Eco-Friendly Synthesis, Characterization and Biological Evaluation of Some Novel Pyrazolines Containing Thiazole Moiety as Potential Anticancer and Antimicrobial Agents

Edrees, Mastoura M.; Melha, Sraa Abu; Saad, Amirah M.; Kheder, Nabila A.; Gomha, Sobhi M.; Muhammad, Zeinab A.

doi:10.3390/molecules23112970

Cited by 51 publications

(24 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Edrees et al documented recently the synthesis and anticancer screening against HepG 2 human hepatocellular carcinoma cell line of a library consisting of 19 pyrazoline derivatives bearing a thiophenyl group at C-3 [ 114 ]. The structures were divided in three groups depending on the exact formula of the thiazole unit; thiazoles incorporating an acyclic nitrogen-nitrogen double bond group, thiazolones, and arylsubstituted thiazoles.…”

Section: 2-pyrazolinesmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

View full text Add to dashboard Cite

Pyrazolines are five-membered heterocycles possessing two adjacent nitrogens. They have attracted significant attention from organic and medicinal chemists due to their potent biological activities and the numerous possibilities for structural diversification. In the last decade, they have been intensively studied as targets for potential anticancer therapeutics, producing a steady yearly rise in the number of published research articles. Many pyrazoline derivatives have shown remarkable cytotoxic activities in the form of heterocyclic or non-heterocyclic based hybrids, such as with coumarins, triazoles, and steroids. The enormous amount of related literature in the last 5 years prompted us to collect all these published data from screening against cancer cell lines, or protein targets like EGFR and structure activity relationship studies. Therefore, in the present review, a comprehensive account of the compounds containing the pyrazoline nucleus will be provided. The chemical groups and the structural modifications responsible for the activity will be highlighted. Moreover, emphasis will be given on recent examples from the literature and on the work of research groups that have played a key role in the development of this field.

show abstract

Section: 2-pyrazolinesmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

View full text Add to dashboard Cite

show abstract

“…[ 29 ] Also, pyrazoline derivatives exhibit pharmacological activities such as antitumor, [ 30 ] antibacterial, [ 31 ] anti‐inflammatory, [ 32 ] antifungal, [ 33 ] and antidepressant activities [ 15 ] (Figure 2). Recent studies have revealed that thiazolyl‐pyrazoline derivatives show potent antifungal, [ 34 ] antibacterial, [ 29 ] and antioxidant [ 35 ] activities, in addition to inhibitory effects on the epidermal growth factor receptor tyrosine kinase as a target for anticancer therapy, [ 36–39 ] among others. [ 18 ] For example, Altintop et al [ 34 ] reported that novel thiazolyl‐pyrazolines bearing thiophenes showed antifungal activity against different Candida spp.…”

Section: Introductionmentioning

confidence: 99%

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Cuartas

Robledo

Vélez

et al. 2020

Archiv der Pharmazie

View full text Add to dashboard Cite

A new series of N-substituted pyrazoline derivatives 6a-g, 7a-g, 8a-g, and 9a-g was synthetized by reaction of hydrazine derivatives and chalcone-thiazole hybrids bearing nitrogen mustard 5a-g. The chalcones 5a-g were obtained by Claisen-Schmidt condensation of thiazole-2-nitrogen mustard 3 and selected acetophenones 4a-g. These new compounds 6/7/8/9a-g were screened for their antifungal activity against Cryptococcus neoformans, with IC 50 values of 3.9-7.8 µg/ml for the N-3, 5-dichlorophenyl pyrazolines 9e-g. Interestingly, those compounds show low cytotoxic effects toward erythrocytes (RBC). In addition, N-acetyl (6a,b) and N-formyl pyrazolines (7a, 7b, 7c, and 7g) showed inhibitory activity against methicillinsusceptible Staphylococcus aureus, methicillin-resistant S. aureus, and vancomycinintermediate S. aureus, with the most important minimum inhibitory concentration values ranging from 31.25 to 125 µg/ml. Regarding the antiprotozoal activity, thiazolyl-pyrazolines 9g, 8f, and 7c display high activity against Plasmodium falciparum, Leishmania (V) panamensis, and Trypanosoma cruzi, with EC 50 values of 11.80, 6.46, and 4.98 μM, respectively, and with 7c being approximately 2.6-fold more potent than benznidazole with a selectivity index of 1.61 on U-937 human cells, showing promising potential as a novel antitrypanosomal agent. K E Y W O R D S antibacterial activity, antifungal activity, antiprotozoal activity, chalcone, pyrazoline

show abstract

“…Among the variety of heterocyclic products, pyrazolines have been the most significant scaffolds among the azole family because of their pharmacological applications . These compounds act as highly beneficial bactericidal and fungicidal agents . Pyrazoles are also found to act as COX‐2/B‐Raf, aurora kinase, EGFR‐TK, and tubulin assembling inhibitors along with their anticancer properties .…”

Section: Introductionmentioning

confidence: 99%

Synthetic and antimicrobial studies of N‐substituted‐pyrazoline‐based new bisheterocycles

Nisa

Yusuf

2020

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

In the present study, the four series of N‐acetyl/N‐carbothioamide/N‐carboxamide/N‐phenyl‐based new bispyrazolines have been synthesized. These symmetrical bisheterocyclic products were prepared efficiently from the ring‐closure reactions of new bischalcones 2a‐d with appropriate cyclizing agents (hydrazine hydrate, thiosemicarbazide, semicarbazide, and phenyl hydrazine) under the alkaline ethanolic conditions. The compounds 2a‐d were obtained by treating hydroxyl‐substituted chalcone 1 with various dihalogenated reagents (α,α′‐dibromo‐o/m/p‐xylene and 4,4′‐bischloromethyl‐diphenyl) in anhydrous K2CO3/dry acetone/Bu4N+I− medium. The structures of all the newly synthesized products have been authenticated with the help of their IR, 1H‐NMR, 13C‐NMR, and ESI‐MS spectral data and their purity was corroborated with the help of elemental analysis and thin‐layer chromatography results. The in vitro antimicrobial screening of the newly synthesized intermediates and final bisheterocycles has also been performed by using the serial tube dilution technique against the selected number of microorganisms. The final bisheterocycles revealed better antibacterial and antifungal potencies as compared to their corresponding bischalcones. Among the symmetrical bisheterocyclic products, N‐acetyl and N‐carbothioamide‐substituted bispyrazolines were found to exhibit potential antimicrobial properties than the other products.

show abstract

Eco-Friendly Synthesis, Characterization and Biological Evaluation of Some Novel Pyrazolines Containing Thiazole Moiety as Potential Anticancer and Antimicrobial Agents

Cited by 51 publications

References 38 publications

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

New thiazolyl‐pyrazoline derivatives bearing nitrogen mustard as potential antimicrobial and antiprotozoal agents

Synthetic and antimicrobial studies of N‐substituted‐pyrazoline‐based new bisheterocycles

Contact Info

Product

Resources

About