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At least 1,207 records · Page 67Linked to original sources
PubMedDate not supplied

Synthesis and biological activity of 6-substituted-3-[2-(5-substituted-2-furfurylidenehydrazino)-4-thiazolyl] coumarins.

A series of coumarin-derivatives (5) were synthesized by the reaction of 5-substituted-2-furfuraldehyde thiosemicarbazones with 3-bromoacetyl-6-substituted coumarins. The structures of newly synthesized compounds were confirmed on the basis of their elemental analysis, NMR and mass spectral data. Some selected compounds were screened for their antibacterial activity employing disc diffusion technique.

Anti-Bacterial Agents↗
PubMed1994

A new class of anti-filariasis compounds: a preliminary look.

Parasitic nematode worms which produce filariasis in humans place approximately one billion people at risk in more than 75 countries. More than 100 million people are infected with these diseases and are recognized as being of significant military importance. During World War II, filariasis was among the leading causes of medical evacuation from the entire South Pacific area. Agents available to treat the diseases exhibit significant toxicity. Better drugs are urgently needed. Data are reported from work using a Mongolian jird animal model on a new class of potential drugs, thiosemicarbazones. These compounds exhibit activity against the parasites which cause both lymphatic filariasis and the "onchocerciasis type" of the disease.

Animals↗
PubMed1992

[Anti-arrhythmic action of some amidinohydrazone substituted benzophenones. 1. Synthesis of new amidinohydrazone and N-phenylamidinohydrazone substituted benzophenones].

The title compounds are synthesized as a rule by condensation of substituted benzophenones and derivatives of aminoguanidine in the presence of up to 2.5 moles of an anorganic acid. They can be obtained alternatively via corresponding hydrazones, thiosemicarbazones or methylthiothiocarbonylhydrazones.

Anti-Arrhythmia Agents↗
PubMedDate not supplied

Tetrazolo[1,5-a] quinoline derivatives as anti-inflammatory and antimicrobial agents [1].

Tetrazolo[1,5-a]quinoline derivatives bearing in the 4-position various thiazolidinone 3a-c, 5a-c and 7a-c, thiazinone 8a,b, thiazoline 9a-d and thiadiazoline 10a,b moieties have been synthesized and evaluated for anti-inflammatory activity and antimicrobial properties. The synthetic routes involved the reaction of tetrazolo[1,5-a]quinoline-4-carboxaldehyde 1 with amines and hydrazines to give the corresponding aniles 2a-c and hydrazones 4a-c respectively The latter compounds when treated with thioglycolic acid, furnished the corresponding thiazolidinone derivatives 3a-c and 5a-c. Moreover; thiosemicarbazone 6a-c derivatives were subsequently cyclized by various reagents giving rise the title compounds. Some of the products proved to possess potent anti-inflammatory and antimicrobial properties.

Animals↗
PubMed2005

Biological activities of isatin and its derivatives.

Isatin is an endogenous compound identified in humans that possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro. A series of p-substituted isatin semicarbazones have shown anticonvulsant activity in MES, scPTZ and scSTY tests. Various isatin-N-Mannich bases of isatin-3-thiosemicarbazones have shown antiviral and tuberculostatic activity. Methisazone is an effective compound against variola and vaccinia viruses. The N-dimethyl and morpholino derivative of 5-methyl isatin and trimethoprim exhibited an EC50 of more than 4.3 and 17.7 mg mL(-1), respectively. Isatin (3-o-nitrophenyl) hydrazone has shown activity against Walker carcinoma-256. Various substituted indolinones showed antitubercular activity against M. tuberculosis H37Rv with MIC ranging from 10-20 microg mL(-1). Isatin derivatives of Mannich bases had fibrinolytic, muscle relaxant, antiallergic, immunosuppressant, and antithrombotic activity. Isatin showed cardioinhibitory effect on frog heart, and hypotensive, respiratory depression and antidiuretic effects.

Animals↗
PubMed1977

[Studies of substances with antiviral activity. VI. Activity on Herpes simplex virus of bis-homoanalogs of nucleosides and of hydrazone derivatives of various aromatic substrates].

Derivatives of different chemical structures, namely hydrazones of aromatic compounds and bis-homoanalogues of pyrimidine and purine nucleosides, have been investigated for inhibiting activity on Herpes simplex virus infection of human HEp-2 cell cultures. Some thiosemicarbazones, nucleoside analogues and guanylhydrazones proved active [compounds (I), (II b), (II c), (III), (IV a), (IV b), (V a), (V b); Fig. 1]. An increase in the number of guanylhydrazone chains linked to a fluorene structure [from 1 to 3: compounds (II a), (II b) and (II c)] increased the "activity index" (i.e., toxic versus active concentrations: Table II). Further in vitro investigations have been carried out on bis-guanylhydrazone of 1-phenyl-2-chloro-3,7-diformylindole (I) and it was found that its activity is of the order of 1 microgram per ml (Fig. 3). The compound completely blocks low multiplicity infections while it only blocks cytopathogenicity, not viral replication, in high multiplicity infections.

Antiviral Agents↗
PubMed1978

[Research on substances with antiviral activity. VIII. Benzindanoncarboxylic acids].

New derivatives (esters, amides, nitriles, amidines, thiosemicarbazones and guanylhydrazones) of 1H-benz[e]indene-2,3-dihydro-5-methyl-1-oxo-3-carboxylic acid and 1H-benz[e]indene-2,3-dihydro-7-methyl-3-oxo-1-carboxylic acid were prepared and tested for antiviral activities in vitro against vaccinia virus, HID stock and parainfluenza type 3 virus, HA-I/CR-8 stock. Four compounds (II g), (II i), (III b), (III g), showed weak activity in vitro against vaccinia virus.

Antiviral Agents↗
PubMed1990

Biopharmaceutical studies of 3-substituted isatin derivatives.

The metabolic fate of isatin hydrazone (Ia), isatin-3-thiosemicarbazone (Ib), isatin-3-semicarbazone (Ic), isatin-3-phenylhydrazone (Id), isatin oxime (Ie) and 3-hydroxy-3-acetonyl oxindole (II) was studied in rabbits. The compounds were administered orally in the dose of 300 mg/kg body wt. Isatin anthranilic acid, tryptophan and nicotinic acid were identified as the major metabolites excreted in urine. The 3-hydroxy-3-acetonyl oxindole (II) gave on additional metabolite, oxindole. The major metabolites were separated and identified unambiguously on thin layer silica gel plate. Metabolic pathways have been proposed to explain the biotransformation of the compounds investigated.

Animals↗
PubMed1990

[The effect of ambazone and ambazone derivatives on immunologic processes in human lymphocytes].

The influence of 1,4-benzoquinone-guanylhydrazone-thio-semicarbazone (1; ambazone), toluquinone-guanylhydrazone-thiosemicarbazone (2; ambazone 82/80) and p-(thio-semicarbacido)-diaminomethylenehydrazino benzene (3; dihydroambazone) on phytomitogen induced stimulation processes of human lymphocytes was studied. Con A- or PHA-stimulated lymphocytes of healthy probands were treated in vitro with the drugs and the DNA synthesis rate was evaluated by the use of the 3H-labelled thymidine incorporation. A concentration dependent inhibition of the DNA synthesis rate in a comparable quantity for all the tested drugs was found. DNA synthesis was inhibited nearly completely by drug application in a concentration range of 10(-4) mol/l. To check for a possible interference of mitogen stimulation and drug action, 3 was added to the lymphocyte cultures either together with PHA, prior to or after addition of the mitogen. Experiments showed, the sooner the drug acted on the stimulation process, the stronger the DNA synthesis was inhibited.

Concanavalin A↗
PubMed1975

Smallpox vaccination reactions, prophylaxis, and therapy of complications.

Smallpox vaccination in the United States is a routine public health measure which has been under intensive review during the last decade. The most frequently occurring adverse reactions to vaccination are benign and require little or no systemic therapy. These reactions include accidental infection, erythematous and urticarial rash, and generalized vaccinia. Chickenpox occurring concurrently with vaccination presents no problem unless vaccinia has widely superinfected the chickenpox lesions. There is no risk to the pregnant woman who is vaccinated, but there is a slight risk that the fetus will develop fetal vaccinia. The vaccinia does not cause congenital malformations. Vaccinia hyperimmune globulin (VIG) in prophylactic dosage may be given to a pregnant woman who is traveling to a smallpox infected or endemic area in order to prevent fetal vaccinia. Vaccinia necrosum and eczema vaccinatum require vigorous systemic therapy with VIG, and often thiosemicarbazone. Post-vaccinial encephalitis, while frequently serious, has not been shown to be ameliorated by VIG therapy, although there are data which suggest VIG has some value in prophylaxis for encephalitis. Prophylaxis, prompt recognition, and proper therapy may reduce the fatality rates of these complications. Revaccination of patients who have suffered a complication is a frequent clinical problem. Revaccination of an individual who has had post-vaccinial encephalitis or vaccinia necrosum is contraindicated unless the risk of contracting smallpox outweighs the risk of the above two diseases. Revaccination of children who have had eczema vaccinatum is not contraindicated. Revaccination of children with a history of accidental infection or erythematous or urticarial rash presents no known or theoretically increased risk.

Eczema↗
PubMed1986

[Dynamic changes in estrogen receptor levels in the cell cycle of human endometrial adenocarcinoma studied by flow cytometry].

Normal endometrial cells and endometrial adenocarcinoma cells were doubly stained with 1-(N)-fluoresceinyl estrone thiosemicarbazone (17-FE) and propidium iodide and the contents of estrogen receptor (ER) and nucleic acids in a single cell were measured by flow cytometry to clarify the changes in ER levels in the cell cycle. In HHUA cells, established from a well differentiated endometrial adenocarcinoma, used as the ER positive tumor model, the cytoplasmic ER (cER) level increased 1.40 times in the S phase and nuclear ER (nER) level increased 1.65 times in the G2/M phase compared with the levels in the G1 phase. In normal endometrial cells, nER content gradually increased from the early proliferative phase to the ovulatory phase with 2.86 +/- 1.12 times higher levels in the G2/M phase than those in the G0G1 phase and remained high until the mid-secretory phase. Human endometrial adenocarcinoma could be classified into 3 types based on nER levels in G1 and G2/M phases; 1) adenocarcinoma with nER accumulation in G2/M phase as in normal proliferative endometrial cells, 2) adenocarcinoma with nER but with failure of nER accumulation in G2/M phase, suggesting acceptor deficiency, and 3) adenocarcinoma with no nER, suggesting a lack of cER and/or acceptor. These results suggest that cell cycle specific nuclear accumulation of ER, especially in the G2/M phase, is principally related to estrogen dependent proliferation of normal and neoplastic cells.

Adenocarcinoma↗
PubMedDate not supplied

Cationic anticancer drugs and their modes of action.

This report focuses on two groups of cationic cancerostatics, anthracycline antibiotics and 1,4-benzoquinone-guanylhydrazone-thiosemicarbazone (ambazone), lining up biophysical and biochemical effects on the level of membranes and membrane constituents. The interaction of both drugs with multilamellar liposomes consisting of phosphatidylcholine used as a simple model membrane system could be ensured by means of steady state and nanosecond time-resolved fluorometric investigations. The biochemical effect on membranes is underlined by the inhibition of the neuraminidase activity of the Sendai virus, modification of the CAMP phosphodiesterase activity of leukemia L 1210 cells of mice and reduction of the lymphocyte blast transformation.

3',5'-Cyclic-AMP Phosphodiesterases↗
PubMed1988

Cross-resistance patterns in hydroxyurea-resistant leukemia L1210 cells.

Hydroxyurea is an inhibitor of ribonucleotide reductase and is specifically directed at the non-heme iron subunit (which contains the free radical) of this enzyme. Leukemia L1210 cells, grown in the presence of increasing concentrations of hydroxyurea, developed resistance to hydroxyurea. For hydroxyurea, the wild-type L1210 cells required a drug concentration of 85 microM to inhibit cell growth by 50%, and the hydroxyurea-resistant (HU-7-S7) cells required a concentration of approximately 2000 microM. The resistant L1210 cells were cross-resistant to 2,3-dihydro-1H-pyrazolo[2,3-a]imidazole/Desferal. However, these HU-7-S7 cells remained sensitive to 4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone and 1-isoquinolylmethylene-N-hydroxy-N'-amino-guanidine tosylate (inhibitors directed at the same subunit as hydroxyurea). The HU-7-S7 cells retained their sensitivity to deoxyadenosine/erythro-9-(2-hydroxy-3-nonyl)adenine and deoxyguanosine/8-amino-guanosine (inhibitors directed at the effector-binding subunit of ribonucleotide reductase). The L1210 cells developed for resistance to hydroxyurea were sensitive to the non-ribonucleotide reductase inhibitors, methotrexate and 1-beta-D-arabinofuranosylcytosine. Ribonucleotide reductase activity was elevated in the HU-7-S7 cells (CDP reductase, 5.5-fold increase; ADP reductase, 13.2-fold increase). The addition of exogenous effector-binding subunit caused much greater stimulation of reductase activities in the extracts from the resistant cells than from the wild-type cells. The reductase activity in cell-free extracts from the resistant cells was inhibited by hydroxyurea, 2,3-dihydro-1H-pyrazolo[2,3-a]imidazole and dATP to the same extent as the activity from the wild-type L1210 cells. These data indicate that resistance to hydroxyurea in these L1210 cells is to some extent related to increased reductase activity. However, the specificity of resistance of these L1210 cells to inhibitors of ribonucleotide reductase depends on the nature of the inhibitor and the subunit at which the inhibitor is directed.

Adenine↗
PubMed1985

Herpes simplex type 1 ribonucleotide reductase. Mechanism studies with inhibitors.

Several known inhibitors of mammalian ribonucleotide reductase were studied for their interactions with herpes simplex virus type 1 (HSV-1) ribonucleotide reductase. MAIQ (4-methyl-5-amino-1-formylisoquinoline thiosemicarbazone) produced apparent inactivation of HSV-1 ribonucleotide reductase. Only catalytically cycling, not resting, enzyme could be inactivated. Double reciprocal replots of the rates of inactivation versus the concentration of MAIQ indicated that a reversible complex with the enzyme was formed prior to inactivation. In the presence of 10 microM CDP, the maximum rate of inactivation was 20 per h (t1/2 = 3 min). The half-maximum rate was achieved at about 15 microM MAIQ. INOX (periodate-oxidized inosine) also appeared to inactivate HSV-1 ribonucleotide reductase. In contrast to MAIQ, it readily inactivated resting as well as cycling enzyme. CDP retarded the rates of inactivation by INOX. An initial reversible complex between INOX and enzyme was not detectable under the conditions used. IMPY (2,3-dihydro-1H-pyrazolo(2,3-a)imidazole) and guanazole (3,5-diamino-1,2,4-triazole) produced reversible inhibition. Although the data with both inhibitors were most consistent with the noncompetitive inhibition model (versus CDP), the data with guanazole were also marginally consistent with the uncompetitive model.

Guanazole↗
PubMed1988

Chemical-analytical characterization of dihydroambazone.

Important properties of p-(thiosemicarbazido)diamino-methylen-hydrazino benzene (1; dihydroambazone) are described. The transformation of this compound into 1,4-benzoquinone guanylhydrazone thiosemicarbazone (2; ambazone) dependent on different aqueous buffer systems was investigated. The spectroscopic behaviour of the transformation product allows us to determine the content of the compound in aqueous solutions, whereas the determination in serum is much more difficult. Furthermore, TLC experiments and oxidation methods are described.

Chemical Phenomena↗
PubMed1988

Synthesis and characterization of new 2-(arylidenehydrazino)-4-methyl-5-(arylazo)thiazoles.

In order to test their insecticidal, fungicidal and herbicidal activities the title compounds 2-20 were prepared from the reactions of various aldehyde-thiosemicarbazones with corresponding alpha-oxo-alpha-methyl-N-(p-substituted phenyl)-ethanehydrazonoyl chloride [1], derived from the coupling of chloroacetone with the diazonium salt of ethyl p-aminobenzoate, p-iodoaniline, sulfanilamide and aniline, respectively. All the synthetized compounds were characterized by their elementary analysis, and by using IR, NMR and mass spectrometry.

Chemical Phenomena↗