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At least 19 recordsLinked to original sources
PubMed1985

Synthesis and pharmacological evaluation of aromatic dihydroxylated spiro[indan-1,3'-pyrrolidine] and spiro[indan-2,2'-pyrrolidine] derivatives.

Aromatic hydroxylated derivatives of the spiro[indan-1,3'-pyrrolidine] and spiro[indan-2,2'-pyrrolidine] ring systems have been synthesized and evaluated for dopaminergic agonist and antagonist activities. None of these conformationally restricted catecholamines possessed any dopaminergic activity, but 5,6-dihydroxy spiro[indan-1,3'-pyrrolidine] hydrobromide exhibited weak dopamine antagonist properties.

Animals↗
PubMed2004

Synthesis of chloro and bromo substituted 5-(indan-1'-yl)tetrazoles and 5-(indan-1'-yl)methyltetrazoles as possible analgesic agents.

Chloro and bromo substututed indanyl tetrazoles (compounds 5a, b) and indanyl methyltetrazoles (compounds 5c, 5d) have been synthesized from their respective acids through amide and nitrile routes, and characterized. The title compounds (5a, 5b, 5c and 5d) were subjected for their analgesic activity in the acetic acid induced writhing test on albino mice. The significant (p < 0.001) analgesic activity, exhibited by the compound 5b at a dose of 50 mg/kg body weight, was comparable to that of phenylbutazone and indometacin at a dose of 100 and 50 mg/kg body weight respectively. The effect of substitution at the benzenoid part of the indan nucleus and chain lenght on analgesic activity was in the following order: bromine > chlorine and tetrazole > methyltetrazole.

Acetic Acid↗
PubMed1966

The metabolism of cis- and trans-indane-1,2-diol.

1. The metabolism of cis-indane-1,2-diol, trans-indane-1,2-diol, indene epoxide and 2-hydroxyindan-1-one in rats has been studied. The substances were administered to the animals by subcutaneous injection. 2. The urine of the dosed animals was examined for the presence of free and conjugated cis- and trans-dihydrodiols, and for each compound it was possible to isolate both cis and trans forms of indane-1,2-diol from the urine. 3. The urines were also examined by paper chromatography for ketones and two ketonic metabolites were detected in the urine of rats dosed separately with cis-indane-1,2-diol, trans-indane-1,2-diol, 2-hydroxyindan-1-one and indene epoxide. The ketones were provisionally identified as (1-oxoindan-2-yl glucosid)uronic acid and 1-oxoindan-2-yl sulphuric acid. 4. (1-Oxoindan-2-yl glucosid)uronic acid was isolated as the 2,4-dinitrophenylhydrazone from the urine of rats dosed separately with cis-indane-1,2-diol and trans-indane-1,2-diol. 5. Possible mechanisms for the interconversion of cis- and trans-indane-1,2-diol are discussed.

Animals↗
PubMed1985

Hypolipidemic activity of indan-1,3-dione derivatives in rodents.

A series of 2-substituted indan-1,3-dione derivatives, including alkyl (C-1-C-5), mono- and disubstituted phenyl, and other 2-aryl derivatives, were tested for hypolipidemic activity of CF1 male mice at 20 mg/kg per day. These derivatives reduced both serum cholesterol and triglycerides after 16 days of administration intraperitoneally. 2-(4-Methoxyphenyl)indan-1,3-dione was one of the more active compounds with 41% reduction of serum cholesterol and 58% reduction of serum triglyceride levels on day 16. This activity was confirmed in the rat after oral administration. 2-(2-Methylphenyl)- and 2-(4-chlorophenyl)indan-1,3-dione were effective in reducing serum triglyceride levels 58% and 53%, respectively, in mice. Serum cholesterol on day 16 was effectively reduced 46% by 2-(2,4-dimethylphenyl)indan-1,3-dione. The indan-1,3-dione derivatives were more effective than clofibrate in lowering lipid levels in mice. A more detailed study on the effects of 2-(4-methoxyphenyl)indan-1,3-dione demonstrated that key enzymes in the de novo synthesis of lipids were inhibited by the drug lowering tissue levels of lipids but raising those in the feces. The alterations in lipid content of rat lipoprotein fractions by the drug appeared favorable.

Animals↗
PubMed2000

Simultaneous determination of ethylbenzene, indan, indene and acenaphthene in air by capillary gas chromatography.

An attempt was made to establish a method for the simultaneous determination of ethylbenzene, indan, indene and acenaphthene by capillary gas chromatography with flame ionization detection. The air was sampled on charcoal tubes and extracted with carbon disulfide-methanol (60:1, v/v). The four analytes were separated by gas chromatography using a capillary column of cross-linked 5% phenylmethylsilicone. Under the applied conditions the method showed detection limits of 1.8 microg/m3 for ethylbenzene, 2.1 microg/m3 for indan, 2.8 microg/m3 for indene and 3.4 microg/m3 for acenaphthene. Relative standard deviations were as follows: ethylbenzene, 6.2%; indan, 9.9%; indene, 13.6%; and acenaphthene, 14.4%. The recoveries for these compounds were 98.6, 97.9, 55.7 and 52.1%, and the accuracies were 2.5, 3.0, 44.3 and 47.8%, a working range of 1.5-30 ng/microl for ethylbenzene and 0.75-15 ng/microl for indan, indene and acenaphthene. The method was found to be suitable for the determination of environmental and occupational analysed ethylbenzene, indan, indene and acenaphthene exposure.

Acenaphthenes↗
PubMed1981

Monophenolic 2-(dipropylamino)indans and related compounds: central dopamine-receptor stimulating activity.

Monophenolic (2-(dipropylamino)indans and related compounds have been synthesized and tested for central dopamine-receptor stimulating activity, using biochemical and behavioral tests in rats and emesis tests in dogs. The active compounds possess similar relative potencies in eliciting the three different dopamine-receptor mediated effects measured. 4-Hydroxy-2-(dipropylamino)indan was the most potent of the new compounds. The corresponding 5-hydroxy analogue was less active. 4-Hydroxy-2-[(dipropylamino)methyl]indan is a new type of dopaminergic agent with a phenylpropylamine moiety in its framework instead of the phenylethylamine structure, common to most dopamine-receptor agonists. This compound was 10-20 times less active than apomorphine. 6,7,8,9-Tetrahydro-1-hydroxy-N,N-dipropyl-5H-6-benzocycloheptenylamine and 5-hydroxy-2-[(dipropylamino)methyl]tetralin were both inactive. Since the intramolecular distances between functional groups in the indans studied here are different from those in, for example, apomorphine, it is concluded that a certain variation of these distances can be accepted by the receptor. It could also be demonstrated that the position of the OH group on the aromatic ring is of importance for the activity and that emetic activity may be associated with dopaminergic agonists of the indan as well as of the tetralin type of structure.

Animals↗
PubMed1983

Synthesis and antianxiety activity of (omega-piperazinylalkoxy)indan derivatives.

A series of (omega-piperazinylalkoxy)indan derivatives has been synthesized and screened for potential antianxiety activities. The effect of structural modification of these molecules on activities has been systemically examined. Antianxiety activity was displayed by 5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (2), 5-[3-[4-(4-fluorophenyl)-1-piperazinyl]-propoxy]indan (8), 6-fluoro-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (33), and 6-methyl-5-[3-(4-phenyl-1-piperazinyl)propoxy]indan (42), as determined in antifighting and anti-morphine tests. These derivatives in antianxiety tests were equipotent or more potent than chlordiazepoxide with less muscle-relaxant effect. They also showed weak neuroleptic-like action.

Animals↗
PubMed1997

Antibacterial activity of two alkylamines integrated an indane scaffold: mimicry of a complementary unit on magainin 2.

Based on the antibacterial activity of 9-phenylnonylamine (pC9a) against Escherichia coli (ATCC29522) and Staphylococcus aureus (ATCC25923), we have further tested the inhibitory ability of the growth of the bacteria by (+/-)1-(4-aminobutyl)-6-benzylindane (PM2) and (+/-)1-benzyl-6-(4-aminobutyl) indane (PM3), that is, two kinds of 1,6-disubstituted indanes. In an in vitro assay, they showed almost the same antibacterial activities against the bacteria as pC9a, as well as that of magainin 2 analogs (i.e., the peptides MSI-78 and 87-ISM), except in the case of 87-ISM against S. aureus. At the MIC (minimum inhibitory concentration) values, however, their killing rate of E. coli is actually quicker than pC9a. This indicates that an indane scaffold, used as a template to mimic a part of the alpha-helical structure of magainin 2, can accelerate the killing rate. At present, however, it is unknown whether either the hydrophobicity or the alpha-helical structure, or both, of the indane scaffold is involved in accelerating the rate. Moreover, these two indanes also showed stronger antibacterial activity against two strains of Helicobacter pylori (ATCC43526, ATCC43579) than either pC9a or magainin 2 related peptides.

Anti-Bacterial Agents↗
PubMed1987

Gas chromatographic/mass spectrometric studies of the urinary metabolites of male rats given indan.

The identified urinary metabolites of male rats exposed to indan are: 1- and 2-indanone; 1-, 2- and 5-indanol; 2- and 3-hydroxyl-1-indanone; and cis- and trans-indan-1,2-diol. Indan causes kidney damage in male rats in a manner similar to the cyclic hydrocarbons cis- and trans-decalin and JP-10. Lesions produced by indan occur only in male rats and not in female or control rats.

Administration, Oral↗
PubMed2005

Examination of the in vitro (anti)estrogenic, (anti)androgenic and (anti)dioxin-like activities of tetralin, indane and isochroman derivatives using receptor-specific bioassays.

Molecules derived from tetralin, indane and isochroman are often used in the synthesis of fragrance materials. The two polycyclic musk fragrances AHTN (6-acetyl-1,1,2,4,4,7-hexamethyltetralin), HHCB (1,2,4,6,7,8-hexahydro-4,6,6,7,8,8-hexamethylcyclopenta-gamma-2-benzopyran) and ADBI (4-acetyl-1,1-dimethyl-6-tert-butylindane) are derived from tetralin, isochroman and indane, respectively. In previous studies, AHTN and HHCB have been shown to antagonize estrogen receptors (ERs), both in vitro and in vivo. Here, we used two newly developed reporter gene assays, to examine the agonistic and antagonistic properties of several indane, tetralin and isochroman derivatives towards the human androgen receptor (AR) and aryl hydrocarbon receptor (AhR). Additionally, we also assessed (anti)estrogenicity of these compounds. A number of compounds showed weak estrogenic activity towards the human ER alpha. Several compounds showed (anti)estrogenic effects, starting at a concentration of 0.1 microM. Surprisingly, almost all compounds were found to be AR antagonists, starting at 0.1 microM. None of the compounds tested, showed either agonism or antagonism towards the AhR. Non-specific effects via crosstalk of the AhR and the ER or AR can therefore be ruled out. As far as we are aware, molecules derived from indane, tetralin and isochroman showing direct interaction with the ER and AR have not been reported previously.

Androgen Receptor Antagonists↗
PubMed1987

Conformational analysis of 2-aminoindans and 2-(aminomethyl)indans in relation to their central dopaminergic effects and a dynamic dopamine receptor concept.

Conformational analyses on differently substituted 2-aminoindans of significant pharmacological interest were carried out by the molecular mechanics method (MM2). An X-ray structure of (R)-4-methoxy-2-aminoindan has shown the ammonium nitrogen [-)-D-tartaric acid salt) in an axial position. From comparison with other, highly potent, centrally acting dopamine (DA) receptor agonists, it can be predicted that the active enantiomer (R)-4-hydroxy-2-(di-n-propylamino)indan should have its nitrogen atom in an equatorial position. This places it close to the aromatic ring plane, which is one of several prerequisites for potent DA receptor agonism. MM2 correctly calculates (R)-4-methoxy-2-aminoindan and (R)-4-hydroxy-2-(dialkylamino)indan to be more stable in the N-axial and N-equatorial conformations, respectively. Conformational analysis of the dimethyl model compound of the moderately potent dopaminergic phenylpropylamine analogue 4-hydroxy-2-[(di-n-propylamino)methyl]indan was also carried out, in order to see if any conformations of this compound satisfy the requirements for dopaminergic agonism. Two such stable conformations were found.

Brain↗
PubMed2000

Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions.

Conformationally constrained cyclic alpha-amino acid derivatives were synthesized under solid-liquid phase-transfer catalysis conditions. This methodology involves the bis-alkylation of ethyl isocyanoacetate with various alpha,alpha'-dibromo-o-xylene derivatives [alpha,alpha'-dibromo-o-xylene 5, 2,3-bis(bromomethyl)-1, 4-dimethoxybenzene 6, 1,2-bis(bromomethyl)-4,5-dibromobenzene 7, 2, 3-bis(bromomethyl)naphthalene 8, 1,8-bis(bromomethyl)-naphthalene 9, 6,7-bis(bromomethyl)-2,2-dimethyl-1H-phenalene-1,3(2H)-dione 10, 2, 3-bis(bromomethyl)-1,4-anthraquinone 11, 6, 7-bis(bromomethyl)quinoxaline 12, 3,4-bis(bromomethyl)furan 13, 1,2, 4,5-tetrakis(bromomethyl)benzene 28, and hexakis(bromomethyl)benzene 30] using potassium carbonate as a base and tetrabutylammonium hydrogensulfate as a phase-transfer catalyst to give corresponding isonitrile derivatives, which upon hydrolysis with HCl in ethanol gave amino esters. Using this method electron-deficient as well as electron-rich and halogen-substituted indan-based alpha-amino acids were prepared. The preparation of bis-indan as well as tris-indan alpha-amino esters is also described.

Acetates↗
PubMed2002

Kinetic resolutions of indan derivatives using bacteria.

Racemic indan derivatives have been resolved by the hydrolysis of amide bonds using Corynebacterium ammoniagenes IFO12612 to produce (S)-amine and (R)-amides. In the kinetic resolution of 1 (N-12-(6-methoxy-indan-1-yl)ethyl]acetamide), it was possible to run the reaction to 44% conversion on a 10-g scale, obtaining (S)-amine 4 ((S)-2-(6-methoxy-indan-1-yl)ethylamine) at >99% enantiomeric excess (ee) and (R)-1 at 98% ee.

Corynebacterium↗
PubMed1992

Evaluation of some newer non-steroidal anti-inflammatory indan-1-acids in various biological systems.

In line of the effort towards development of some newer indanyl non-steroidal anti-inflammatory agents and providing comprehensive SAR among this class of compounds some significantly active derivatives with low ulcerogenic potential were identified. Dealing with various long chain and branched chain compounds among this series, 3-(5, 6-dimethoxy indan-1-yl) propionic acid, 2-(5, 6-dimethoxy indan-1-yl) propionic acid and 3-(6-methoxy indan-1-yl) propionic acid were observed to have encouraging biological activity. Screening in various animal models of inflammation suggests their longer duration of action and lower ulcerogenic liability.

Animals↗
PubMed2006

Hypolipidemic activity of Indan--1--acetic acids.

To study the hyoplipidemic activity of non-methoxy and methoxy substituted--alkyl indan acetic acids in normogenic and hypergenic animal models. The hyoplipidemic activity was evaluated using normogenic and hypergenic rat models. Indan acids synthesized in our laboratory (50 mg/kg) and the standard drug clofibrate (50 mg/kg) were used for this study. Dimethoxy substituted -methyl and -ethyl indan acetic acids (9 & 10) exhibited significant hypocholesterolemic activity in both animal models. Clofibrate showed cholesterol lowering activity of 18% in normogenic rats while test agents 9 and 10 produced a similar activity of 20% and 17% respectively. Liver cholesterol and liver weight of the animals tested were found normal in case of the test compounds while liver weight was increased by 15% in clofibrate treated rats. LDL and VLDL cholesterol levels were also affected by compounds No. 9 and 10. Compounds having a smaller alkyl groups (R = CH3, C2H5) at--carbon atom of the acetic acid moiety exhibited significant hypocholesterolemic activity.

Acetates↗
PubMedDate not supplied

Studies on anti-inflammatory, analgesic and antipyretic activities of some indan acids.

A series of indan-1 acids were synthesized and screened for anti-inflammatory activity. All the reported compounds showed varying degrees of anti-inflammatory activity in carrageenin-induced paw oedema test. They also exhibited appreciable antipyretic and analgesic activity in various animal test models. Among these compounds 6-methoxy-indan-1-acetic acid (compound 11) and 5,6-dimethoxy-indan-1-acetic acid (compound 12) showed activity profile close to that of phenylbutazone having prolonged action and lower toxicity than the latter.

Animals↗