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PubMed2004

Stable gold(III) complexes with thiosemicarbazone derivatives.

Novel thiosemicarbazonato complexes of gold(III) have been prepared from reactions of [Au(damp-C1,N)Cl2(damp- = 2-(N,N-dimethylaminomethyl)phenyl) or [NBu4][AuCl4] with 2-pyridineformamide thiosemicarbazones (HL). The thiosemicarbazones deprotonate and coordinate as mononegative, tridentate NNS ligands to gold to give [Au(Hdamp-C1)(L)]Cl2 or [AuCl(L)]Cl complexes. The organometallic damp- ligand is protonated during the reactions and the Au-N bond is cleaved. The [AuCl(L)]+ cations represent the first gold(III) complexes with thiourea derivatives which are not stabilised by an additional organometallic ligand. Reactions of [NBu4][AuX4](X = Cl, Br) with diphenylthiocarbazone (dithizone) result in reduction of the metal and the formation of gold(I) complexes of the composition [AuX(SCN4-3,4-Ph2)] where SCN4-3,4-Ph2 is 3,4-diphenyltetrazole thione which is formed from cyclisation of dithizone.

Crystallography, X-Ray↗
PubMed2005

Synthesis and evaluation of the antibacterial and antitubercular activity of some N1-aral-N4-(3-chloro-4-fluorophenyl)thiosemicarbazones and their copper(I) complexes.

New N1-aral-N4- (3-chloro-4-fluorophenyl)thiosemicarbazones (2a-h) and their Cu(I) complexes (3a-h) have been prepared and characterized by elemental analysis and spectral methods (IR and 1H-NMR). Thiosemicarbazones 2a-h bind to copper(I) as bidentate ligand via nitrogen and thione sulphur centers to afford 3a-h. Both ligands and their complexes are screened against Escherichia coli (National Collection of Type Culture 10418) and Staphylococcus aureus (National Collection of Type Culture 5571) to evaluate their antibacterial properties and against human virulent H37Rv strain of Mycobacterium tuberculosis for their antitubercular properties. Ligands 2d-h showed promising antibacterial activity while their Cu(I) complexes 3d-h exhibited excellent activity. The compounds 2a, 2d, 2f, 2g and their Cu(I) complexes 3a, 3d, 3f and 3g were evaluated for their antitubercular activity. It was observed that compounds 2a, 2g, 3a, 3d showed moderate activity while 3f and 3g exhibited promising antitubercular activity.

Anti-Bacterial Agents↗
PubMed1977

Inhibition of vesicular stomatitis virus by kethoxal bis (thiosemicarbazone).

Kethoxal bis (thiosemicarbazone) (KTS) inhibited replication of, and plaque formation by, vesicular stomatitis virus (VSV) in chick embryo cells. No other thiosemicarbazones tested were effective. Virus-specific m-RNA and protein synthesis were inhibited by KTS. However, virion RNA-dependent RNA synthesis was not inhibited by the drug. Treatment of VSV virions directly with KTS produced enhancement, rather than inactivation, of plaque formation. KTS inhibited cellular DNA and RNA synthesis by 67 and 25% respectively. Since cellular DNA and RNA synthesis are not required for VSV replication, the inhibition of these processes is probably unrelated to the antivirial activity of KTS. Cellular protein synthesis was inhibited 24% by KTS. Unexpectedly, synthesis of four proteins was induced in KTS-treated uninfected cells.

Animals↗
PubMed1982

Correlations between structure and antimycobacterial activity in a series of 2-acetylpyridine thiosemicarbazones.

The antimycobacterial activity of a new series of 2-acetylpyridine thiosemicarbazones was determined in vitro using Mycobacterium smegmatis ATCC 607. The resulting log minimal inhibitory concentration (mumol l-1) values were plotted against the partition coefficient (log P) values for each compound, and fell on a parabolic distribution curve having a log P opt of 3.0. Compounds having partition coefficients outside the range 2.0 to 4.0 were inactive against M. smegmatis. When similar assays were carried out using M. tuberculosis, M. kansasii, M. marinum, M. simiae, M. avium and M. intracellulare, a similar series of parabolic activity curves were obtained having log P opt values around 4.0. The significance of this shift in the log P opt value obtained using the slow-growing pathogenic mycobacteria compared to that observed with the rapid-growing M. smegmatis is discussed in relation to the structures of the variable substituents of these new 2-acetylpyridine thiosemicarbazone compounds.

Anti-Bacterial Agents↗
PubMed1980

Inhibition of clinically significant bacterial organisms in vitro by 2-acetylpyridine thiosemicarbazones.

Antibacterial activity of 65 2-acetylpyridine thiosemicarbazones and related compounds was determined by using clinical isolates of nine bacterial genera. Minimal inhibitory concentrations (MICs) of 0.002 to 0.062 micrograms/ml were obtained with 23% of the compounds for Neisseria gonorrhoeae and 0.016 to 0.062 micrograms/ml with 17% of the compounds for N. meningitidis. Staphylococcus aureus was inhibited in the MIC range of 0.125 to 0.5 micrograms/ml by 18% of the thiosemicarbazones, whereas 26% inhibited group D enterococcus with an MIC of 0.25 to 2.0 micrograms/ml. Poor antibacterial activity was shown toward the gram-negative bacilli, i.e., Pseudomonas, Klebsiella-Enterobacter, Shigella, Escherichia coli, and Proteus.

Bacteria↗
PubMed1981

Preferential inhibition of ribonucleic acid synthesis by a new thiosemicarbazone possessing antibacterial and antiparasitic properties.

We determined the influence of the azacycloheptane derivative (H) of a 2-acetylpyridine thiosemicarbazone on growth and macromolecular synthesis in Escherichia coli AT-9. Thiosemicarbazone H caused bacteriostasis and a primary inhibition of ribonucleic acid synthesis; secondary effects included inhibition of deoxyribonucleic acid and protein synthesis. Addition of cooper or other transition elements was not necessary for these inhibitions.

Anti-Bacterial Agents↗
PubMed1986

Antibacterial properties of 2-acetylpyridine-1-oxide thiosemicarbazones.

We have investigated the in vitro antibacterial activity of 13 2-acetylpyridine-1-oxide thiosemicarbazones and 5 thiosemicarbazides against 80 clinically significant bacterial cultures, including 13 isolates with known antibiotic resistance. Of the thiosemicarbazones tested, 5 had minimal inhibitory concentrations (MICs) of 0.25 microgram/ml for Neisseria gonorrhoeae isolates; 1 of these had an MIC range of 0.25-0.5 microgram/ml for the Neisseria meningitidis cultures, and 2 had MICs of 2 and 2-4 micrograms/ml for Staphylococcus aureus and Streptococcus faecalis isolates, respectively. Two of the thiosemicarbazides had MICs of 0.25 microgram/ml for N. gonorrhoeae, whereas 2 others had MICs of 2-4 and 4-8 micrograms/ml for S. aureus and S. faecalis isolates, respectively. The test compounds were ineffective against the gram-negative enteric cultures and the Pseudomonas isolates.

Bacteria↗
PubMedDate not supplied

Relationships between structure and antiretroviral activity of thiosemicarbazone derivatives.

In an attempt to develop anti-AIDS drugs, the compound isatin beta-thiosemicarbazone has been subjected to systematic structural modifications. The resulting synthesized thiosemicarbazone derivatives (TSCDs) were examined for their ability to act as antiretrovirus agents in a model system--2M3/M cell system--consisting of B lymphocytes transformed by the v-abl oncogene and chronically infected with a retrovirus, the Moloney leukemia virus (M-MuLV). The efficacy of the synthesized TSCDs against retroviruses was determined by assaying the therapeutic index (TI) values of the compounds. The results enabled the classification of TSCD groups based on the relationship between chemical structure and antiretroviral activity. The compound N-allylisatin-beta':4'-diallylthiosemicarbazone showed the highest TI value and efficiently suppressed the chronic infection of M-MuLV in continuous long-term treatment.

B-Lymphocytes↗
PubMed1982

Activity of 2-acetylpyridine and 2-acetylquinoline thiosemicarbazones tested in vitro in combination with other antituberculous drugs.

Determinations of minimal inhibitory concentrations (MIC) were carried out using three new 2-acetylpyridine and two new 2-acetylquinoline thiosemicarbazones tested against Mycobacterium tuberculosis, M. kansasii, M. simiae, M. avium, and M. intracellulare. Two of the compounds (Compounds L and 3I) exhibited MIC less than or equal to 5 micrograms per ml for all of the test organisms, except for M. simiae, which was resistant to most antituberculous drugs. The other thiosemicarbazones (Compounds 3L, 2N, 3G, and 2H) were relatively inactive against the nontuberculous mycobacteria. Rifampin, amikacin, and clofazimine were active when tested singly or in combination with Compounds L and 3I. Addition of compound 3I to a mixture of rifampin, amikacin, and clofazimine resulted in combination MIC of less than 0.6 microgram/ml against all of the nontuberculous mycobacteria, suggesting that combinations of this type may be suitable for the treatment of infections caused by these highly drug-resistant organisms.

Antitubercular Agents↗
PubMed2005

[Study of the characterization of beta-cyclodextrin-acetylferrocene-thiosemicarbazone inclusion complex and micro-environmental effects].

Inclusion complex of acetylferrocene-thiosemicarbazone(TAF) with beta-cyclodextrin(beta-CD) has been prepared by using kneading method. Elemental analysis and the solubility determination proved that 1:1 inclusion complex has been formed. Characterization of the inclusion complex was studied by UV, FTIR, and X-ray diffractometry. The association constant was calculated to be 227 L x mol(-1) from the straight portion of the phase-solubility diagram. Furthermore, the influence of different solvents and pH on UV spectrum of acetylferrocene-thiosemicarbazone and beta-CD -TAF was discussed respectively. The results show that different micro-environment has apparently different effects on electric spectra of guest and inclusion complexes.

Ferrous Compounds↗
PubMed1977

[Research on substances with antiviral activity. VII. Activity and lipophilic of property N-alkyl-2-chloro-3-formylindole thiosemicarbazone].

Thiosemicarbazones of N-alkyl-2-chloroindole-3-carboxaldehydes were synthesized and investigated for antiviral activity against RNA virus (parainfluenza type 3, HA-I/CR-8 stock) and DNA virus (vaccinia virus, HID stock). The effect of lipophilicity on the activity against vaccinia virus was considered. Relative lipophilicities were measured by a reversed phase thin-layer chromatographic technique. The most active compound N-isopropyl-2-chloroindole-3-carboxaldehyde thiosemicarbazone appeared comparable for its activity to methisazone.

Antiviral Agents↗
PubMed1990

[Synthesis of 2-formyl (acetyl) substituted quinoline thiosemicarbazones].

A series of 2-formyl (acetyl) substituted quinoline thiosemicarbazones (III, XII, XIII) were prepared in order to evaluate their antimalarial activity. Oxidation of substituted quinolines (IV) with selenium dioxide gave 2-formyl substituted quinolines (V). 2-Acetyl substituted quinoline (IX) was obtained from IV by oxidation, esterification, Claisen condensation and decarboxylation. III1-9 were synthesized by two methods; one was by condensation of 2-formyl (acetyl) substituted quinolines with methyl hydrazinecarbodithioat to form methyl-3-[1-(2-quinolinyl)-alkylidene] hydrazinecarbodithioate (XI), then the S-methyl group of XI was displaced by substituted amines to form the desired substituted thiosemicarbazones. The other was by condensation of 2-formyl (acetyl) substituted quinolines with 4-substituted-3-thiosemicarbazide (X) to afford directly III1-9, III10-12 were obtained by selective reduction of corresponding nitro compounds with stannous chloride and XII as a by-product was obtained by the nonselective reduction of III7 with stannous chloride. 3-Hexyl-4-oxothiazolin-2-yl(2-formyl or acetyl substituted quinoline) hydrazones (XIII1,2) were prepared from III1,4 via cyclization under sodium acetate condition. Eighteen compounds were found to be inactive in mice infected with ANKA strain of Plasmodium berghei.

Animals↗
PubMed1985

Substituted benzaldehyde thiosemicarbazone with antiviral activity against poliovirus.

A series of eight benzaldehyde thiosemicarbazone derivatives with a variable number of -OH substituents at different positions on the aromatic ring were prepared and evaluated for in vitro antiviral activity against poliovirus types I, II and III. Some of the compounds significantly inhibited the replication of poliovirus at a mean ED50 of 2, 5.7, 10.5 and 9.7 micrograms/ml. A comparison between chemical structure and biological activity suggests that the inhibitory effect depends on the relative position of the -OH and the thiosemicarbazone group. The compounds possess antiviral action only when the two groups are distant enough to prevent the formation of intramolecular hydrogen bonds.

Animals↗
PubMed1988

Copper(II) bis(thiosemicarbazone) complexes as potential tracers for evaluation of cerebral and myocardial blood flow with PET.

Wider application of positron emission tomography would be facilitated by the availability of positron-emitting radiopharmaceuticals labeled with nuclides, like 62Cu, that are available from parent/daughter generator systems. Using a longer-lived copper isotope (67Cu) we have examined three derivatives of copper(II) pyruvaldehyde bis(thiosemicarbazone) as potential tracers for evaluation of cerebral and myocardial blood flow: Cu(PTS), Cu(PTSM), and Cu(PTSM2) (where PTS = pyruvaldehyde bis(thiosemicarbazone), PTSM = pyruvaldehyde bis(N4-methylthiosemicarbazone), and PTSM2 = pyruvaldehyde bis(N4-dimethylthiosemicarbazone). All three lipophilic radiocopper complexes were obtained in high yield via a procedure that could be adapted to a "kit" formulation. In animal model systems Cu(PTSM) and Cu(PTSM2) show excellent uptake in the brain and heart following i.v. injection. These tracers differ in that Cu(PTSM) exhibits microsphere-like retention in the brain and heart, whereas Cu(PTSM2) substantially clears from these organs. The relative cerebral pharmacokinetics of [67Cu]Cu(PTSM) and [67Cu]Cu(PTSM2) are consistent with their known reactivity towards intracellular sulfhydryl groups.

Animals↗
PubMed1986

[The synthesis and biologic activity of analogs of 1,4-benzoquinone-guanylhydrazone-thiosemicarbazone. 2. Substitution at the quinone ring by alkyl groups].

Because of the anticancer activity of 1,4-benzoquinone-guanylhydrazone-thiosemicarbazone (1a) some analogues were synthesized, containing alkyl groups at the quinone moiety. If necessary, the structure of the obtained compounds was confirmed by 1H-NMR-spectroscopy. The anticancer and the antibacterial activities were investigated. The guanylhydrazone-thiosemicarbazones of tolu-,p-xylo-and thymo-quinone showed much lower activities not only against the murine leukemias L 1210 and P 388, but also against Bacillus subtilis ATCC 6633. No correlation could be found between the biological activity and the redox potential.

Animals↗
PubMed1981

[Substances with antiviral. XVI. Thiosemicarbazones containing benzofuran and 1H-indene moieties].

A few hydrazones with benzofuran and 1H-indene moieties were synthesized and screened in vitro against vaccinia virus strain IHD, parainfluenza type 3 virus strain HA-1/CR-8, and the MP mutant of herpes simplex virus type 1 [HSV-1 (MP)]. Only the thiosemicarbazones were active. The thiosemicarbazone of 3-chloro-2-formyl-1H-indene inhibited vaccinia virus to a greater extent than methisazone, used as reference standard. Furthermore, this compound was active also against parainfluenza and herpes viruses.

Antiviral Agents↗
PubMed1984

A quantitative analysis of steric and hydrophobic effects in ribonucleoside diphosphate reductase inhibition by thiosemicarbazones.

Ribonucleoside diphosphate reductase (RDR) inhibitory activity of 2-formylpyridine and 1-formylisoquinoline thiosemicarbazones is quantitatively analysed in relation to a steric parameter (van der Waals volume, VW) and the hydrophobic parameter logP. The activity is found to be significantly correlated with VW and very poorly with logP. On the basis of this, it is inferred that RDR inhibition by thiosemicarbazones is very sensitive to steric effects and is little influenced by the hydrophobic character of the molecules.

Chemical Phenomena↗