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PubMed2005

[Synthesis and insulinotropic activity of 2-benzylidenesuccinic acid derivatives].

AIM: To design and synthesize new compounds of prandial glucose regulator with more simple structure. METHODS: The target compounds were synthesized from diethyl succinate and benzaldehyde or 4-fluorobenzaldehyde by four-step reactions. Thus 18 compounds were synthesized. Their structures were comfirmed by NMR, MS and IR. RESULTS: Seventeen compounds had different hypoglycemic activity in mice, among them, 9 compounds had higher hypoglycemic activity and 6 compounds had character of prandial glucose regulator. CONCLUSION: Part of the compounds have higher hypoglycemic activity deserve to be further investigated.

Animals↗

PubMed2005

N-acetyl-4-[(2-hydroxybenzylidene)amino]benzenesulfonamide monohydrate and N-acetyl-4-[(5-bromo-2-hydroxybenzylidene)amino]benzenesulfonamide monohydrate.

Molecules of the title compounds, C15H14N2O4S.H2O and C15H13BrN2O4S.H2O, adopt an E configuration about the azomethine C=N double bond. In both molecules, the two benzene rings and the azomethine group are practically coplanar, as a result of intramolecular hydrogen bonds involving the hydroxy O atom and azomethine N atom. The angular disposition of the bonds about the S atom deviates significantly from that of a regular tetrahedron. In the crystal structures, both compounds form two-dimensional layers parallel to the (100) plane.

Benzylidene Compounds↗

PubMed1999

In vivo effects of new inhibitors of catechol-O-methyl transferase.

1. The effects of two new synthetic compounds showing in vitro catechol-O-methyl transferase (COMT) inhibitor properties were studied in vivo and compared with the effects of nitecapone and Ro-41-0960. 2. QO IA (3-(3-hydroxy-4-methoxy-5-nitrobenzylidene)-2,4-pentanedione), QO IIR ([2-(3,4-dihydroxy-2-nitrophenyl)vinyl]phenyl ketone), nitecapone and Ro-41-0960 (30 mg kg(-1), i.p.) were given to reserpinized rats 1 h before the administration of L-DOPA/carbidopa (LD/CD, 50:50 mg kg(-1), i.p.). Locomotor activity was assessed 1 h later. All the COMT inhibitors (COMTI), with the exception of QO IA, markedly potentiated LD/CD reversal of reserpine-induced akinesia. Similar results were obtained when the COMTI were coadministered with LD/CD. The effect of compound QO IIR was dose-dependent (7.5-30 mg kg(-1), i.p.). 3. The COMTI (30 mg kg(-1), i.p.) potentiated LD/CD reversal of both catalepsy and hypothermia of reserpinized mice. 4. QO IIR, nitecapone and Ro-41-0960 (30 mg kg(-1), i.p.) reduced striatal 3-methyl-DOPA (3-OMD) levels and increased dopamine (DA) and dihydroxyphenylacetic acid (DOPAC) levels. Compound QO IA was devoid of any effect on striatal amine levels. In contrast to the other inhibitors, Ro-41-0961 reduced HVA levels as well. The effect of QO IIR on striatal amine levels was dose-dependent (7.5-60 mg kg(-1), i.p.) 5. These results suggest that the new compound QO IIR is an effective peripherally acting COMT inhibitor in vivo.

Animals↗

PubMed1998

GTS-21, a nicotinic agonist, attenuates multiple infarctions and cognitive deficit caused by permanent occlusion of bilateral common carotid arteries in rats.

We examined the effects of GTS-21 [3-(2,4-dimethoxybenzylidene)-anabaseine dihydrochloride], a nicotinic agonist, on histopathological changes of the brain and radial maze learning performance in rats with permanent occlusion of the bilateral common carotid arteries (2VO) and elucidated whether this compound has a protective effect against the neuronal degeneration and spatial cognitive deficit caused by chronic ischemia. Rats were administered GTS-21 (1 and 10 mg/kg, p.o.) or vehicle 24 hr and 30 min before the 2VO operation and then once daily for 2 months after the operation. The 2VO rats given vehicle had multiple infarctions in the cerebral cortex, hippocampus and striatum and rarefaction in the white matter at 2 months after the operation, although the number and distribution of infarctions varied among individual animals. In addition, the 2VO rats given vehicle showed a higher rate of errors in the acquisition trials of the 8-arm radial maze task than sham-operated controls. However, 2VO rats treated with GTS-21 (1 and 10 mg/kg, p.o.) showed significantly decreased neuropathological changes and less errors in the acquisition trials compared to the vehicle-treated 2VO rats. These results indicate that GTS-21 attenuates impairment of spatial cognitive deficit and progressive neuronal degeneration induced by 2VO and suggest that this compound is beneficial for the treatment of neurodegenerative diseases following chronic cerebral hypoperfusion.

Animals↗

PubMed1990

An evaluation of the acute in vivo toxicity of benzylidenechroman-4-ones, 1-thiobenzylidenechroman-4-ones and benzylidenetetralones.

A series of new compounds were evaluated for acute in vivo toxicity. Their synthesis and antifungal activity have previously been described by us. The naturally occurring class of compounds to which they belong - the benzylidenechroman-4-ones - have been identified as a potential source of new antifungal agents. These compounds were found to be less toxic, as judged by acute toxicity, than existing commercially available antifungals. A number of conclusions can be drawn about the relationship of structural changes in this series of compounds to increases or decreases in acute toxicity.

Animals↗

PubMed2004

Inhibitory effects of multi-substituted benzylidenethiazolidine-2,4-diones on LDL oxidation.

Multi-substituted benzylidenethiazolidine-2,4-diones 3a-h were synthesized by Knoevenagel condensation of di- or tri-substituted 4-hydroxybenzaldehydes [or 1-(3,5-di-tert-butyl-4-hydroxyphenyl)ethanone] 1 with thiazolidine-2,4-dione (2) and evaluated for antioxidant activities of Cu(2+)-induced oxidation of human low-density lipoproteins (LDL). Among compounds 3a-h, 3a was superior to probucol in LDL-antioxidant activities and found to be ninefold more active than probucol. Due to its potency, compound 3a was tested for complementary in vitro investigations, such as TBARS assay (IC(50) = 0.1 microM), lag time (240 min at 1.5 microM), relative electrophoretic mobility (REM) of ox-LDL (inhibition of 83% at 10 microM), fragmentation of apoB-100 (inhibition of 61% at 5 microM), and radical DPPH scavenging activity on copper-mediated LDL oxidation. In macrophage-mediated LDL oxidation, the TBARS formation was also inhibited by compound 3a.

Antioxidants↗

PubMed1991

Structure of (+)-[S-(E)]-N-(alpha-methylbenzylidene)-p-toluenesulfinamide.

C15H15NOS, Mr = 257.35, monoclinic, P2(1), a = 7.710 (2), b = 5.903 (5), c = 14.700 (3) A, beta = 91.48 (2) degrees, V = 668.8 (6) A3, Z = 2, Dx = 1.278 g cm-3, lambda(Mo K alpha) = 0.71069 A, mu = 2.18 cm-1, F(000) = 272, T = 296 K, R = 0.043, 944 unique observed reflections. This is the first structure determination of an N-alkylidenesulfinamide. The C = N bond is distorted and lengthened presumably because of the steric interaction and electron-withdrawing effect of the sulfinyl group. The nonplanar conformation is also a result of repulsive steric interaction. The configuration at C = N is trans. The title compound was obtained from the displacement reaction of (-)-1-methyl (S)-p-toluenesulfinate with methyllithium.

Benzylidene Compounds↗

PubMed1995

Tyrphostins suppress the growth of psoriatic keratinocytes.

Tyrosine kinase inhibitors of the tyrphostin family which block EGF receptor kinase are reported to arrest the growth of psoriatic keratinocytes in vitro. Three tyrphostins with the potency ratio AG555 >> AG18 >> AG814 were found to arrest growth with no adverse cytotoxic effects. The potency ratio to inhibit keratinocyte proliferation follows their potency to inhibit EGF receptor kinase activity in vitro. These compounds represent novel leads for the therapy of psoriasis.

Benzylidene Compounds↗

PubMed1997

Synthesis and antimicrobial activities of 2-[(alpha-methylbenzylidene)-hydrazino]benzoxazoles.

New 2-[(alpha-methylbenzylidene)hydrazino]benzoxazole derivatives have been synthesized by reacting ortho or para substituted acetophenones with 2-hydrazinobenzoxazole in ethanol. The structures of the synthesized compounds were confirmed by microanalysis, IR and NMR spectral data. Antimicrobial activities of the compounds were investigated by the microdilution susceptibility test in Mueller-Hinton broth and Sabouraud liquid medium. Test organisms: Staphylococcus aureus ATCC 29213 and Enterococcus faecalis ATCC 29212 as Gram (+) bacteria, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa, ATCC 27853 as Gram (-) bacteria, and Candida albicans, Candida stellatoidea, Candida parapsilosis and Candida pseudotropicalis as yeasts. Among the compounds tested 2-[(alpha-methyl-4-chlorobenzylidene)hydrazino]benzoxazole (compounds 4) and 2-[(alpha-methyl-4-nitrobenzylidene)hydrazino]benzoxazole (compound 8) showed the most favorable activity.

Anti-Bacterial Agents↗

PubMed1996

Synthesis and antiproliferative activity of tyrphostins containing quinoline moieties.

Tyrphostins are a series of benzylidenemalononitrile derivatives synthesized by condensing aromatic aldehydes with malononitrile derivatives. The use of heteroaromatic aldehydes in this process has received little attention. Accordingly, 27 tyrphostins containing a 2-, 3- or 4-substituted quinoline moiety were synthesized, of which 21 are novel compounds Compounds containing the 2-aminoethene-1, 1-dinitrile moiety in each series were the most potent inhibitors of the EGF receptor kinase in a cell-free enzyme assay (compounds 2, 11 and 20), having IC50 values of 1.7, 27.0 and 4.7 microM respectively. For each R group substitution the order of potency was 2-quinolines > 4-quinolines > 3-quinolines. Compounds 2, 11 and 20 were unable to inhibit the epidermal growth factor (EGF) receptor autophosphorylation in intact cells; however, they were able to inhibit the EGF-dependent phosphorylation of a 50 kDa protein. These three compounds were able to inhibit EGF-dependent proliferation in a fibroblast cell more efficiently than serum-stimulated proliferation, suggesting that their mechanism of action may be linked to the EGF receptor signalling pathway. Compound 2 exhibited a degree of cell line selectivity in the US National Cancer Institute in vitro human tumour cell line panel. The majority of non-small cell lung cancer lines were relatively resistant to compound 2, while most of the colon, CNS, melanoma and renal lines were relatively sensitive. Further work is required to elucidate the mechanism of action of this interesting group of substituted-quinoline compounds and to determine whether for compounds 2, 11 and 20 this is related to inhibition of EGF receptor function.

Adenocarcinoma↗

PubMed1994

A nicotinic agonist (GTS-21), eyeblink classical conditioning, and nicotinic receptor binding in rabbit brain.

The septo-hippocampal cholinergic system is of demonstrated involvement in eyeblink classical conditioning (EBCC). To determine if a nicotinic cholinergic agonist, GTS-21, would facilitate acquisition of EBCC in older rabbits, three doses (0.1, 0.5, 1.0 mg/kg) in sterile saline vehicle and vehicle alone were administered to older rabbits (n = 48; mean age = 29.8 months). A control group of vehicle-treated young rabbits (n = 12; mean age = 3.5 months) was included. Rabbits were conditioned for fifteen 90-trial sessions in the 750 ms delay paradigm with a tone conditioned stimulus and corneal airpuff unconditioned stimulus. Dependent measures of trials to learning criterion, percentage of conditioned responses (CRs) and CR amplitude consistently showed significant improvement in older rabbits treated with 0.5 and 1.0 mg/kg of GTS-21. Acquisition was similar in vehicle-treated young and GTS-treated older rabbits. Vehicle-treated older rabbits conditioned more poorly than vehicle-treated young rabbits. No non-associative learning effects were observed in GTS-21 treated animals. Nicotinic receptor binding was similar in all groups of older rabbits, indicating that GTS-21 administration over a 15-day period did not affect nicotinic receptors. Alzheimer's disease (AD) has been associated with significant loss of nicotinic cholinergic receptors, and patients diagnosed with probable AD are seriously impaired on EBCC. These results demonstrating that the nicotinic agonist, GTS-21, facilitated EBCC in older rabbits suggest that the compound should receive additional investigation for its potential to affect cognition in AD.

Aging↗

PubMed2002

Antimycobacterial activity of 5-arylidene aromatic derivatives of hydantoin.

Various 5-(chlorobenzylidene)-2-isoniazido and 5-(chlorobenzylidene)-2-amino substituted derivatives of imidazoline-4-one were synthesized and evaluated in the primary assay for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv. Eight of them exhibited > 90% inhibition in the primary screening at 12.5 microg/ml. For these primarily selected compounds the actual MIC and IC50 values were determined. Two of the isoniazid derivatives, for which MIC < 3.13 microg/ml and SI > 10, were selected for further screening and investigated for efficacy in vitro in a TB-infected macrophage model. The most promising compound, 5-(3-chlorobenzylidene)-2-(isonicotinoylhydrazino)-imidazoline-4-one, with activity in vitro comparable with rifampin (MIC = 0.8 microg/ml. SI > 78) was tested in vivo in the animal tuberculosis model but exhibited insignificant activity. For several compounds the primary screening of antimycobacterial activity against Mycobacterium avium (ATCC 25291) was conducted as well, but none of them demonstrated satisfactory activity.

Animals↗

PubMed2006

Antieosinophilic activity of orazipone.

Orazipone is a novel sulfhydryl-reactive compound that has been previously shown to reduce lung eosinophilia in guinea pigs and rats and to inhibit degranulation in mast cells and cytokine production in monocytes and T-cells. However, the effects of orazipone on granulocyte longevity are unknown. Orazipone and its derivative 3-(4-chloro-3-nitro-benzylidene)-pentane-2,4-dione (OR-2370) reversed interleukin-5-afforded survival of human eosinophils by inducing apoptosis. In contrast, orazipone did not affect granulocyte macrophage-colony-stimulating factor-induced survival of human neutrophils. The effect of orazipone on eosinophil apoptosis is different from that of glucocorticoids in that even high con-centrations of interleukin-5 were not able to overcome the effect of orazipone. Orazipone further enhanced spontaneous apoptosis as well as that induced by CD95 ligation without inducing primary necrosis. OR-2370-induced DNA fragmentation was shown to be dependent on caspases 3 and 6 and c-jun-N-terminal kinase, whereas extracellular regulated kinase, p38 mitogen-activated protein kinase, and phosphatidylinositol 3-kinase as well as caspases 4, 8, and 9 seem not to mediate its actions. Our results suggest that orazipone and its derivative OR-2370 possess strong antieosinophilic activity and thus may have anti-inflammatory efficacy in the treatment of asthma and/or allergic conditions.

Apoptosis↗

PubMed1998

Selective alpha7-nicotinic agonists normalize inhibition of auditory response in DBA mice.

Abnormal sensory inhibition is a measurable indicator of a sensory processing deficit which is observed in schizophrenia, and other disorders, and which may be heritable. This deficit has also been observed in certain inbred mouse strains where the intensity of the deficit has been correlated with reduction in the number of hippocampal alpha-bungarotoxin-sensitive nicotinic receptors. Nicotine and certain nicotinic agonists produce brief periods of normal sensory inhibition in these mice. Similarly, nicotine also transiently normalizes sensory inhibition in schizophrenics. The present study assessed the effects of a novel nicotinic partial agonist (GTS-21), selective for the alpha-bungarotoxin site, on sensory inhibition in DBA mice, a strain with no sensory inhibition under routine experimental conditions. GTS-21 produced a dose-dependent normalization of sensory inhibition which was blocked by alpha-bungarotoxin but not mecamylamine. In contrast to other nicotinic agonists, normalization of sensory inhibition by GTS-21 and two related anabaseine compounds, DMAB-anabaseine and DMAC-anabaseine, was observed when administered a second time to the animal, after a 40-min delay. Our results indicated that the anabaseine compounds increase sensory inhibition through alpha7 nicotinic receptors, and that their ability to act repeatedly on these receptors may be less affected by desensitization.

Anabasine↗

PubMed1996

Simultaneous determination of GTS-21 and its metabolite in rat plasma by high-performance liquid chromatography using solid-phase extraction.

It has been suggested that GTS-21 can improve the learning deficits and inhibit the neuro-degeneration in patients with Alzheimer's disease. This paper describes a reversed-phase high-performance liquid chromatographic assay with visible detection at 405 nm for determination of GTS-21 and its metabolite, 4-hydroxy-GTS-21 in rat plasma. The method uses solid-phase extraction with a Bond Elut C18 column. A quantitation limit of 1.0 ng/ml was achieved using 0.5 ml of rat plasma. In the validation study, the coefficients of variation and the relative errors of each compound were less than 10%. Also freeze-thaw and storage stability were confirmed. This method has proved to be applicable to the pharmacokinetic study of GTS-21 in rats.

Animals↗

PubMed2001

Novel seco cyclopropa[c]pyrrolo[3,2-e]indole bisalkylators bearing a 3,3'-arylenebisacryloyl group as a linker.

We synthesized the novel seco cyclopropa[c]pyrrolo[3,2-e]indole (CPI) bisalkylators and evaluated their antitumor activity. Among these derivatives, 11a (AT-760), in which the two seco 3-methoxycarbonyl-2-trifluoromethyl CPI (MCTFCPI) moieties are connected with a 3,3'-(1,4-phenylene)bisacryloyl group, was found to exhibit more potent cytotoxicity and antitumor activity against HeLaS3 human uterine cervix carcinoma cells and Colon 26 adenocarcinoma cells, respectively, than 8 (bizelesin, U-77,779). It also appeared that compound 11a exhibits improved in vivo efficacy in the human colon CX-1 model when compared to either compound 8 or mitomycin C (MMC). Efficacious doses for 11a were found to be 2-fold lower than those for 8.

Animals↗

PubMed2004

Possible role of the phosphoinositide pathway for signal transduction in changes in the sensitivity of delta-opiate receptors during diabetes mellitus.

We studied the effects of selective delta-opiate receptor agonists and antagonists on the phosphoinositide pathway in lymphocytes from healthy donors and patients with diabetes mellitus. The test compounds probably play a role in changes in the sensitivity to pharmacological substances binding to delta-opiate receptors during diabetes mellitus.

Benzylidene Compounds↗

PubMed1986

Antihypertensive activity of arylidenaminoguanidine derivatives.

The synthesis of new benzylidenaminoguanidine compounds is described. Some of these compounds were tested for antihypertensive activity in conscious unrestrained spontaneously hypertensive rats. The compounds examined possess a significant antihypertensive activity, qualitatively different from that of clonidine. For the tested compounds, the absence of the transient rise in blood pressure, which appears immediately after administration of clonidine-like drugs, is noteworthy.

Animals↗