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. 2023 Jul 13;8(29):25698-25709.
doi: 10.1021/acsomega.2c07539. eCollection 2023 Jul 25.

Antiproliferative Activity of New Pyrazole-4-sulfonamide Derivatives: Synthesis and Biological Evaluation

Panasa Mahesh  1 , Parameswari Akshinthala  2 , Naresh Kumar Katari  1   3 , Lavleen Kumar Gupta  4 , Dikshita Panwar  4 , Manoj Kumar Sharma  4 , Sreekantha Babu Jonnalagadda  3 , Rambabu Gundla  1
Affiliations

Antiproliferative Activity of New Pyrazole-4-sulfonamide Derivatives: Synthesis and Biological Evaluation

Panasa Mahesh et al. ACS Omega. .

Abstract

Pyrazole and sulfonamide constitute an important class of drugs, with several types of pharmacological agents. Facile synthesis of two new series of 3,5-dimethyl-1H-pyrazole-4-sulfonamide and 1,3,5-trimethyl-1H-pyrazole-4-sulfonamide derivatives was designed and synthesized. These pyrazole-4-sulfonamide derivatives are characterized by Fourier transform infrared (FT-IR), 1H NMR, 13C NMR, and elemental analysis, and their biological evolution data are presented. This paved way for the development of new pyrazole-4-sulfonamide derivatives. These compounds are tested for their in vitro antiproliferative activity against U937 cells by the CellTiter-Glo Luminescent cell viability assay using Mitomycin C. Cytotoxicity detection is based on the measurement of LDH activity, while these compounds did not exhibit cytotoxic activity on these cells. Half maximal inhibitory concentration (IC50) was calculated by Graph Pad Prism software for each dose. Their structure-activity relationships were obtained and discussed.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Pharmaceutical drugs in the market with pyrazole heterocyclic and sulfonamide moieties.
Scheme 1
Scheme 1. Synthesis of 3,5-Dimethyl-1H-pyrazole-4-sulfonyl Chloride and 1,3,5-Trimethy-1H-pyrazole-4-sulfonyl Chloride
Reagents and conditions: (a) 85% hydrazine hydrate, methanol, 25–30 °C, yield 95%; (b) potassium tert-butoxide, CH3I, THF, yield 78%; (c) chlorosulfonic acid, SOCl2, CHCl3, 60 °C, yield 90%.
Scheme 2
Scheme 2. Synthesis of 3,5-Dimethyl-N-phenethyl-1H-pyrazole-4-sulfonamide and 1,3,5-Trimethyl-N-phenethyl-1H-pyrazole-4-sulfonamide
Figure 2
Figure 2
FT-IR spectra of N-(2-(cyclohex-1-en-1-yl)ethyl)-1,3,5-trimethyl-1H-pyrazole-4-sulfonamide (MR-S1-2) in CDCl3.
Figure 3
Figure 3
1H NMR spectra of N-(2-(cyclohex-1-en-1-yl)ethyl)-1,3,5-trimethyl-1H-pyrazole-4-sulfonamide (MR-S1-2) in CDCl3.
Figure 4
Figure 4
13C NMR spectra of N-(2-(cyclohex-1-en-1-yl)ethyl)-1,3,5-trimethyl-1H-pyrazole-4-sulfonamide (MR-S1-2) in CDCl3.
Figure 5
Figure 5
HRMS spectra of N-(2-(cyclohex-1-en-1-yl)ethyl)-1,3,5-trimethyl-1H-pyrazole-4-sulfonamide (MR-S1-2).
See this image and copyright information in PMC

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