- Mixed bis(morpholine-4-dithiocarbamato-S,S)antimony(III) complexes: Synthesis, characterization and biological studies
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Some mixed bis(morpholine-4-dithiocarbamato-S,S)antimony(III) complexes [(OC4H8NCS2)2SbL] with oxygen or sulfur donor ligands [L = -OOCCH3 (1), -OOCC6H5 (2), -SOCCH3 (3), -SCH2COOH (4), -OOCC6H 4(OH) (5), -SCH2CH2CH3 (6), -OC 6H5 (7), SCH2CH2S- (8)] have been synthesized by reacting the chloro-bis(morpholine-4-dithiocarbamato-S,S) antimony(III) with corresponding oxygen or sulfur donor ligands in 1:1 or 2:1 stoichiometries. These have been characterized by melting point, molecular weight determination (cryoscopically), antimony (iodometrically) and sulfur (gravimetrically) estimation, elemental analyses (C, H and N), UV-visible, FT-IR, far IR, multinuclear NMR (1H and 13C)], TG/DTA analysis, ESI-mass and powder X-ray diffraction studies. The splitting of the strong band observed at 1046-1066 cm-1 due to (C-S) indicated anisobidentate mode of binding of the dithiocarbamate group, which was further supported by a 13C NMR signal appearing at around δ 200 due to NCS2 moiety. The base peak observed at m/z 444.9 supports the strong chelating nature of the morpholine-4-dithiocarbamate compared to the other hetero ligands used. TGA revealed that, complexes 21 and 4 were decomposed in three steps; also 6 was decomposed in two steps, followed by the formation of Sb2S3. The results obtained by antimicrobial screening tests indicate that complex 3 showed a maximum zone of inhibition (20 mm) against Trichoderma ressie at a concentration of 200 μg ml-1. Complexes 2, 3 and 8 are most active (zone of inhibition (ZI) 17-20 mm) against both of the fungal species Aspergillus niger and Trichoderma ressie as well as complex 4 (ZI 17 mm) and 6 (ZI 18 mm) against Trichoderma ressie. Copyright
- Chauhan,Carpenter, Jaswant,Joshi, Sapana
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- Synthesis, chemical characterization and cancer cell growth-inhibitory activities of Cu(ii) and Ru(iii) aliphatic and aromatic dithiocarbamato complexes
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In this paper, we focused on the analysis of the effects mediated by different cyclic dithiocarbamic ligands (DTC) on three classes of antiproliferative coordination compounds, namely, Ru(iii) complexes with the general formulae [Ru(DTC)3] and [Ru2(DTC)5]Cl, and the neutral Cu(ii) derivatives of the type [Cu(DTC)2]. In particular, we present the synthesis and characterization of a library of total 23 coordination compounds containing Ru(iii) or Cu(ii) as the biologically-active metal center and two or more dithiocarbamato (DTC) ligands derived from cyclic amines (aliphatic or aromatic). Several techniques including elemental analysis, X-ray crystallography, ESI-MS, 1H-NMR spectroscopy, FT-IR and UV-Vis spectrophotometry were used to characterize the compounds, which highlighted the different electronic behaviors generated by the substituents within the DTC moiety. Moreover, the synthesized compounds were tested for their stability in order to investigate their antiproliferative activity against 3 human cancer cell lines, namely, HeLa, HepG2 and HepG2/SB3. In particular, HepG2/SB3 was chosen for its aggressiveness due to upregulation of the anti-apoptotic protein SerpinB3. Finally, the most promising compounds are studied in terms of log?P. Overall, the results reveal the drug-likeness of some of the derivatives of copper(ii) and ruthenium(iii).
- Brustolin,Nardon,Pettenuzzo,Zuin Fantoni,Quarta,Chiara,Gambalunga,Trevisan,Marchiò,Pontisso,Fregona
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supporting information
p. 15477 - 15486
(2018/11/20)
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- Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents
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A series of dual dithiocarbamates were synthesized and evaluated for their in-vitro anticancer activities on human non-small cell lung cancer cell line H460. Nine compounds exhibited significant antiproliferative activities with IC50 less than 1 μM. Among them, compound 14m showed the highest inhibitory activity against H460 cell and inhibited the growth of nine types of tumor cells with IC50 values less than 1 μM. It also achieved IC50 of 54 nM and 23 nM against HepG2 and MCF-7 cell lines, respectively. Preliminary structure-activity relationship study indicated that: a) when the methyl group (region A) is substituted with benzene rings, ortho substitution on the benzene ring is favored for activity; b) substitution with heterocyclic structures at region A exhibited greater impact on the anti-tumor activity of compounds, in which pyridine ring, thiazole ring, coumarin and benzo[b]thiophene are favored and quinoline ring is the most favored; c) substitution with different amines (region B) also showed marked effect on the activity of compounds and dimethylamine and morpholine are preferred to other tested amines.
- Li, Ri-Dong,Wang, Hui-Ling,Li, Ying-Bo,Wang, Zhong-Qing,Wang, Xin,Wang, Yi-Tao,Ge, Ze-Mei,Li, Run-Tao
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p. 381 - 391
(2015/03/04)
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- Synthesis and antitumor activity of tetrahydrocarbazole hybridized with dithioate derivatives
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The present study reported the synthesis of tetrahydrocarbazoles hybridized with dithioate derivatives. Three series were synthesized namely alkyl dithiocarbonates (4a-d), heterocyclic dithiocarbamates (6a-g) and dialkyl dithiocarbamate (7). The synthesized compounds were tested in vitro on human breast adenocarcinoma cell line (MCF7) and the human colon tumor cell line (HCT116). Most of the synthesized compounds exploited potent antitumor activity, especially compound 6f [4-chlorophenylpiperazine derivative], which showed cytotoxic activity against MCF7 superior to doxorubicin with IC50 value of 7.24 nM/mL.
- El-Nassan, Hala Bakr
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p. 308 - 315
(2015/04/14)
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- Lanthanide(III) morpholine 4-dithiocarbamate complexes: Pr(III) derivative shows first example of polymeric lanthanide(III) dithiocarbamate
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Three lanthanide(iii) morpholine 4-dithiocarbamate complexes [Ln(Phen)(Mph-Dtc)3]·xCH2Cl2 [Ln = Pr (1), Nd (2) and Eu (3); Mph-Dtc = morpholine 4-dithiocarbamate; x = 2 (1) or 1 (2, 3)] have been prepared from the reaction of the potassium salt of morpholine 4-dithiocarbamate with lanthanide nitrates and phenanthroline. Complexes 1-3 were characterized by various analytical techniques and their solid state structures were established by single crystal X-ray diffraction analysis. The Ln(iii) ions are nine or eight coordinated in 1 and 2, 3 respectively. Interestingly, oxygen atom of one of the three coordinated Mph-Dtc ligands is further coordinated to a Pr(iii) ion of the adjacent molecule. Thus, it results in the formation of an one-dimensional (1D) polymeric structure. Thermal stability and optical properties of 1-3 have been investigated.
- Mahato, Mamata,Jana, Partha P.,Harms, Klaus,Nayek, Hari Pada
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p. 62167 - 62172
(2015/08/03)
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- Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors
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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.
- Kapanda, Coco N.,Muccioli, Giulio G.,Labar, Geoffray,Poupaert, Jacques H.,Lambert, Didier M.
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experimental part
p. 7310 - 7314
(2010/07/14)
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- Synthesis and antimicrobial activities of some 1-[(N,N- disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines
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The increasing clinical importance of drug-resistant fungal and bacterial pathogens has lent additional urgency to microbiological research and new antimicrobial compound development. For this purpose, new pyrazoline derivatives were synthesized and evaluated for antimicrobial activity. Some 1-[(N,N-disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines derivatives were synthesized by reacting 1-(chloroacetyl)-3,5-diaryl-2- pyrazolines with appropriate potassium salts of secondary amine dithiocarbamic acids. The chemical structures of the compounds were elucidated by IR, 1H-NMR, and FAB+-MS spectral data. Their antimicrobial activities against Staphylococcus aureus (B-767), Escherichia coli (B-3704), Pseudomonas aeruginosa (ATCC 27853), Proteus vulgaris (NRLL B-123), and Candida albicans (NRRL-27077) were investigated. The results showed that some of the compounds have notable activity against S. aureus and C. albicans. Copyright Taylor & Francis Inc.
- Turan-Zitouni, Guelhan,Oezdemir, Ahmet,Kaplancikli, Zafer Asim,Chevallet, Pierre,Tunali, Yagmur
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p. 2717 - 2724
(2007/10/03)
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- Synthesis and anticonvulsant activity of some new hexahydropyrimidine-2,4- dione derivatives
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In this study, twelve new hexahydropyrimidine-2,4-dione derivatives were synthesized and screened for their anticonvulsant activities. All the compounds (7a-l) which have 6-arylhexahydropyrimidine-2,4-dione and N,N-disubstituted dithiocarbamate structures were prepared by the reaction with appropriate 3-(2-chloroethyl)-6-arylhexahydropyrimidine-2,4-diones and the corresponding N,N-disubstituted dithiocarbamate potassium salts. The structure of the synthesized compounds was confirmed by UV, IR, 1H-NMR and elemental analysis. Their anticonvulsant activities were determined by maximal electroshock (MES), subcutaneous pentetrazol (metrazol, scMet) and rotorod toxicity tests for neurological deficits. According to the activity studies, 6-(4-chlorophenyl)hexahydropyrimidine-2,4-dione derivatives (7e-h) were found to be highly protective against MES and scMet. Neurotoxicity was not observed in any of the tested compounds.
- Septioglu, Ebubekir,Aytemir, Mutlu Dilsiz,Calis, Uensal
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p. 259 - 264
(2007/10/03)
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- Triphenyl phosphine adducts of platinum(IV) and palladium(II) dithiocarbamates complexes: A spectral and in vitro study
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Triphenyl phosphine adducts of dithiocarbamate complexes of platinum(IV) and palladium(II) of the type [Pt(L)2PPh3Cl2] and [Pd(L)2PPh3] [L: morpholine dithiocarbamate (L 1), aniline dithioc
- Manav,Mishra,Kaushik
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p. 3087 - 3092
(2007/10/03)
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- Synthesis and in vitro antifungal activity of some N,N-disubstituted dithiocarbamic acid esters derived from 2-methylquinazolinones
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A series of 2-[(N,N-disubstituted thiocarbamoylthio)methyl]quinazolinones 9a-g; 10a; 10d; 11a-d and 12a were synthesized and evaluated for potential antifungal activity against a variety of fungal species. The synthesis of the target compounds was achieved by reaction of the potassium salts of disubstituted dithiocarbamic acids 8a-g and the respective 2-bromomethyl-4(3H)-quinazolinone 4 or 3-aryl-2- chloromethyl-4(3H)-quinazolinones 5-7. The dithiocarbamic acid derivatives were synthesized in a one step reaction from the appropriate amine, alcoholic potassium hydroxide solution and carbon disulfide. TLC and elemental analyses ascertained the purity of the synthesized compounds and their structures were confirmed by IR and 1H-NMR spectroscopy, 2-Methyl-4(3H)-quinazolinone 2, the precursor of the 2-bromomethyl intermediate 4, was selected as representative example for detailed spectroscopic investigations, including 300 MHz 1H- and 13CNMR in addition to HH COSY; APT and 1H13C HETCOR spectra, with the aim of establishing correct assignment of the spectral data of related compounds. The synthesized disubstituted dithiocarbamates 9a-g; 10a,d; 11a-d and 12a as well as tolnaftate and clotrimazole, as reference drugs, were tested in vitro at 2 and 5% concentrations against 23 pathogenic fungi. The study revealed that compound 9a exhibited broad spectrum inhibitory activity that is superior or comparable to that of the reference drugs against the tested fungal isolates. Selective fungistatic activity against Candida species was elicited by compound 9e and against Microsporum species as well as Trichophyton mentagrophytes was also observed for compound 9g. As a general pattern it might be postulated that some of the synthesized dithiocarbamate derivatives showed broad spectrum antifungal activity as compared with tolnaftate, the clinically used thiocarbamate compound, and also exhibited comparable activity to clotrimazole against Candida species and F. Solani.
- Farghaly,Moharram
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p. 280 - 289
(2007/10/03)
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- Synthesis and pharmacology of new dithiocarbamic acid esters derived from phenothiazine and diphenylamine
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2-Methylthio-10-[N,N-disubstituted-thiocarbamoylthio)acetyl]- phenothiazines (4a-g) and N-(3-methylthiophenyl)-N-[(N,N-disubstituted- thiocarbamoylthio)acetyl]phenylamines (5a-g) were synthesized by subsequent treatment of 2-methylthio-10-chloroacetylphenothiazines (1) and N-(3- methylthiophenyl)-N-chloroacetylphenylamine (2) with potassium salts of N,N- disubstituted dithiocarbamic acid derivatives (3a-i). The structures of the compounds were determined by analytical and spectral (IR, 1H NMR, 13C NMR, EIMS) methods. The antihistaminic and anticholinergic activities of 4a, 4c, 4e-g, 5a-c 5e, and 5g were evaluated in comparison with H1-receptor antagonist mepyramine and nonselective cholinergic antagonist atropine. In the first series of experiments, the cumulative concentration-response curves to histamine (10-8-10-4 M) and acetylcholine (10-8-10-4 M) were constructed in separate fundus strips. The test compounds exhibited marked antihistaminic activity at 10-6 M concentration but compounds did not influence acetylcholine induced contractions. Concentration-related experiments carried out on 4g and 5g revealed that a moderate antihistaminic activity was present at 10-7 M concentration of the compounds and became strong at higher concentrations. In the second series of experiments, the cumulative concentration-response curve to histamine (10-9-10-4 M) was constructed in guinea-pig ileum segments. Maximal responses were obtained by 10-6-3 x 10-6 M concentrations of histamine in ileum segments. Similar inhibitions of histamine contractions were also obtained with the test compounds. Their inhibitory effectiveness was evaluated by comparing the pA2 values.
- Karali, Nilguen,Apak, Idil,Oezkirimli, Sumru,Guersoy, Aysel,Dogan, Soenmez Uydes,Eraslan, Aylin,Oezdemir, Osman
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p. 422 - 426
(2007/10/03)
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- Synthesis, characterization and in-vitro antifungal evaluation of some dithiocarbamic acid derivatives
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Some new N, N-disubstituted dithiocarbamates derived from α-acetonaphthone and their precursors, potassium salts of dithiocarbamic acid, were prepared and evaluated for antifungal activity. Synthesis involved the reaction of α-chloro-2-acetonaphthone or α-chloro-4-methoxy-1-acetonaphthone with the potassium salts of N, N-disubstituted dithiocarbamic acid (5a-g). Compounds 5a-g were readily produced by reaction of equivalent amounts of the appropriate secondary amine, potassium hydroxide and carbon disulphide. The purity of the final derivatives, N, N-disubstituted dithiocarbamates 6a-g and 7a-g, was determined elemental analyses and TLC, and assignment of structures was confirmed by IR, 1H NMR, 13C NMR and MS. Preliminary evaluation of the antifungal activity of derivatives 5a-g, 6a-g and 7a-g was determined in-vitro at a 2.5 or 5.0% concentration against different fungal species using tolnaftate as a reference drug. The potassium salts 5a-g were the most potent derivatives of the tested series. Compounds 5a-g showed significant broad spectrum antifungal activity. Combination of the dithiocarbamate with acetonaphthonyl moiety, represented by the 6a-g and 7a-g series, resulted in a decrease in or complete loss of antifungal activity in certain derivatives. Compounds derived from 4-methoxy-1-acetonaphthone (7a-g) were generally superior to their 4-nonsubstituted congeners (6a-g). The morpholino dithiocarbamate derivative 7e was equipotent or superior to the reference drug against the tested dermatophytes species and Rhodotorula rubra at a 5% concentration. In addition, 7e exhibited inhibitory activity against Chrysosporium tropicum, Emericella nidulans, Penicillium aurantiogriseum and Aspergillus sydowii. Some derivatives of both series showed selective activity against certain fungi, (e.g. 6f against Phoma glomerata and Scopulariopsis acremonium; 6g against Emericella nidulans and Phoma glomerata; 7c against Geotrichum candidum and Mucor circinelloides; 7d against Geotrichum candidum, Penicillium aurantiogriseum and Rodotorula rubra and 7f against Mucor circinelloides).
- Mahfouz, Nadia M.,Moharram, Ahmad M.
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p. 315 - 322
(2007/10/03)
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- Synthesis characterization and biological evaluation of 2-methyl-3-(N-substituted thiocarbamoylthio)acetamido-4(3H)-quinazolinones
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Reaction of 3-chloroacetamido-2-methyl-4(3H)-quinazolinones (1 and 2) with appropriately substituted potassium dithiocarbamates (3) furnished 2-methyl-3-(N-substituted thiocarbamoylthio)acetamido-4(3H)-quinazolinones (4 and 5) which exist as isomeric mixtures. The structures of 4 and 5 were determined by analytical and spectral (IR, 1H-NMR, EIMS, CIMS(CH4 or NH3)) methods. All the compounds except for 4g and 5g were tested for antimicrobial activity against some bacteria und fungi. Only 4b and 4c were found active against Staphylococcus aureus (MIC 100 μg/ml). 4d, 4e, 4g, 4h, 5a-f and 5h were also evaluated for anticonvulsant activity but were found inactive.
- Capan,Ergenc,Buyuktimkin,Yulug
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p. 243 - 250
(2007/10/02)
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- Separation and Determination of Selenium(IV) and Tellurium(IV) by using Morpholine-4-carbodithioate
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The separation and determination of selenium(IV) and tellurium(IV), when present together in a mixture, has been carried out by employing morpholine-4-carbodithioate in presence of aqueous ammonia and sulphur dioxide.The complexes were weighed as Se(C5H8ONS2)4 and Te(C5H8ONS2)2, respectively, after drying and 110-115 deg.The interference by NiII, ZnII, CdII, CoII, FeIII, InIII, TIIII, SnII and UIV has been avoided by using an ammoniacal mixture of EDTA and tartrate (1:1 molar ratio) as a masking agent.The metal carbodithioates were characterised by elemental and thermogravimetric analysis.
- Singh, Nepal,Rastogi, Kalpana,Agrawal, R. C.
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p. 394 - 396
(2007/10/02)
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