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PubMed1983

Thiosemicarbazones of 2-acetylpyridine, 2-acetylquinoline, 1- and 3-acetylisoquinoline and related compounds as inhibitors of clinically significant bacteria in vitro.

Antibacterial activity of 64 thiosemicarbazones of 2-acetylpyridine, 2-acetylquinoline, 1- and 3-acetylisoquinoline and related compounds was determined by testing clinical isolates of ten bacterial genera, including some which were antibiotic resistant. Minimal inhibitory concentrations (MICs) of 0.016 to 0.125 microgram/ml were obtained with 26% of the compounds for Neisseria meningitidis and 0.002 to 0.25 microgram/ml with 19% of the compounds for N. gonorrhoeae. Staphylococcus aureus was inhibited in the MIC range of 0.062 to 0.5 microgram/ml by 34% of the thiosemicarbazones, whereas 26% inhibited Streptococcus faecalis with an MIC range of 0.25 to 1.0 microgram/ml. Less antibacterial activity was shown toward the Gram-negative bacilli, i.e., Pseudomonas, Klebsiella-Enterobacter, Shigella, Escherichia coli, Serratia marcescens and Proteus.

Anti-Bacterial Agents↗
PubMed1981

[Substances with antiviral activity. XX. Thiosemicarbazones of 1-substituted 3-formyl-2-ethoxycarbonyl(carboxy)indoles].

A series of 3-formyl-2-ethoxycarbonyl(carboxy)indole thiosemicarbazones 1-substituted were synthesized and evaluated for in vitro antiviral activity against vaccinia virus strain IHD. The thiosemicarbazone of 1-(m-chlorobenzoyl)-3-formyl-2-ethoxycarbonylindole [(II g); Table II] was the most active compound. Some structure activity relationships are discussed.

Antiviral Agents↗
PubMed1995

Species-dependent binding of copper(II) bis(thiosemicarbazone) radiopharmaceuticals to serum albumin.

UNLABELLED: Copper-62-labeled pyruvaldehyde bis(N4-methylthiosemicarbazonato)-copper(II) (Cu-PTSM) is a generator-based PET radiopharmaceutical under investigation for use in evaluation of tissue perfusion. Despite promising results from animals, problems have been encountered in the use of 62Cu-PTSM to quantitate myocardial perfusion in humans at high flow rates, possibly due to species-dependent interactions of the tracer with serum albumin. METHODS: Ultrafiltration and plasma/erythrocyte partitioning studies were performed to assess the protein binding of 67Cu-labeled Cu-PTSM and six related copper(II) bis(thiosemicarbazone) complexes. RESULTS: These studies reveal significant interspecies variability in the strength of Cu-PTSM binding to serum albumin, with 67Cu-PTSM binding much more strongly to human albumin than to dog albumin. Most of the related Cu(II)-bis(thiosemicarbazone) complexes examined exhibit interspecies variability of albumin binding similar to that observed with Cu-PTSM. Two such complexes, Cu-ETS and Cu-n-PrTS, however, were identified that exhibit no preferential association with human serum albumin. CONCLUSION: Copper-62-PTSM exhibits substantial interspecies variability in the strength of its binding to serum albumin, which appears to explain the problems encountered in using animal data to predict 62Cu-PTSM behavior in humans. The 62Cu-ETS and 62Cu-n-PrTS complexes may be viable alternatives to 62Cu-PTSM for PET studies to evaluate quantitatively myocardial blood flow in humans.

Animals↗
PubMedDate not supplied

Antibacterial activity of metal complexes of benzil and benzoin thiosemicarbazones.

The metal (II) complexes of benzyl and benzoin thiosemicarbazones have been synthesized and characterized. They were studied for their antibacterial, antifungal and amoebicidal activity in vitro and for their toxicity in vivo. The ligands and their metal complexes exhibited low antibacterial and amoebicidal activity. The metal chelates of benzoin thiosemicarbazone seem to be the most active compounds.

Animals↗
PubMedDate not supplied

A study on ester thiosemicarbazones.

The cyclization of ester thiosemicarbazones to two different heterocycles was studied for some new thiosemicarbazones, and only the formation of 1,2,4-triazol-5-thiols was attributed to the regioselectivity of the ring closure reaction, due to a steric hindrance of bulky groups. Next, some of the new compounds were tested for their in vitro antimicrobial and antitumor activities.

Antibiotics, Antitubercular↗
PubMed1976

The antiviral activity of isatin beta-thiosemicarbazone derivatives on vaccinia virus infection in mice.

Newly synthetized compounds of Mannich bases isatin-beta-thiosemicarbazone derivatives: N,N'-bis-(beta-thiosemicarbazone-isatinmethyl)-2-methylpiperazine (TSKI-VI); N,N'-bis (beta-thiosemicarbazoneisatinmethyl)-cis-2,5-dimethylpiperazine (TSKI-VII) and N,N'-bis (beta-thiosemicarbazoneisatinmethyl)-trans-2,5-dimethylpiperazine (TSKI-VII), showed protective effect on mice infected i.c. with neurovaccinia virus. Antiviral activity was shown already at doses of 1-25 mg/kg increased with the concentrations of the administratered compounds. TSKI-VI given prophylactically also showed protective effect, similar to metisazone in mice later infected i.c. with vaccinia virus.

Animals↗
PubMed2006

In vitro and in vivo evaluation of isatin-beta-thiosemicarbazone and marboran against vaccinia and cowpox virus infections.

It has been reported previously that some thiosemicarbazone compounds have prophylactic activity against smallpox disease and therapeutic activity against vaccinia virus (VV) infections. In these studies, isatin-beta-thiosemicarbazone (IBT) and marboran were administered once daily by intraperitoneal (ip) injection to mice using 30, 10 or 3 mg/kg for 5 days beginning 24, 48 or 72 h after inoculation with VV or cowpox virus (CV). Both compounds were highly effective (p < 0.01) at preventing mortality due to VV even when treatment was delayed up to 72 h postinfection. In CV-infected mice, neither IBT nor Marboran were effective in preventing mortality at any dosage tested when administered at 24 h postinoculation. Viral replication in liver, spleen and kidney was delayed or reduced by 100-to 10,000-fold by 10 mg/kg of marboran, but not IBT, in VV infections. Neither compound was effective against CV infection. Neither IBT nor marboran treatment of mice cutaneously infected with VV or CV reduced viral replication or clinical disease. These results suggest that this class of compound has little therapeutic potential for orthopoxvirus infections since the in vivo activity against CV, a surrogate virus for variola, is lacking.

Animals↗
PubMed2005

Synthesis, spectral studies and in vitro assessment for antiamoebic activity of new cyclooctadiene ruthenium(II) complexes with 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones.

We report here the synthesis, characterization and in vitro antiamoebic activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones (TSC), 1-5, and their bidentate complexes [Ru(eta(4)-C(8)H(12))(TSC)Cl(2)] 1a-5a. The biological studies of these compounds were investigated against HK-9 strain of Entamoeba histolytica and the concentration causing 50% cell growth inhibition (IC(50)) was calculated in the micromolar range. The ligands exhibited antiamoebic activity in the range (2.05-5.29microM). Screening results indicated that the potencies of the compounds increased by the incorporation of ruthenium(II) in the thiosemicarbazones. The complexes 1a-5a showed antiamoebic activity with an IC(50) of 0.61-1.43microM and were better inhibitors of growth of E. histolytica, based on IC(50) values. The most promising among them is Ru(II) complex 2a having 1,2,3,4-tetrahydroquinoline as N(4) substitution.

Amebicides↗
PubMed2005

Investigation into 64Cu-labeled Bis(selenosemicarbazone) and Bis(thiosemicarbazone) complexes as hypoxia imaging agents.

BACKGROUND: Cu-diacetyl-bis(N4-methylthiosemicarbazone) [Cu-ATSM], although excellent for oncology applications, may not be suitable for delineating cardiovascular or neurological hypoxia. For this reason, new Cu hypoxia positron emission tomography (PET) imaging agents are being examined to search for a higher selectivity for hypoxic or ischemic tissue at higher oxygen concentrations found in these tissues. Two approaches are to increase alkylation or to replace the sulfur atoms with selenium, resulting in the formation of selenosemicarbazones. METHODS: Three 64Cu-labeled selenosemicarbazone complexes were synthesized and one was screened for hypoxia selectivity in vitro using EMT-6 mouse mammary carcinoma cells. Rodent biodistribution and small animal PET images were obtained from BALB/c mice implanted with EMT-6 tumors. One alkylated thiosemicarbazone was synthesized and examined. RESULTS: Of the three bis(selenosemicarbazone) ligands synthesized and examined, only 64Cu-diacetyl-bis(selenosemicarbazone) [64Cu-ASSM] was isolated in high-enough radiochemical purity to undertake cell uptake experiments where uptake was shown to be independent of oxygen concentration. The bis(thiosemicarbazone) complex synthesized, 64Cu-diacetyl-bis(N4-ethylthiosemicarbazone) [64Cu-ATSE], showed hypoxia selectivity similar to 64Cu-ATSM although at a higher oxygen concentration. Biodistribution studies for 64Cu-ASSM and 64Cu-ATSE showed high tumor uptake at 20 min (64Cu-ASSM, 10.33+/-0.78% ID/g; 64Cu-ATSE, 7.71+/-0.46% ID/g). PET images of EMT-6 tumor-bearing mice visualized the tumor with 64Cu-ATSE and revealed hypoxia selectivity consistent with the in vitro data. CONCLUSION: Of the compounds synthesized, only 64Cu-ASSM and 64Cu-ATSE could be examined in vitro and in vivo. Although the stability of bis(selenosemicarbazone) complexes increased upon addition of methyl groups to the diimine backbone, the fully alkylated species, 64Cu-ASSM, demonstrated no hypoxia selectivity. However, the additional alkylation present in Cu-ATSE modifies the hypoxia selectivity and in vivo properties when compared with Cu-ATSM.

Animals↗
PubMed2005

EPR, mass, IR, electronic, and magnetic studies on copper(II) complexes of semicarbazones and thiosemicarbazones.

Copper(II) complexes having the general composition Cu(L)(2)X(2) [where L = isopropyl methyl ketone semicarbazone (LLA), isopropyl methyl ketone thiosemicarbazone (LLB), 4-aminoacetophenone semicarbazone (LLC), and 4-aminoacetophenone thiosemicarbazone (LLD) and X = Cl(-), 1/2SO(4)(2-)] have been synthesized. All the Cu(II) complexes reported here have been characterized by elemental analyses, molar conductance, magnetic moment susceptibility, EI mass, (1)H NMR, IR, EPR, and electronic spectral studies. All the complexes were found to have magnetic moments corresponding to one unpaired electrons. The possible geometries of the complexes were assigned on the basis of EPR, electronic, and infrared spectral studies.

Chlorides↗
PubMed2002

Metal-induced cyclization of thiosemicarbazones derived from beta-keto amides and beta-keto esters: open-chain and cyclized ligands in zinc(II) complexes.

The reactions of Zn(OAc)(2) with acetoacetanilide, methyl acetoacetate, o-acetoacetanisidide, and ethyl 2-methylacetoacetate thiosemicarbazones (HTSC(1), HTSC(2), HTSC(3), and HTSC(4), respectively) were explored in methanol. With HTSC(1), HTSC(2), and HTSC(3), following isolation of the corresponding zinc(II) thiosemicarbazonates [Zn(TSC(x))(2)] (x = 1, 2, 3), the mother liquors afforded pyrazolonate complexes [ZnL(1)(2)(H(2)O)] (HL(1) = 2,5-dihydro-3-methyl-5-oxo-1H-pyrazole-1-carbothioamide) that had been formed by cyclization of the corresponding TSC(-). The reaction of HTSC(4) with zinc(II) acetate gave only the pyrazolonate complex [ZnL(2)(2)(H(2)O)] (HL(2) = 2,5-dihydro-3,4-dimethyl-5-oxo-1H-pyrazole-1-carbothioamide). All compounds were studied by IR and NMR spectroscopy, and HTSC(3), [Zn(TSC(3))(2)] x DMSO, [ZnL(1)(2)(H(2)O)] x 2DMSO, and [ZnL(2)(2)(H(2)O)] x 2DMSO were also studied by X-ray diffractometry, giving a thorough picture of the cyclization process. In preliminary tests of the effects of HL(1) and [ZnL(1)(2)(H(2)O)] on rat paw inflammatory edema induced by carrageenan, HL(1) showed antiinflammatory activity.

Amides↗
PubMed2005

Mono- and dinuclear tricarbonyltechnetium(I) complexes with thiosemicarbazones.

[NEt4]2[Tc(CO)3Cl3] reacts with thiosemicarbazones derived from 2,2'-dipyridyl ketone (HL3) and 4-acetylpyridine (HL4) to form stable technetium(I) complexes of the compositions [Tc(CO)3Cl(HL3-Npy,Npy)] and [Tc2(CO)6Cl2(micro-HL4-Npy,S)]. Whereas exclusively the pyridine nitrogen atoms are involved in coordination in the monomeric complex, the binuclear compound represents the first technetium complex with a coordinated thiosemicarbazone functionality.

Journal Article↗
PubMed2004

Reactions of thiosemicarbazones derived from beta-keto amides and beta-keto esters with Zn(II) and Cd(II) acetates: influence of metal, substitution, reagent ratio and temperature on metal-induced cyclization.

Zinc(II) and cadmium(II) acetates were reacted in methanol under various experimental conditions with thiosemicarbazones derived from beta-keto amides or beta-keto esters (HTSC). Some of these reactions afforded thiosemicarbazonate complexes [M(TSC)2] with IR and NMR spectra compatible with N,S-coordination, but most gave complexes [ML2], where HL is a substituted 2,5-dihydro-5-oxo-1H-pyrazole-1-carbothioamide resulting from cyclization of the HTSC. Some of these pyrazolonates and two of the HL ligands were studied by X-ray diffractometry, and their structures are discussed. Surprisingly, the reactions of zinc(II) acetate with HTSC in 1:1 mol ratio usually gave a third, previously unreported type of complex with a dideprotonated ligand, [Zn(L-H)], which was also formed when [ZnL2] and Zn(OAc)2 interacted at room temperature in 1:1 mol ratio. These L-H complexes are highly insoluble in all common solvents, which hinders their characterization but suggests that they are polymeric in nature.

Journal Article↗
PubMed2006

Chiral aggregation and spontaneous resolution of thiosemicarbazone metal complexes.

Chiral aggregation and spontaneous resolution of thiosemicarbazone metal complexes MnL2 (1 and 1') (HL = acetylpyrazine thiosemicarbazone) were achieved through cooperation of hydrogen bonding and pi-pi stacking interactions. Compound 1 crystallized in a chiral space group P4(1)2(1)2 and the molecules exhibited lambda-configuration. Head-to-tail pyrazine-amino hydrogen bonding linked the molecules together presenting a two-dimensional homochiral sheet. The interlayer pi-pi stacking interactions linked the layers in a homochiral array and extended the 2D homochirality to a three-dimensional network. Compound 1 crystallized in space group P4(3)2(1)2, the opposite handedness of P4(1)2(1)2. The molecules, the two-dimensional hydrogen-bonded sheets and the three-dimensional network all exhibited the opposite chiralities to those of 1. Solid state CD spectra measurements confirmed the occurrence of spontaneous resolution of MnL2 and demonstrated that one of the enantiomers of the compound was always in excess. The zinc complexes (2 and 3) and nickel complex 4 crystallized in the chiral space group P4(3)2(1)2. Similar two-dimensional pyrazine-amine hydrogen bonded chiral sheets and three-dimensional networks were found in the crystal packing patterns. The cadmium complex 5 crystallized in a chiral space group P2(1)2(1)2(1), however, it exhibited a similar chiral packing pattern. The only difference was that enlarged Cd-S and Cd-N bond lengths induced the potential 4(1) symmetry. All results indicated that the supramolecular synthon, the cooperation of the pyrazine-amino hydrogen bonding and the pi-pi stacking interactions, were robust enough so that the orientation of the molecules in the solid state could be predicted to a reasonable degree of accuracy.

Journal Article↗
PubMed1992

In vitro antibacterial studies of some newly synthesized phenacyl-thiosemicarbazones.

Four different phenacyl-thiosemicarbazone compounds were studied for their antibacterial activity against seventeen different species/strains. Of the four compounds under study, O-methoxy- phenacyl-thiosemicarbazone was found to be highly active against almost all the cultures under study. The other compounds were also found to possess antibacterial spectrum, but in very high concentrations for some of the cultures.

Journal Article↗
PubMed1963

A case of vaccinia necrosum (or progressive vaccinia), with severe hypogammaglobulinaemia, treated with n-methyl isatin beta-thiosemicarbazone (33T57).

A fatal case of vaccinia necrosum treated with antivaccinial gamma globulin and N-methyl isatin beta-thiosemicarbazone (33T57) is described. Histological abnormalities found at necropsy included intranuclear as well as cytoplasmic inclusion bodies, absence of lymphoid germinal centres, grey hepatization, and bronchiolar epithelial hyperplasia. Virus titres were highest in the original skin lesion; virus was also found in the lymph node draining it and in the kidney and the brain. No toxic effects could be clearly attributed to the drug used in treatment.

Agammaglobulinemia↗
PubMed1998

The cytotoxicity of 2-formyl and 2-acetyl-(6-picolyl)-4N-substituted thiosemicarbazones and their copper(II) complexes.

2-Acetyl-(6-picolyl)-4N-substituted thiosemicarbazones and their copper(II) complexes were shown to be potent antineoplastic and cytotoxic agents against murine and human cultured cells. Numerous derivatives were as active against solid tumor growth as clinically useful agents. The agents inhibited L1210 DNA and RNA syntheses with inhibition of key regulatory enzyme activities of the purine pathway as well as nucleoside kinase activities. d[NTP] pools were reduced and DNA strand scission occurred. These agents were DNA topoisomerase II inhibitors with lower IC50 values than that of VP-16. However, they did not cause L1210 DNA protein linked breaks and actually protected against those breaks afforded by VP-16. The agents were not synergistic with VP-16 in reducing cell growth or DNA synthesis although they did reduce growth of L1210 cells in agar suspended media.

Animals↗