64268-93-5

Usage

Uses

Used in Pharmaceutical Industry:
1-[(4-NITROPHENYL)SULFONYL]PIPERIDINE is used as a building block in the synthesis of pharmaceuticals for its anti-inflammatory and analgesic properties, making it a promising candidate for drug development.
Used in Agrochemical Industry:
1-[(4-NITROPHENYL)SULFONYL]PIPERIDINE is used as a building block in the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural chemicals.
Used in Materials Science:
1-[(4-NITROPHENYL)SULFONYL]PIPERIDINE is used as a corrosion inhibitor in metalworking and industrial applications, providing protection against metal corrosion and enhancing the durability of materials.

InChI:InChI=1/C11H14N2O4S/c14-13(15)10-4-6-11(7-5-10)18(16,17)12-8-2-1-3-9-12/h4-7H,1-3,8-9H2

Upstream product

• 110-89-4 piperidine 
• 155164-61-7 2-(4-nitrobenzenesulfonyl)-4,5-dichloropyridazin-3-one 
• 156840-00-5 2,4-dinitrophenyl 4-nitrobenzenesulfonate 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 173778-68-2 1,5-pentanediyl bis(diphenylphosphinite) 
• 111-29-5 1 ,5-pentanediol 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 1441409-91-1 (E)-ethyl 2-cyano-2-(4-nitrophenylsulfonyloxyimino)acetate 
• 30362-87-9 p-Nitrophenyl p-nitrobenzenesulphonate 

Downstream Products

• 952-97-6 4-nitrophenyl phenyl sulfide 
• 1601403-39-7 3-oxo-N-(4-(piperidin-1-ylsulfonyl)phenyl)benzo[d]isothiazole-2(3H)-carboxamide 
• 790691-27-9 N-[4-(isocyanato)phenylsulfonyl]piperidine 
• 6336-68-1 4-(piperidin-1-ylsulfonyl)aniline 

Relevant academic research and scientific papers

Antimicrobial action of arylsulfonamides bearing (aza)norbornane and related motifs: evaluation of new promising anti-MRSA agents

Arylsulfonamides bearing (aza)norbornane and related motifs were evaluated for: (1) antimicrobial activity toward five key ESKAPE pathogenic bacteria, one Gram‐positive bacteria methicillin‐resistant Staphylococcus aureus (MRSA, ATCC 43300), four Gram‐neg

Structure-activity relationship studies in substituted sulfamoyl benzamidothiazoles that prolong NF-κB activation

In the face of emerging infectious diseases, there remains an unmet need for vaccine development where adjuvants that enhance immune responses to pathogenic antigens are highly desired. Using high-throughput screens with a cell-based nuclear factor κB (NF-κB) reporter assay, we identified a sulfamoyl benzamidothiazole bearing compound 1 that demonstrated a sustained activation of NF-κB after a primary stimulus with a Toll-like receptor (TLR)-4 agonist, lipopolysaccharide (LPS). Here, we explore systematic structure–activity relationship (SAR) studies on compound 1 that indicated the sites on the scaffold that tolerated modification and yielded more potent compounds compared to 1. The selected analogs enhanced release of immunostimulatory cytokines in the human monocytic cell line THP-1 cells and murine primary dendritic cells. In murine vaccination studies, select compounds were used as co-adjuvants in combination with the Food and Drug Administration approved TLR-4 agonistic adjuvant, monophosphoryl lipid A (MPLA) that showed significant enhancement in antigen-specific antibody titers compared to MPLA alone. Additionally, our SAR studies led to identification of a photoaffinity probe which will aid the target identification and mechanism of action studies in the future.

VACCINE ADJUVANT

Compounds useful as an adjuvant, e.g., formulas (I)-(VI) and uses thereof, for example, with immunogenic moieties or other adjuvants, are provided.

Functionalization of Piperidine Derivatives for the Site-Selective and Stereoselective Synthesis of Positional Analogues of Methylphenidate

Rhodium-catalyzed C?H insertions and cyclopropanations of donor/acceptor carbenes have been used for the synthesis of positional analogues of methylphenidate. The site selectivity is controlled by the catalyst and the amine protecting group. C?H functionalization of N-Boc-piperidine using Rh2(R-TCPTAD)4, or N-brosyl-piperidine using Rh2(R-TPPTTL)4 generated 2-substitited analogues. In contrast, when N-α-oxoarylacetyl-piperidines were used in combination with Rh2(S-2-Cl-5-BrTPCP)4, the C?H functionalization produced 4-susbstiuted analogues. Finally, the 3-substituted analogues were prepared indirectly by cyclopropanation of N-Boc-tetrahydropyridine followed by reductive regio- and stereoselective ring-opening of the cyclopropanes.

1,2-Benzisothiazol-3-one derivatives as a novel class of small-molecule caspase-3 inhibitors

A novel series of 1,2-benzisothiazol-3-one derivatives was synthesized and their biological activities were evaluated for inhibiting caspase-3 and -7 activities, in which some of them showed low nanomolar potency against caspase-3 in vitro and significant protection against apoptosis in a camptothecin-induced Jurkat T cells system. Among the tested compounds, compound 5i exhibited the most potent caspase-3 inhibitory activity (IC50 = 1.15 nM). The molecular docking predicted the interactions and binding modes of the synthesized inhibitor in the caspase-3 active site.

Sulfonamide synthesis via oxyma-O-sulfonates - Compatibility to acid sensitive groups and solid-phase peptide synthesis

A milder and more efficient procedure for the synthesis of sulfonamides by activating sulfonic acid groups as the corresponding sulfonate esters of ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) is reported. This method is greener than all other existing protocols for the purpose. Other important advantages lie in (a) its applicability to less nucleophilic anilines under ambient and milder conditions and (b) its compatibility with solid phase peptide synthesis and acid-labile groups such as trityl (Trt) and tBu, which empowers the solid phase synthesis of sulfonamides of various peptides. To illustrate this, the syntheses of three sulfonamide derivatives of the peptide GAILG-NH2, which is relevant in the context of drug design against type 2 diabetes, are demonstrated by using Fmoc-based solid-phase peptide synthesis (SPPS). The activation of sulfonic acids as their corresponding O-sulfonate esters facilitates sulfonamide synthesis, which can be applied to those substrates that possess acid-labile functional groups and is compatible with solid phase synthesis. Copyright

Potent non-nucleoside inhibitors of the measles virus RNA-dependent RNA polymerase complex

Measles virus (MV) is one of the most infectious pathogens known. In spite of the existence of a vaccine, approximately 350000 deaths/year result from MV or associated complications. Antimeasles compounds could conceivably diminish these statistics and pr

Bisaryl-sulfonamides

Compounds, compositions and methods are provided that are useful in the treatment or prevention of a condition or disorder mediated by PPARγ or PPARδ. In particular, the compounds of the invention modulate the function of PPARγ or PPARδ. The subject methods are particularly useful in the treatment and/or prevention of diabetes, obesity, hypercholesterolemia, rheumatoid arthritis and atherosclerosis.

A new method for the preparation of nitrogen-containing cyclic compounds from p-nitrobenzenesulfonamide and alkyl bis(diphenylphosphinite)s by oxidation-reduction condensation using 1-azidoadamantane

A new and efficient method was established for the preparation of nitrogen-containing cyclic compounds from p-nitro-benzenesulfonamide, bisphosphinites, and 1-azidoadamantane in good yields under neutral conditions. Copyright