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PubMed1975

Regulators of cell division in plant tissue. XXIII. The identity of an unusual metabolite of 6-benzylaminopurine.

When the cytokinin 6-benzylaminopurine was supplied to de-rooted radish seedings, the principal metabolites formed were the 7- and 9-glucosides. However the cytokinin activity of these glucosides was much less than that of a minor metabolite. This metabolite was purified (yield 550 mug from 40 600 seedings), identified as 6-benzylamino-3beta-D-glucopyranosylpurine and synthesized. It is the first compound with a glycosidic linkage at position 3 of a purine ring to be isolated from a plant tissue.

Benzyl Compounds↗
PubMed2003

Steroidal compounds from in vitro regenerated shoots of Datura metel.

Regeneration of adventitious shoots from young leaves of Datura metel is described. Shoot buds developed on MS medium with 2 mg/l and elongated on hormone-free solid basal medium. The microshoots failed to produce alkaloids, but a number of steroidal compounds were detected. The C(28) sterol 3beta,24xi-dihydroxy-ergosta-5,25-dienolide, regarded as the precursor of withanolides and related steroidal lactones, was identified. The withanolide 12-deoxywithastramonolide was also detected.

Benzyl Compounds↗
PubMed1976

Substituted alpah-methylbenzyl and tricyclic arylalkyl lactamimides as inhibitors of blood platelet aggregation.

N-[1-(p-Phenoxyphenyl)ethyl]hexahydro-2H-azepin-2-imine hydrochloride (10) and N-[1-(2-dibenzothienyl)-ethyl]hexahydro-2H-azepin-2-imine hydrochloride (22) were found to inhibit in vitro aggregation of human blood platelets induced by ADP with minimal release of procoagulant platelet factor 3. The compounds were selected from a series of substituted alpha-methylbenzyl and tricyclic arylalkyl lactamimides that were free of hypoglycemic and diuretic effects. Compounds 10 and 22, as well as N-[1-(1-naphthyl)ethyl]hexahydro-2H-azepin-2-imine hydrochloride (I) and N-(2,2-diphenylpentyl)hexahydro-2H-azepin-2-imine hydrochloride (II), were evaluated for effects on ADP-induced platelet aggregation after repeated oral administration to guinea pigs. Compound II (RMI 12,366A) showed in vivo activity in this system 2 h after the last of four daily doses of 100 mg/kg po.

Adenosine Diphosphate↗
PubMed2002

[Analysis of 1H-NMR fingerprint in stem of Dendrobium loddigesii].

OBJECTIVE: To analyse the 1H-NMR finger-print of the stem of Dendrobium loddigesii. METHOD: Silica gel column chromatography was used to separate the chemical constituents of SCE A of the stem of D. loddigesii. The characteristic signals of the H-NMR finger-print were analysed after determining the structures of the compounds isolated from SCE A. RESULT: 1H-NMR finger-prints of the samples of D. loddigesii collected from different regions showed highly characteristic features and reproducibility. Four compounds predominant in SCE A were isolated and their structures were determined by spectral analysis as 1, 2, 3 and 4, respectively. CONCLUSION: Compound 3 and 4 were isolated from D. loddigesii for the first time. The 1H-NMR finger-print of CGE A of the stem of D. loddigesii showed mainly the characteristic signals of the above four compounds and might be utilized for the original authentication of this plant.

Benzyl Compounds↗
PubMed2000

Characterization of Lonidamine and AF2785 blockade of the cyclic AMP-activated chloride current in rat epididymal cells.

It has been shown previously that the antifertility agents Lonidamine and its analogue AF2785, [1-(2,4-dichlorobenzyl)-indazole-3-acrylic acid] are potent inhibitors of the cAMP-activated chloride channel (CFTR) in rat epididymal cells. In this study, we further characterized the blocking actions of these two compounds and compared them with the known chloride channel blocker diphenylamine-2-carboxylate (DPC). Results show that the order of potency in blocking the cAMP-activated current is AF2785 > Lonidamine > DPC. All three compounds shared similar blocking characteristics. Firstly, their blockade of the current exhibited voltage dependence; all three agents blocked the current more markedly at negative than at positive membrane potentials. Secondly, they blocked the channels from the outside of the cell. Thirdly, their blocking efficacies were maximal at low extracellular pH. Lastly, the time course of the block by AF2785 and DPC appeared to be more rapid than that of Lonidamine. It is hoped that further studies with other indazole compounds will add knowledge to the physiology and pharmacology of CFTR in the epididymis. Such information will be of great importance to our quest for novel male contraceptives.

Animals↗
PubMed1986

Molecular basis for the anti-sickling activity of aromatic amino acids and related compounds: a proton nuclear magnetic resonance investigation.

High-resolution proton nuclear magnetic resonance spectroscopy and relaxation techniques have been used to investigate the interactions of sickle cell hemoglobin (Hb S) and human normal adult hemoglobin (Hb A) with p-bromobenzyl alcohol, L-phenylalanine, L-tryptophan, and L-valine. With the exception of valine, all these compounds inhibit the polymerization of deoxy-Hb S [Noguchi, C. T., & Schechter, A. N. (1978) Biochemistry 17, 5455)). Using transferred nuclear Overhauser effects among the proton resonances of the compound of interest and the corresponding longitudinal relaxation rates (T1(-1], we have shown that the binding of each of the compounds investigated to deoxy-Hb S is comparable to that to deoxy-Hb A. Intermolecular transferred nuclear Overhauser effects have been observed between proton resonances of the anti-sickling compounds and specific protons situated in the heme pockets of Hb. On the basis of these results, we suggest that one binding site, common to all compounds with anti-sickling activity, is at or near the heme pockets in the alpha and beta chains of both deoxy-HB S and deoxy-Hb A. The proton T1(-1) values of the histidyl residues situated over the surface of the hemoglobin molecule indicate that a second binding site is located at or near the beta 6 position, containing the mutation in Hb S (beta 6Glu----Val). The binding of the compounds investigated to the latter site induces conformational changes in the amino-terminal domains of the beta chains.(ABSTRACT TRUNCATED AT 250 WORDS)

Antisickling Agents↗
PubMed2005

Selective herbicide activity of 2,5-di(benzylamine)-p-benzoquinone against the monocot weed Echinochloa crusgalli. An in vivo analysis of photosynthesis and growth.

Six 2,5-diamino-p-benzoquinone derivatives previously characterized as photosystem I electron acceptors were tested for their postemergence herbicide activity. By induction kinetics of chlorophyll a fluorescence performed in vivo it was determined that 2,5-di(benzylamine)-p-benzoquinone diverted electrons at the reducing side of the chloroplast photosystem I. This derivative decreased the efficiency of photosystem II as evidenced by the decrease in the F(v)/F(m) change in Echinochloa crusgalli leaf disks. In addition, 2,5-di(benzylamine)-p-benzoquinone was a CO(2) assimilation inhibitor to Rubisco: the A/C(i) curve analysis indicates that 2,5-di(benzylamine)-p-benzoquinone affected both the carboxylation reaction itself and the regeneration of RuBP. 2,5-di(benzylamine)-p-benzoquinone did not exhibit any effect on the dicot plants Phaseolus vulgaris and Physalis ixocarpa or the monocot Zea mays. These species may have metabolized the herbicide to an inactive compound. Thus, 2,5-di(benzylamine)-p-benzoquinone was found to be a selective herbicide against the monocot weed E. crusgalli.

Benzoquinones↗
PubMed2006

Development of the first potential covalent inhibitors of anandamide cellular uptake.

On the basis of the chemical structures of two previously developed metabolically stable and relatively potent inhibitors of anandamide uptake, OMDM-1,2, two series of potential covalent inhibitors of anandamide cellular reuptake, which might be used for the molecular characterization of the protein(s) involved in the membrane transport of endocannabinoids, have been designed and synthesized. Most of the compounds inhibited uptake to a varied extent and in a generally enantio-sensitive manner when co-incubated with [(14)C]anandamide, but only three of them, the photoactivatable 1a (OMDM-37), 1b (OMDM-39), and 8(Lo395), also produced a significant inhibition of uptake following the preincubation only of the cells, and this effect was significantly enhanced following UV exposure only in the case of 8. None of the new compounds inhibited [(14)C]anandamide hydrolysis with IC(50) < 50 microM, except for 1b.

Amidohydrolases↗
PubMed1993

Antioxidant action of benzylisoquinoline alkaloids.

The antioxidant action of a series of benzylisoquinoline alkaloids has been investigated. Laudanosoline, protopapaverine, anonaine, apomorphine, glaucine, boldine, bulbocapnine, tetrahydroberberine and stepholidine produced a dose-dependent inhibition of microsomal lipid peroxidation induced by Fe2+/ascorbate, CCl4/NADPH or by Fe3+ ADP/NADPH. Apomorphine exerted the highest inhibitory effects in the three systems of induction used, with a potency higher than propyl gallate. Laudanosoline was particularly effective in the first system, while bulbocapnine and anonaine were more potent when CCl4/NADPH or Fe3(+)-ADP/NADPH were used as inducers. Laudanosoline, protopapaverine, apomorphine, tetrahydroberberine and stepholidine were also potent inhibitors of nitroblue tetrazolium (NBT) reduction. The presence of a free hydroxyl group or preferably of a catechol group is a feature relevant for inhibition of lipid peroxidation and NBT reduction, nevertheless the antioxidant activity of benzylisoquinoline alkaloids cannot be only ascribed to the formation of phenoxy radicals and other free radical species may be formed during aporphine and tetrahydroprotoberberine oxidation. The influence of this series of compounds on the time course of lipid peroxidation suggests that some of them, like apomorphine and boldine act as chain-breaking antioxidants.

Alkaloids↗
PubMed2000

Lonidamine and analogue AF2785 block the cyclic adenosine 3', 5'-monophosphate-activated chloride current and chloride secretion in the rat epididymis.

The cystic fibrosis transmembrane conductance regulator (CFTR) or the small conductance cAMP-activated chloride channel encoded by the CFTR gene has been shown to play an important role in the formation of the epididymal fluid microenvironment. Mutation of the gene has led to widespread effects on male reproduction. Like other ion channels, CFTR is amenable to pharmacological intervention. Blocking CFTR in the epididymis could in principle lead to disruption of the epididymal fluid environment. We report for the first time two indazole compounds: lonidamine and 1-(2, 4-dichlorobenzyl)-indazole-3-acrylic acid (AF2785) are potent blockers of CFTR in the epididymis. When added to the external solution under whole-cell patch clamp conditions, AF2785 and lonidamine inhibited the cAMP-activated chloride current in rat epididymal cells with apparent IC(50) values of 170.6 and 631.5 microM, respectively; by comparison the IC(50) value for diphenylamine-2-carboxylate, a well-known chloride channel blocker was 1294 microM. In cultured rat epididymal epithelia mounted in a Ussing chamber, AF2785 and lonidamine inhibited the cAMP-stimulated short-circuit current (a measure of chloride secretion) when added to the apical bathing solution with potency greater than any known chloride channel studied. It is proposed that in view of the important role CFTR plays in male reproduction, further study with these and other new indazole compounds for their CFTR blocking actions can provide a new avenue of research into the development of novel male contraceptives.

Animals↗
PubMed1976

Compounds designed to fit a site of known structure in human haemoglobin.

1 The three-dimensional coordinates of the atoms in human haemoglobin are known, and there is a specific site in the deoxygenated form of the protein at which 2,3-diphosphoglycerate (DPG) interacts. 2 Molecular models of this site have been constructed and used to design compounds which should bind to the deoxy conformation and stabilize it. These compounds should therby promote oxygen liberation, as does DPG. 3The compounds so designed were found to promote oxygen liberation. Their relative potencies, as assessed by sigmoidal dose-response curves, are in the predicted sequence.

Benzyl Compounds↗
PubMed2006

Synthesis and in vitro antitumor activity of novel series 2-benzylthio-4-chlorobenzenesulfonamide derivatives.

Three series of novel 2-benzylthio-4-chloro-5-R1-benzenesulfonamides bearing the N-(benzoxazol-2-yl) (10-19), N-(benzothiazol-2-yl) (20-21) or N-(1,3-dihydro-2H-benzimidazol-2-ylidene) (22-25) moiety were synthesized by reacting N-(2-benzylthio-4-chloro-5-R1-benzenesulfonyl)cyanamide potassium salts (5-9) with 2-aminophenols, 2-aminothiophenol and o-phenylenediamines, respectively. Compounds with carbamoyl substituent at position 5 (14-16, 21 and 25, R1=CONH2) were further dehydrated to the corresponding nitriles (26-30, R1=CN). The in vitro antitumor activity of the compounds obtained was determined at the National Cancer Institute (NCI), and the structure-activity relationships were discussed. N-(2-benzoxazolyl)-2-benzylthio-4-chloro-5-(4-fluorophenylcarbamoyl)benzenesulfonamide (18) is the prominent of the compounds due to its remarkable activity and selectivity toward non-small cell lung cancer (NCI-H522) and melanoma (SK-MEL-2) cell lines (GI50=0.1 microM, TGI=0.5-0.6 microM).

Antineoplastic Agents↗
PubMed2003

Novel selective and metabolically stable inhibitors of anandamide cellular uptake.

Novel aromatic analogues of N-oleoylethanolamine and N-arachidonoylethanolamine (anandamide, AEA) were synthesized and, based on the capability of similar compounds to interact with proteins of the endocannabinoid and endovanilloid signaling systems, were tested on: (i) cannabinoid CB(1) and CB(2) receptors; (ii) vanilloid VR1 receptors; (iii) anandamide cellular uptake (ACU); and (iv) the fatty acid amide hydrolase (FAAH). The (R)- and, particularly, the (S)-1'-(4-hydroxybenzyl) derivatives of N-oleoylethanolamine and AEA (OMDM-1, OMDM-2, OMDM-3, and OMDM-4) inhibited to a varied extent ACU in RBL-2H3 cells (K(i) ranging between 2.4 and 17.7 micro M), the oleoyl analogues (OMDM-1 and OMDM-2, K(i) 2.4 and 3.0 micro M, respectively) being 6- to 7-fold more potent than the arachidonoyl analogues (OMDM-3 and OMDM-4). These four compounds exhibited: (i) poor affinity for either CB(1) (K(i)> or = 5 micro M) or CB(2) (K(i)>10 micro M) receptors in rat brain and spleen membranes, respectively; (ii) almost no activity at vanilloid receptors in the intracellular calcium assay carried out with intact cells over-expressing the human VR1 (EC(50)> or = 10 micro M); and (iii) no activity as inhibitors of FAAH in N18TG2 cell membranes (K(i)>50 micro M). The oleoyl- and arachidonoyl-N'-(4-hydroxy-3-methoxybenzyl)hydrazines (OMDM-5 and OMDM-6), inhibited ACU (K(i) 4.8 and 7.0 micro M, respectively), and were more potent as VR1 agonists (EC(50) 75 and 50nM, respectively), weakly active as CB(1) receptor ligands (K(i) 4.9 and 3.2 micro M, respectively), and inactive as CB(2) ligands (K(i)>5 micro M) as well as on FAAH (K(i)> or = 40 micro M). In conclusion, we report two novel potent and selective inhibitors of ACU (OMDM-1 and OMDM-2) and one "hybrid" agonist of CB(1) and VR1 receptors (OMDM-6). Unlike other compounds of the same type, OMDM-1, OMDM-2, and OMDM-6 were very stable to enzymatic hydrolysis by rat brain homogenates.

Amidohydrolases↗
PubMed2003

Camptothecin biosynthetic genes in hairy roots of Ophiorrhiza pumila: cloning, characterization and differential expression in tissues and by stress compounds.

Camptothecin derivatives are clinically used anti-tumor compounds that biogenetically belong to a group of monoterpenoid indole alkaloids (TIA). We have already established a hairy root culture of Ophiorrhiza pumila (Rubiaceae) that produces camptothecin. The present study describes the cloning and characterization of cDNAs encoding strictosidine synthase (OpSTR; EC 4.3.3.2) and tryptophan decarboxylase (OpTDC; EC 4.1.1.28), two key enzymes in the biosynthesis of TIA from hairy roots of O. pumila. We also isolated the cDNA coding for NADPH:cytochrome P450 reductase (OpCPR; EC 1.6.2.4) that is presumed to be indirectly involved in camptothecin synthesis. The recombinant OpSTR and OpTDC proteins exhibit STR and TDC activities, respectively, when expressed in Escherichia coli. The tissue-specific and stress-inducible expression patterns of OpSTR and OpTDC were quite similar, unlike those of OpCPR. The high expression of OpSTR and OpTDC observed in hairy roots, roots and stems were closely correlated with STR protein accumulation as observed by immunoblot analysis. Plant stress compounds like salicylic acid repressed expression of OpSTR and OpTDC, suggesting coordinate regulation of these genes for camptothecin biosynthesis.

Acetates↗
PubMed2003

Synthesis and antimelanoma activity of tertiary amide analogues of N-acetyl-4-S-cysteaminylphenol.

The biosynthetic pathway to melanin is a realistic target for therapeutic intervention in the development of new drugs to combat malignant melanoma. N-Acetyl-4-S-cysteaminylphenol (1) is an analogue of a biosynthetic intermediate in the pathway to melanin. It probably acts as a prodrug and is oxidized selectively in melanocytes to an o-quinone, which can alkylate cellular nucleophiles resulting in interference with cell growth and proliferation. We previously synthesized a range of more lipophilic analogues of 1 by varying the acyl portion and introducing substitution alpha to the nitrogen. Most of the new compounds displayed greater cytotoxicity than the original lead compound 1. We have now prepared 12 new compounds with varying acyl portions and three different substituents on the nitrogen of the amide in order to increase lipophilicity and to reduce the possibility of hydrolysis of the amides. Most of the tertiary amides showed greater cytotoxicity towards five representative melanoma cell lines than the parent secondary amide. The highest cytotoxicity, comparable to cisplatin, was observed for the benzyl substituted compounds 4, 8, 12, and 16 and the cyclohexylacetamide derivatives 13-15 against these five cell lines. The moderate activity of 13-16 against SK-Mel-24 (non-tyrosinase containing) and an ovarian cell line suggests that interference with the melanin pathway may not be the only mode of action of these new compounds.

Amides↗
PubMed2006

Luminescent property and catalytic activity of Ru(II) carbonyl complexes containing N, O donor of 2-hydroxy-1-naphthylideneimines.

The reaction of the chelating ligands (obtained by the condensation of 2-hydroxy-1-naphthaldehyde with various primary amines) with [RuHCl(CO)(EPh3)2(B)] (where E=P; B=PPh3, py or pip: E=As; B=AsPh3) in benzene afforded new stable ruthenium(II) carbonyl complexes of the general formula [Ru(Cl)(CO)(EPh3)(B)(L)] (L=anion of bidentate Schiff bases). The structure of the new complexes was investigated using elemental analyses, spectral (FT-IR, UV-vis and 1H NMR) and electrochemical studies and is found to be octahedral. All the metal complexes exhibit characteristic MLCT absorption and luminescence bands in the visible region. The luminescence efficiency of the ruthenium(II) complexes was explained based on the ligand environment around the metal ion. These complexes catalyze oxidation of primary and secondary alcohols into their corresponding carbonyl compounds in the presence of N-methylmorpholine-N-oxide (NMO) as the source of oxygen. The formation of high valent Ru(IV)=O species as a catalytic intermediate is proposed for the catalytic process.

Alcohols↗
PubMed2005

Synthesis and biological evaluation of 2- and 7-substituted 9-deazaadenosine analogues.

A series of 2-halogen and 7-alkyl substituted analogues of 9-deazaadenosine and 2'-deoxy-9-deazaadenosine was synthesized by new efficient methodology involving transformation of corresponding 9-deazaguanosine and 2'-deoxyguanosine, which in turn were synthesized by direct C-glycosylation of 1-benzyl-9-deazaguanine with 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose and methyl 2-deoxy-3,5-di-O-(p-toluoyl)-D-ribofuranoside, respectively. Deoxychlorination of C6 and diazotization/chloroor fluoro-dediazoniation of the sugar-protected 9-deazaguanosine, followed by selective ammonolysis at C6 and deprotection of the sugar moiety, gave 2-chloro- and 2-fluoro-9-deazaadenosine (6 and 9). Substitution of the 7-position of the dihalogen-intermediate with alkyl groups, followed by ammonolysis and deprotection, provided 2-chloro-7-alkyl-9-deazaadenosines (13a-e) and 2-fluoro-7-benzyl-9-deazaadenosine (13f). Catalytic hydrogenation of 13a-e gave 7-alkyl-9-deazaadenosines 14a-e. Similarly, 2-chloro-2'-deoxy-9-deazaadenosine (21), 2-chloro-2'-deoxy-7-methyl-9-deazaadenosine (25), 2'-deoxy-9-deazaadenosine (22), and 2'-deoxy-7-methyl-9-deazaadenosine (26) were prepared from sugar-protected 2'-deoxy-9-deazaguanosine. Among these compounds, 7-benzyl-9-deazaadenosine (14b) showed the most potent cytotoxic activity, with IC50 values of 0.07, 0.1, 0.2 and 1.5 microM, while both 7-methyl-9-deazaadenosine (14a) and 2-fluoro-9-deazaadenosine (9) also demonstrated significant cytotoxic activity with IC50 values of 0.4, 0.7, 0.3, and 1.5 microM, and 1.5, 0.9, 0.3, and 5 microM against L 1210 leukemia, P388 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma cells, respectively.

Antineoplastic Agents↗