20443-75-8

Usage

Uses

Used in Pharmaceutical Industry:
4'-Nitro-biphenyl-4-sulfonyl chloride is used as an intermediate for the synthesis of various drugs, contributing to the development of new pharmaceuticals with potential therapeutic applications.
Used in Organic Synthesis:
4'-Nitro-biphenyl-4-sulfonyl chloride is used as a reagent in organic synthesis for the preparation of various organic compounds, facilitating the creation of new chemical entities with diverse properties and applications.
Used in Agrochemical Production:
As an important building block, 4'-Nitro-biphenyl-4-sulfonyl chloride is utilized in the production of agrochemicals, aiding in the development of effective and targeted pest control solutions.
Used in Dye and Pigment Manufacturing:
4'-Nitro-biphenyl-4-sulfonyl chloride is employed in the manufacturing of dyes and pigments, contributing to the creation of vibrant and stable colorants for various industries.
Safety Precautions:
It is important to handle 4'-Nitro-biphenyl-4-sulfonyl chloride with care, as it is corrosive and can cause skin and eye irritation upon contact. Proper safety measures, such as wearing protective gear and working in a well-ventilated area, should be taken to minimize potential hazards.

Upstream product

• 91493-72-0 4-nitrobiphenylsulfonic acid 
• 92-93-3 1-phenyl-4-nitrobenzene 

Downstream Products

• 116748-59-5 4'-Nitro-biphenyl-4-sulfonic acid 2-formyl-phenyl ester 
• 857078-06-9 N-({4'-[(1-benzofuran-2-ylcarbonyl)amino]-1,1'-biphenyl-4-yl}sulfonyl)glycine t-butyl ester 

Relevant academic research and scientific papers

Biaryl sulfonamides and methods for using same

The present invention relates to biaryl sulfonamides and their use as, for example, metalloproteinase inhibitors.

Identification of potent and selective MMP-13 inhibitors

A potent, selective series of MMP-13 inhibitors has been derived from a weak (3.2 μM) inhibitor that did not bear a zinc chelator. Structure-based drug design strategies were employed to append a Zn-chelating group to one end of the molecule and functionality to enhance selectivity to the other. A compound from this series demonstrated rat oral bioavailability and efficacy in a bovine articular cartilage explant model.

Synthesis of radiolabeled biphenylsulfonamide matrix metalloproteinase inhibitors as new potential PET cancer imaging agents

Novel matrix metalloproteinase (MMP) inhibitor radiotracers, (S)-3-methyl-2-(2′,3′,4′-methoxybiphenyl-4-sulfonylamino)- butyric acid [11C]methyl ester (1a-c), (S)-3-methyl-2-(2′,3′,4′-fluorobiphenyl-4-sulfonylamino)- butyric acid [11C]methyl ester (1d-f), and (S)-3-methyl-2-(4′-nitrobiphenyl-4-sulfonylamino)-butyric acid [11C]methyl ester (1g), a series of substituted biphenylsulfonamide derivatives, have been synthesized for evaluation as new potential positron emission tomography (PET) cancer imaging agents.

Structure-activity relationships and pharmacokinetic analysis for a series of potent, systemically available biphenylsulfonamide matrix metalloproteinase inhibitors

A series of biphenylsulfonamide derivatives of (S)-2-(biphenyl-4- sulfonylamino)-3-methylbutyric acid (5) were prepared and evaluated for their ability to inhibit matrix metalloproteinases (MMPs). For this series of compounds, our objective was to systematically replace substituents appended to the biphenyl and α-position of 5 with structurally diverse functionalities to assess the effects these changes have on biological and pharmacokinetic activity. The ensuing structure-activity relationship (SAR) studies showed that biphenylsulfonamides substituted with bromine in the 4'- position (11c) significantly improved in vitro activity and exhibited superior pharmacokinetics (C(max), t(1/2), AUCs), relative to compound 5. Varying the lipophilicity of the α-position by replacing the isopropyl group of 11c with a variety of substituents, in general, maintained potency versus MMP-2, -3, and -13 but decreased the oral systemic availability. Subsequent evaluation of its enantiomer, 11c', showed that both compounds were equally effective MMP inhibitors. In contrast, the corresponding hydroxamic acid enantiomeric pair, 16a (S-isomer) and 16a' (R-isomer), stereoselectivity inhibited MMPs. For the first time in this series, 16a' provided nanomolar potency against MMP-1, -7, and -9 (IC50'S = 110, 140, and 18 nM, respectively), whereas 16a was less potent against these MMPs (IC(50)'S = 24, 78, and 84 μM, respectively). However, unlike 11c, compound 16a' afforded very low plasma concentrations following a single 5 mg/kg oral dose in rat. Subsequent X-ray crystal structures of the catalytic domain of stromelysin (MMP-3CD) complexed with inhibitors from closely related series established the differences in the binding mode of carboxylic acid-based inhibitors (11c,c') relative to the corresponding hydroxamic acids (16a,a').