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At least 19 recordsLinked to original sources
PubMed2005

Idesolide: a new spiro compound from Idesia polycarpa.

[structure: see text]. Idesolide, a new spiro compound possessing tetrahydrobenzodioxole structure, was isolated from the fruits of Idesia polycarpa Maxim. Its structure was established by NMR and MS spectroscopic analysis with single-crystal X-ray experiments. Idesolide significantly reduced nitric oxide production induced by lipopolysaccharide in BV2 microglial cells.

Anti-Inflammatory Agents↗
PubMed1977

Estrogen potentiating activity of two spiro compounds having approximately similar molecular dimensions to stilbestrol.

Pharmacological investigation of members of a series of synthetic spiro derivatives with similar molecular dimensions to stilbestrol revealed that two compounds, spiro[cyclohexane-1,2'-tetralin]-1,4'-dione and spiro[cyclohexane-1,2'-indan]-1,4'-diol, exhibited a marked ability to potentiate stilbestrol at doses which had no intrinsic estrogenic activity. It is postulated that such compounds may be of use in reducing the side effects associated with estrogen therapy.

Animals↗
PubMed2004

Inhibition of inducible TNF-alpha expression by oxaspirodion, a novel spiro-compound from the ascomycete Chaetomium subspirale.

In a search for compounds inhibiting the inducible TNF-alpha promoter activity in T cells, a new spiro-compound, designated oxaspirodion, was isolated from fermentations of the ascomycete Chaetomium subspirale. Oxaspirodion inhibited TNF-alpha promoter-driven luciferase reporter gene expression with an IC50 value of 2.5 microg/ml (10 microM) in TPA/ionomycin-stimulated Jurkat T cells. Studies on the mode of action of the compound revealed that the inhibition of the TNF-alpha promoter activity is caused by an inhibition of the phosphorylation of the ERK1/2 kinases. In addition, oxaspirodion inhibited the activation of the transcription factor NF-kappaB, which is involved in the inducible expression of many proinflammatory genes.

Animals↗
PubMed2002

Electroauxiliary-assisted sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen: application to the synthesis of spiro compounds.

The sequential introduction of two carbon nucleophiles on the same alpha-carbon of nitrogen by using selective oxidative cleavage of two silyl groups as electroauxilialies has been accomplished. The combination of this expedient transformation and ring-closing metathesis enables reliable and straightforward syntheses of nitrogen-containing spiro compounds, such as cephalotaxine.

Alkylation↗
PubMed1977

Synthesis and pharmacological screening of certain spiro compounds.

The synthesis of certain azaspirodione, azaspirane and bis-azaspirodione derivatives is described. Fusing equimolecular amounts of 3-oxaspiro[5.5]undecane-2.4-dione with certain amino compounds afforded the corresponding N-substituted azaspirodiones. Reduction of the N-harolaryl azaspirodiones gave the oxygen-free analogues. Reacting 3-azaspiro[5.5]undecane-2.4-dione with certain secondary amines under the Mannich conditions yielded the expected bases. Reacting one equivalent of ethylene-diamine with two equivalents of 2-oxaspiro[4.4]nonane-1.3-dione and the next higher homologues, viz, the decane and undecane afforded the respective ethylene bis-azaspirodiones. Likewise, on applying the Mannich conditions to the nitrogen analogues of the before-mentioned oxaspirodiones using piperazine as the secondary amine, bis-azaspirodions were obtained. The result of the pharmacological screening of some of the synthesized spiro compounds is included.

Animals↗
PubMed1990

Studies on heterocyclic compounds: spiro [indole-3,2'-thiazolidine] derivatives. II. Antimicrobial activity of halogenated 3'-phenylspiro 3H-indole-3,2'-thiazolidine -2,4 (1H)-diones.

The following polyhalogenated 3'-phenyl 3H-indole-3,2'-thiazolidine -2,4' (1H)-dione of general formula (A) were synthesized and screened for antimicrobial activity. (formula: see text) where: X = H (I, III, V, VII, IX, XI), CH3 (II, IV, VI, VIII, X, XII); Y = H (I, II), 2,4-F2 (III, IV), 2,4-Cl2 (V, VI), 3,4-Cl2 (VII, VIII), 2,6-Cl2 (IX, X), 2,4,6-Cl3 (XI, XII). The general synthetic route involves the preparation of variously substituted isatin-3-imines, which are subjected to cyclocondensation with thioglycolic acid to give compounds I, III, V, VII, IX, XI, or thiolactic acid to give compounds II, IV, VI, VII, X, XII. The prepared compounds were screened against S. aureus, B. cereus, M. paratuberculosis, E. coli, Pr. mirabilis, Ps. aeruginosa, C. albicans, S. cerevisiae, A. niger by a disk-diffusion assay (Kirby-Bauer modified). The results of the antimicrobial screening showed that the polyhalogenated derivatives of type (A) exhibited varying degrees of activity against Gram-positive, Gram-negative bacteria, and fungi. Compound (III) showed a significant activity toward A. niger, moreover compound (IV) was active toward C. albicans. Compound (IX) was very active toward S. typhi and Ps. aeruginosa. Compounds (VII), (IX) and (XII) were very active toward M. paratuberculosis.

Anti-Bacterial Agents↗
PubMed1976

Synthesis of certain spiro compounds.

The synthesis of certain N-substituted azaspirodiones and azaspiranes is described. Fusing equimolecular amounts of 2-oxaspiro [4.4]nonane-1.3-dione with a number of amino compounds afforded the corresponding N-substituted azaspirodiones. However, with certain o-substituted anilines, no condensation took place. Reduction of the N-haloaryl azaspirodiones gave the corresponding oxygen free compounds. Other azaspiranes were isolated as the quaternary methiodides. Applying the Mannich conditions to 2-azaspiro[4.4]nonane-1.3-dione yielded the N-Mannich bases.

Chemical Phenomena↗
PubMed1990

Studies on heterocyclic compounds: spiro [indole-3,2'-thiazolidine] derivatives. Antimicrobial activity of monohalogenated 3'-phenylspiro 3H-indole-3,2'-thiazolidine-2,4' (1H)-diones.

The following halogenated 3'-phenyl [3H-indole-3,2'-thiazolidine]-2,4'(1H)-dione of general formula (A) were synthesized and screened for antimicrobial activity. (formula: see text) where: X = H (I, III, V, VII, IX, XI, XIII, XV), CH3 (II, IV, VI, VIII, X, XII, XIV, XVI); Y = H (I, II), 3-F (III, IV), 2-Cl (V, VI), 3-Cl (VII, VIII), 4-Cl (IX, X), 2-Br (XI, XII), 3-Br (XIII, XIV), 4-Br (XV, XVI). The synthetic approach involves the preparation of variously substituted Schiff-bases of indol-2,3-dione, which then are subjected to cyclocondensation with alpha-mercaptoalkanoic acids, to give spirothiazolidinones of type (A). The prepared compounds were screened against S. aureus, B. cereus, M. paratuberculosis, E. coli, S. typhi, Pr. mirabilis, Ps. aeruginosa, C. albicans, S. cerevisiae, A. niger by a disk-diffusion assay (Kirby-Bauer modified. The results of the antimicrobial screening showed that the prepared compounds exhibited varying degrees of activity against Gram-positive, Gram-negative bacteria, and fungi. 3-Fluoro-derivative (III) showed inhibitory activity especially toward S. aureus and C. albicans. Chloroderivatives (VII) and (VIII) showed broad-spectrum "in vitro" antimicrobial activity, and were especially inhibitory toward S. aureus, E. coli, and S. Typhi. Fluoro-derivative (IV) and bromo-derivatives (XIII) and (XIV) possessed marked antimicrobial activity against M. paratuberculosis.

Anti-Bacterial Agents↗
PubMed1993

Delaminomycins, novel extracellular matrix receptor antagonist. IV. Structure-activity relationships of delaminomycins and derivatives.

Delaminomycins A, B, C and their derivatives were prepared and investigated biological activities of them. Among these compounds, spiro compounds (A2, B2 and C2) showed stronger inhibitory activity than natural products (A1, B1 and C1) on B16 melanoma cells adhesion assay and Con A-induced proliferation of murine splenic lymphocytes assay. In MLCR and antimicrobial assay, however, A1, B1 and C1 showed more potent inhibitory activity than spiro compounds (A2, B2 and C2). On the other hand, as to C-5' substituents of pyrrolidine ring, the order of inhibitory activity was R = OH > R = OCH3 > R = H on Con A-induced proliferation of murine splenic lymphocytes assay. In MLCR and antimicrobial assay, however, the order of inhibitory activities were R = H > R = OCH3 > R = OH. Inhibitory activities of A4 which was lacked pyrrolidine ring were reduced on B16 melanoma cells adhesion assay and on cytotoxicity against tumor cells in vitro in comparison with those of A1.

Animals↗
PubMed1994

Synthesis of some new heterobicyclic compounds containing spiro-1,2,4-triazine moiety as potential anti HIV and anticancer agents.

A number of heterobicyclic compounds such as 1,3,5-thiazine, thiazolidinone, pyrimidine, pyrimidinedione, imidazole, quinazolinone and 1,2,4-triazinone derivatives have been synthesized by interaction of 1,6-dihydro-3 (2H)-thioxo-6-spiro-(9'-fluorene)-1,2,4-triazin-5(4H)-one (1) with sulphur/nitrogen compounds in neutral or alkaline medium. Structure elucidation of the new compounds has been carried out with the help of elemental analysis and spectral data. Some of these compounds were tested for in vitro anti HIV and anticancer activities.

Antineoplastic Agents↗
PubMed1978

Synthesis of 2-aryl-4,4-spiro-morpholinium compounds of possible biologic interest.

The preparation of some 2-hydroxy-2-aryl-4,4-polymethylenemorpholinium bromides (II) by ring closure of the corresponding N-phenacyl-N-hydroxy-ethylpiperidinium (pyrrolidinium) bromide (III) and the synthesis of 2-ethoxy (IV) and of 2,3-dehydro derivatives (VI) are described. The synteshis of 2-phenyl-4,4-pentamethylene-morpholinium bromide (VII) from the hydrogenation of either the 2-phenyl or 2-p-bromophenyl-2,3-dehydromorpholinium derivativies (VI) is also reported. Proof of the chemical structures is provided by IR, UV, and NMR spectroscopy. The synthesized compounds did not present any significant pharmacologic activity.

Animals↗