370883-85-5Relevant academic research and scientific papers
New sulphonamide pyrolidine carboxamide derivatives: Synthesis, molecular docking, antiplasmodial and antioxidant activities
Onoabedje, Efeturi A.,Ibezim, Akachukwu,Okoro, Uchechukwu C.,Batra, Sanjay
, (2021/03/16)
Carboxamides bearing sulphonamide functionality have been shown to exhibit significant lethal effect on Plasmodium falciparum, the causative agent of human malaria. Here we report the synthesis of thirty-two new drug-like sulphonamide pyrolidine carboxami
Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
, p. 1377 - 1384 (2021/06/06)
We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a sulfonyl radical, and coupling of sulfonyl radical with a benzyl radical formed via hydrogen abstraction by sulfate anion radical. The practicality of the present reaction is demonstrated by a gram-scale synthesis and one-step synthesis of anticancer-active compound. The mechanism studies are conducted using radical scavengers and deuterated toluene.
Synthesis, molecular docking and pharmacological investigation of some 4-methylphenylsulphamoyl carboxylic acid analogs
Egbujor, Melford C.,Okoro, Uchechukwu C.,Okafor, Sunday N.,Amasiatu, Ifeanyi S.,Amadi, Ugochukwu B.,Egwuatu, Pius I.
, p. 5357 - 5366 (2020/10/12)
Compounds bearing sulphonyl and amino acid moieties are considered the basis for sulfa drug development. The synthesis of 4-methylphenylsulphamoyl carboxylic acids and the evaluation of their pharmacological activities are reported. The synthesis of these
Phenotypic Screening of Chemical Libraries Enriched by Molecular Docking to Multiple Targets Selected from Glioblastoma Genomic Data
Aryal, Uma K.,Bailey, Barbara J.,Bum-Erdene, Khuchtumur,Corson, Timothy W.,Fishel, Melissa L.,Lee, Jonathan A.,Liu, Sheng,Meroueh, Samy O.,Pollok, Karen E.,Sishtla, Kamakshi,Wan, Jun,Wells, Clark D.,Xu, David,Zhou, Donghui
, p. 1424 - 1444 (2020/07/15)
Like most solid tumors, glioblastoma multiforme (GBM) harbors multiple overexpressed and mutated genes that affect several signaling pathways. Suppressing tumor growth of solid tumors like GBM without toxicity may be achieved by small molecules that selec
α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization
Kanyiva, Kyalo Stephen,Hamada, Daisuke,Makino, Sohei,Takano, Hideaki,Shibata, Takanori
supporting information, p. 5905 - 5909 (2018/09/14)
We developed a silver-catalyzed strategy for the generation of sulfonyl radicals from sulfonamides derived from α-amino acids. The reaction proceeded via a decarboxylation, N–S bond cleavage and radical cyclization sequence and allows the difunctionalization of alkynes and the synthesis of 3-sulfonylated coumarins. The reaction tolerated a broad scope of substrates and functional groups and could be extended to the synthesis of oxindoles and an isoquinolinedione by the capturing of the sulfonyl radical with an alkene moiety. Moreover, the proposed mechanism was supported experimentally and by DFT calculations.
Novel Phenoxazinones as potent agonist of PPAR-α: Design, synthesis, molecular docking and in vivo studies
Ugwu, David I.,Okoro, Uchechukwu C.,Mishra, Narendra K.,Okafor, Sunday N.
, (2018/05/30)
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.
New antiprotozoal agents: Synthesis and biological evaluation of different 4-(7-chloroquinolin-4-yl) piperazin-1-yl)pyrrolidin-2-yl)methanone derivatives
Ansari, Mohammad Fawad,Hayat, Faisal,Inam, Afreen,Kathrada, Fatima,van Zyl, Robyn L.,Coetzee, Maureen,Ahmad, Kamal,Shin, Dongyun,Azam, Amir
supporting information, p. 460 - 465 (2017/01/16)
In an endeavor to develop efficacious antiprotozoal agents 4-(7-chloroquinolin-4-yl) piperazin-1-yl)pyrrolidin-2-yl)methanone derivatives (5–14) were synthesized, characterized and biologically evaluated for antiprotozoal activity. The compounds were scre
Br?nsted acid-assisted intramolecular aminohydroxylation of N -alkenylsulfonamides under heavy metal-free conditions
Moriyama, Katsuhiko,Izumisawa, Yuta,Togo, Hideo
, p. 9846 - 9851 (2013/01/15)
The intramolecular aminohydroxylation of N-alkenylsulfonamides proceeded under heavy metal-free conditions to give substituted prolinol derivatives in high yields. Oxone activated by catalytic Br?nsted acid worked well as an electrophilic oxidant for this reaction.
Does an axial propeller shape on a dirhodium(III,III) core affect equatorial ligand chirality?
Doyle, Michael P.,Shabashov, Dmitry,Zhou, Lei,Zavalij, Peter Y.,Welch, Christopher,Pirzada, Zainab
experimental part, p. 3619 - 3627 (2011/09/20)
The dirhodium(III,III) tetrakis(1-aza-2-cyclooctanoate) framework, which exists solely in a propeller conformation, has been prepared with nonidentical apical aryl ligands. The presence of these nonidentical ligands on the propeller conformation was expec
N-(9-(9-phenylfluorenyl))homoserine-derived cyclic sulfamidates: Novel chiral educts for the synthesis of enantiopure γ-substituted α-amino acids
Atfani, Mohamed,Wei, Lan,Lubell, William D.
, p. 2965 - 2967 (2007/10/03)
matrix presented nucleophile: NaN3, RNH2, RR'NH, ArNH2, KSCN, NaSAr, NaOAr (4S)-tert-Butyl 2,2-dioxo-3-PhF-1,2,3-oxathiazainane-4-carboxylate reacted effectively with nitrogen, sulfur, and oxygen nucleophiles to provide en
