Facile synthesis and in vitro anticancer evaluation of a new series of tetrahydroquinoline

Fathy, Usama; Salam, Hayam A. Abd El; Fayed, Eman A.; Elgamal, Abdelbaset M.; Gouda, Ahmed

doi:10.1016/j.heliyon.2021.e08117

Cited by 9 publications

(4 citation statements)

References 35 publications

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“…22 Next, compound 9 was treated with NaI to yield compound 10 in the presence of methanol and potassium carbonate under 70 °C. 23 In addition, compound 10 was reacted with compound 8 to obtain compound 11 under an ice-salt bath. Finally, compounds 12−35 were synthesized via the reaction of compound 11 with diverse acid chloride derivatives in an alkaline environment.…”

Section: Resultsmentioning

confidence: 99%

“…Then compound 8 was synthesized via the reaction of compound 7 with CS 2 under an ice-salt bath with slow stirring for 1 h. The synthesis of compound 9 involved the introduction of p -toluenesulfonyl chloride to compound 1 in dichloromethane . Next, compound 9 was treated with NaI to yield compound 10 in the presence of methanol and potassium carbonate under 70 °C . In addition, compound 10 was reacted with compound 8 to obtain compound 11 under an ice-salt bath.…”

Section: Results and Discussionmentioning

confidence: 99%

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Design, Synthesis, Biological Evaluation, and Molecular Docking Studies of Pleuromutilin Derivatives Containing Thiazole

Li,

Lin,

et al. 2024

ACS Infect. Dis.

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In this study, we designed and synthesized a series of pleuromutilin derivatives containing thiazole. The in vitro antimicrobial efficacy of these synthesized compounds was examined by using four strains. Compared with tiamulin (MIC = 0.25 μg/mL), compound 14 exhibited potency in inhibiting MRSA growth (MIC = 0.0625 μg/mL) in these derivatives. Meanwhile, the time-killing kinetics further demonstrated that compound 14 could efficiently inhibit the MRSA growth. After exposure at 4 × MIC, the postantibiotic effect (PAE) of compound 14 was 1.29 h. Additionally, in thigh-infected mice, compound 14 exhibited a more potent antibacterial efficacy (−1.78 ± 0.28 log 10 CFU/g) in reducing MRSA load compared to tiamulin (−1.21 ± 0.23 log 10 CFU/g). Moreover, the MTT assay on RAW 264.7 cells demonstrated that compound 14 (8 μg/mL) had no significant cytotoxicity. Docking studies indicated the strong affinity of compound 14 toward the 50S ribosomal subunit, with a binding free energy of −9.63 kcal/mol. Taken together, it could be deduced that compound 14 was a promising candidate for treating MRSA infections.

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Section: Resultsmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Design, Synthesis, Biological Evaluation, and Molecular Docking Studies of Pleuromutilin Derivatives Containing Thiazole

Li,

Lin,

et al. 2024

ACS Infect. Dis.

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“…Cells were injected into ACEA Novocyte™flow cytometer (ACEA Biosciences Inc., San Diego, CA, USA) to test presence of apoptosis cells with 2 fluorescence signal detector (λex/em 488/530 nm for FITC and λex/em 535/617 nm for PI). Each sample was injected three times and analyzed by the quadrant plot [56] …”

Section: Methodsmentioning

confidence: 99%

Design, Synthesis, Cytotoxic Activity and Molecular Docking Studies of Naphthyl Pyrazolyl Thiazole Derivatives as Anticancer Agents

et al. 2023

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Novel series of heterocycliccompounds pairing hybrids pyrazole, naphthalene and pyrazoline/thiazoldinemoieties were synthesized. The starting compounds pyrazolyl hydrazinecarbothioamidewere synthesized by the reaction of the 4‐formyl pyrazole derivatives with thiosemicarbazide to afford the substituted carbothioamide in good yields. The carbothioamideswere used as starting materials for synthesis of a variety of pyrazolylhydrazinylthiazole derivativesandpyrazolylhydrazonothiazolidin derivatives. The structures of the newly synthesized compounds were deduced depending on their spectrum data and elemental analysis. The cytotoxicity of the selected compounds was screened in vitro against three human breast cancer cell lines. The four compounds showed a gradual decrease in cell viability and theonly compound thiazolidin‐4‐one10b showed IC5010.16, 8.25 and 4.88 μM against the above cell lines, respectively. Thus, it was selected for further in vitro biological investigations. The Structure‐activity relationship for these compounds was interpreted in terms of molecular docking.

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“…Caspase 3 is the most important protein in the caspase family that is highly conserved and functions as a central apoptosis regulator in multicellular organisms. Thus, it has become an attractive strategy for the treatment of cancer in critical regulators of apoptosis to induce apoptosis in cancer cells [11,[15][16][17][18][19]. The molecular mechanisms used by cancer cells for apoptosis are multifarious [20].…”

Section: Introductionmentioning

confidence: 99%

Novel fluorinated pyrazole-based heterocycles scaffold: cytotoxicity, in silico studies and molecular modelling targeting double mutant EGFR L858R/T790M as antiproliferative and apoptotic agents

Fayed

Gohar²,

Bayoumi

et al. 2023

Med Chem Res

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Hepatocellular carcinoma (HCC), also known as hepatoma, is the most prevalent type of primary liver cancer. It begins in the hepatocytes, the liver’s major cell type. Cancer that began in another region of the body but has spread to the liver is known as secondary cancer of life; several still unmet demands for better, less toxic therapy to treat this malignant tumor. Several novel pyrazolo[1,5-a]pyrimidine derivatives were synthesized as part of our goal to develop promising anticancer drugs. All the synthesized hybrids have been screened for their cytotoxicity effect against three cancer cell lines which are; HepG-2, HCT-116, and MCF-7. The liver cancer cells were found to be the most sensitive to the effect of the new molecules. A subsequent set of in vitro biological evaluation studies has been conducted on the most promising derivatives to identify their effect on such a cancer type. In HepG-2 cells, four derivatives (8a, 8b, 10c, and 11b) demonstrated good anticancer activity. The most efficacious compounds were 8b and 10c, which had IC50 values of 2.36 ± 0.14 and 1.14 ± 0.063 μM, respectively, higher than the reference medication Imatinib. The latter’s putative molecular effect has been investigated further by looking at its influence on the cell cycle, EGFR, and specific apoptotic and anti-apoptotic markers in HepG-2 cells. These findings indicated that 8b and 10c could trigger apoptosis by upregulating BAX and caspase-3 and cell cycle at the Pre-G1 and G2-M stages. The compounds 8b and 10c showed high potency for EGFR with IC50 equal to 0.098 and 0.079 μM, respectively. Compound 10c had the most effective inhibitory activity for EGFR L858R-TK with IC50 (36.79 nM). Additionally, in silico ADMET and docking studies were done for the most active hits, representing good results. Graphical Abstract

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Facile synthesis and in vitro anticancer evaluation of a new series of tetrahydroquinoline

Cited by 9 publications

References 35 publications

Design, Synthesis, Biological Evaluation, and Molecular Docking Studies of Pleuromutilin Derivatives Containing Thiazole

Design, Synthesis, Biological Evaluation, and Molecular Docking Studies of Pleuromutilin Derivatives Containing Thiazole

Design, Synthesis, Cytotoxic Activity and Molecular Docking Studies of Naphthyl Pyrazolyl Thiazole Derivatives as Anticancer Agents

Novel fluorinated pyrazole-based heterocycles scaffold: cytotoxicity, in silico studies and molecular modelling targeting double mutant EGFR L858R/T790M as antiproliferative and apoptotic agents

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