71107-76-1

Upstream product

• 75-15-0 carbon disulfide 
• 108-91-8 cyclohexylamine 

Downstream Products

• 75-15-0 carbon disulfide 
• 108-91-8 cyclohexylamine 
• 1025836-01-4 Cyclohexyl-hydroxymethyl-dithiocarbamic acid hydroxymethyl ester 
• 41967-03-7 5-carboxymethyl-3-cyclohexyl-1,3,5-thiadiazinane-2-thione 
• 200422-61-3 [2-(5-Cyclohexyl-6-thioxo-[1,3,5]thiadiazinan-3-yl)-acetylamino]-acetic acid 
• 1122-82-3 isothiocyanatocyclohexane 
• 14882-56-5 bis(N-cyclohexyldithiocarbamato)zinc 
• 1251935-63-3 bis(N-cyclohexyldithiocarbamato)cobalt(II) 
• 15699-97-5 bis(N-cyclohexyldithiocarbamato)copper(II) 
• 113588-56-0 bis(N-cyclohexyldithiocarbamato)nickel(II) 

Relevant academic research and scientific papers

Structure-activity relationships of mononuclear metal-thiosemicarbazone complexes endowed with potent antiplasmodial and antiamoebic activities

A useful concept for the rational design of antiparasitic drug candidates is the complexation of bioactive ligands with transition metals. In view of this, an investigation was conducted into a new set of metal complexes as potential antiplasmodium and an

Dithiocarbamates combined with copper for revitalizing meropenem efficacy against NDM-1-producing Carbapenem-resistant Enterobacteriaceae

The worldwide prevalence of NDM-1-producing Gram-negative pathogens has drastically undermined the clinical efficacy of carbapenems, prompting a need to devise an effective strategy to preserve their clinical value. Here we constructed a focused compound library of dithiocarbamates and systematically evaluated their potential synergistic antibacterial activities combined with copper. SA09-Cu exhibited excellent inhibition against a series of clinical NDM-1-producing carbapenem-resistant Enterobacteriaceae (CRE) in restoring meropenem effect, and slowed down the development of carbapenem resistance. Enzymatic kinetic and isothermal titration calorimetry studies demonstrated that SA09-Cu was a noncompetitive NDM-1 inhibitor. The electron paramagnetic resonance (EPR) and X-ray photoelectron spectroscopy (XPS) revealed a novel inhibition mechanism, which is that SA09-Cu could convert NDM-1 into an inactive state by oxidizing the Zn(II)-thiolate site of the enzyme. Importantly, SA09-Cu showed a unique redox tuning ability, and avoided to be reduced by intracellular thiols of bacteria. In vivo experiments indicated that SA09 combined with CuGlu could effectively potentiate MER's effect against NDM-1-producing E. coli (EC23) in the murine infection model. This study provides a highly promising scaffold in developing novel inhibitors to combat NDM-1-producing CREs.

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

Liquid phase organic synthesis of 3,5-disubstituted 1,3,5-thia-diazinane-2- thione derivatives on polyethylene glycol (PEG) support

An efficient liquid-phase synthesis of 3,5-disubstituted 1,3,5-thiadiazinane-2-thione derivatives (THTT) is described using soluble polymer support polyethylene glycol (PEG) 5000 via one-pot condensation of PEG-bound free amino acid or PEG-bound tripeptid

Spectral, thermal and in vitro antimicrobial studies of cyclohexylamine-N-dithiocarbamate transition metal complexes

Transition metal complexes of the type [M(L)2] and those containing monodentate phosphines of the type [M(L)2(PPh 3)] {M = Ni, Co, Cu and Zn; L = cyclohexylamine-N-dithiocarbamate; PPh3 = triphenylphosphine} have been synthesized. The complexes were characterized using IR, UV-vis, NMR spectroscopy, and thermal analysis (TGA). The 1H NMR, 13C NMR and 31P NMR showed the expected signals for the dithiocarbamate and triphenylphosphine moieties. The spectral studies in all compounds revealed that the coordination of metals occurs via the sulphur atom of the dithiocarbamate ligand in a bidentate fashion. Thermal behavior of the complexes showed that the complexes were more stable than their parent ligands. The ligand moiety is lost in the first step and the rest of the organic moiety decomposes in the subsequent steps. Furthermore, the ligand and their metal complexes were screened in vitro for their antibacterial activity against Escherichia coli, Staphylococcus aureus, Salmonella typhi, Enterococcus faecalis, Pseudomonas aeruginosa and Bacillus cereus and antifungal activities against Aspergillus flavus, Aspergillus carbonarius, Aspergillus niger and Aspergillus fumigatus. The metal complexes exhibited higher antimicrobial activity than the parent ligands. Generally, the zinc complexes were effective against the growth of bacteria with Zn(L) 2 displaying broad spectrum bacteriocidal activity at concentrations of 50 μg/mL; and Ni(L)2 was more effective against the growth of fungi at concentrations of 100-400 μg/mL under laboratory conditions.

Synthesis of 3-substituted-5-(4-carboxycyclohexylmethyl)-tetrahydro-2h-1,3, 5-thiadiazine-2-thione derivatives as antifibrinolytic and antimicrobial agents

A series of 3-substituted-5-(4-carboxycyclohexylmethyl)-tetrahydro-2H-1,3, 5-thiadiazine-2-thione derivatives was prepared and examined for antifibrinolytic and antimicrobial activities. Their structures were elucidated by spectral methods. Antifibrinolytic activities of these compounds, were investigated in vitro and compared to tranexamic acid (CAS 1197-18-8). Among the synthesized compounds, 3-methyl-5-(4-carboxycyclohexylmethyl)-tetrahydro-2H-1, 3,5-thiadiazine-2-thione (Ia) was the most prominent one (104 %) when compared to tranexamic acid. Besides, 3-ethyl-5-(4-carboxycyclohexyl-methyl)-tetrahydro- 2H-1,3,5-thiadiazine-2-thione (Ib), 3-isopropyl-5-(4-carboxycyclohexylmethyl)- tetrahydro-2H-1,3,5-thiadiazine-2-thione (Id) and 3-isobutyl-5-(4- carboxycyclohexyl-methyl)-tetrahydro-2H-1,3,5-thiadiazine-2-thione (Ig) showed antifibrinolytic activity similar to tranexamic acid. Antibacterial activities of these compounds against Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis), Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa) and yeast-like fungi (Candida albicans, Candida tropicalis) were investigated by the micro-dilution method and compared with the activity of tranexamic acid, ofloxacin and fluconazole. By this way their minimal inhibitory concentration (MIC), minimal bactericidal concentration (MBC) and minimal fungicidal concentration (MFC) values were determined. Compound Ia exhibited almost equally potent activity against B. subtilis (MIC and MBC: 6.25 μg/mL). Compounds Ib-Id, If-Ig and In exhibited similar bactericidal activity against B. subtilis (MBC: 12.5 μg/mL). Compounds Ik and Im showed bacteriostatic activity against S. aureus. None of the compounds exhibited activity against Gram-negative bacteria. On the other hand, all compounds had potent antifungal activities against the yeast utilized. Among the synthesized compounds, 3-methyl-5-(4-carboxycyclohexylmethyl) -tetrahydro-2H-1,3,5-thiadiazine-2-thione (Ia) seems to be the most effective compound with antifibrinolytic and antimicrobial activity. ECV Editio Cantor Verlag.

Synthesis and antimicrobial activity of new thiazole-2(3H)-thiones containing 1,1,3-trisubstituted cyclobutane

The reaction of potassium salts of RNHCSSK with 2-chloro-1-(3-methyl-3- phenylcyclobutyl)ethan-1-one in ethanol at 78-80°C afforded new 1,3-thiazole-2(3H)-thiones containing 1,1,3-trisubstituted cyclobutane rings at C-4. The antimicrobial activities of these compounds were also investigated against seven different microorganisms, and some of them were found to be active against several of the microorganisms at higher concentrations.

Synthesis and antimycobacterial activity of 3,5-disubstituted thiadiazine thiones

A series of 3,5-disubstituted thiadiazine thiones (4-24) have been synthesized by reaction of primary amines with carbon disulphide followed by cyclocondensation of the resulting intermediate with formaldehyde and primary amines or amino acids. The compounds were screened for antitubercular activity in vitro against Mycobacterium tuberculosis H37Rv. Three compounds 4, 12 and 18 showed antimycobacterial activity with MIC 12.5 μg/mL. Compound 4, was tested in vitro against five multidrug resistant (MDR) strains of M. tuberculosis and was found to be active. Compound 4 also exhibited activity in vivo. While all the mice died in the untreated group, the mean survival time (MST) of the compound treated mice was enhanced, 33% mice were surviving in treated group and the load of bacilli in the lung was considerably less in the compound treated group than in the untreated control group.

New 2H-tetrahydro-1,3,5-thiadiazine-2-thiones incorporating glycine and glycinamide as potential antifungal agents

The new title derivatives (4 b-h and 5 a-i) were synthesized by reaction of the appropriate primary amine, carbon disulphide, and formaldehyde. These derivatives were prepared in order to study the effects of introducing polar groups at N3 or N5 or at both positions on the biological activity. The compounds were tested for their antifungal activity in vitro against pathogenic (Trichophyton rubrum and Candida albicans), phytopathogenic (Penicillum expansum, Trichoderma hazianum, and Fasarium oxysporum), and aflatoxin-producing (Aspergillus flavus) fungi. These compounds exhibited varied inhibitory effects on growth or sporulation of some tested fungal species.

Synthesis and antiprotozoan properties of new 3,5-disubstituted- tetrahydro-2H-1,3,5-thiadiazine-2-thione derivatives

In a search for antiprotozoan compounds, 34 new 3,5-disubstituted- tetrahydro-2H-1,3,5-thiadiazine-2-thione derivatives were synthesized and tested in vitro against Trypanosoma cruzi and Trichomonas vaginalis. Some of them showed important antiprotozoan a