Hydrazine Carbodithioate Research Articles

Novel Piperidone Hydrazine Carbodithioate Derivative: Synthesis, In Silico Drug-Likeness Analysis and Anticancer Properties

An efficient synthesis of a novel compound of hydrazine carbodithioate derivative of piperidone, (E)-methyl-2-(3-methyl-2,6-diphenylpiperidin-4-ylidene)hydrazinecarbodithioate (1), was performed using methyl dithiocarbazinate and 3-methyl-2,6-diphenylpiperidin-4-one as the starting materials. The reaction was carried out in an acidic medium using methanol as a solvent. The novel compound was characterized by FTIR, Mass, and NMR spectral techniques. The hydrazine carbodithioate derivative (1) was then tested for its anticancer activity against the liver cancer cell line, Hep G2, using the MTT assay. The IC50 values of the newly synthesized compound were found to be 34.33 ± 0.79 µM (24 hours) and 27.64 ± 1.42 µM (48 hours). The in vitro antitumor studies demonstrated that the novel compound (1) exhibited good inhibitory activity against the Hep G2 cancer cells. Furthermore, in silico properties such as lipophilicity, water solubility, pharmacokinetic properties, drug likeness, and medicinal chemistry were analyzed using the SwissADME tool.

Synthesis and Antibacterial Activity of Azo-Sulfa-Based Disperse Dyes and Their Application in Polyester Printing

For conjugating sulfa drug moieties with Schiff’s bases scaffold in the same build through an azo linker to take advantage of the bioactive feature of both motifs, we designed and synthesized a series of bioactive disperse dyes. The target disperse dyes, methyl 2-(E-2-hydroxy-5-((E)-(4-sulfa-derivative) diazenyl)benzylidene) hydrazine-1-carbodithioates 4a–e have been synthesized via the acidic reaction of azo dyes 3a–e with methyl hydrazine carbodithioate. Structures of the synthesized dyes were clarified based on their spectral and elemental analyses. The effectiveness of the dyes was initially tested as an antibacterial toward Staphylococcus aureus ATCC 6538-P and Escherichia coli ATCC 25933. Dyes that were proven to be effective against bacteria have been used as disperse dyes to print polyester fabrics. The color properties of the dyes and their fastness properties counting washing, perspiration, light, rubbing, and sublimation fastness were also examined. The printed polyester fabrics were evaluated for their antibacterial activity via colony-forming unit (CFU) technique. Fabric samples treated with 4c, 4d, and 4b had promising anti-Gram-positive activities against S. aureus. Whereas 4c-, 4d-, and 4b-treated fabrics exhibited moderate anti-Gram-negative activities against the test bacterium E. coli.

Nitroisatin dithiocarbazate: Synthesis, structural characterization, DFT, and docking studies

The reaction between 5-nitroisatin with S-benzyl dithiocarbazate affords a new isatindithio carbazate so-called NO2Isadtc (Benzyl 2-(5-nitro-2-oxoindolin-3-ylidene)hydrazinecarbodi thioate) which was characterized by means of 1H NMR, FT-IR, UV-visible and single crystal X-ray diffraction - Crystal data for C16H12N4O3S2 (M =372.42 g/mol): triclinic space group P-1, (n°. 02), a = 6.640 Å, b = 8.256 Å, c = 15.908 Å, V = 849.6 Å3, Z = 2, T = 293 K, μ(MoKα) = 0.337 mm-1, Dcalc = 1.456 g/cm3, 27515 reflections measured (2.499° ≤ 2Θ ≤ 26.524°), 3518 unique (Rint = 0.0533, Rsigma =0.0222) which were used in all calculations. The final R1 was 0.0367 (I > 2σ(I)) and wR2 was 0.1045 (all data). Computational methods were applied to NO2Isadtc and its nonsubstituted parent compound Isadtc for structure optimization, electronic distribution, and infrared calculations using B3LYP functional with 6-31G(d,p) basis set in ethanol as a polarizable continuum model. Furthermore, docking studies using human thioredoxin reductase 1 (TrxR) as enzyme target also were performed using NO2Isadtc and the optimized structure of Isadtc. The results demonstrated that both NO2Isadtc and Isadtc may act as inhibitors of TrxR, having different interactions detected, highlighting the contact between the NO2 group and the S111 at the helix which is found for NO2Isadtc.

Synthesis, Characterization and Antibacterial Activity Study of Cobalt(II), Nickel(II), Copper(II), Palladium(II), Cadmium(II) and Platinum(IV) Complexes with 4-Amino-5-(3,4,5-trimethoxyphenyl)-4<i>H</i>-1,2,4-triazole-3-thione

New transition metal complexes of cobalt(II), nickel(II), copper(II), palladium(II), cadmium(II), and platinum(IV) with bidentate ligand 4-amino-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole-3-thiol were synthesized and characterized by microelemental analyses (CHNS), Fourier-transform infrared (FT-IR), UV-Visible spectra, molar conductance, magnetic susceptibility and thermal analyses (TG-DSC). The ligand was synthesized by ring closure of potassium-2-(3,4,5-trimethoxybenzoyl) hydrazine carbodithioate with an excess amount of hydrazine, and then was acidified using hydrochloric acid. The ligand was used as Lewis bases to prepare metal complexes through the reaction of ratio (1:2) metal:ligand. The ligand was characterized by 1H-NMR and 13C-NMR and the previously described methods to identify the complexes. The results obtained from spectra and elemental analyses indicated the tetrahedral geometry around Cd(II) ion, square-planar for Cu(II) and Pd(II), and octahedral geometry around Co(II), Ni(II), and Pt(IV). All the metal complexes showed significant antibacterial activity in comparison with the free ligand. The antibacterial test of the platinum(IV) complex showed higher activity than other metal complexes against bacteria Staphylococcus aureus (G-positive) and Escherichia coli (G-negative).

A Facile synthesis of some novel 1,3,4-thiadiazoles and pyridines linked to benzofuran as antimicrobial agents.

In the present study, a new series of benzofuran-integrated 1,3,4-thiadiazoles were prepared starting from pyrazol-4-carboxaldehyde derivatives 3a,b. Thus, reaction of compound 3a,b with benzyl hydrazine carbodithioate afforded hydrazine carbodithioate derivatives 4a,b. Treatment of compound 4a with hydrazonoyl halides 5e,f afforded 1,3,4-thiadiazoles 6a, b while the reaction of 4b with hydrazonoyl halides 5a-d yielded 1,3,4-thiadiazoles 7a,b. on the other hand, new pyridine derivatives can be synthesized via the reaction from the reaction of chalcone 8 with different C-nucleophile such as ethyl acetoacetate, benzoyl acetonitrile or acetyl acetone. All the new derivatives were characterized by spectral data. Some of the newly prepared compounds were investigated against different pathogenic microbes. The results of the antimicrobial activity revealed that all the tested compounds showed no activity except compound 6a which showed weak activity against all tested microorganisms. Compound 6b was weak active against B. subtilis and compound 7c was intermediate active against E. coli.

One-Step Dyeing and Antimicrobial Finishing of PET Fabric with Novel 4-Arylazopyrazolone Disperse Dyes

Azopyrazole disperse dyes 8–12 could be synthesized either by condensing ethyl 3-hydroxy-2-aryldiazenyl butenoates 3–7 with S-methyl hydrazine carbodithioate 1 or by coupling the parent pyrazole 2 with diazotized aniline, p-substituted anilines and/or 4-aminoantipyrine. These dyes were applied to polyester fabrics using a high-temperature dyeing method at 120 °C and displayed yellow to orange hues. Raman spectra of the dyed samples undoubtedly excluded ring dyeing and were found to agree with the proposed structures. The synthesized disperse dyes were found to possess very good dyeing properties, as indicated by color strength measurements, and all of them except dye 12 had a color strength (K/S) value ranging from 19–23. The dyed fabrics exhibited excellent fastness to washing and dry and wet rubbing as well as light fastness, which varied from moderate to very good. The antimicrobial activities of the synthesized pyrazoles 2 and 8–12 as well as the dyed fabric samples against Escherichia coli and Staphylococcus aureus were measured, and the results showed very good activity.

2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

The complete mol-ecule of the title hydrazine carbodi-thio-ate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bis-ects the di-sulfide bond. The mol-ecule is twisted about this bond with the C-S-S-C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the mol-ecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN2C residue as there is a twist about the N-N bond [C-N-N-C torsion angle = -166.57 (15)°]. An intra-molecular hydroxyl-O-H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, methyl-ene-C-H⋯π(tol-yl) contacts assemble mol-ecules into a supra-molecular layer propagating in the ab plane: the layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H⋯H contacts, which contribute 46.7% of all contacts followed by H⋯C/C⋯H contacts [25.5%] reflecting, in part, the C-H⋯π(tol-yl) contacts. The calculation of the inter-action energies confirm the importance of the dispersion term and the influence of the stabilizing H⋯H contacts in the inter-layer region.

Synthesis, Structural Properties of Hydrazine Carbodithioate Schiff Base and Their Metal Complexes and Evaluation of Their Biological Activity

A new series of [Ni(II)L2](1), [Cu(II)L2](2) and [Co(II)L2](3)(L = benzyl-2-((1E,4E)-1,5-diphenylpenta-1,4-dien-3-ylidene) hydrazine carbodithioate) Schiff base metal complexes have been synthesized. The ligand and its metal complexes were characterized by elemental analysis, 1H NMR, UV-Vis, FT-IR and magnetic moment, molar conductance and thermal analysis. The electrochemical behaviors of these complexes were investigated by cyclic voltammetry in DMF. The spectroscopic analyses and magnetic moment value suggested four coordinated geometry for three metal complexes, tetrahedral structure of complex 1 and square planer structure of complex 2 and 3. The ligand and its metal complexes were evaluated for their antibacterial (Bacillus cereus, Bacillus subtilis, Escherichia coli) activities. The complex 1 and Complex 2 revealed moderate activity against both gram positive bacteria (B. cereus and B. subtilis) with the minimum inhibitory concentration (MIC) value of 256 microg/mL.

Design and Synthesis of Some New Analgesic Azole Derivatives Containing Tramadol Moiety

Some new triazole, thiadiazole, oxadiazole, thiazole, oxazole, and imidazole derivatives have been synthesized via the reaction of tramadol bearing a hydrazide, hydrazine carbodithioate, and/or acetic acid group with certain reagents. Molecular docking study had been carried out to demonstrate the reactivity of these synthetic compounds for interaction with Cytochrome P450 2D6 (CYP2D6).

Bis{4-methylbenzyl 2-[4-(propan-2-yl)benzyl-idene]hydrazine-carbodi-thio-ato-κ2N2,S}nickel(II): crystal structure and Hirshfeld surface analysis.

The complete mol-ecule of the title hydrazine carbodi-thio-ate complex, [Ni(C19H21N2S2)2], is generated by the application of a centre of inversion. The NiII atom is N,S-chelated by two hydrazinecarbodi-thio-ate ligands, which provide a trans-N2S2 donor set that defines a distorted square-planar geometry. The conformation of the five-membered chelate ring is an envelope with the NiII atom being the flap atom. In the crystal, p-tolyl-C-H⋯π(benzene- i Pr), i Pr-C-H⋯π(p-tol-yl) and π-π inter-actions [between p-tolyl rings with inter-centroid distance = 3.8051 (12) Å] help to consolidate the three-dimensional architecture. The analysis of the Hirshfeld surface confirms the importance of H-atom contacts in establishing the packing.

Synthesis, crystal structure, biomolecular interactions and anticancer properties of Ni(II), Cu(II) and Zn(II) complexes bearing S-allyldithiocarbazate

A new series of bivalent Ni(II), Cu(II) and Zn(II) metal complexes containing Schiff base ligand [H-emk-sadtc] [(E)-allyl 2-(butan-2-ylidene) hydrazine carbodithioate)] were synthesized and characterized by different spectroscopic techniques. The molecular structure of the ligand and its complexes 1 [(E)-allyl 2-(butan-2-ylidene) hydrazine carbodithioato nickel(II)], complex 2 [(E)-allyl 2-(butan-2-ylidene) hydrazine carbodithioato copper(II)], complex 3 [(E)-allyl 2-(butan-2-ylidene) hydrazine carbodithioato zinc(II)] were confirmed by single crystal X-ray crystallography. XRD data of the complexes had revealed a distorted square planar geometry around the metal ion, satisfied by N2S2 fashion. Density functional calculations of all the compounds in gas phase were performed by using DFT (B3LYP) with 6-311G basis set. The calculated FT-IR and structural data are in good agreement with the experimental results and confirmed by the experimental one. The interactions of calf thymus (CT) DNA and bovine serum albumin (BSA) with complexes 1–3 were explored by emission spectra. Catecholase and phosphatase-like activities of all the complexes were also investigated. An in vitro cytotoxicity study of the complexes had shown significant activity against human cervical cancer cell line (HeLa) with the best results of complex 2, which was found to be more toxic to cancer cells with a few micromolar concentrations, as the IC50 value, but significantly less toxic to normal cell lines. Additionally, the cell death analysis was carried out by AO/EB and DAPI staining methods.

Catechol Oxidase, Phosphatase-Like Activity, DNA/BSA Binding Studies of RuII Complexes of S-Allyldithiocarbazate: Synthesis and Spectral Studies

New ruthenium(II) complexes with formulae [RuCl(CO)(PPh3)2L1] and [RuCl(CO)(PPh3)2L2] (L1 = S-allyl-4-methoxy benzylidene hydrazine carbodithioate, L2 = S-allyl-1-naphthylidene hydrazine carbodithioate) have been synthesized and characterized by elemental analysis, Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR), UV-Vis, electrospray ionization (ESI)-mass spectral studies. Both the Schiff base ligands are coordinated to ruthenium through azomethine nitrogen (C=N) and thiolato sulfur donor atoms in the thiolate form. On the basis of spectral data obtained, an octahedral structure has been assigned to all the new complexes, satisfied by coordination of donor atoms N and S. The stability of complexes in solution was determined by molar conductivity measurements. The interaction of the two complexes with calf thymus (CT) DNA was investigated by fluorescence spectroscopic and viscometric methods. Bovine serum albumin (BSA) protein was examined by fluorescence spectroscopic methods. These techniques indicate that the two metal complexes bind to DNA via intercalation mode and BSA bind with static interaction. Catecholase and phosphatase like activities promoted by these two complexes under physiological conditions have been studied. In vitro anticancer activities have been demonstrated by 3,4,5-dimethylthiazolyl-2-2,5-diphenyltetrazolium bromide (MTT) assay, acridine orange/ethidium bromide (AO/EB) and diamidino-2-phenylindole (DAPI) staining against HeLa cancer cell line.

Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents.

Coumarin derivatives containing pyrazolo[1,5-a]pyrimidine, tetrazolo[1,5-a]pyrimidine, imidazo[1,2-a]pyrimidine, pyrazolo[3,4-d]pyrimidine, 1,3,4-thiadiazoles and thiazoles were synthesized from 6-bromo-3-(3-(dimethylamino)acryloyl)-2H-chromen-2-one, methyl 2-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene)hydrazine carbodithioate, 2-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene)hydrazine carbothioamide and each of heterocyclic amine, hydrazonoyl chlorides and hydroximoyl chlorides. The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Moreover, selected newly synthesized products were evaluated for their antitumor activity against a liver carcinoma cancer cell line (HEPG2-1). The results revealed that pyrazolo[1,5-a]pyrimidine 7c, thiazole 23g and 1,3,4-thiadiazole 18a (IC50 = 2.70 ± 0.28, 3.50 ± 0.23 and 4.90 ± 0.69 µM, respectively) have promising antitumor activity against liver carcinoma (HEPG2-1) while most of the tested compounds showed moderate activity.

Synthesis, characterization and bio-activity of nickel(II) and copper(II) complexes of a bidentate NS Schiff base of S-benzyl dithiocarbazate

The reaction of S-benzyldithiocarbazate (SBDTC) with 3-hydroxyacetophenone afforded a bidentate NS Schiff base HL (HL=benzyl-3-(3-hydroxyphenyl methyl ethylene)hydrazine carbodithioate) which on further reaction with nickel(II) and copper(II) salt yielded bis-chelated inner complexes, NiL2 and CuL2, respectively with deprotonated L ligand. The ligand and its complexes were characterized by physico-chemical techniques, viz., molar conductance, magnetic susceptibility measurement, IR, NMR, UV–Vis spectroscopy and mass spectroscopic techniques. The crystal structure of all the compounds was also characterized by single crystal X-ray crystallography. The ligand exists in its thione tautomeric form both in solution and in the solid state. In the complexes the two deprotonated ligands chelate the metal through the azomethine nitrogen and the thione sulfur atom with cis arrangement generating a tetrahedrally distorted square planar geometry around the metal center. Only complex CuL2 showed moderate analgesic activity at 60min compared to Diclofenac sodium, while all the test compounds exhibited good anti-inflammatory activity as compared to standard drug Indomethacin.

Syntheses, spectral and structural characterization of trinuclear and mononuclear Zn(II) complexes of N′-benzoyl hydrazine carboperthioate and 5-phenyl-1,3,4-oxadiazole-2-thione: An approach to DFT calculation, antibacterial and thermal studies

Potassium N′-(benzoyl)-hydrazine carbodithioate forms novel complexes [Zn3(μ-bhcp)2(py)4] (1) and [Zn(phot)2(en)2] (2) containing newly generated ligands N′-benzoyl hydrazinecarboperthioate (bhcp)3− and 5-phenyl-1,3,4-oxadiazole-2-thione (phot)− which have been characterized by elemental analyses, m.p, IR, NMR and single crystal X-ray data. During complexation, potassium N′-(benzoyl)-hydrazine carbodithioate is converted to N′-benzoyl hydrazinecarboperthioate (oxidized ligand having a S-S linkage) and 5-phenyl-1,3,4-oxadiazole-2-thione in the presence of pyridine and ethylenediamine (en), respectively which act as secondary ligands. The crystal structure of complex 1 reveals that the ligand is acting as trinegative pentadentate ON2S2, bonded to terminal zinc as ONS dinegative tridentate and to the other as NS uninegative bidentate. In the trinuclear complex 1, both terminal zinc atoms have distorted square pyramidal geometry and the middle zinc has tetrahedral geometry. Complex 2 has distorted octahedral geometry where central atom is bounded to two en and two oxadiazoles anions. The geometry of the complexes has also been optimized by the DFT method and the results of which are presented and compared with the X-ray diffraction data. The ligand has been also optimized and analyzed for its reactive site. In addition to this, frontier molecular orbitals (FMO) were also calculated. Raman analyses give the evidence of the binding of zinc with the newly generated oxadiazole and acyclic perthio ligands and the results corroborate with the IR and XRD data. Solid state electrical conductivity, bactericidal and thermal properties have been analyzed. The bioefficacy of the ligand and complexes has been examined against the growth of bacteria in vitro to evaluate their anti-microbial potential.

Physico-Chemical and In-vitro Microbial Studies of Newly Synthesis Organometallic Complexes

Drugs normally synthesized to use as medication to treat diseases like cancer and microbial infections, these synthesized drugs were interested more than naturally-derived drugs which have been shows low activity or not as efficient against diseases. A new ligand 3-methylbenzyl (2Z)-2-[1-(pyridin-4-yl)ethylidene]hydrazine carbodithioate (PE3MBC) and its Cd(II), Cu(II), Co(II) and Zn(II) metal complexes. The new ligand and metal complexes were characterized via various physico-chemical and spectroscopic techniques. Cd(II) complex show more activity against microbes and against cancer cell line MCF-7, while other complexes does not shows activity like cadmium complex, all the complexes does not shows any activity against MDAMB-231 cell line. The fatal of the cancer and the microbes cell was due to inhibition of DNA synthesis which was probably due to chelating with metals complexes, or could be referred to lipophilicity, presence of hydrophobic moiety in the complex molecule, also could be due to steric effects and electronic effects.

Synthesis, characterization and bio-activity of a bidentate NS Schiff base of S-allyldithiocarbazate and its divalent metal complexes: X-ray crystal structures of the free ligand and its nickel(II) complex

Transition metal complexes ML2 (2–6) [where M = Ni(II), Cu(II), Zn(II), Cd(II), Pd(II) and HL = allyl-2-(4-benzyloxyphenylmethylene)hydrazine carbodithioate (1)] have been prepared by the reaction of the ligand with metal ions in 2:1 molar ratio and characterized by physicochemical techniques and spectroscopic methods. The crystal structures of the free ligand and its nickel(II) complex 2 have been determined by X-ray diffractometry. The ligand exists in its thione tautomeric form both in solution and in the solid state. In complex 2, square-planar coordination of nickel(II) was achieved by two chelating ligand moieties coordinating through the azomethine nitrogen and the deprotonated thione sulphur atom. Based on the crystal structures of analogous dithiocarbazate species, a square-planar geometry was assumed for the copper(II) and palladium(II) complexes, and a tetrahedral coordination sphere for the zinc(II) and cadmium(II) derivatives. The in vitro bactericidal activity suggests that the palladium(II) complex is strongly active against two bacteria. The cadmium(II) complex is moderately cytotoxic with an LC50 value of 409 μg/ml, but less active than gallic acid, LC50 = 78 μg/ml.

Preparation and Spectroscopic Study of New NS Ligand and its Cd(II) and Zn(II) Metal Complexes

A new nitrogen sulphur Schiff base has been prepared from the condensation 1-(pyridin-4-yl) ethanone with 3-methylbenzyl hydrazinecarbodithioate leading the formation of new ligand 3-methylbenzyl (2Z)-2-[1-(pyridin-4-yl)ethylidene]hydrazine carbodithioate (PE3MBC). The ligand was reacted with Cd(II) and Zn(II) metal salts to form new coordinated complexes. The new ligand and its metal complexes were characterized via various physico-chemical and spectroscopic techniques and conductivity, magnetic susceptibility of metal complexes based on the data analysis the metal complexes are expected to be tetrahedral in geometry.

Synthesis of New Indeno[1,2‐c]pyrazole‐Based Heterocycles and Evaluation of Their Protective Effect against DNA Damage Induced by Bleomycin–Iron

image Reaction of potassium 2‐(1‐phenyl‐1,4‐dihydroindeno[1,2‐c]pyrazole‐3‐carbonyl)hydrazine carbodithioate (2) with hydrazine hydrate, phenacyl bromides, and hydrazonoyl chlorides afforded the corresponding 1,2,4‐triazole, 1,3‐thiazole, and 1,3,4‐thiadiazole derivatives 3, 5, and 7, respectively. Reaction of 3‐mercapto‐4‐amino‐1,2,4‐triazole 3 with phenacyl bromides 4a–c and hydrazonoyl chlorides 6a,b afforded the corresponding 1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazine derivatives 10a–c and 13a,b, respectively, whereas its reaction with 2‐chloro‐N‐arylacetamide derivatives 11a–d afforded the corresponding 2‐(4‐amino‐5‐(1‐phenyl‐1,4‐dihydroindeno[1,2‐c]pyrazol‐3‐yl)‐4H‐1,2,4‐triazol‐3‐ylthio)‐N‐arylacetamide derivatives 12a–d. All of the new compounds were tested for their protection activity against DNA damage induced by bleomycin–iron complex. Compounds 7a and b showed the highest protection activity through diminishing chromogen formation between the damaged DNA and thiobarbituric acid.

Synthesis and Evaluation of Antibacterial Activities of some Important Bridge-head Nitrogenous Heterocyclic Compounds

The key intermediates in the present study to synthesize the title bridge-head nitrogen heterocycle compounds were N-substituted semicarbazides 2(a-c), which prepared by hydrazinolysis of the ethyl substituted carbamates 1(a-c) with hydrazine hydrate. These carbamates were prepared by the reaction of proper amines and ethylchloroformate. The reaction of these semicarbazides with ethanolic solution of carbon disulfide under strong basic conditions at room temperature, followed by acidification resulted in the formation of the corresponding potassium (2-arylcarbamoyl)hydrazine carbodithioate 3(a-c), while refluxing the ethanolic solution for three hours afforded 5-(arylamino)-1,3,4-oxadiazole-2- thioles 4(a-c). The potassium salts 3(a-c) were cyclized with hydrazine hydrate to 4-amino-5-arylamino-1,2,4-triazole-3-thiones(thioles) 5(a-c). Compounds 5(a-c) were excellent precursors for 3-(arylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 6(a-c) by dehydrative ring closure of the proper triazole with formic acid in benzene in presence of phosphorous oxychloride or using microwave irradiation technique. Also, refluxing of the proper triazoles with carbon disulfide under basic conditions afforded 3-(arylamino)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole-6-thiones 7(a-c). Finally 4-amino-3-(4-(5-(4-amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-ylamino)-1,3,4-thiadiazol-2-yl)phenylamino)-1H-1,2,4-triazole-5(4H)-thione 5(d) were synthesized by the same procedures that were followed to synthesize its analogs starting from 5-(4-aminophenyl)-1,3,4-thiadiazole-2-amine and duplicated all the scales of the reactants. The structures of these compounds were confirmed by their physical properties in addition to the IR, UV and NMR spectra. All synthesized compounds were tested for their in vitro growth inhibitory activity against a panel of standard strains of pathogenic microorganism including bacteria Staphylococcus, Streptococcus and Salmonella. All these compounds were practically inactive against the tested microorganisms.