Novel Ethyl 1,5-Disubstituted-1H-Pyrazole-3-Carboxylates as a New Class of Antimicrobial Agents

Radwan, A E; Ghorab, Mostafa M.; Alsaid, Mansour S.; Alanazi, Fars K.

doi:10.2478/acph-2014-0028

Cited by 11 publications

(6 citation statements)

References 21 publications

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“…The combined extracts were washed with brine (100 mL), dried (MgSO 4 ), and concentrated. The obtained solid was recrystallized from methanol to procure compounds 2a – e and the produced compounds were used in the next step without further purification [ 2 , 4 , 55 , 56 , 57 ].…”

Section: Methodsmentioning

confidence: 99%

Development and Assessment of 1,5–Diarylpyrazole/Oxime Hybrids Targeting EGFR and JNK–2 as Antiproliferative Agents: A Comprehensive Study through Synthesis, Molecular Docking, and Evaluation

Abdelrahman,

Hassan,

Abdel-Aziz

et al. 2023

Molecules

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New 1,5-diarylpyrazole oxime hybrid derivatives (scaffolds A and B) were designed, synthesized, and then their purity was verified using a variety of spectroscopic methods. A panel of five cancer cell lines known to express EGFR and JNK-2, including human colorectal adenocarcinoma cell line DLD-1, human cervical cancer cell line Hela, human leukemia cell line K562, human pancreatic cell line SUIT-2, and human hepatocellular carcinoma cell line HepG2, were used to biologically evaluate for their in vitro cytotoxicity for all the synthesized compounds 7a–j, 8a–j, 9a–c, and 10a–c. The oxime containing compounds 8a–j and 10a–c were more active as antiproliferative agents than their non-oxime congeners 7a–j and 9a–c. Compounds 8d, 8g, 8i, and 10c inhibited EGFR with IC50 values ranging from 8 to 21 µM when compared with sorafenib. Compound 8i inhibited JNK-2 as effectively as sorafenib, with an IC50 of 1.0 µM. Furthermore, compound 8g showed cell cycle arrest at the G2/M phase in the cell cycle analysis of the Hela cell line, whereas compound 8i showed combined S phase and G2 phase arrest. According to docking studies, oxime hybrid compounds 8d, 8g, 8i, and 10c exhibited binding free energies ranging from −12.98 to 32.30 kcal/mol at the EGFR binding site whereas compounds 8d and 8i had binding free energies ranging from −9.16 to −12.00 kcal/mol at the JNK-2 binding site.

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Section: Methodsmentioning

confidence: 99%

Development and Assessment of 1,5–Diarylpyrazole/Oxime Hybrids Targeting EGFR and JNK–2 as Antiproliferative Agents: A Comprehensive Study through Synthesis, Molecular Docking, and Evaluation

Abdelrahman,

Hassan,

Abdel-Aziz

et al. 2023

Molecules

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show abstract

“…The combined extracts were washed with brine (100 mL), dried over anhydrous Na2SO4, and concentrated. The obtained solid was crystallized from methanol to obtain pure compounds 2a-c [57,58].…”

Section: 11general Procedures For the Synthesis Of (Z)-ethyl 2hydroxy-4-oxo-4-substituted Phenylbut-2-enoate Derivatives (2a-c)mentioning

confidence: 99%

Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel 1,5-Diarylpyrazole Carboxamide Derivatives as Antiproliferative Agents

Shoman

Soltan

Nagaoka

et al. 2021

Journal of advanced Biomedical and Pharmaceutical Sciences

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A series of novel 1,5-diarylpyrazole carboxamide derivatives was designed and synthesized. All the synthesized compounds were biologically evaluated for their in vitro cytotoxic activities against a panel of five cancer cell lines namely, DLD, Hela, K-562, SUIT and HepG-2. The results revealed that compound 5c exhibited the most prominent cytotoxic effect against four tested cell lines with growth inhibition percentages ranged from 75.95 to 123 % and IC50 values of 17.20 and 21.20 μM comparable to that of daunorubicin as a control drug (IC50 values of 13.30 and 22 μM) against K-562 and Hep-G2 cell lines, respectively. Molecular docking study suggested the ability of the tested compounds to inhibit EGFR-TK. Data showed that 5c possess the ability to bind to erlotinib binding site forming a stable complex with energy scores -7.73 compared to -7.63 for erlotinib. It potentially forms three hydrogen bonds with LYS 721 and GLU 638 residues. Data suggests that compound 5c is a promising lead in the design of further EGFR inhibitors.

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“…The combined extracts were washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated. The obtained solid was recrystallized from methanol to give compounds 3a-c [29,30].…”

Section: General Procedures For Synthesis Of Ethyl 4-(substituted Phenyl)-2-hydroxy-4-oxobut-2-enoates 2a-cmentioning

confidence: 99%

Design, synthesis, molecular docking and biological evaluation of novel 1,5-diarylpyrazole-N,O-dimethyl hydroxamate derivatives as antiproliferative agents.

Hassan

Abdelrahman

Abdel‐Aziz

et al. 2021

Journal of advanced Biomedical and Pharmaceutical Sciences

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A series of novel hybrid of 1,5-diarylpyrazole-N,O-dimethylhydroxamate derivatives were designed and synthesised in synthetically acceptable yields. All the new synthesized compounds were biologically evaluated for their in vitro cytotoxicity against a panel of five cell lines namely human colorectal adenocarcinoma cell line DLD1, human cervical cancer cell line Hela, human leukemia cell line K562, human pancreatic cancer cell line Suit-2 and human hepatocellular carcinoma cell line HepG2. Compound 7a showed a significant cytotoxicity against Hela cell line with IC50 value of 16 µM and a good cytotoxicity against DLD1 and HepG2 with IC50 values of 69.9 µM and 78.8µM. Also, compound 7a displayed a potent EGFR inhibitory activity with IC50= 4.00 µM, which was comparable to positive reference drug sorafenib (IC50 = 3.5 µM). Moreover, in-silico studies showed that compound 7a has excellent binding affinity to the active site of EGFR with binding score better than a multitarget kinase drug sorafenib and good binding affinity to JNK-2, which explains the anticancer activity of compound 7a.

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Novel Ethyl 1,5-Disubstituted-1H-Pyrazole-3-Carboxylates as a New Class of Antimicrobial Agents

Cited by 11 publications

References 21 publications

Development and Assessment of 1,5–Diarylpyrazole/Oxime Hybrids Targeting EGFR and JNK–2 as Antiproliferative Agents: A Comprehensive Study through Synthesis, Molecular Docking, and Evaluation

Development and Assessment of 1,5–Diarylpyrazole/Oxime Hybrids Targeting EGFR and JNK–2 as Antiproliferative Agents: A Comprehensive Study through Synthesis, Molecular Docking, and Evaluation

Design, Synthesis, Molecular Modeling and Biological Evaluation of Novel 1,5-Diarylpyrazole Carboxamide Derivatives as Antiproliferative Agents

Design, synthesis, molecular docking and biological evaluation of novel 1,5-diarylpyrazole-N,O-dimethyl hydroxamate derivatives as antiproliferative agents.

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