68005-71-0Relevant articles and documents
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, Characterization, In vivo, Molecular Docking, ADMET and HOMO-LUMO study of Juvenile Hormone Analogues having sulfonamide feature as an Insect Growth Regulators
Sharma, Priyanka,Awasthi, Pamita
, (2021/02/09)
The search for a simple and efficient method for the synthesis of sulfonamide derivatives as an Insect Growth Regulators (IGRs) under mild and eco-friendly conditions is of our interest. Here, we report a simple, efficient, and eco-friendly method for the
Concise Asymmetric Synthesis of Kweichowenol A
Konrad, David B.,Kicin, Bilal,Trauner, Dirk
supporting information, p. 383 - 386 (2019/02/26)
An asymmetric 11-step synthesis of the polyoxygenated cyclohexene natural product kweichowenol A from the traditional Chinese medicinal herb Uvaria kweichowesis is reported. The oxygenation pattern was installed on a linear precursor by exploiting the acyclic stereocontrol of the Kiyooka aldol reaction, as well as Cram chelate-controlled Grignard reactions. Ring-closing metathesis and a selective benzoylation then gave the natural product.
Diverse structural assemblies of U-shaped hydrazinyl-sulfonamides: experimental and theoretical analysis of non-covalent interactions stabilizing solid state conformations
Andleeb, Hina,Khan, Imtiaz,Franconetti, Antonio,Tahir, Muhammad Nawaz,Simpson, Jim,Hameed, Shahid,Frontera, Antonio
, p. 1780 - 1793 (2019/03/19)
The present study describes the synthesis of five new hydrazinyl-sulfonamide derivatives incorporating linear and branched alkyl chains. An efficient and straightforward synthetic approach was used to achieve these sulfonamide compounds in good yields. Th
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.
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.
Gold-Catalyzed Aminoalkenylation of β-Amino-1,n-Diynols to Cycloalkyl-, Piperidinyl- and Pyranyl-Fused Pyrroles
Kothandaraman, Prasath,Zhao, Yichao,Lee, Bo Ra,Le Ng, Clarrisa Jia,Lee, Jun Yi,Ayers, Benjamin James,Chan, Philip Wai Hong
supporting information, p. 1385 - 1391 (2016/05/19)
A synthetic method to prepare cycloalkyl-, piperidinyl- and pyranyl-fused pyrroles efficiently by gold(I)-catalyzed dehydrative aminoalkenylation of β-amino-1,n-diynols under mild conditions at room temperature is described.
In silico and bio assay of juvenile hormone analogs as an insect growth regulator against Galleria mellonella (wax moth)-Part i
Sharma, Priyanka,Thakur, Sunil,Awasthi, Pamita
, p. 1061 - 1078 (2016/05/09)
Juvenile hormone (JH) analogs are nowadays in use to control harmful pests. In order to develop new bioactive molecules as potential pesticides, we have incorporated different active structural features like sulfonamide, aromatic rings, amide group, and a
Metal complexes of tosyl sulfonamides: Design, X-ray structure, biological activities and molecular docking studies
Khan, Najm Ul Hassan,Zaib, Sumera,Sultana, Kishwar,Khan, Imtiaz,Mougang-Soume, Berline,Nadeem, Humaira,Hassan, Mukhtiar,Iqbal, Jamshed
, p. 30125 - 30132 (2015/05/13)
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-
Improved total synthesis and biological evaluation of potent apratoxin S4 based anticancer agents with differential stability and further enhanced activity
Chen, Qi-Yin,Liu, Yanxia,Cai, Weijing,Luesch, Hendrik
, p. 3011 - 3029 (2014/05/06)
Apratoxins are cytotoxic natural products originally isolated from marine cyanobacteria that act by preventing cotranslational translocation early in the secretory pathway to downregulate receptor levels and inhibit growth factor secretion, leading to pot
