74159-80-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-Chloro-4-(ethylsulfonyl)-2-nitrobenzene is used as a chemical intermediate for the synthesis of pharmaceuticals and agrochemicals. Its unique structure allows it to be a key component in the production of various organic compounds, contributing to the development of new drugs and agricultural products.
Used in Dye and Pigment Manufacturing:
In the dye and pigment industry, 1-Chloro-4-(ethylsulfonyl)-2-nitrobenzene is utilized as a raw material. Its chemical properties make it suitable for the creation of dyes and pigments, enhancing the color and performance of these products.
Used in Industrial Product Manufacturing:
This versatile compound is also used as a raw material in the manufacturing of other industrial products. Its properties allow it to be incorporated into various formulations, improving the performance and characteristics of the final products.
Used in Agricultural Applications:
1-Chloro-4-(ethylsulfonyl)-2-nitrobenzene is employed as a pesticide and herbicide ingredient in some agricultural applications. Its ability to control pests and weeds contributes to increased crop yields and improved agricultural productivity.

InChI:InChI=1/C8H8ClNO4S/c1-2-15(13,14)6-3-4-7(9)8(5-6)10(11)12/h3-5H,2H2,1H3

Upstream product

• 7205-80-3 1-(ethylsulfonyl)-4-chlorobenzene 
• 5120-72-9 p-chlorophenyl ethyl sulfide 
• 98-60-2 4-chlorobenzenesulfonyl chloride 

Downstream Products

• 1067155-93-4 C₁₉H₂₉N₃O₆S 
• 886049-24-7 4-(ethylsulfonyl)-2-nitro-N-(tetrahydro-2H-pyran-4-ylmethyl)aniline 
• 84996-11-2 4-(ethylsulfonyl)-2-nitro-phenol 
• 1067155-96-7 C₁₉H₃₁N₃O₄S 

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.

COMPOUNDS AND COMPOSITIONS FOR TREATMENT OF BREAST CANCER

The present invention provides novel methods of treating triple-negative breast cancer (TNBC). In certain embodiments, the methods of the invention do not require the use of ionizing radiation therapies. In other embodiments, the methods of the invention do not harm non-cancerous cells.

Synthetic method of 2-amino-4-(ethylsulfonyl) phenol

The invention provides a synthetic method of 2-amino-4-(ethylsulfonyl) phenol. The method comprises the following steps that firstly, 4-ethylsulfonyl-2-nitro-chlorobenzene and alkali are subjected to a reaction in a solvent to obtain 4-(ethylsulfonyl)-2-nitro-phenol; then, the 4-(ethylsulfonyl)-2-nitro-phenol obtained in the last step is reduced to obtain 2-amino-4-(ethylsulfonyl) phenol. The novel synthesis route is designed, no high temperature or high pressure is needed in the reaction process, reaction conditions are mild, and the reaction yield and product purity are high, so that the production cost of the product is lowered, the product quality is improved, the preparation technology is more reasonable, and large batch industrial production is facilitated.

Syntheses and In Vitro Anticancer Properties of Novel Radiosensitizers

Series of 4-(ethylsulfonyl)-1-halogen-2-nitrobenzene (3a-e) and 1-(4-halogen-3-nitrophenyl) propan-1-one (5a-d) analogs designed as novel radiosensitizers using bromonitropropiophenone and bromonitrobenzonitrile as lead compounds were synthesized. The anticancer activities of the compounds were evaluated in vitro using human prostate cancer (DU-145) and breast cancer (MCF-7) cell lines and the MTT assay. From the series, six compounds (3b-e, 5b-c) exhibited potent growth inhibitory effects against both cell lines. The most active, compound 3d, is an iodosulfone and is significantly more potent than the lead compound 5c at 10μm. Compounds were then compared with doxorubicin, a clinically used anticancer compound for breast and prostate cancers. Our most active compound 3d is more effective than doxorubicin at the dose level of 10μm at 3days after radiation, cell viabilities of 18%, 13% compared to 87%, 94% against MCF-7, and 15%, 20% compared to 60%, 75% against DU-145 without and with radiation, respectively. At 10μm, compound 5c had no effects as compared to control, whereas compound 3d reduced DU-145 cell viability to 16% and that of MCF-7 cells to 9% even at 5days after radiation. These results are very encouraging. Future studies include testing the compounds in vivo with and without radiation. Our most active compound 3d is significantly more effective than doxorubicin or lead compound 5c at the dose level of 10μm, without and with radiation; and in MCF-7 and DU-145 cell lines. These results are very encouraging. Future studies include testing the compounds in vivo without and with radiation.

5-Sulfonyl-benzimidazoles as selective CB2 agonists

A novel series of benzimidazole CB2-receptor agonists was synthesized and the structure-activity relationship explored. The results showed agonistic activities with an EC50 up to 0.5 nM and excellent selectivity (>4000-fold) over the CB1 receptor. The size of the substituent on the 2-position determined the level of agonism, ranging from inverse agonism to partial agonism to full agonism, which was more pronounced for the rat CB2 receptor. A wide variation of sulfonyl substituents at the benzimidazole 5-position was tolerated, which was used to optimize the drug-like properties. This resulted into lead compound 14j that can be used to investigate the potential of a selective, peripherically acting CB2 agonist. The in vitro profile of key compounds is displayed using pie bar charts (VlaaiVis).

Sulfonyl benzimidazole derivatives

This invention relates to compounds of the formula (I): or a pharmaceutically acceptable salt thereof, wherein A, B, R1, R2 and R3 are each as described herein, and compositions containing such compounds, and the use of such compounds in the treatment of a condition mediated by CB2 receptor activity such as, but not limited to, inflammatory pain, nociceptive pain, neuropathic pain, fibromyalgia, chronic low back pain, visceral pain, acute cerebral ischemia, pain, chronic pain, acute pain, post herpetic neuralgia, neuropathies, neuralgia, diabetic neuropathy, HIV-related neuropathy, nerve injury, rheumatoid arthritic pain, osteoarthritic pain, back pain, cancer pain, dental pain, fibromyalgia, neuritis, sciatica, inflammation, neurodegenerative disease, cough, broncho constriction, irritable bowel syndrome (IBS), inflammatory bowel disease (IBD), colitis, cerebrovascular ischemia, emesis such as cancer chemotherapy-induced emesis, rheumatoid arthritis, asthma, Crohn's disease, ulcerative colitis, asthma, dermatitis, seasonal allergic rhinitis, GERD, constipation, diarrhea, functional gastrointestinal disorders, irritable bowel syndrome, cutaneous T cell lymphoma, multiple sclerosis, osteoarthritis, psoriasis, systemic lupus erythematosus, diabetes, glaucoma, osteoporosis, glomerulonephritis, renal ischemia, nephritis, hepatitis, cerebral stroke, vasculitis, myocardial infarction, cerebral ischemia, reversible airway obstruction, adult respiratory disease syndrome, COPD, cryptogenic fibrosing alveolitis and bronchitis.