Ultrasound-Promoted Synthesis, Structural Characterization and in vitro Antimicrobial Activity of New 5-Aryl-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamides

Pyrazoline plays an important role in the development of heterocyclic chemistry theory and is widely used as a synthesis useful in organic synthesis. The structure of the pyrazoline derivative compound contains a 5-membered heterocyclic framework with two nitrogen atoms and one endocyclic double bond. The function of pyrazoline as a fragment was stable enough in the bioactive group to synthesize new compounds with various biological activities. Various methods that could be used for the synthesis of pyrazole derivatives were ultrasonic irradiation, microwave assistance, ionic liquids, grinding techniques, and conventional methods. However, the synthesis of pyrazoline derivatives using conventional methods had many problems, one of which is the product yield, which was <70%. Therefore, this article will discuss the importance of optimizing the synthesis reaction conditions by taking into account several synthesis parameters to get the best organic product results based on conventional methods. A literature search was conducted by employing PubChem, Chemspider Google Scholar, Research Gate, Science Direct, and Elsevier by selecting pyrazoline synthesis based on physicochemical profile, reaction mechanism, and synthesis method.

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“…This method could promote the synthesis of pyrazoline derivate with a short reaction time and good results. [ 27 28 29 ]…”

Section: Synthesis Methods Of Pyrazoline Derivatementioning

confidence: 99%

Comparison of various synthesis methods and synthesis parameters of pyrazoline derivates

Praceka

Megantara

Maharani

et al. 2021

Journal of Advanced Pharmaceutical Technology &Amp; Research

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“…Danilo et al conducted cyclo condensation reaction of heteroaryl enones (63a-m) and aminoguanidines hydrochloride adduct (62) under sonochemical irradiations to synthesize amidino pyrazolines (64a-m) (Scheme 14) [30].…”

Section: S C H E M E 5 a Synthesis Of Azidobenzothiazoles Under Ultra...mentioning

confidence: 99%

Ultrasound assisted synthesis of 5–7 membered heterocyclic rings in organic molecules

Shabir

Shafique

Saeed

2022

Journal of Heterocyclic Chem

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Ultrasound synthesis is a powerful technique that is being used increasingly to accelerate organic reactions as a green synthetic approach. Ultrasonication has offered advantages over conventional methods in terms of enhanced yields, shorter reaction time, high selectivity and minimal side reaction. The current investigation is the review of papers published from 2016 to 2022 for the synthesis of organic heterocycles under the effect of ultrasound irradiation. It is a comprehensive compilation of sonochemical processes as a versatile technique to achieve synthesis of numerous organic scaffolds from simple carbocyclic compounds to complex and biologically active heterocyclic structural molecules. This review encompasses the examples of ultrasound supported synthetic reactions of multicomponent one pot processes as well as different steps flow synthesis. Ultrasound assisted synthesis have been proved as an ecofriendly and benign approach for the synthesis of 5-7 membered heterocyclic rings, with one to three hetero atoms. Moreover Ultrasound synthesis has offered excellent yield in a vast majority of reactions under mild conditions without involving complicated purification procedures.

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“…Thirty-seven pyrazoline derivatives from three studies were served as the validation dataset of the recently built docking model. We deliberately selected studies that conducted the antibacterial assay on the same bacterial strain in our research, ATCC 25923, to be more precise [24][25][26]. The molecules from these studies were applied to our docking model, then the docking score would be recorded.…”

Section: Validating the Docking Modelmentioning

confidence: 99%

Computer-aided structural optimization, synthesis, evaluation of the antimicrobial and cytotoxic activity of some pyrazoline derivatives

Nguyen¹,

Ly²,

Tuoi³

et al. 2022

MedPharmRes

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Introduction: In the last few decades, pyrazoline-based substances have emerged as potential antimicrobial and anticancer candidates. In concern with antimicrobial activity, this study aims to build a docking model to predict the structure of potential 2-pyrazoline derivatives. The cytotoxicity of some compounds was also evaluated to get insight into the structure–anticancer activity relationship of the 2-pyrazoline derivatives. Methods: Docking models were built on virtual FabH enzymes using FlexX platform with 2-pyrazoline derivatives served as test sets. Afterward, derivatives with high docking scores were chemically synthesized and evaluated for antibacterial activity using the agar dilution method. Furthermore, MTT assay was used to assess the cytotoxicity of these compounds. Results: The docking score and the in vitro minimum inhibitory concentration (MIC) value on Staphylococcus aureus (S. aureus) bacteria strongly correlate with an R-square value of 0.6751 (p < 0.0001). Four 2 pyrazoline derivatives were synthesized and evaluated for antimicrobial activity. Their MIC values on S. aureus range between 4 and 16 μg/mL, consistent with ones predicted by the docking model. Apropos cytotoxic properties, a series of 2-pyrazolines exhibit a moderate activity on HepG2, RD, and MDA-MB-231. The most active compound, HP10, has the IC50 values on these cell lines. which are 26.62 μM, 17.74 μM, 14.47 μM, respectively. Conclusion: Our research built a docking model on the virtual S. aureus FabH enzyme with high potential in predicting antibacterial activities of different 2-pyrazoline derivatives. Moreover, our cytotoxicity results provided data for further studies on the anticancer activity of these promising derivatives.

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Ultrasound-Promoted Synthesis, Structural Characterization and in vitro Antimicrobial Activity of New 5-Aryl-3-(2-hydroxyphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamides

Cited by 4 publications

References 14 publications

Comparison of various synthesis methods and synthesis parameters of pyrazoline derivates

Comparison of various synthesis methods and synthesis parameters of pyrazoline derivates

Ultrasound assisted synthesis of 5–7 membered heterocyclic rings in organic molecules

Computer-aided structural optimization, synthesis, evaluation of the antimicrobial and cytotoxic activity of some pyrazoline derivatives

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