587850-67-7

Usage

Biological Activity

c7280948 is a novel prmt1 inhibitor with ic50 value of 12.75 μm [1].protein arginine methyltransferase 1 (prmt1) is a histone methyltransferase specific for histone h4. prmt1 catalyzes the transfer of the methyl group from sam to the guanidine nitrogen atoms of arginine residues to produce monomethyl arginines (mma) and asymmetric dimethyl arginines (adma) [2].c7280948 is a novel prmt1 inhibitor. c7280948 interacts with aromatic residues at the hprmt1 substrate binding pocket (tyr 147 and tyr 160) [1]. c7280948 inhibited hprmt1 with ic50 value of 26.7 μm [3].

references

[1]. heinke r, spannhoff a, meier r, et al. virtual screening and biological characterization of novel histone arginine methyltransferase prmt1 inhibitors. chemmedchem, 2009, 4(1): 69-77. [2]. itoh y, suzuki t, miyata n. small-molecular modulators of cancer-associated epigenetic mechanisms. mol biosyst, 2013, 9(5): 873-896. [3]. bissinger em, heinke r, spannhoff a, et al. acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hprmt1. bioorg med chem, 2011, 19(12): 3717-3731.

Upstream product

• 289061-22-9 N-(4-(N-phenethylsulfamoyl)phenyl)acetamide 
• 52374-24-0 N-(4-nitrobenzenesulfonyl)-2-phenylethylamine 
• 64-04-0 phenethylamine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 60-12-8 2-phenylethanol 
• 63-74-1 sulfanilamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Downstream Products

• 1314230-52-8 4-amino-N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 600129-08-6 N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 600129-24-6 4-chloro-N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 600131-72-4 N-[4-(phenethylsulfamoyl)phenyl]-4-phenyl-benzamide 
• 587846-64-8 4-nitro-N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 606922-74-1 4-chloro-N-[4-(phenethylsulfamoyl)phenyl]benzenesulfonamide 
• 600131-24-6 3,4-dichloro-N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 600129-12-2 4-bromo-N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 651296-94-5 N-[4-(phenethylsulfamoyl)phenyl]-2-phenyl-acetamide 
• 1314230-51-7 4-iodo-N-[4-(phenethylsulfamoyl)phenyl]benzamide 
• 1456736-81-4 N-phenethyl-4-(4-((p-tolyloxy)methyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide 
• 1456736-80-3 4-(4-((naphthalen-2-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide 
• 1456736-79-0 4-(4-((naphthalen-1-yloxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide 
• 1456736-78-9 N-phenethyl-4-(4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Discovery of secondary sulphonamides as IDO1 inhibitors with potent antitumour effects in vivo

Indoleamine 2,3-dioxygenase 1 (IDO1) as a key rate-limiting enzyme in the kynurenine pathway of tryptophan metabolism plays an important role in tumour immune escape. Herein, a variety of secondary sulphonamides were synthesised and evaluated in the HeLa cell-based IDO1/kynurenine assay, leading to the identification of new IDO1 inhibitors. Among them, compounds 5d, 5l and 8g exhibited the strongest inhibitory effect with significantly improved activity over the hit compound BS-1. The in vitro results showed that these compounds could restore the T cell proliferation and inhibit the differentiation of na?ve CD4+ T cell into highly immunosuppressive FoxP3+ regulatory T (Treg) cell without affecting the viability of HeLa cells and the expression of IDO1 protein. Importantly, the pharmacodynamic assay showed that compound 5d possessed potent antitumour effect in both CT26 and B16F1 tumours bearing immunocompetent mice but not in immunodeficient mice. Functionally, subsequent experiments demonstrated that compound 5d could effectively inhibit tumour cell proliferation, induce apoptosis, up-regulate the expression of IFN-γ and granzyme B, and suppress FoxP3+ Treg cell differentiation, thereby activate the immune system. Thus, compound 5d could be a potential and efficacious agent for further evaluation.

Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HTS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial β-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure-activity relationships of these compounds were explored.

Method for synthesizing C-7280948

The invention discloses a method for synthesizing C-7280948. The method comprises the following steps that sulfanilamide, phenethyl alcohol, a complex catalyst and alkali are added into a reaction container, after the reaction mixture reacts for several h

Synthesis and molecular docking of 1,2,3-triazole-based sulfonamides as aromatase inhibitors

Abstract A series of 1,4-disubstituted-1,2,3-triazoles (13-35) containing sulfonamide moiety were synthesized and evaluated for their aromatase inhibitory effects. Most triazoles with open-chain sulfonamide showed significant aromatase inhibitory activity

Novel 1,4-naphthoquinone-based sulfonamides: Synthesis, QSAR, anticancer and antimalarial studies

A novel series of 1,4-naphthoquinones (33-44) tethered by open and closed chain sulfonamide moieties were designed, synthesized and evaluated for their cytotoxic and antimalarial activities. All quinone-sulfonamide derivatives displayed a broad spectrum o

Effective Recognition of Different Types of Amino Groups: From Aminobenzenesulfonamides to Amino-(N-alkyl)benzenesulfonamides via Iridium-Catalyzed N-Alkylation with Alcohols

(Chemical Equation Presented). A simple, highly efficient, and general strategy for the direct synthesis of amino-(N-alkyl)benzenesulfonamides has been accomplished via direct N-alkylation of aminobenzenesulfonamides bearing both different types of amino groups with alcohols as alkylating agents. Notably, this research exhibited the potential for the recognition of different types of amino groups in the N-alkylation of complex molecules with alcohols, facilitating the progress of the transition-metal-catalyzed "hydrogen autotransfer (or hydrogen-borrowing) process."

Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1- yl)-N-phenethylbenzenesulfonamides

A new series of 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N- phenethylbenzenesulfonamide derivatives 5 were synthesized through the Click approach and evaluated for their cytotoxic activity against four cancer cell lines (HuCCA-1, HepG2, A549, and MOLT-3)

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.

SULFONAMIDO COMPOUNDS THAT ANTAGONISE THE VANILLOID TRPV1 RECEPTOR

The invention relates to sulfonamido derivatives of formula (I) wherein R1-R7 are as defined in the description. Compounds (I) antagonize the 10 vanilloid receptor and can be used for the preparation of medicaments for the treatment of inflammatory states.

Novel lead structures for antimalarial farnesyltransferase inhibitors

Through the combination of nitrophenylfurylacryloyl moiety which has been designed to occupy an aryl binding site of farnesyltransferase with several AA(X)-peptidomimetic substructures some novel farnesyltransferase inhibitors were obtained. Evaluation of their antimalarial activity and some initial modifications yielded a 4-benzophenone- and a sulfonamid-based novel lead for antimalarial farnesyltransferase inhibitors.