23306-60-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(Ethylsulphonyl)-2-nitroaniline is used as a chemical intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Dye Industry:
In the dye industry, 4-(ethylsulphonyl)-2-nitroaniline is utilized as a precursor in the production of dyes, providing a range of color options for various applications.
Used in Agrochemical Industry:
4-(Ethylsulphonyl)-2-nitroaniline is employed as an intermediate in the synthesis of agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.
Safety and Handling:
Due to its potential mutagenic and carcinogenic properties, 4-(ethylsulphonyl)-2-nitroaniline should be handled with caution, ensuring proper safety measures are in place during its use and disposal. This includes the use of personal protective equipment, safe storage, and responsible disposal methods to minimize exposure and environmental impact.

InChI:InChI=1/C8H10N2O4S/c1-2-15(13,14)6-3-4-7(9)8(5-6)10(11)12/h3-5H,2,9H2,1H3

Upstream product

• 74159-80-1 1-chloro-4-(ethylsulphonyl)-2-nitrobenzene 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 7205-80-3 1-(ethylsulfonyl)-4-chlorobenzene 

Downstream Products

• 2976-31-0 1-(ethylsulfonyl)-3-nitrobenzene 

Relevant academic research and scientific papers

Design, synthesis and anticancer/antiestrogenic activities of novel indole-benzimidazoles

Indole-benzimidazoles have recently gained attention due to their antiproliferative and antiestrogenic effects. However, their structural similarities and molecular mechanisms shared with selective estrogen receptor modulators (SERMs) have not yet been investigated. In this study, we synthesized novel ethylsulfonyl indole-benzimidazole derivatives by substituting the first (R1) and fifth (R2) positions of benzimidazole and indole groups, respectively. Subsequently, we performed 1H NMR, 13C NMR, and Mass spectral and in silico docking analyses, and anticancer activity screening studies of these novel indole-benzimidazoles. The antiproliferative effects of indole-benzimidazoles were found to be more similar between the estrogen (E2) responsive cell lines MCF-7 and HEPG2 in comparison to the Estrogen Receptor negative (ER-) cell line MDA-MB-231. R1:p-fluorobenzyl group members were selected as lead compounds for their potent anticancer effects and moderate structural affinity to ER. Microarray expression profiling and gene enrichment analyses (GSEA) of the selected compounds (R1:p-fluorobenzyl: 48, 49, 50, 51; R1:3,4-difluorobenzyl: 53) helped determine the similarly modulated cellular signaling pathways among derivatives. Moreover, we identified known compounds that have significantly similar gene signatures to that of 51 via queries performed in LINCS database; and further transcriptomics comparisons were made using public GEO datasets (GSE35428, GSE7765, GSE62673). Our results strongly demonstrate that these novel indole-benzimidazoles can modulate ER target gene expression as well as dioxin-mediated aryl hydrocarbon receptor and amino acid deprivation-mediated integrated stress response signaling in a dose-dependent manner.