Syntheses, characterization, crystal structure and antifungal activity of four tetraphenylphosphonium bis(N-R-sulfonyldithiocarbimato)zincate(II) salts

Amim, Raquel S.; Oliveira, Marcelo R. L.; Janczak, Jan; Rubinger, Mayura M. M.; Vieira, Lígia Maria Mendonça; Alves, Leonardo Corrêa; Zambolim, Laércio

doi:10.1016/j.poly.2010.12.003

Cited by 14 publications

(16 citation statements)

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“…The S1-C1-N1 and S5-C3-N2 angles are significantly greater than S2-C1-N1 and S4-C3-N2 due to the repulsive interactions between the two SO 2 CF 3 groups and the S1 and S5 atoms, respectively, which are cis in relation to the C1-N1 and C3-N2 bonds. Similar behavior is observed for other zinc complexes with dithiocarbimato ligands (Amim et al, 2011;Alves et al, 2009;Oliveira et al, 2007;Perpétuo et al, 2003). The torsion angles of C1-N1-S3-C2 and C3-N2-S6-C4 describing the conformation of the dithiocarbimato ligands are -175.9 (3)° and 180.0 (3)°, respectively.…”

Section: S1 Commentsupporting

confidence: 76%

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Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ²S,S′]zincate(II)

et al. 2011

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The title salt, (C24H20P)2[Zn(C2F3NO2S3)2], consists of a complex dianion and two tetraphenylphosphonium cations. The ZnII ion displays a distorted tetrahedral coordination environment with four S atoms from two S,S′-chelated N-(trifluoromethylsulfonyl)dithiocarbimate anions. In the crystal, besides the ionic interaction of the oppositely charged ions, intermolecular C—H⋯O interactions between cations and anions are observed. One of the cations interacts with an inversion-related equivalent by π–π stacking between phenyl rings, with a centroid–centroid distance of 3.932 (4) Å.

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Section: S1 Commentsupporting

confidence: 76%

“…The title complex is a new member of the class of Zn complexes with general formula [Zn(RSO 2 N═CS 2 ) 2 ] 2- (Amim et al, 2011;Alves et al, 2009;Mariano et al, 2007;Perpétuo et al, 2003). The literature describes only one complex of this class having an alkyl group (methyl) attached to the SO 2 moiety (Oliveira et al, 2007).…”

Section: S1 Commentmentioning

confidence: 99%

Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ²S,S′]zincate(II)

et al. 2011

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“…These results indicated that this activity was due to the cation only, making it a candidate for enhancing the recently discovered activity of the dithiocarbimates. 11,12 The new compounds 1-4 containing both the tris(1,10-phenanthroline)iron(II) cation and the zinc-dithiocarbimate anions were active against C. Gloeosporioides and inactive against both Candida albicans and Candida tropicalis. These results indicate that the mode of action of the dithiocarbimates is specific for filamentous fungi.…”

Section: Biological Assaymentioning

confidence: 99%

“…10 In recent studies, we have demonstrated that the dithiocarbimate compounds A 2 [Zn(RSO 2 N=CS 2 ) 2 ] and A 2 [Sn(Bu) 2 (RSO 2 N=CS 2 ) 2 ] (A = tetrabutylammonium cation or tetraphenylphosphanium cation, Bu = n-butyl and R = 4-FC 6 H 4 , 4-ClC 6 H 4 , 4-BrC 6 H 4 and 4-IC 6 H 4 ) are active against Colletotrichum gloeosporioides. [11][12][13] It was also observed that the cations Bu 4 N + and Ph 4 P + were inactive.…”

Section: Introductionmentioning

confidence: 99%

Syntheses, characterization and antifungal activity of tris(1,10-phenanthroline)iron(ii) bis(n-r-sulfonyldithiocarbimate)zincate(ii)

Bottega¹,

Oliveira²,

Garcia³

et al. 2013

Quím. Nova

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Recebido em 24/8/12; aceito em 7/1/13; publicado na web em 24/5/13Four new compounds with the general formula [Fe(phen) 3 ][Zn(RSO 2 N=CS 2 ) 2 ], where phen = 1,10-phenanthroline, R = 4-FC 6 H 4 (1), 4-ClC 6 H 4 (2), 4-BrC 6 H 4 (3) and 4-IC 6 H 4 (4), respectively, were obtained by the reaction of the appropriate potassium N-R-sulfonyldithiocarbimate (RSO 2 N=CS 2 K 2 ) and tris(1,10-phenanthroline)iron(II) sulfate, with zinc(II) acetate dihydrate in dimethylformamide. The elemental analyses and the IR data were consistent with the formation of the expected complexes salts. The 1 H and 13 C NMR spectra showed the signals for the cationic iron(II) complex and dithiocarbimate moieties. The molar conductance data were consistent with the 1:1 cation:anion complexes in 1-4. The antifungal activities of the compounds were tested in vitro against Candida albicans, Candida tropicalis and Colletotrichum gloeosporioides.Keywords: dithiocarbimates; metal complexes; antifungal activity. INTRODUCTIONFungal infections in humans have increased in recent years predominantly affecting immunocompromised patients. 1,2 Fungi from the Candida genus can infect the oral and vaginal cavities, skin and, more seriously, essential organs. 1,3 Colletotrichum gloeosporioides is known to infect a wide variety of hosts, including vegetables, field and forage crops, fruit trees, and ornamental shrubs. 4 C. gloeosporioides infections in humans can cause keratitis in healthy or immunocompromised individuals and can induce phaeohyphomycosis in patients with hematologic malignancies and iatrogenic immunosuppression. [5][6][7] Several dithiocarbamate and N-substituted dithiocarbamate complexes and salts (Scheme 1a) have been used as agrochemicals mainly due to their high efficiency in controlling plant fungal diseases, and their relatively low toxicity. 8,9 The literature reports that dithiocarbamate complexes are also active against Candida spp. 10In recent studies, we have demonstrated that the dithiocarbimate compounds A 2 [Zn(RSO 2 N=CS 2 ) 2 ] and A 2 [Sn(Bu) 2 (RSO 2 N=CS 2 ) 2 ] (A = tetrabutylammonium cation or tetraphenylphosphanium cation, Bu = n-butyl and R = 4-FC 6 H 4 , 4-ClC 6 H 4 , 4-BrC 6 H 4 and 4-IC 6 H 4 ) are active against Colletotrichum gloeosporioides. 11-13 It was also observed that the cations Bu 4 N + and Ph 4 P + were inactive.Unlike dithiocarbamate analogues, the bis(dithiocarbimate) metal(II) complexes are anionic species (Scheme 1), offering potentially useful modulation of this activity. For example, enhanced antifungal activity should be possible either by the use of active counter ions, or by varying the solubility of the salts of the complexes through the use of different cations.Considering these possibilities, the activities of some salts were tested in order to find an appropriate active cation to deepen the investigation into the antifungal potential of dithiocarbimates. This search revealed that tris(phenantholine)iron(II) perchlorate is active against Colletotrichum gloeosporioides. Here we describe the s...

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“…However, the use of these compounds in rubber vulcanizates is associated with two problems, the short scorch time and N‐nitrosamines liberation, which are well documented mutagenic and carcinogenic substances, on heating . The synthesis and characterization of dithiocarbimates, especially the zinc complexes, have been reported recently, although the application of these compounds as vulcanization accelerators is still little explored …”

Section: Introductionmentioning

confidence: 99%

Optimizing Properties of Natural Rubber Compounds Using Tetrabutylammonium bis(N‐phenylsulfonyldithiocarbimate)zincate(II) as Accelerator

Arruda

Visconte

Linhares

et al. 2018

Macromolecular Symposia

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The rheometric properties of natural rubber compounds containing the compound tetrabutylammonium bis(N‐phenylsulfonyldithiocarbimate)zincate(II) as the accelerator are modulated by means of the response surface methodology (RSM), where the Face Centred Central Composite Design (FCCD) with three factors and three levels was chosen with the objective to obtain the relationship among the evaluated properties and factor levels. The factors in the experimental design are the amounts of both accelerator and sulfur and the vulcanization temperature. The compounds are evaluated as for the scorch time, optimum vulcanization time, and maximum torque. For each of these properties the Regression analysis, the pareto diagram and the fitted surface are obtained. Concerning the scorch and optimum vulcanization times, the most important factors are the vulcanization temperature and the amount of accelerator, respectively. Regarding the maximum torque, the most significant factors are the amounts of sulfur and accelerator. Considering the optimum vulcanization time a regression model with good accuracy could be obtained. The function desirability is used to obtain an optimum condition for an adequate cure system related to a set of desired intervals for the properties of interest.

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Syntheses, characterization, crystal structure and antifungal activity of four tetraphenylphosphonium bis(N-R-sulfonyldithiocarbimato)zincate(II) salts

Cited by 14 publications

References 12 publications

Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ²S,S′]zincate(II)

Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ²S,S′]zincate(II)

Syntheses, characterization and antifungal activity of tris(1,10-phenanthroline)iron(ii) bis(n-r-sulfonyldithiocarbimate)zincate(ii)

Optimizing Properties of Natural Rubber Compounds Using Tetrabutylammonium bis(N‐phenylsulfonyldithiocarbimate)zincate(II) as Accelerator

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Syntheses, characterization, crystal structure and antifungal activity of four tetraphenylphosphonium bis(N-R-sulfonyldithiocarbimato)zincate(II) salts

Cited by 14 publications

References 12 publications

Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ2S,S′]zincate(II)

Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ2S,S′]zincate(II)

Syntheses, characterization and antifungal activity of tris(1,10-phenanthroline)iron(ii) bis(n-r-sulfonyldithiocarbimate)zincate(ii)

Optimizing Properties of Natural Rubber Compounds Using Tetrabutylammonium bis(N‐phenylsulfonyldithiocarbimate)zincate(II) as Accelerator

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Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ²S,S′]zincate(II)

Bis(tetraphenylphosphonium) bis[N-(trifluoromethylsulfonyl)dithiocarbimato(2−)-κ²S,S′]zincate(II)