Synthesis of some novel pyrazoline‐thiazole hybrids and their antimicrobial activities

Masoud, Doaa M.; Azzam, Rasha A.; Hamdy, Fatma; Mekawey, Amal A. I.; Abdel‐Aziz, Hatem A.

doi:10.1002/jhet.3698

Cited by 16 publications

(36 citation statements)

References 48 publications

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“…The chalcones intermediate 3a-c were prepared through a condensation reaction of different acetophenones 1a-c with 4-flourobenzaldehyde 2 via the reported procedures. 48 The previously prepared chalcones 3a-c subjected to heterocyclization with thiosemicarbazide in basic condition (using NaOH) to furnish the pyrazoline derivatives 4a-c . The pyrazoline derivatives 4a-c were further cyclized with ethyl bromoacetate in absolute ethyl alcohol to produce the key thiazolidenone intermediates 5a-c .…”

Section: Resultsmentioning

confidence: 99%

Novel 2-(5-Aryl-4,5-Dihydropyrazol-1-yl)thiazol-4-One as EGFR Inhibitors: Synthesis, Biological Assessment and Molecular Docking Insights

Al‐Warhi¹,

Kerdawy²,

Said³

et al. 2022

DDDT

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Introduction Epidermal growth factor receptor (EGFR) regulates several cell functions which include cell growth, survival, multiplication, differentiation, and apoptosis. Currently, EGFR kinase inhibitors are of increasing interest as promising targeted antitumor therapeutic agents. Methods Different thiazolyl-pyrazoline derivatives ( 7a-o ) were synthesized and were first tested for anti-proliferative effect towards the A549 lung cancer cell line and the T-47D breast cancer cell line in MTT assay. Thereafter, thiazolyl-pyrazolines ( 7b, 7g, 7l , and 7m ) were subsequently evaluated for their PK inhibition for EGFR. Moreover, representative promising derivatives ( 7g and 7m ) in cytotoxic and PK inhibition assays were tested to investigate their impact on the apoptosis and cell cycle phases in T-47D cells in order to explore more insights into the antitumor actions of the target thiazolyl-pyrazolines. Furthermore, docking studies were accomplished to evaluate the patterns of binding of thiazolyl-pyrazolines 7b, 7g, 7l , and 7m in the EGFR active pocket (PDB ID: 1M17). Results Testing the thiazolyl pyrazoline compounds 7a-o on A549 and T-47D cell lines showed IC 50 arrays between 3.92 and 89.03 µM, and between 0.75 and 77.10 µM, respectively. Also, the tested thiazolyl-pyrazolines ( 7b, 7g, 7l , and 7m ) demonstrated significant sub-micromolar EGFR inhibitory actions with IC 50 values 83, 262, 171 and 305 nM, respectively, in comparison to erlotinib (IC 50 =57 nM). Discussion Generally, it was observed that the tested thiazolyl pyrazolines showed more potent antiproliferative activity toward breast cancer cells T-47D than toward lung cancer cell lines A549. In particular, thiazolyl pyrazolines 7g and 7m showed the best activity against A549 cells (IC 50 = 3.92 and 6.53 µM) and T-47D cells (IC 50 = 0.88 and 0.75 µM). Compounds 7g and 7m provoked a sub-G1 phase arrest and cell apoptosis which are in agreement with the expected outcome of EGFR inhibition. Finally, the molecular docking of 7g and 7m in the active site of EGFR revealed a common binding pattern similar to that of erlotinib which involves the accommodation of the 1,3 thiazol-4-one ring and pyrazoline ring of target compounds in the binding region of erlotinib’s quinazoline ring and anilino moiety.

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Section: Resultsmentioning

confidence: 99%

Novel 2-(5-Aryl-4,5-Dihydropyrazol-1-yl)thiazol-4-One as EGFR Inhibitors: Synthesis, Biological Assessment and Molecular Docking Insights

Al‐Warhi¹,

Kerdawy²,

Said³

et al. 2022

DDDT

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“…The title compounds were synthesized by Claisen-Schmidt condensation in accordance with the procedure reported [25,42] in the literature. All of these intermediate compounds (3a-j) were recorded in the literature [43][44][45][46][47][48][49]. Briefly, a mixture of suitable acetophenone (1 mmol) and benzo[d] [1,3]dioxole-5-carbaldehyde (1 mmol) was dissolved in ethanol (5 mL).…”

Section: Synthesis Of Chalcone Compounds 3a-j 3-(benzo[d][13]dioxol-5-yl)-1-arylprop-2-en-1-one (Figure 2)mentioning

confidence: 99%

Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors

Tuğrak¹,

Gül²,

Sakagami³

et al. 2021

Turk J Chem

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IntroductionCancer is a disease characterized by the continuous growth of cells without obeying the rules that normal healthy cells do. It is second amongst the reasons for death after cardiovascular diseases [1][2][3][4]. Based on the World Healthy Organization (WHO) report in 2018, 18.1 million people around the world had cancer, and 9.6 million died from the disease. It will reach 29.4 million in 2040. Although several therapeutic approaches are available, such as chemotherapy, which includes drug therapy and has great importance, development of new chemotherapeutics is needed since the available drugs in the market have numerous side effects, resistance development to itself, or selectivity problems [1,3,5].Oral cancer is ranked as the sixth most common malignancy worldwide [6][7][8]. The main carcinogens for oral squamous cell carcinoma (OSCC) are cigarette and alcohol products [9,10]. Understanding the molecular mechanisms of tumorigenesis and metastasis process for OSCC can lead researchers to discover new chemotherapeutic strategies and improve the treatment of oral cancer.Although there are several types of anticancer therapeutic products, novel aryl sulphonamides have recently been reported to have anticancer properties and can be used to treat different types of cancers. Among them, pazopanib, a tyrosine kinase inhibitor for renal cell carcinoma and soft tissue sarcoma, belinostat, a histone deacetylase inhibitor for peripheral T-cell lymphoma, and dabrafenib, a BRAF inhibitor for metastatic melanoma, have been approved for in the clinic treatment of patients [11] (Figure 1).As another well-known pharmacophore in drugs or bioactive compounds are pyrazoline and its analogs. Their numerous bioactivities have been reported including their anticancer/cytotoxic activities [12][13][14].

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“…Meanwhile, indole derivatives have broad-spectrum biological activities, such as antibacterial, − anti-inflammatory, − and antiviral. − Therefore, commercial products with an indole backbone can be continually searched for in research and development in pesticides and pharmaceuticals. Recent studies have shown that the antiviral mechanism of most indole-containing compounds increases the plant body’s autoimmunity to fulfill disease rebellion. − As a promising moiety in this category, 4,5-dihydro-1 H -pyrazoline exhibits diverse activities, which have led to the development of numerous commercially available drugs for application to insecticides, − antivirals, − herbicides, − and fungicides. − Thiourea is likewise an active structure, and its most well-known feature is its ability to serve as a hydrogen bond former, which helps strengthen the molecule’s binding to the probable target. As a result, such fragments, when properly introduced into the target chemical, might considerably increase the related activity. , …”

Section: Introductionmentioning

confidence: 99%

Splicing Indoles and 4,5-Dihydro-1H-pyrazoline Structure Gave Birth to Novel Antiviral Agents: Design, Synthesis, and Mechanism Study

Bai

Wei

Shen

et al. 2023

J. Agric. Food Chem.

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The specific conation of our research is to invent a series of indole derivatives containing a 4,5-dihydro-1H-pyrazoline motif with effective antiviral activity. The anti-potato virus Y (PVY) activities of target compounds were systematically investigated. Most target compounds exhibited good PVY activities. Compound D40, which exhibited outstanding anti-PVY activities, was sieved using a three-dimensional quantitative structure–activity relationship. Based on the anti-PVY activity assessments, the curative and protective activities of D40 were found to be 64.9 and 60.8%, respectively, which were superior to those of the commercial drug Ningnanmycin (50.2 and 50.7%, respectively). In addition, defensive enzyme activities and proteomics results indicate that D40 can increase the three crucial defense-related enzyme activities and regulate the carbon fixation pathway in photosynthetic organisms to intensify the resistance of plants to PVY. Therefore, our study suggests that compound D40 might be used as a suitable crop protection pesticide.

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Synthesis of some novel pyrazoline‐thiazole hybrids and their antimicrobial activities

Cited by 16 publications

References 48 publications

Novel 2-(5-Aryl-4,5-Dihydropyrazol-1-yl)thiazol-4-One as EGFR Inhibitors: Synthesis, Biological Assessment and Molecular Docking Insights

Novel 2-(5-Aryl-4,5-Dihydropyrazol-1-yl)thiazol-4-One as EGFR Inhibitors: Synthesis, Biological Assessment and Molecular Docking Insights

Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors

Splicing Indoles and 4,5-Dihydro-1H-pyrazoline Structure Gave Birth to Novel Antiviral Agents: Design, Synthesis, and Mechanism Study

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