example, peptide synthesis, medicinal chemistry, as chiral sources, and polymer materials .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel phthalazine derivatives as pharmacological activities

Wasfy

Aly

Behalo

et al. 2019

Journal of Heterocyclic Chem

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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.

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Section: Introductionmentioning

confidence: 99%

Synthesis of novel phthalazine derivatives as pharmacological activities

Wasfy

Aly

Behalo

et al. 2019

Journal of Heterocyclic Chem

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“…The synthesis of α‐trifluoromethyl azelastine 36 started with the synthesis of N ‐methyl trifluoromethyl pyrrolidine 37 issued from the reduction of the N ‐Cbz pyrrolidine 12 ′ (LiAlH 4 , THF, reflux) (Scheme ). The N ‐methyl pyrrolidine 37 was then submitted to the ring‐expansion conditions using 38 as the nucleophile. The desired trifluoromethyl azelastine 36 was formed and isolated with a good yield of 70 %.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of 2‐Fluoroalkyl 4‐Substituted Azepanes

et al. 2019

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Synthesis of di‐ and tri‐substituted fluoroalkylated azepanes was achieved by ring expansion of pyrrolidines via a regioselective attack of nucleophiles on a bicyclic azetidinium intermediate. A broad scope of azepanes, substituted at C4 and bearing a α‐trifluoromethyl, α‐difluoromethyl or α‐perfluorobutyl group, can be synthesized by this method by using a wide variety of nucleophiles.

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“…Among them, the compound 4-(4-chlorobenzyl)-2-methylphthalazin-1(2H)-one (6) exhibited a remarkable antifungal activity against standardised strains of dermatophytes and Cryptococcus neoformans, as well as against some clinical isolates. The compound 5 revealed its conformational and electronic characteristics, providing us with useful data for the future design of antifungal analogues (Derita et al, 2013).…”

Section: Pharmacological Activitiesmentioning

confidence: 99%

Pharmacological activities of various phthalazine and phthalazinone derivatives

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2019

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Various pthalazine derivatives have been synthesized and tested for their diverse biological activities. Pthalazine derivatives have been exhibited pharmacological activities like antitumor, PARP-1 inhibitors, antimicrobial, antivirus, antihistamine-H1, antiallergic rhinitis, antifungal, anti-inflammatory, anti-proliferative, COX-2 inhibitor, LOX-5 inhibitor, antidiabetes, and other biological activities like imaging agent. Pthalazine derivatives were also used as agrochemicals and chemicals. Various synthetic aspects indicate that pthalazines derivatives are easy to synthesize which can produce a wide variety of activity.

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Synthesis, Bioevaluation and Structural Study of Substituted Phthalazin-1(2H)-ones Acting as Antifungal Agents

Cited by 14 publications

References 24 publications

Synthesis of novel phthalazine derivatives as pharmacological activities

Synthesis of novel phthalazine derivatives as pharmacological activities

Synthesis of 2‐Fluoroalkyl 4‐Substituted Azepanes

Pharmacological activities of various phthalazine and phthalazinone derivatives

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