- Nickel complexes with phosphines and N-R-sulfonyldithiocarbimates ligands: New antifungals for the control of Hemileia vastatrix and Phakopsora pachyrhizi
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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.
- 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.
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p. 724 - 732
(2018/12/11)
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- Synthesis of Sultams and Cyclic N-Sulfonyl Ketimines via Iron-Catalyzed Intramolecular Aliphatic C-H Amidation
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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.
- Zhong, Dayou,Wu, Di,Zhang, Yan,Lu, Zhiwu,Usman, Muhammad,Liu, Wei,Lu, Xiuqiang,Liu, Wen-Bo
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supporting information
p. 5808 - 5812
(2019/08/26)
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- THIAZOLIDINONE COMPOUNDS AND USE THEREOF
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A pharmaceutical composition containing a compound of Formula (I) for treating an opioid receptor-associated condition. Also disclosed is a method for treating an opioid receptor-associated condition using such a compound. Further disclosed are two sets of thiazolidinone compounds of formula (I): (i) compounds each having an enantiomeric excess greater than 90% and (ii) compounds each being substituted with deuterium.
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Paragraph 0054; 0389-0390
(2017/09/21)
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- Cu-catalyzed aerobic oxidative three-component coupling route to N -sulfonyl amidines via an ynamine intermediate
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Cu-catalyzed aerobic oxidative three-component coupling of a terminal alkyne, secondary amine, and sulfonamide enables efficient synthesis of amidines. The use of Cu(OTf)2 (5 mol %) produces amidines selectively without Glaser-Hay alkyne homocoupling products. Preliminary studies suggest that the reaction pathway involves initial oxidative coupling of the terminal alkyne with the secondary amine, followed by hydroamidation of the ynamine intermediate with the sulfonamide.
- Kim, Jinho,Stahl, Shannon S.
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p. 2448 - 2454
(2015/04/14)
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- 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
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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.
- 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
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- Synthesis and investigation of inhibition effect of fluorinated sulfonamide derivatives on carbonic anhydrase
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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.
- Benfodda, Zohra,Guillen, Franck,Romestand, Bernard,Dahmani, Abdelkader,Blancou, Hubert
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experimental part
p. 1225 - 1229
(2010/04/29)
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- Syntheses, crystal structure and spectroscopic characterization of bis(dithiocarbimato)-nickel(II)-complexes: A new class of vulcanization accelerators
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The compounds (Ph4P)2[Ni(RSO2NCS 2)2] [Ph4P+= tetraphenylphosphonium cation; R = CH3 (1b), CH3CH2 (2b), CH 3(CH2)3/su
- Gomes Cunha, Leandro Marcos,Magalh?es Rubinger, Mayura Marques,Sabino, José Ricardo,Visconte, Leila Léa Yuan,Leite Oliveira, Marcelo Ribeiro
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experimental part
p. 2278 - 2282
(2010/09/06)
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- Analogs of isovaleramide, a pharmaceutical composition including the same, and a method of treating central nervous system conditions or diseases
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An isovaleramide analog having at least one of an increased potency, an increased half-life, and an increased stability compared to isovaleramide. The isovaleramide analog is a cyclic analog or a noncyclic analog. The isovaleramide analog is formulated into a pharmaceutical composition. A method of treating a central nervous system condition or disease is also disclosed. The method comprises administering an isovaleramide analog to a patient suffering from the central nervous system condition or disease.
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Page/Page column 7-8
(2010/02/15)
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- Intramolecular asymmetric amidations of sulfonamides and sulfamates catalyzed by chiral dirhodium(II) complexes
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Enantioselective intramolecular amidation of aliphatic sulfonamides was achieved for the first time by means of chiral carboxylatodirhodium(II) catalysts in conjunction with PhI(OAc)2 and MgO in high yields and with enantioselectivities of up to 66% (Scheme 3, Table 1). The best results were obtained with [Rh2{(S)-nttI)4] and [Rh 2{(R)-ntv)4] as catalysts ((S)-nttl = (αS)-α- (tert-butyl)-1,3-dioxo-2H-benz[de]isoquinoline-2-acetato, (R)-nto = (αR)-α-isopropyl-1,3-dioxo-2H-benz[de] isoquinoline-2-acetato). In addition, these carboxylatodirhodium(II) catalysts were also efficient in intramolecular amidations of aliphatic sulfamates esters, although the enantioselectivity of these latter reactions was significantly lower (Scheme 4, Table 3).
- Fruit, Corinne,Mueller, Paul
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p. 1607 - 1615
(2007/10/03)
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- Pyridyl-containing spirocyclic compounds as inhibitors of fibrinogen-dependent platelet aggregation
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Disclosed are certain substituted or unsubstituted pyridyl-containing spirocyclic compounds substituted with both basic and acidic functionality, which are useful in inhibiting platelet aggregation, inhibiting the binding of fibrinogen to blood platelets, and preventing or treating thrombosis
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- A mild, efficient method for the synthesis of aromatic and aliphatic sulfonamides
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A two-step method was developed for the synthesis of aromatic and aliphatic sulfonamides from the corresponding sulfinates using bis(2,2,2-trichloroethyl)azodicarboxylate as the electrophilic nitrogen source. The intermediate sulfonylhydrazides were obtained in very good yields and were cleaved under reductive conditions to deliver the desired sulfonamides. A variety of substituents in the aromatic ring are well tolerated as well as heterocycles.
- Chan, Wing Yan,Berthelette, Carl
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p. 4537 - 4540
(2007/10/03)
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- Discovery of IRL 3461: A novel and potent endothelin antagonist with balanced ET(A)/ET(B) affinity
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IRL 3461, N-butanesulfonyl-[N-(3,5-dimethylbenzoyl)-N-methyl-3-[4-(5- isoxazolyl)-phenyl]-alanyl]-(L)-valineamide, a potent and bifunctional (ET(A) + ET(B)) [Ki(ET(A))=1.8 nM, Ki(ET(B))=1.2 nM] antagonist was discovered by structural modification of IRL 2500, an ET(B) selective antagonist. IRL 3461 was found to be stable on incubation with human, rat, mouse, and guinea pig plasmas.
- Sakaki, Junichi,Murata, Toshiki,Yuumoto, Yoko,Nakamura, Ikushi,Frueh, Thomas,Pitterna, Thomas,Iwasaki, Genji,Oda, Kyoko,Yamamura, Takaki,Hayakawa, Kenji
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p. 2241 - 2246
(2007/10/03)
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- Antagonists of endothelin receptors
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The present invention provides novel compounds having pharmacological properties represented by the general formula I STR1 processes for the manufacture, pharmaceutical compositions and the use of the compounds of formula I and salts thereof.
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- Unconventional Regiospecific Syntheses of Aromatic Carbonamides and Thiocarbonamides by Means of Tin-Mediated Friedel-Crafts Reactions
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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.
- Arnswald, Martin,Neumann, Wilhelm P.
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p. 7022 - 7028
(2007/10/02)
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- Toners and yellow dye compounds used therein
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Novel cyano hydroxy pyridone monoazo yellow dye compounds are useful in thermoplastic electrostatographic toners. They absorb at the desired wavelength, are lightfast and have high tinctorial strength. They resist decomposition, sublimation and bleeding upon being thermally fixed to a substrate. For use in color transparencies, these dyes form a transparent toner image.
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