17328-16-4

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-[Sulfonylbis(1,4-phenylene)]bis(chloroacetamide) is used as an inhibitor of human PRMT1 for its selective action over other arginine methyltransferases like CARM1 and the lysine methyltransferase Set7/9. This selective inhibition makes it a valuable tool in the development of targeted therapies for various diseases, including cancer.
Used in Cancer Treatment:
N,N'-[Sulfonylbis(1,4-phenylene)]bis(chloroacetamide) is used as an anti-cancer agent, particularly in the treatment of breast cancer (MCF-7a) and prostate cancer (LNCaP) cell lines. It demonstrates growth inhibition at low concentrations (GI50s = 1.97 and 4.49 μM, respectively) and has the potential to disrupt androgen-dependent gene transcription, which may be beneficial in hormone-responsive cancer types.
Used in Antimalarial Applications:
N,N'-[Sulfonylbis(1,4-phenylene)]bis(chloroacetamide) is used as an antimalarial agent, with properties that help eradicate Plasmodium berghei in mice when administered at a dosage of 80 mg/kg. This suggests its potential use in the development of new treatments for malaria.

References

1) Bissinger?et al. (2011),?Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methytransferase hPRMT1; Bioorg. Med. Chem.,?19?3717

Upstream product

• 79-04-9 chloroacetyl chloride 
• 80-08-0 dapsone 

Downstream Products

• 2731-67-1 bis-[4-(2-morpholino-acetylamino)-phenyl]-sulfone 
• 865439-31-2 2-azido-N-{4-[4-(2-azido-acetylamino)-benzenesulfonyl]-phenyl}-acetamide 
• 2731-65-9 bis-(4-piperidinoacetylamino-phenyl)-sulfone 

Relevant academic research and scientific papers

Design and synthesis of new sulfonamides–based flt3 inhibitors

Background: Flt3 is an oncogenic kinase involved in different leukemias. It is most prominently associated with acute myeloid leukemia (AML). Flt3-specific inhibitors have shown promising results in interfering with AML. Methods: The crystallographic structures of two inhibitors complexed within Flt3, namely, quizartinib and F6M, were used to guide the synthesis of new sulfonamide-based Flt3 inhibitors. Results: One of the prepared compounds showed low micromolar anti-Flt3 bioactivity, and interestingly, low micromolar bioactivity against the related oncogenic kinase VEGFR2.

Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1

Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes.

Size-specific ligands for RNA hairpin loops

The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo. Copyright

2-Amino-4'(phenylsulfonyl) acetanilides

A method of modulating the immune response system in a warm-blooded animal by the administration of N-substituted-phenylthioanilines, N-substituted-phenylsulfinylanilines, and N-substituted-phenylsulfonylanilines, certain of which are new compounds.