- Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
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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.
- Kanyiva, Kyalo Stephen,Shibata, Takanori,Uchida, Kanako
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p. 1377 - 1384
(2021/06/06)
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- Synthesis, Characterization, In vivo, Molecular Docking, ADMET and HOMO-LUMO study of Juvenile Hormone Analogues having sulfonamide feature as an Insect Growth Regulators
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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
- Sharma, Priyanka,Awasthi, Pamita
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- Diverse structural assemblies of U-shaped hydrazinyl-sulfonamides: experimental and theoretical analysis of non-covalent interactions stabilizing solid state conformations
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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
- Andleeb, Hina,Khan, Imtiaz,Franconetti, Antonio,Tahir, Muhammad Nawaz,Simpson, Jim,Hameed, Shahid,Frontera, Antonio
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p. 1780 - 1793
(2019/03/19)
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- Novel Phenoxazinones as potent agonist of PPAR-α: Design, synthesis, molecular docking and in vivo studies
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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.
- Ugwu, David I.,Okoro, Uchechukwu C.,Mishra, Narendra K.,Okafor, Sunday N.
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- α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization
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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.
- Kanyiva, Kyalo Stephen,Hamada, Daisuke,Makino, Sohei,Takano, Hideaki,Shibata, Takanori
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supporting information
p. 5905 - 5909
(2018/09/14)
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- In silico and bio assay of juvenile hormone analogs as an insect growth regulator against Galleria mellonella (wax moth)-Part i
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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
- Sharma, Priyanka,Thakur, Sunil,Awasthi, Pamita
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p. 1061 - 1078
(2016/05/09)
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- Metal complexes of tosyl sulfonamides: Design, X-ray structure, biological activities and molecular docking studies
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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-
- Khan, Najm Ul Hassan,Zaib, Sumera,Sultana, Kishwar,Khan, Imtiaz,Mougang-Soume, Berline,Nadeem, Humaira,Hassan, Mukhtiar,Iqbal, Jamshed
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p. 30125 - 30132
(2015/05/13)
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- Asymmetric synthesis of N-tosyl amino acids from N-sulfinyl α-amino-1,3-dithioketals
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Hydrolysis of diastereomerically pure N-sulfinyl α-amino-1,3- dithianes with 1,3-dibromo-5,5-dimethylhydantoin gives N-tosyl α-amino aldehydes which when subjected to a Pinnick-type oxidation gave N-tosyl α-amino acids without epimerization.
- Davis, Franklin A.,Ramachandar, Tokala,Chai, Jing,Qiu, Hiu
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experimental part
p. 17 - 26
(2010/09/05)
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- Synthesis of α-amino acids by reaction of aziridine-2-carboxylic acids with carbon nucleophiles
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A variety of homochiral α-amino acids have been prepared in good yield via regioselective reaction of higher order cuprates with (2S)-N-para-toluenesulfonylaziridine-2-carboxylic acid 4. The reaction was much less regioselective and low yielding when higher order cuprates were reacted with the more hindered aziridine carboxylic acid 30, the principal products being protected β-amino acids. Reaction of lithium trimethylsilylacetylide with the aziridine acid 30, however, gave a protected α-amino acid which was converted to the protected isoleucine ester 37. The Royal Society of Chemistry 2006.
- Beresford, Kenneth J. M.,Church, Nicola J.,Young, Douglas W.
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p. 2888 - 2897
(2008/02/08)
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- PROCESS FOR MAKING N-SULFONATED-AMINO ACID DERIVATIVES
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This invention relates to a process for preparing optically active α -amino acid substrates which are used to make potent lethal factor (LF) inhibitors for the treatment of anthrax. This invention further relates to a process for synthesis of potent LF-inhibitors for the treatment of anthrax. Specifically, the invention concerns a novel, high-yielding and highly enantioselective asymmetric hydrogenation reaction of a tetrasubstituted ene-sulfonamide acid or ester.
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Page/Page column 33-34
(2008/06/13)
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- Asymmetric hydrogenation of N-sulfonylated-α-dehydroamino acids: Toward the synthesis of an anthrax lethal factor inhibitor
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(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.
- Shultz, C. Scott,Dreher, Spencer D.,Ikemoto, Norihiro,Williams, J. Michael,Grabowski, Edward J. J.,Krska, Shane W.,Sun, Yongkui,Dormer, Peter G.,DiMichele, Lisa
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p. 3405 - 3408
(2007/10/03)
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- Amino acids in the syntheses of heterocyclic systems: Syntheses and radiostability of novel biologically active triazoles containing the sulfonamide moiety
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A number of novel triazoles 2a-f, 4, 9, 10, 12, 15; triazolothiadiazoles 6, 8, 11, 16; triazolothiadizine 5; and triazolotriazine 14 were synthesized and characterized by elemental analyses and spectral data. Six of the compounds showed antifungal activity compared with the fungicide Mycostatine. Radiosterilization of the biologically active compounds 4, 8, 9b, and 10 in the dry state may prove to be applicable at the sterile dose 25 kGy.
- El-Sharief,Ghorab,El-Gaby,Mohamed,Ammar
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p. 316 - 323
(2007/10/03)
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- Aminoacids in the synthesis of heterocyclic systems: The synthesis of triazinoquinazolinones, triazepinoquinazolinones and triazocinoquinazolinones of potential biological interest
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A number of novel triazinoquinazolinones (5b,c and 8), triazepinoquinazolinones(5a, 6b, 7 and 9) and triazocinoquinazolinones (6a and 10) were obtained via nucleophilic interaction of 3-aminoquinazolinone derivatives 3 with different reagents.
- El-Sharief,Ammar,Zahran,Ali,El-Gaby
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p. 267 - 278
(2007/10/03)
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- Asymmetric Synthesis of Functionalized Secondary Alcohols by Catalytic Ring-Cleavage Reactions of Cyclic Acetals Derived from (R)-1,3-Butanediol
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In the presence of a catalytic amount (0.1-0.2 molar amount) of a 2-phenyl-1,3,2-oxazaborolidin-5-one, prepared by the reaction of dichlorophenylborane and N-(trifluoromethylsulfonyl)-L- phenylalanine, and enol silyl ethers ((R2)2C=C-(R3)OTMS; R3 = t-BuS, EtS, EtO, Ph) (1.1-1.5 molar amount), chiral cyclic acetals 6 derived from (R)-1,3-butanediol and aldehydes undergo an efficient ring-cleavage reaction with the inversion of the stereochemistry at the acetal carbon to give the anti isomer of the corresponding products with high stereoselectivity. The reaction is applicable to acetals derived from aromatic, aliphatic, and α,β-unsaturated aldehydes. Not only enol silyl ethers, but also methallyltrimethylsilane and allyltributyltin, can be employed as nucleophiles, leading to the selective formation of the anti isomer of the corresponding allylated ring-cleavage products. Removal of the chiral auxiliary from these ring-cleavage products by a two-step sequence ((i) PCC (ii) Bn2NH2(CF3CO2)) furnishes enantiomerically enriched β-hydroxy carbonyl compounds and homoallyl alcohols. A modest level of kinetic resolution is observed in the ring cleavage of a racemic acetal catalyzed by a phenylboron compound derived from N-mesyl-L-phenylalanine.
- Kinugasa, Motoharu,Hanada, Toshiro,Egusa, Takayuki,Fujita, Katsuhiro,Oku, Akira
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p. 3639 - 3650
(2007/10/03)
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- Synthesis of α-Amino Acids by Ring Opening of Aziridine-2-carboxylates with Carbon Nucleophiles
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Excellent regiospecificity has been achieved in the reaction of carbon nucleophiles with N-para-toluenesulfonylaziridine-2-carboxylic acid (6, R=H) protected as the anion.This has been developed into a general and high yielding synthesis of optically pure α-amino acids containing one chiral centre.When the aziridine (20) containing a second chiral centre was used, only lithium trimethylsilylacetylide gave the desired α-amino acid.Reaction with higher order cuprates gave lower yields, the principal products being the protected β-amino acids (22) and (23).
- Church, Nicola J.,Young, Douglas W.
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p. 151 - 154
(2007/10/02)
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