34235-81-9

Usage

InChI:InChI=1/C13H19NO4S/c1-4-10(3)12(13(15)16)14-19(17,18)11-7-5-9(2)6-8-11/h5-8,10,12,14H,4H2,1-3H3,(H,15,16)

Upstream product

• 73-32-5 DL-isoleucine 
• 98-59-9 p-toluenesulfonyl chloride 
• 73-32-5 L-isoleucine 
• 104-15-4 toluene-4-sulfonic acid 
• 319-78-8 isoleucine 
• 959215-79-3 (2RS,3S)-2-amino-3-methylpentanoic acid 

Downstream Products

• 26465-78-1 (2-methylbutane-1,1-diyl)dibenzene 
• 26613-38-7 1,2-diphenyl-2-methylbutane 
• 1303530-13-3 2-[(2-bromobenzyl)(toluene-4-sulfonyl)amino]-3-methylpentanoic acid methyl ester 
• 1303530-21-3 N-(2-bromobenzyl)-N-(1-hydroxymethyl-2-methylbutyl)-4-methylbenzenesulfonamide 
• 932725-33-2 3-sec-butyl-4-(toluene-4-sulfonyl)-2,3,4,5-tetrahydrobenzo[f][1,4]oxazepine 
• 1361127-81-2 (E)-ethyl 3-(N-((3S,4S)-1-diazo-4-methyl-2-oxohexan-3-yl)-4-methylphenylsulfonamido)acrylate 
• 1361126-99-9 (2S,3S)-2-(N-((E)-3-ethoxy-3-oxoprop-1-enyl)-4-methylphenylsulfonamido)-3-methylpentanoic acid 
• 1254592-72-7 C₁₅H₂₅N₃O₄PdS*H₂O 
• 1428989-73-4 C₂₃H₂₅N₃O₄PdS 
• 898558-08-2 (2S,3S)-N-(4-toluenesulfonyl)-2-amino-3-methyl-pentanol 
• 1018897-52-3 [Cu(N-(p-toluenesulfonyl)-isoleu(-2H))(NH₃)2] 

Relevant academic research and scientific papers

Isoleucine with secondary sulfonamide functionality as anticancer, antibacterial and antifungal agents

Isoleucine substituted analogues with secondary sulfonamide group (I1–I6) have been synthesized. Structures of synthesized analogues have been confirmed by Fourier Transform-Infrared Red, Nuclear Magnetic Resonance (1H and 13C) and ESI-MS spectroscopic tools. Cytotoxic screenings of synthesized analogues have been done on MCF-7 (breast), Prostate Cancer-3 (PC-3) and A549 (lung) cancer cell lines. N-(1-isobutyl-2-oxo-2-anilinoethyl) p-toluene sulfonamide (I5) screened to be better cytotoxic agent on MCF-7 and A549 cell lines whereas N-(1-isobutyl-2-oxo-2-p-chloroanilino ethyl) benzene sulfonamide (I3) against PC-3 cell line. Cell cycle analysis of N-(1-isobutyl-2-oxo-2-anilinoethyl) p-toluene sulfonamide (I5) analogue has been carried out on A549 cell line in comparison to control and Vinblastine (standard drug). Complete arrest in G0 and G1 phase along with mild disturbance in S-phase of cell cycle has been observed. The screened analogues (I1–I6) also showed good antifungal and antibacterial potential against gram positive as well as gram negative strains. Computer simulation indicated good bioactivity prediction by the ‘Lipinski rule’ and synthesized analogues did not violate this rule. Docking study of isoleucine sulfonamide analogues (I1–I6) were carried out to determine the possible interaction sites of the analogues with p53 tumor suppressor-DNA complex and demonstrate that the analogues confirmed binding and inhibition with the most mutated residues of p53. Density functional theory has been used to correlate the electronic and chemical properties of analogues and they were found to be stable and chemically reactive. Thus the results suggest that isoleucine substituted sulfonamide analogues can serve as a structural model for the design of anticancer agents, antibacterial agents as well as antifungal agents with better inhibitory potential. Communicated by Ramaswamy H. Sarma.

Novel Phenoxazinones as potent agonist of PPAR-α: Design, synthesis, molecular docking and in vivo studies

Background: The use of statin, a 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor for the treatment of dyslipidemia has been associated with dose limiting hepatoxicity, mytotoxicity and tolerability due to myalgias thereby necessitating the synthesis of new drug candidates for the treatment of lipid disorder. Methods: The reaction of appropriate benzenesulphonamide with substituted phenoxazinone in the presence of phenylboronic acid gave the targeted compounds. The molecular docking study were carried out using autodock tool against peroxisome proliferator activated receptor alpha. The in vivo lipid profile were assayed using conventional methods. The kidney and liver function test were carried out to assess the effect of the derivatives on the organs. The LD50 of the most active derivatives were determined using mice. Results: The targeted compounds were successfully synthesized in excellent yields and characterized using spectroscopic techniques. The results of the molecular docking experiment showed that they were good stimulant of peroxisome proliferator activated receptor alpha. Compound 9f showed activity at Ki of 2.8 nM and binding energy of 12.6 kcal/mol. All the compounds tested reduced triglyceride, total cholesterol, low density lipoprotein cholesterol and very low density lipoprotein cholesterol level in the mice model. Some of the reported compounds also increased high density lipoprotein cholesterol level in the mice. The compounds did not have appreciable effect on the kidney and liver of the mice used. The LD50 showed that the novel compounds have improved toxicity profile. Conclusion: The synthesis of fifteen new derivatives of carboxamides bearing phenoxazinone and sulphonamide were successful. The compounds possessed comparable activity to gemfibrozil. The reported compounds had better toxicity profile than gemfibrozil and could serve as a replacement for the statins and fibrate class of lipid agents.

NMR-based assignment of isoleucine: Vs. allo -isoleucine stereochemistry

A simple 1H and 13C NMR spectrometric analysis is demonstrated that permits differentiation of isoleucine and allo-isoleucine residues by inspection of the chemical shift and coupling constants of the signals associated with the proton and carbon at the α-stereocentre. This is applied to the estimation of epimerisation during metal-free N-arylation and peptide coupling reactions.

Metal complexes of tosyl sulfonamides: Design, X-ray structure, biological activities and molecular docking studies

The present study reports the synthesis of Zn(ii) complexes of tosyl sulfonamide derivatives obtained by the reaction of tosyl chloride with l-amino acids. The ligands and their complexes were characterized by IR, 1H and 13C-NMR, GC-

Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor

(Chemical Equation Presented) A novel and highly enantioselective Ru-catalyzed hydrogenation of N-sulfonylated-α-dehydroamino acids has been discovered and demonstrated in the synthesis of an anthrax lethal factor inhibitor (LFI). Herein, this methodology is used to prepare N-sulfonylated amino acids in up to 98% ee. This unprecedented hydrogenation uses a chiral Ru catalyst rather than Rh as typical for acylated dehydroamino acids and esters, and this work reports the first asymmetric hydrogenation of a tetrasubstituted dehydroamino acid derivative using a Ru catalyst.