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PubMed1981

Binding (in vitro) of some antimitotic isatin derivatives to human serum albumin.

The binding of isatin and its mustard N-Mannich base, considerably biologically active compounds, to human serum albumin has been studied by equilibrium dialysis and ultrafiltration. The influences of ligand and macromolecule concentration, temperature and pH of the incubation medium have been demonstrated. The Scatchard plot of isatin binding to albumin shows a biphasic curve which indicates the presence of at least two different binding sites on albumin molecule. One site with a higher affinity, K1 = 2.25 X 10(3) M and n1= 25, and the other site with a lower affinity, i.e. higher capacity. In the cases of mustard Mannich base we could demonstrate the same type of curve, K1 = 2.20 X 10(5) M and n1 = 1.0, whereas another site has a lower affinity and greater number of binding sites.

Humans↗
PubMed2001

Synthesis and pharmacological activities of hydrazones, Schiff and Mannich bases of isatin derivatives.

Schiff bases and phenyl hydrazone of isatins were prepared by reacting isatin and the appropriate aromatic primary amine/hydrazines. A new series of the corresponding N-mannich bases were synthesized by reacting them with formaldehyde and diphenylamine. The chemical structures were confirmed by means of their 1H-NMR, IR spectral data and elemental analysis. The compounds were screened for analgesic, antiinflammatory and antipyretic activity. 1-Diphenylaminomethyl-3-(1-naphthylimino)-1,3-dihydroindol-3-one (4), 3-(1-naphthylimino)-5-bromo-1,3-dihydroindol-2-one (2) and 1-diphenylaminomethyl-3-(4-methylphenylimino)-1,3-dihydroindol-3-one (7) were found to exhibit the highest analgesic, anti-inflammatory and antipyretic activity respectively. 1-Diphenylaminomethyl-3-(4-methylphenylimino)-1,3-dihydroindol-3-one (7) was found to be the most active compound of the series.

Acetic Acid↗
PubMedDate not supplied

[The reaction of 3-(R-phenyl)-6-hydrazine pyridazines with substituted isatins (II)].

This paper presents the synthesis of six hydrazones from isatin and 1-morpholinomethyl-isatin and also of their six cooper's complex salts. Their structure was confirmed by the results of the quantitative elemental analysis and by IR, UV-VIS spectral analysis. The biological tests point out that cooper's complex salt of 3-(3'-phenyl-pyridazinylhydrazono)-5-methyl-indoline-2-one (1:2) (VI a) has the smallest toxicity (DMT over 800 mg/kg.w. p.o.), a remarkable anti-inflammatory activity (inhibition 57.1%, IAR 1.1) and also a gastroprotector coefficient of 43.3%. In the mean time, the cooper's complex salt of 3-(3'-p-anisyl-pyridazinyl-hydrazono)-5-methyl-ind oline-2-one (1:2) (VI b) has a gastroprotector coefficient of 76.3% and a lower anti-inflammatory activity than the first derivative (inhibition 36.9%).

Animals↗
PubMedDate not supplied

Synthesis of isatin semicarbazones as novel anticonvulsants--role of hydrogen bonding.

PURPOSE: A series of substituted isatin semicarbazones and related bioisosteric hydrazones were designed and synthesised to meet the structural requirements essential for anticonvulsant properties. METHODS: The structures of all synthesised compounds were confirmed by means of infrared, proton magnetic resonance spectroscopy and by elemental analyses. All compounds were evaluated for their anticonvulsant activity by maximal electroshock (MES), subcutaneous metrazol (ScMet) and subcutaneous strychnine (ScSty) induced seizure methods and their neurotoxic effects were determined by rotorod test. RESULTS: A number of isatin semicarbazones exhibited significant protection after intraperitoneal administration at the dose of 100 and 300mg/kg. Some of them showed good anticonvulsant activity in MES test in rats after per oral administration at the dose of 30mg/kg. The bioisosteric hydrazone derivatives were inactive in all tests. Compound 6-chloroisatin-3- (4-bromophenyl)-semicarbazone has emerged as the most active analogue of the series showing good activity in all the three tests and was more active than phenytoin and valproic acid. CONCLUSIONS: The results evidenced the importance of hydrogen bonding and suggested a new pharmacophore model with four binding sites essential for anticonvulsant activity.

Administration, Oral↗
PubMed2004

Anticonvulsant activity of Schiff bases of isatin derivatives.

Schiff bases of N-methyl and N-acetyl isatin derivatives with different aryl amines have been synthesized and screened for anticonvulsant activities against maximal electroshock (MES) and subcutaneous metrazole (ScMet). N-methyl-5-bromo-3-(p-chlorophenylimino) isatin (2) exhibited anticonvulsant activity in MES and ScMet with LD50 > 600 mg kg(-1), showing better activity than the standard drugs phenytoin, carbamazepine and valproic acid. Thus, compound 2 may be chosen as a prototype for development of new anticonvulsants.

Animals↗
PubMedDate not supplied

[The effect of long-term administration of isatin and himantan to mice on sensitivity of brain monoamine oxidase B to inhibition by deprenyl in vivo and in vitro].

Chronic administration of a low dose of reversible monoamine oxidase (MAO) B inhibitors isatin or himantane (20 mg/kg) to mice during 21 day did not influence the enzyme activity assayed in isolated brain mitochondria. However in vivo sensitivity of brain MAO B to irreversible mechanism-based inhibitor deprenyl injected to animals right after the last administration of the reversible inhibitor sharply decreased. This suggests accumulation of these compounds (or their metabolites?) in the brain accompanied by increased protection of active site of MAO B against specific irreversible inhibitor. deprenyl. In vitro inhibition of MAO B activity in mitochondria isolated from brain of mice treated with isatin or himantane was somewhat higher than in control mitochondria. The latter suggests that long-term treatment of animals with reversible easily dissociating inhibitors may influence regulatory properties of MAO B.

Adamantane↗
PubMed2005

Aminopyrimidinimino isatin analogues: design of novel non- nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum chemotherapeutic properties.

PURPOSE: HIV is the most significant risk factor for many opportunistic infections such as tuberculosis, hepatitis, bacterial infections and others. In this paper, we describe an aminopyrimidinimino isatin lead compound as a novel non-nucleoside reverse transcriptase inhibitor with broad-spectrum chemotherapeutic properties for the effective treatment of AIDS and AIDS-related opportunistic infections. METHODS: The synthesis of various aminopyrimidinimino isatin derivatives was achieved in two steps and evaluated for anti-HIV, anti-HCV, antimycobacterial and antibacterial activities. RESULTS: Compound 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7[[N4-[3'-(4'-amino-5'-trimethoxybenzylpyrimidin-2'-yl)imino-1'-isatinyl] methyl]N1-piperazinyl]-3-quinoline carboxylic acid (14) emerged as the most potent broad-spectrum chemotherapeutic agent active against HIV, HCV, M. tuberculosis and various pathogenic bacteria. Among the synthesized compounds compound 14 and 15 emerged as more promising broad-spectrum chemotherapeutic agents.

Aminopyridines↗
PubMed1985

The response of some intravascular and intracellular lipid parameters of the rat after treatment with isatin.

The effect of isatin on serum lipid concentrations, the activity of lipoprotein lipase, the activity of lipogenic enzymes and the oxidation rate of fatty acids of female Wistar rats were investigated. A decrease of the triglyceride concentrations could be observed after one week of treatment of the group of sucrose-rich alimented animals, after two weeks this was also the case with the group fed with standard food. There were no changes in the cholesterol concentrations. Post-heparin lipolytic activity was not influenced. The liver enzymes malic enzyme, glucose-6-phosphate dehydrogenase and 6-phosphogluconate dehydrogenase showed a remarkable increase in activity. The simultaneous rise of the oxidation rate of 14C-palmitate in the liver was measured. On the basis of the present findings the accelerated degradation rate could be responsible for the hypolipemic effect of the substance. The possible participation of the carnitine shuttle in the lipid-lowering action is discussed on the basis of changed concentrations of total carnitine, free carnitine and acylcarnitine in pooled serum samples after treatment with isatin.

Animals↗
PubMedDate not supplied

Effect of administration of isatin on alkaline phosphatase of various organs of rat.

In vivo administration of isatin (200 mg/kg) significantly lowered the activity of rat kidney alkaline phosphatase after 5 hr but enhanced the activity of rat duodenal and jejunal enzyme after 2 and 5 hr (P less than 0.01). The increased activity of the duodenal and jejunal alkaline phosphatase might be due to the induction of the enzyme by isatin.

Alkaline Phosphatase↗
PubMed2003

Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation.

This paper reports the results of our thermochemical/calorimetric determination of the enthalpies of combustion, phase change, and formation of isatin, isatoic anhydride, and N-methylisatin. The density functional calculations accompanied by vibrational and thermal corrections were also performed for these compounds and N-methylisatoic anhydride. Through a combination of theoretical calculations and associated isodesmic reactions, we have deduced that isatin has some antiaromatic character and isatoic anhydride enjoys some aromatic stabilization.

Journal Article↗
PubMed1968

The metabolism of C-labeled isatin and anthranilate in pisum stem sections.

Isatin, previously shown to promote growth in green and etiolated pea stems, is converted mainly to anthranilate in those tissues; small quantities of isatate are also formed. Fed anthranilate is converted mainly to its beta-d-glucoside; smaller amounts are metabolized to anthranilamide, tryptophan and kynurenine. These data provide some basis for understanding the growth promoting activity of isatin.

Journal Article↗
PubMed1999

Antiproliferative action of isatine-beta-thiocarbohydrazone and N-ethylisatine-beta-thiocarbohydrazone on human PBMC and on two neoplastic cell lines.

The antiproliferative action of two synthetic compounds, isatine-b-thiocarbohydrazone (IsTCH) and N-ethyl isatine-beta-thiocarbohydrazone (N-Et-IsTCH), towards healthy human peripheral blood mononuclear cells (PBMC) and two neoplastic cell lines in vitro, was investigated. IsTCH and N-Et-IsTCH were dissolved in DMSO and then diluted with nutrient medium to desired final concentration. Target cells were PBMC, as well as human cervix carcinoma - HeLa cells, and murine melanoma B16 cells. Five different concentrations (3 microM to 50 microM) of investigated agents were applied on target cells. Cell survival was determined 72 h after the agent's action using MTT test. Results obtained showed that both investigated compounds exerted a dose dependent antiproliferative action to neoplastic cell lines. Their action was only cytostatic; trypan blue exclusion test did not show any sign of direct drug cytotoxicity when drugs concentration were less than 50 microM. ICs50 +/- SD for IsTCH antiproliferative action were 61.69 +/- 4.25 microM for HeLa cells; 34.1 +/- 7.15 microM for B16 cells: 17.62 +/- 7.11 microM for nonstimulated and 30.0 +/- 9.46 microM for stimulated (by 5 mg/ml PHA) PBMC. ICs50 +/- SD for the action of N-Et-IsTCH were 21.86 +/- 1.77 microM for HeLa cells; 10.37 +/- 1.55 microM for B16 cells; >47 microM for both, nonstimulated and for stimulated, PBMC. Nonstimulated human PBMC appeared to be the most sensitive to the cytostatic IsTCH action; while HeLa cells were the most resistant. N-Et-IsTCH showed more than two or five fold stronger antiproliferative effect toward B16 cells than on HeLa or PBMC cells, respectively, and more than three times intensive activity compared to IsTCH, indicating specificity of N-Et-IsTCH towards inhibition of melanoma cell growth. While increasing concentrations of IsTCH led to decrease in the the PBMC induced suppression of HeLa cell survival; N-Et-Is-TCH in the difference from IsTCH, in dose dependent way contributed to the PBMC induced suppression of HeLa cell survival. In conclusion, the activity of N-Et-Istch on malignant melanoma cells deserves further investigation.

Adult↗
PubMed2002

Anticonvulsant and sedative-hypnotic activities of N-substituted isatin semicarbazones.

A series of N-methyl/acetyl, 5-(un)-substituted isatin-3-semicarbazones were screened for anticonvulsant and sedative-hypnotic activities. The results revealed that protection was obtained in all the screens i.e., MES, scPTZ, and scSTY. Compounds 2, 4, 6, 10 but not 1 and 3 showed low neurotoxicity when compared to clinically used drugs. Compounds 5, 7, 8 and 9 were completely non-toxic. Compound 6 showed good activity in the rat oral MES screen. Among all the compounds, 3 and 6 emerged as the most active compounds as indicated by the protection they exhibit in MES, scSTY, and scPTZ screens. All the compounds showed significant sedativehypnotic activity.

Animals↗