68502-19-2

Basic information

• Product Name: 4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine
• Synonyms: 4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine;5-(Ethylsulfonyl)-2-(MethylaMino)phenylaMine
• CAS NO: 68502-19-2
• Molecular Formula: C₉H₁₄N₂O₂S
• Molecular Weight: 214
• Mol File: 68502-19-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine(68502-19-2)
• EPA Substance Registry System: 4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine(68502-19-2)

Safety Data

• Hazardous Substances Data: 68502-19-2(Hazardous Substances Data)

Usage

General Description

4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine, also known as sulfaethidole, is a chemical compound with the molecular formula C10H16N2O2S. It is an organic compound with a sulfonamide group, which is often used as a sulfonamide antibiotic in veterinary medicine to treat a variety of bacterial infections. Sulfaethidole works by inhibiting the growth of bacteria by interfering with the synthesis of folic acid, a necessary component for bacteria to grow and multiply. It is also used as a food preservative and in the production of certain dyes. However, its use as an antibiotic in human medicine has declined due to the availability of more effective and less toxic alternatives. Overall, 4-(ethylsulfonyl)-N1-methylbenzene-1,2-diamine has multiple industrial and medicinal applications, but its use is now limited in human medicine due to concerns about toxicity and the availability of safer alternatives.

Upstream product

• 21355-86-2 (4-Ethanesulfonyl-2-nitro-phenyl)-methyl-amine 
• 74159-80-1 1-chloro-4-(ethylsulphonyl)-2-nitrobenzene 
• 98-60-2 4-chlorobenzenesulfonyl chloride 
• 7205-80-3 1-(ethylsulfonyl)-4-chlorobenzene 

Relevant articles and documents

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.