16022-65-4

Usage

InChI:InChI=1/C5H9NOS2.K/c8-5(9)6-1-3-7-4-2-6;/h1-4H2,(H,8,9);/q;+1/p-1

Upstream product

• 110-91-8 morpholine 
• 75-15-0 carbon disulfide 

Downstream Products

• 100515-82-0 2-N-morpholino-dithiocarbamoyl-propanoic acid 
• 729-46-4 4,4'-(dithiodicarbonothioyl)dimorpholine 

Relevant academic research and scientific papers

Mixed bis(morpholine-4-dithiocarbamato-S,S)antimony(III) complexes: Synthesis, characterization and biological studies

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

Synthesis, chemical characterization and cancer cell growth-inhibitory activities of Cu(ii) and Ru(iii) aliphatic and aromatic dithiocarbamato complexes

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).

Discovery and optimization of novel dual dithiocarbamates as potent anticancer agents

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.

Synthesis and antitumor activity of tetrahydrocarbazole hybridized with dithioate derivatives

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.

Lanthanide(III) morpholine 4-dithiocarbamate complexes: Pr(III) derivative shows first example of polymeric lanthanide(III) dithiocarbamate

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.

Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors

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.

Synthesis and antimicrobial activities of some 1-[(N,N- disubstitutedthiocarbamoylthio)acetyl]-3,5-diaryl-2-pyrazolines

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.

Synthesis and anticonvulsant activity of some new hexahydropyrimidine-2,4- dione derivatives

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.

Triphenyl phosphine adducts of platinum(IV) and palladium(II) dithiocarbamates complexes: A spectral and in vitro study

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

Synthesis and in vitro antifungal activity of some N,N-disubstituted dithiocarbamic acid esters derived from 2-methylquinazolinones

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.