Synthesis, characterization and in vitro antibacterial activity of novel phthalazine sulfonamide derivatives

Abbasi, Marzieh; Nazifi, S. Mohamad Reza; Nazifi, Zahra Sadat; Massah, Ahmad Reza

doi:10.1007/s12039-017-1337-8

Cited by 27 publications

(7 citation statements)

References 29 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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“…A lot of phthalazine-containing compounds showed potent antimicrobial activity. Therefore, the phthalazine skeleton can be considered as a promising antimicrobial pharmacophore. , Based on the principle of analogue design and the hybridized combination strategy of double pharmacophores, we designed one novel 2-phenylphthalazin-2-ium skeleton ( C ) (Figure ) by replacing the 3,4-dihydropyridine moiety of the analogue A (Figure ) with a pyridazine unit. The skeletons C and A possess some obvious similarities such as the same molecular length and width, the presence of one polar iminium moiety (CN + ), and planar or approximately planar molecules, suggesting that the two compounds should have a similar pharmacological activity.…”

Section: Resultsmentioning

confidence: 99%

Simple Analogues of Quaternary Benzo[c]phenanthridine Alkaloids: Discovery of a Novel Antifungal 2-Phenylphthalazin-2-ium Scaffold with Excellent Potency against Phytopathogenic Fungi

Cui

Zhou

et al. 2020

J. Agric. Food Chem.

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Inspired by sanguinarine and chelerythrine, a novel antifungal 2-phenylphthalazin-2-ium scaffold as a simple analogue was designed. Most of the 30 compounds showed excellent inhibition activity against almost all eight phytopathogenic fungi, far superior to sanguinarine and chelerythrine. A third of the compounds were more active than azoxystrobin in most cases. Compounds 26 and 27 showed the highest total activity against all the fungi with EC50 means of ca. 4.6 μg/mL. Fusarium solani showed the highest susceptibility with an EC50 mean of 3.62 μg/mL to 19 compounds. A concentration of 25.0 μg/mL 27 can fully control the Colletotrichum gloeosporioides infection in apples over 9 days. Electron microscopic observations showed that 27 was able to damage the structures of the hypha and cell membrane. The structure–activity relationship showed that the presence of electron-withdrawing groups on the C-ring increases the activity against most of the fungi. Thus, 2-phenylphthalazin-2-ium compounds represent promising leads for the development of novel fungicides.

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“…Therefore, the development of efficient, convenient, environmentally benign, and recyclable catalyst is essential. In continuing to our previous works on synthesis and catalyst, [28][29][30][31][32][33][34][35] herein, we introduce Diatomite-Si-Pr-TAT-Bis-(AZY-MY)(Cu) Phenol as a heterogeneous catalyst for the one-pot threecomponent synthesis of pyranopyrans and chromenes.…”

Section: Introductionmentioning

confidence: 98%

Dual Copper (II) Complex Supported on Diatomite as a Novel and Green Catalyst for the Synthesis of Dihydropyrano[3;2‐b]Chromenediones and Aminopyranopyrans

2021

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Immobilized copper (II) complex, namely, 2,2'-((1E,1'E)-((6-(l2azaneyl)-1,3,5-triazine-2,4-diyl)bis(azaneylylidene))bis (methaneylylidene))diphenol, supported on diatomite (Diatomite-Si-Pr-TAT-Bis-(AZY-MY)(Cu)Phenol) was introduced as a robust and heterogeneous catalyst for the synthesis of dihydropyrano[3;2-b]chromenediones and aminopyranopyrans. The Diatomite-Si-Pr-TAT-Bis-(AZY-MY)(Cu)Phenol catalyst was synthesized by complexation of copper (II) acetate with TAT-Bis-(AZY-MY)Phenol as a ligand with oxygen and nitrogen ligation sites that were anchored on diatomite through 3chloropropyltrimethoxysilane. The prepared catalyst was characterized using different microscopic and spectroscopic techni-ques including SEM, TEM, EDX, XRD, FT-IR, TGA and ICP. The diatomite is available and cheap support with a high specific surface area and a large amount of hydroxyl group on the surface. A large amount of dual copper (II) complexes were supported on diatomite through covalent bonds. The Diatomite-Si-Pr-TAT-Bis-(AZY-MY)(Cu)Phenol showed good catalytic activity for the synthesis of dihydropyrano[3;2-b] chromenediones and aminopyranopyrans using aromatic aldehyde, kojic acid, dimedone, or malononitrile. In addition, this catalyst system was reusable for five consecutive catalytic cycles without loss of their catalytic activity.

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Synthesis, characterization and in vitro antibacterial activity of novel phthalazine sulfonamide derivatives

Cited by 27 publications

References 29 publications

Synthesis of novel phthalazine derivatives as pharmacological activities

Synthesis of novel phthalazine derivatives as pharmacological activities

Simple Analogues of Quaternary Benzo[c]phenanthridine Alkaloids: Discovery of a Novel Antifungal 2-Phenylphthalazin-2-ium Scaffold with Excellent Potency against Phytopathogenic Fungi

Dual Copper (II) Complex Supported on Diatomite as a Novel and Green Catalyst for the Synthesis of Dihydropyrano[3;2‐b]Chromenediones and Aminopyranopyrans

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