65501-71-5Relevant articles and documents
Nickel complexes with phosphines and N-R-sulfonyldithiocarbimates ligands: New antifungals for the control of Hemileia vastatrix and Phakopsora pachyrhizi
Vidigal, Antonio E.C.,Rubinger, Mayura M.M.,de Queiroz, Luan F.,da Silva, Lucas F.,Zambolim, Laércio,Guilardi, Silvana,Souza, Rafael A.C.,Ellena, Javier,Wetler, Emiliana B.,Oliveira, Marcelo R.L.
, p. 724 - 732 (2018/12/11)
Nickel(II) complexes of general formula [Ni(RSO2N = CS2)(PPh3)2] (2a–h) or [Ni(RSO2N = CS2)dppe] (3a–h), where R = methyl (a), ethyl (b), butyl (c), octyl (d), phenyl (e), 4-isopropylphenyl (f), 4-tert-butylphenyl (g), 2-naphthyl (h), PPh3 = triphenylphosphine and dppe = 1,2-bis(diphenylphosphine)ethane were prepared, from which six are new substances (2f–h and 3f–h). The new compounds were characterized by elemental analysis of C, H, N and Ni, and by IR, UV–Vis and 1H, 13C and 31P NMR spectroscopies. The data were consistent with the formation of square planar nickel(II) complexes with mixed ligands, what was confirmed by single crystal X-ray diffraction studies on compounds 2f and 2h. These complexes present intramolecular Ni–H–C anagostic interactions. All complexes inhibited the germination of Hemileia vastatrix and Phakopsora pachyrhizi, the causal agents of devastating diseases on soybean and coffee cultures. The most active compounds presented IC90 values as low as 405 μM against H. vastatrix, and 280 μM against P. pachyrhizi. Thus, the title compounds are target molecules for the development of new agrochemicals against the Asian soybean rust and Coffee leaf-rust diseases.
Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation
Zhong, Dayou,Wu, Di,Zhang, Yan,Lu, Zhiwu,Usman, Muhammad,Liu, Wei,Lu, Xiuqiang,Liu, Wen-Bo
supporting information, p. 5808 - 5812 (2019/08/26)
Cyclic sulfonamides (sultams) play a unique role in drug discovery and synthetic chemistry. A direct synthesis of sultams by an intramolecular C(sp3)-H amidation reaction using an iron complex in situ derived from Fe(ClO4)2 and aminopyridine ligand is reported. This strategy features a readily available catalyst and tolerates a broad variety of substrates as demonstrated by 22 examples (up to 89% yield). A one-pot iron-catalyzed amidation/oxidation procedure for the synthesis of cyclic N-sulfonyl ketimines is also realized with up to 92% yield (eight examples). The synthetic utility of the method is validated by a gram-scale reaction and derivatization of the products to ring-fused sultams.
Synthesis, characterization, and antifungal activity of novel (Z)-N-(2-cyano-3-phenylprop-2-en-1-yl)-alkyl/aryl-sulfonamides derived from a Morita-Baylis-Hillman adduct
Tavares, Eder C.,Rubinger, Mayura M.M.,Zacchi, Carlos H.C.,Silva, Simone A.,Oliveira, Marcelo R.L.,Guilardi, Silvana,Alcantara, Ant?nio F. De C.,Piló-Veloso, Dorila,Zambolim, Laércio
, p. 43 - 51 (2014/04/17)
A series of allyl sulfonamides prepared from the reaction of the Morita-Baylis-Hillman adduct 2-[hydroxy(phenyl)methyl]acrylonitrile with primary sulfonamides (RSO2NH2), where R = C6H 5 (1), 4-FC6H4 (2), 4-ClC6H 4 (3), 4-BrC6H4 (4), 4-NO2C 6H4 (5), CH3 (6), CH3CH2 (7), CH3(CH2)3 (8), and CH3(CH 2)7 (9), were characterized by IR, 1H and 13C NMR spectroscopies, mass spectrometry and elemental analyses. BLYP/6-31G* calculations suggested stereoselective reactions, resulting in the exclusive formation of the thermodynamically more stable Z-products. The Z-configuration of the products was confirmed by NOE difference spectroscopy and single crystal X-ray diffraction measurements. The allyl sulfonamides were active against Colletotrichum gloeosporioides, an important agent of anthracnose in plants.
Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase
Benfodda, Zohra,Guillen, Franck,Romestand, Bernard,Dahmani, Abdelkader,Blancou, Hubert
experimental part, p. 1225 - 1229 (2010/04/29)
Series of perfluoroalkanesulfonamides 1, sodium salt of perfluoroalkanesulfonamides 2 and polyfluoroalkanesulfonamides 3 derivatives were synthesized and characterized by 1H NMR, 13C NMR, 19F NMR, IR and HRMS. Inhibition effects of these compounds on bovine carbonic anhydrase (bCA) and human carbonic anhydrase isoenzyme II (hCA) have been investigated. Comparing IC50 values of the synthesized molecules 1, 2 and 3, it has been found that compound 2b is a more potent inhibitor than acetazolamide on hCA. Moreover 2b does not present cellular toxicity on sheep red globules.
Syntheses, crystal structure and spectroscopic characterization of bis(dithiocarbimato)-nickel(II)-complexes: A new class of vulcanization accelerators
Gomes Cunha, Leandro Marcos,Magalh?es Rubinger, Mayura Marques,Sabino, José Ricardo,Visconte, Leila Léa Yuan,Leite Oliveira, Marcelo Ribeiro
experimental part, p. 2278 - 2282 (2010/09/06)
The compounds (Ph4P)2[Ni(RSO2NCS 2)2] [Ph4P+= tetraphenylphosphonium cation; R = CH3 (1b), CH3CH2 (2b), CH 3(CH2)3/su
Pharmaceutical Compositions Based on Fluorinated Sulphamides and Sulphinimides
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Page/Page column 9, (2008/06/13)
Pharmacuetical composition comprising compounds of formula (I): [in-line-formulae]NZ1Z2Z3 ??(I) [/in-line-formulae] in which: Z1, Z2, Z3 each independently of the others represents: a hydrogen atom; C1-C6-alkyl group; a group —SO2R3 wherein R3 represents a linear or branched C1-C12-alkyl, -alkenyl or -alkynyl group, a C3-C10-cycloalkyl group or a C6-C10-aryl group, a (C1-C6)-alkyl-(C6-C14)-aryl group, or a C5-C10-heteroaryl group; it being understood that at least one of the groups Z1, Z2, Z3 represents a group of formula (II) [in-line-formulae]X—RF—(CH2)n—SO2—??(II) [/in-line-formulae] X, RF and n being as defined in claim 1.
Novel N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides with periodic acid catalyzed by chromium(III) acetate hydroxide
Xu, Liang,Zhang, Suhong,Trudell, Mark L.
, p. 1901 - 1904 (2007/10/03)
Chromium(III) acetate hydroxide has been found to be an efficient catalyst for N-dealkylation of N-alkyl sulfonamides and N,N-dialkyl sulfonamides to furnish sulfonamides in good to excellent yields with periodic acid in acetonitrile at room temperature.
Endothelin antagonists
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, (2008/06/13)
A compound of the formula (I): or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.
Radical-chain reactions of sulfonyl azides and of ethyl azidoformate with allylstannanes: Homolytic allylation at nitrogen
Dang, Hai-Shan,Roberts, Brian P.
, p. 1493 - 1498 (2007/10/03)
4-Methylbenzenesulfonyl azide reacts with allyltriphenylstannane (ATPS) in refluxing benzene, in the presence of 2,2′-azobis(2-methylpropionitrile) as initiator, to give N-allyl-4-methylbenzenesulfonamide in good yield after hydrolytic work-up. Small amounts of allyl 4-methylphenyl sulfone were also formed. The reaction follows a free-radical chain mechanism which involves competitive addition of Ph5Sn? to Na and to Nc of the azido group in ArSO2NaNbNc. Addition to Na followed by loss of nitrogen gives ArSO2NSnPh3, the precursor of the N-allylarenesulfonamide, while addition to Nc leads to the formation of ArSO2 and thence to the allyl aryl sulfone. Allyltrimethylstannane behaves in a similar way to ATPS, but allyltributylstannane gives only a low yield of N-allylarenesulfonamide and the major product is the unsubstituted sulfonamide MeC6H4SO2NH2, which results because the radical ArSO2NSnBu3 undergoes intramolecular 1,5-hydrogen-atom transfer in preference to adding to the allylstannane. 2-Methylallyltriphenylstannane reacts in an analogous way to ATPS, but allylstannanes containing non-terminal double bonds do not react successfully. The arenesulfonyl azides 4-XC6H4SO2N3 (X = H, MeO, F) react in a similar way to tosyl azide, but the reaction is very sluggish when X = NO2? With 1-octanesulfonyl azide, reaction with Ph3Sn? is much less selective and products arising from attack at Na and Nc are formed in comparable yields. Ethyl azidoformate reacts with allylstannanes in a similar manner to, although more slowly than, tosyl azide and gives good yields of the corresponding allylic carbamates.
Unconventional Regiospecific Syntheses of Aromatic Carbonamides and Thiocarbonamides by Means of Tin-Mediated Friedel-Crafts Reactions
Arnswald, Martin,Neumann, Wilhelm P.
, p. 7022 - 7028 (2007/10/02)
Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group.Thus, unconventionally substituted aromatic carbonamides can be obtained.The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings.The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22.One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29.Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28.From the reactions of 1 with ethoxycarbonyl isocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible.The scope, limitations, and mechanism of these electrophilic substitutions are outlined.
