- Unexpected complexation of allylpseudothiohydantoin hydrochlorides towards CuX (X?=?Cl, NO3, ClO4, BF4, 1/2SiF6). The first known examples of joint CuI(Cl,ClO4) and CuI(Cl,BF4) π-complexes
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By means of alternating current-electrochemical synthesis starting from a mixture of 2-imino-3-(prop-2-en-1-yl)-1,3-thiazolidin-4-one (3-allylpseudothiohydantoin, napt) and 2-allylamino-1,3-thiazol-4(5H)-one (allylaminopseudothiohydantoin, aapt) hydrochlorides and corresponding copper(II) salts five new π-complexes, [Cu(napt)Cl] (1), [Cu2(aapt)2Cl]NO3 (2), [Cu2(aapt)2Cl]BF4 (3), [Cu2(aapt)2Cl]ClO4 (4) and [Cu2(aapt)2Cl]2SiF6·2H2O (5), were obtained and studied by X-ray single crystal diffraction and IR-spectroscopy. Napt and aapt molecules are selectively coordinated to Cu+ depending on the anion type. In crystals of 1 and 5, the organic ligands are attached to the metal in a chelating N,(C=C)-bidentate mode. The aapt molecule in 2-4 acts as a tridentate chelating ligand, being coordinated to the copper(I) ion through the heterocyclic N atom, carbonyl O atom, and C=C?bond of allyl group, forming an original cationic [Cu2(aapt)2Cl]+ fragment with both a bridging Cl– ion and O atom of the C=O group. In the presence of the doubly charged SiF6 2– anion, Cu(I) in 5 prefers to be bonded with two bridging Cl– ions, rather than the C=O group, causing [Cu2(aapt)2Cl]+ units to associate into the infinite cationic chains. Crystals of 3 and 4 are the first known examples of the simultaneous BF4 –/Cl– or ClO4 –/Cl– participation in copper(I) π-complex formation.
- Fedorchuk,Kinzhybalo,Slyvka, Yu. I.,Goreshnik,Bednarchuk,Lis,Mys’kiv
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- NG-Allyl- and NG-Cyclopropyl-L-arginine: Two Novel Inhibitors of Macrophage Nitric Oxide Synthase
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NG-Methyl-L-arginine has recently been shown to inactivate the inducible murine macrophage nitric oxide (.NO) synthase (Olken, N.M.; Rusche, K.M.; Richards, M.K.; Marletta, M.A.Biochem.Biophys.Res.Commun. 1991, 177, 828-833).NG-Allyl-L-arginine and NG-cyclopropyl-L-arginine were synthesized as potential mechanism-based enzyme inhibitors to exploit the chemistry presumed to occur at the active site.NG-Cyclopropyl-L-arginine was found to be a potent reversible inhibitor with a Ki = 7.7 μM.NG-Allyl-L-arginine was found to be both a potent reversible (Ki = 2.1 μM) and irreversible inhibitor of the enzyme.The irreversible inhibition demonstrated pseudo-first-order inactivation kinetics with kinact = 0.026 min-1 and Ki = 3.4 μM.Stereospecific protection of the inactivation was afforded by L-arginine, and saturability of the inactivation rate was observed.Our studies indicate that both reversible and irreversible inhibition of the inducible .NO synthase can be achieved with relatively simple modifications of the substrate L-arginine.
- Olken, Norman M.,Marletta, Michael A.
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Read Online
- ANTIVIRAL COMPOUNDS AND USE THEREOF
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The present invention relates to compounds of formula (I), their use as medicaments, in particular as broad spectrum antiviral agents, their combination with a further antiviral agent and relative pharmaceutical compositions. In particular, the compounds of the invention are useful in the treatment of a disease caused by an enveloped virus.
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Page/Page column 36; 39-40
(2019/10/04)
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- Reactions of N-alkenyl Thioureas with p-alkoxyphenyltellurium Trichlorides
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N-Аlkenyl thioureas, under the action of aryltellurium trichlorides, form the addition products N-{2-chloro-3-[dichloro(4-alkoxyphenyl)-tellanyl]propyl} thioureas or the intramolecular cyclization products 5-{dichloro(4-alkoxyphenyl)-telluromethyl}-2-phenylamino-4,5-dihydro-1,3-thiazole hydrochlorides. The reaction route depends on the nature of the substituent in the thiourea. The Fukui function reactivity indexes identify the electrophilic/nucleophilic centers and explain the possible cyclization reaction in the case of phenyl substituted thioureas. In the case of other substituents, the calculated values of partial atomic charges clearly predict that the addition reaction is more possible.
- Kut, Mykola,Fizer, Maksym,Onysko, Mikhajlo,Lendel, Vasil
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p. 2284 - 2290
(2018/09/06)
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- A pharmaceutical intermediate propenyl thiourea synthesis method (by machine translation)
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A pharmaceutical intermediate propenyl thiourea synthesis method, comprises the following steps: in the reaction container by adding 5 L sodium chloride solution, 4 μM of 3 - methyl isobutyl ketone sulfur cyanic acid benzene, raising the temperature of the solution to 60 - - 65 °C, adding 5 — 6 μM of acrylamide and 6 L acetone solution, reflux 90 - 120 min, layered, take out the oil layer, potassium bromide solution for washing 5 — 7 times, be propylene isothiocyanate, desiccant dehydration, filtering, the filtrate is distilled under reduced pressure, collecting 80 — 86 °C fraction, obtained propylene thiocyanate; the resulting thiocyanate of propylene added to the 5 — 6 μM benzene acetamide, adding 2 L aqueous solution, raising the temperature of the solution to 50 — 60 °C, reaction 50 — 70 min, reduce the temperature of the solution to 10 — 15 °C, separating out crystal, filtering, washing toluene solution, butanone solution washing, dehydrating agent dehydration, to get finished propenyl thiourea. (by machine translation)
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Paragraph 0011; 0013; 0014; 0015
(2018/07/30)
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- Synthesis, molecular docking and biological evaluation of N,N-disubstituted 2-aminothiazolines as a new class of butyrylcholinesterase and carboxylesterase inhibitors
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A series of 31 N,N-disubstituted 2-amino-5-halomethyl-2-thiazolines was designed, synthesized, and evaluated for inhibitory potential against acetylcholinesterase (AChE), butyrylcholinesterase (BChE) and carboxylesterase (CaE). The compounds did not inhibit AChE; the most active compounds inhibited BChE and CaE with IC50 values of 0.22-2.3 μM. Pyridine-containing compounds were more selective toward BChE; compounds with the para-OMe substituent in one of the two dibenzyl fragments were more selective toward CaE. Iodinated derivatives were more effective BChE inhibitors than brominated ones, while there was no influence of halogen type on CaE inhibition. Inhibition kinetics for the 9 most active compounds indicated non-competitive inhibition of CaE and varied mechanisms (competitive, non-competitive, or mixed-type) for inhibition of BChE. Docking simulations predicted key binding interactions of compounds with BChE and CaE and revealed that the best docked positions in BChE were at the bottom of the gorge in close proximity to the catalytic residues in the active site. In contrast, the best binding positions for CaE were clustered rather far from the active site at the top of the gorge. Thus, the docking results provided insight into differences in kinetic mechanisms and inhibitor activities of the tested compounds. A cytotoxicity test using the MTT assay showed that within solubility limits (30 μM), none of the tested compounds significantly affected viability of human fetal mesenchymal stem cells. The results indicate that a new series of N,N-disubstituted 2-aminothiazolines could serve as BChE and CaE inhibitors for potential medicinal applications.
- Makhaeva, Galina F.,Boltneva, Natalia P.,Lushchekina, Sofya V.,Serebryakova, Olga G.,Stupina, Tatyana S.,Terentiev, Alexey A.,Serkov, Igor V.,Proshin, Alexey N.,Bachurin, Sergey O.,Richardson, Rudy J.
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p. 1050 - 1062
(2016/02/19)
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- Substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one as CB 1 cannabinoid receptor ligands: Synthesis and pharmacological evaluation
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A set of 30 substituted 5,5′-diphenyl-2-thioxoimidazolidin-4-one (thiohydantoins) derivatives was synthesized, and their affinity for the human CB1 cannabinoid receptor has been evaluated. These compounds are derived from the previously described cannabinoid ligands 5,5′- diphenylimidazolidine-2,4-dione (hydantoins). The replacement of the oxygen by a sulfur leads to an increase of the affinity while the function-i.e., inverse agonism-determined by [35S]-GTPγS experiments remains unaffected. Finally, to evaluate the molecular parameters that could influence the affinity of the thiohydantoins, molecular electrostatic potential as well as lipophilicity calculations were undertaken on representative thiohydantoins and hydantoins derivatives. In conclusion, 5,5′-bis-(4-iodophenyl)-3-butyl-2- thioxoimidazolidin-4-one (31) and 3-allyl-5,5′-bis(4-bromophenyl)-2- thioxoimidazolidin-4-one (32) possess the highest affinity for the CB 1 cannabinoid receptor described to date for the hydantoin and thiohydantoins series when compared in a same bioassay.
- Muccioli, Giulio G.,Martin, Diana,Scriba, Gerhard K. E.,Poppitz, Wolfgang,Poupaert, Jacques H.,Wouters, Johan,Lambert, Didier M.
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p. 2509 - 2517
(2007/10/03)
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- A convenient and efficient method for the synthesis of mono- and N,N-disubstituted thioureas
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A convenient method for the synthesis of mono- and N,N-disubstituted thioureas by the debenzoylation of N-substituted- and N,N-disubstituted- N′-benzoylthioureas with hydrazine hydrate under solvent-free conditions has been developed. N-Substituted-N′-benzoylthioureas and hydrazine hydrate were mixed, and stirred at room temperature without a solvent to give the corresponding N-substituted thioureas in high yields.
- Kodomari, Mitsuo,Suzuki, Masato,Tanigawa, Keiko,Aoyama, Tadashi
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p. 5841 - 5843
(2007/10/03)
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- A General Procedure for Synthesis of NG-Alkyl, and NG-Aryl-L-Arginines as Potential Nitric Oxide Synthase Inhibitors
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A general procedure for the synthesis of NG-alkyl, and NG-aryl-L-arginines with relatively high overall yield is reported. The key step involved the coupling of protected L-ornithine 4 with isothiourea 7 to give the fully protected NG-aryl-L-arginine derivative 8. Subsequent deprotection of 8 in acidic condition provided the final target compound 9 with an overall yield of more than 80%.
- Chen, Bor-Cherng,Shiu, Shi,Yang, Ding-Yah
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p. 549 - 553
(2007/10/03)
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- Kinetics of electron transfer between bis(2,2'-bipyridine)manganese(III)complex and thioureas in aqueous perchlorate media
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Kinetics of the redox interactions of thiourea and its N-substituted derivatives with manganese(III) complex of 2,2'-bipyridine has been investigated in aqueous solution by stopped-flow technique in the acid range +>, 0.10-0.50 mol dm-3 at I=1.0 mol dm-3 (NaClO4) and at 30 deg C.A rapid initial increase in absorbance is followed by a slower decay of the formed species for all the four thioureas.Both the reaction steps are analysed and an inner sphere mechanism has been proposed for these reactions.The reactivity order for these thiourea derrivatives is: ptu>tu>mtu>atu, and this bears a consequence to their substituent effects.
- Ali, Mahammad,Gangopadhyay, Sumana,Dutta, Amitava,Banerjee, Pradyot
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- ZINC SULFIDE PRECIPITATION FROM AN N-ALLYLTHIOUREA SOLUTION
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The constant of N-allylthiourea hydrolysis in an alkaline medium at 25 deg C was determined experimentally.Thermodynamic analysis was performed on the conditions for zinc sulfide precipitation by allylthiourea from alkaline solutions of zinc complex salts.The conditions of ZnS precipitation were found experimentally.The structure of the precipitates was determined by means of x-ray phase analysis.
- Kitaev, G. A.,Uritskaya, A. A.,Yatlova, L. E.,Mirolyubov, V. R.
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p. 1415 - 1418
(2007/10/03)
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- Effects of pH and Ferrous Ion on the Degradation of Glucosinolates by Mirosinase
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During the enzymatic degradation of sinigrin, the relase of glucose and the formation of allyl isothiocyanate via subsequent cleavage of the aglucon were studied in the presence or absence of ferrous ion over a pH range of 3.5-7.5.The liberation of glucose increased linearly with the time of enzymatic cleveage of sinigrin for the first 20 min at the pHs used, and no inhibition of glucose liberation was caused by ferrous ion at the concentration tried.On the other hand, the effects of ferrous ion on the formation of the isothiocyanate changed greatly with changes of pH of the reaction medium.At pH 4.5 and 5.5, formation of isothiocyanate was strongly inhibited by ferrous ion, while such an effect of ferrous ion was notably depressed at pH 6.5 and disappeared at pH 7.5.These results were also confirmed by gas chromatographic analysis of the volatile cleveage products of the glucosinolates prepared from the seed meal of hakuran (an artificial variety of Brassica napus).From these results, it was suggested that ferrous ion is not involved in the enzymatic liberation of glucose from glucosinolate but in the subsequent degradation of the aglucon.
- Uda, Yasushi,Kurata, Tadao,Arakawa, Nobuhiko
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p. 2735 - 2740
(2007/10/02)
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- Synthesis of Heterocyclic Compounds via Enamines. Part 8. Acid-catalysed Transformations in 4,4,6-Trimethyl-1,4-Dihydropyrimidine-2(3H)-thione Derivatives and Related Compounds
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1-Substituted 4,4,6-trimethyl-1,4-dihydropyrimidine-2(3H)-thiones (2) on heating in 11M-HCl at 100-110 deg C are converted into the corresponding 2-substituted-amino-4,6,6-trimethyl-6H-1,3-thiazines (4) and/or thioureas.But at 95-100 deg C, Dimroth rearrangement products, e.g. the corresponding 2-substituted-amino-4,4,6-trimethyl-4H-1,3-thiazenes (3) are formed.
- Singh, Harjit,Singh, Paramjit
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p. 1013 - 1018
(2007/10/02)
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- Cephalosporin displacement reaction
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The present invention is directed to a process for the displacement of the acetoxy group of a cephalosporanic acid by a sulfur nucleophile, in an organic solvent and under essentially anhydrous conditions.
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- Pesticidal compositions containing phosphoric esters and divalent sulphur compounds
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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.
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