97-74-5Relevant academic research and scientific papers
Substituted carbamothioic amine-1-carbothioic thioanhydrides as novel trichomonicidal fungicides: Design, synthesis, and biology
Mandalapu, Dhanaraju,Kushwaha, Bhavana,Gupta, Sonal,Krishna, Shagun,Srivastava, Nidhi,Shukla, Mahendra,Singh, Pratiksha,Chauhan, Bhavana S.,Goyani, Ravi,Maikhuri, Jagdamba P.,Sashidhara, Koneni V.,Kumar, Brijesh,Tripathi, Renu,Shukla, Praveen K.,Siddiqi, Mohammad I.,Lal, Jawahar,Gupta, Gopal,Sharma, Vishnu L.
, p. 632 - 645 (2017/12/08)
Sexually transmitted diseases like trichomoniasis along with opportunistic fungal infections like candidiasis are major global health burden in female reproductive health. In this context a novel non-nitroimidazole class of substituted carbamothioic amine-1-carbothioic thioanhydride series was designed, synthesized, evaluated for trichomonacidal and fungicidal activities, and was found to be more active than the standard drug Metronidazole (MTZ). Compounds were trichomonicidal in the MIC ranges of 4.77–294.1 μM and 32.46–735.20 μM against MTZ-susceptible and -resistant strains, respectively. Further, compounds inhibited the growth of at least two out of ten fungal strains tested at MIC of 7.50–240.38 μM. The most active compound (20) of this series was 3.8 and 9.5 fold more active than the MTZ against the two Trichomonas strains tested. Compound 20 also significantly inhibited the sulfhydryl groups present over Trichomonas vaginalis and was found to be more active than the MTZ in vivo. Further, a docking analysis carried out with cysteine proteases supported their thiol inhibiting ability and preliminary pharmacokinetic study has shown good distribution and systemic clearance.
Room-temperature carbon-sulfur bond formation from Ni(II) σ-aryl complex via cleavage of the S-S bond of disulfide moieties
Okamoto, Ken,Housekeeper, Jeremy B.,Luscombe, Christine K.
, p. 639 - 643 (2013/11/19)
The formation of ArSY (Y: C(= S)NMe2, Ph, P(= O)(OEt) 2) by reductive elimination from σ-aryl complexes (M(PPh 3)2PhBr, M = Ni, Pd), associated with disulfides (YS-SY, Y: C(=S)NMe2 (1), Ph (2), P(=O)(OEt)2 (3)), at ambient temperature, has been investigated. Various mechanistic features of disulfide bond (S-S) cleavage have been elucidated using disulfide 1 by 31P NMR spectroscopy and matrix-assisted laser desorption/ionization-time of flight mass spectrometric investigations. Based upon the results of nucleophilic cleavage of the S-S bond by PPh3, studies of the reductive elimination process show that when M(PPh3)2PhBr is mixed with disulfide 1, competitive reactions occur between the PPh3 ligand, disulfide 1 and a trace amount of water, leading to low C-S coupling yields; an oxidation reaction of PPh3 with disulfide and water occur prior to C-S cross-coupling, and phosphonium ion intermediates are likely involved. However, when the disulfide 1 is pretreated with PPh3, the Ni(II) σ-aryl complex affords the C-S coupling product nearly quantitatively at room temperature. The pretreatment method is also effective for the coupling reaction of disulfide 2 and Ni(II) σ-aryl complex. The difference between Ni(II) and Pd(II) σ-aryl complexes on C-S bond formation by reductive elimination can be explained by the affinity of metal for the thiolate ligands derived from the cleaved disulfide. Copyright 2013 John Wiley & Sons, Ltd. The formation of ArSY (Y: C(= S)NMe2, Ph, P(= O)(OEt)2) by reductive elimination from σ-aryl complexes (M(PPh3)2PhBr, M = Ni, Pd) at ambient temperature, has been investigated, a result that shows an effective C-S cross-coupling reaction. Copyright
Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors
Kapanda, Coco N.,Muccioli, Giulio G.,Labar, Geoffray,Poupaert, Jacques H.,Lambert, Didier M.
experimental part, p. 7310 - 7314 (2010/07/14)
Monoglyceride lipase (MGL) inhibition may offer an approach in treating diseases in which higher 2-arachidonoyglycerol activity would be beneficial. We report here the synthesis and pharmacological evaluation of bis(dialkylaminethiocarbonyl)disulfide derivatives as irreversible MGL inhibitors. Inhibition occurs through interactions with MGL C208 and C242 residues, and these derivatives exhibit high inhibition selectivity over fatty acid amide hydrolase, another endocannabinoid-hydrolyzing enzyme. 2009 American Chemical Society.
The synthesis of 1-thia-6-oxa-6aλ4-seleno-3-azapentalene and a 3H-1,2,4-dithiazole
Koketsu, Mamoru,Otsuka, Toshihiro,Swenson, Dale,Ishihara, Hideharu
, p. 613 - 616 (2008/03/27)
The reaction of thiocarbamoyl isoselenocyanate with a carbanion gave 1-thia-6-oxa-6aλ4-seleno-3-azapentalene, which has a hypervalent selenium, as the major product. The by-products 3-diacylmethylidene- 5-dimethylamino-3H-1,2,4-dithiazole and thiocarbamate thioanhydride were also formed. This journal is The Royal Society of Chemistry.
Studies of phosphorus ylides with tetramethylthiuram disulfide
Abdou,Yakout
, p. 6411 - 6418 (2007/10/02)
In contrast to the behaviour of the entitled disulfide (1) toward Wittig reagents (2a, b), which undergoes direct and simple nucleophilic displacement reactions giving 71, b, 8 and 9 as the final products, an extensive decomposition occurred when the same disulfide was treated with ylides 2c, d, furnishing the adducts 7c, d, 8 and 12 or 14, respectively. The given structures were based upon analytical, chemical and spectroscopic results.
Aminosilylation of heterocumulenes and the intramolecular decomposition of their silyl-functionalized adducts
Corriu, R. J. P.,Lanneau, Gerard F.,Mehta, V. D.
, p. 9 - 26 (2007/10/02)
Heteroorganic amidosilanes are readily obtained by interaction of CO2, CS2 and other heterocumulenes with pentacoordinated diaminosilanes.A comparison is made with the corresponding reactions of tetracoordinated species.Decompositon of these bifunctional organosilanes gives 2-substituted ureido derivatives and base-stabilized low coordinated silicon species, seemingly by a unimolecular thermal β-elimination.
Pesticidal compositions containing phosphoric esters and divalent sulphur compounds
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, (2008/06/13)
Pesticidal composition comprising: a pesticidal, phosphoric ester the molecule of which has at least one alkyl group of 1 to 3 carbon atoms, 0.05 to 10% of an agent stabilizing the said ester against decomposition by protonisation, together with adjuvants characterized in that the stabilizing agent comprises at least one sulphur compound containing per molecule at least one divalent sulphur atom of which one valence is bonded to an atom chosen from sulphur, carbon, nitrogen, hydrogen, and metals capable of giving a salt, the other valence being bonded to an atom chosen from hydrogen, the carbon atom already noted, a second carbon atom, the nitrogen atom already noted, a second nitrogen atom, the metal atom already noted in the case of a metal of valence greater than one, a second atom of metal and oxygen when the first valence is not attached to an atom of hydrogen, the proportion of sulphur calculated with reference to the weight of the sulphur compound being between 5 and 99%. Process for stabilizing a phosphoric ester of which the molecule possesses at least one alkyl group containing 1 to 3 carbon atoms characterized in that there is added to the phosphoric ester or to a mixture which contains it, 0.05 to 10% calculated on the weight of the phosphoric acid ester of an agent capable of stabilizing the said phosphoric ester against protonisation and comprising at least one sulphur compound such as that defined thereupon.
