ChemInform Abstract: 3,5‐Diphenyl‐1H‐pyrazole Derivatives. Part 2. N‐Substituted 1‐(2‐Aminoethyl)‐3,5‐diphenyl‐1H‐pyrazoles and Their 4‐Bromo Derivatives with Analgesic and Other Activities.

Bondavalli, Francesco; Bruno, Olga; Ranise, Angelo; Schenone, P; Russo, Saverio; Loffreda, A.; Novellis, Vito de; Sasso, C. Lo; Marmo, E

doi:10.1002/chin.198929136

Cited by 2 publications

(3 citation statements)

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“…The ATR-FTIR and NMR data, as well as the elemental analysis results of the main intermediates (the uncharged inner scaffold (G4OH) and the tert -butyloxycarbonyl (Boc)-protected lysine dendrimer (G4BK)) and of the final lysine dendrimer hydrochloride salt (G4K) have been reported in Section 2.2.1 , Section 2.2.2 , and Section 2.2.3 , respectively. BBB4 was prepared according to the procedure schematized in Section 3.2 [ 5 ]. The ATR-FTIR and NMR data, as well as the elemental analysis results, confirmed its structure and purity and have been reported in Section 2.2.4 .…”

Section: Methodsmentioning

confidence: 99%

“…To confirm this scenario, several previously synthetized 3,5-diphenylpyrazole derivatives, including 2-(4-bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4, Figure 2 ), showed several pharmacological activities [ 5 ]. In particular, BBB4 showed analgesic, hypotensive, anti-inflammatory, local anaesthetic, and motor activity inhibition effects in mice and rats, while showing mild platelet antiaggregating action in vitro [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

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Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative

et al. 2021

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2-(4-Bromo-3,5-diphenyl-pyrazol-1-yl)-ethanol (BBB4) was synthetized and successfully evaluated concerning numerous biological activities, except for antimicrobial and cytotoxic effects. Due to the antimicrobial effects possessed by pyrazole nucleus, which have been widely reported, and the worldwide need for new antimicrobial agents, we thought it would be interesting to test BBB4 and to evaluate its possible antibacterial effects. Nevertheless, since it is water-insoluble, the future clinical application of BBB4 will remain utopic unless water-soluble BBB4 formulations are developed. To this end, before implementing biological evaluations, BBB4 was herein re-synthetized and characterized, and a new water-soluble BBB4-based nano-formulation was developed by its physical entrapment in a biodegradable non-cytotoxic cationic dendrimer (G4K), without recovering harmful solvents as DMSO or surfactants. The obtained BBB4 nanoparticles (BBB4-G4K NPs) showed good drug loading (DL%), satisfying encapsulation efficiency (EE%), and a biphasic quantitative release profile governed by first-order kinetics after 24 h. Additionally, BBB4-G4K was characterized by ATR-FTIR spectroscopy, NMR, SEM, dynamic light scattering analysis (DLS), and potentiometric titration experiments. While, before the nanotechnological manipulation, BBB4 was completely water-insoluble, in the form of BBB4-G4K NPs, its water-solubility resulted in being 105-fold higher than that of the pristine form, thus establishing the feasibility of its clinical application.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative

et al. 2021

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“…When 2 was assayed with various amines under different reaction conditions, the expected 5'-amine derivatives of AZT were not obtained, 15,16 leading to tricyclic analog (3) (Figure 1). Although total conversion of 2 took place, only 50% yield of 3 was obtained as side reaction products were formed, which were not identified, except AZT, the main co-product.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and antiretroviral evaluation of derivatives of zidovudine

Raviolo

Trinchero-Hernández

Turk

2009

J. Braz. Chem. Soc.

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Uma série de novos carbamatos de zidovudina (AZT, 1) foi sintetizada, caracterizada e avaliada em relação a sua atividade anti-HIV e citotoxicidade. O grupo hidroxila da posição 5' do AZT foi derivatizado usando-se N, N'-carbonildiimidazol e diferentes aminas para gerar os respectivos 5'-O-carbamatos. Além disso, dois derivados já conhecidos foram sintetizados, um 5'-O-tosilato e um derivado tricíclico (AZT-Cycl), empregando-se métodos mais rápidos e simples do que os previamente reportados. Embora os novos derivados tenham apresentado menor toxicidade do que o AZT, essa redução na citotoxicidade foi concomitante com a marcada diminuição para inibir a replicação do vírus, com exceção do AZT-Cycl, o qual, mesmo apresentando IC 50 = 1 µmol L -1 , não demonstrou sinais de citotoxicidade com valores de CCID 50 (µmol L -1 ) > 1000.A series of zidovudine (AZT, 1) derivatives have been synthesized and their anti-HIV activity and cytotoxicity have been determined. The 5'-OH function of AZT was derivatized using N, N'-carbonyldiimidazole and different amine compounds leading to their 5'-O-carbamates. In addition, two known AZT derivatives 5'-O-tosylate and a tricyclic one (AZT-Cycl) were also obtained by a simpler procedure than those previously reported. Although these AZT derivatives were less toxic than AZT, their reduced cytotoxicity was concomitant with an inability to inhibit HIV-1 replication, except in the case of AZT-Cycl, which showed an IC 50 = 1 µmol L -1 without cytotoxicity with values of CCID 50 (µmol L -1 ) > 1000.

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ChemInform Abstract: 3,5‐Diphenyl‐1H‐pyrazole Derivatives. Part 2. N‐Substituted 1‐(2‐Aminoethyl)‐3,5‐diphenyl‐1H‐pyrazoles and Their 4‐Bromo Derivatives with Analgesic and Other Activities.

Abstract: The diphenyl pyrazoles (I) are transformed into the tosylates (III).

Cited by 2 publications

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Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative

Preparation and Physicochemical Characterization of Water-Soluble Pyrazole-Based Nanoparticles by Dendrimer Encapsulation of an Insoluble Bioactive Pyrazole Derivative

Synthesis and antiretroviral evaluation of derivatives of zidovudine

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