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PubMed2007

Tandem oxidation of allylic and benzylic alcohols to esters catalyzed by N-heterocyclic carbenes.

N-heterocyclic carbenes catalyze the oxidation of allylic, propargylic, and benzylic alcohols to esters with manganese(IV) oxide in excellent yields. A variety of ester derivatives can be synthesized, including protected carboxylates. This one-pot tandem oxidation represents the first organocatalytic oxidation of alcohols to esters. Saturated esters can also be accessed from aldehydes using this method. Through the utilization of a chiral catalyst, the acyl-heteroazolium intermediate becomes a chiral acylating agent, which can desymmetrize meso-1,2-diols. [reaction: see text].

Allyl Compounds↗
PubMed1975

Synthesis of threo-4,5-dihydroxy diastereomers of sphinganine;.

The threo-4,5-dihydroxy diastereomers of sphinganine were prepared by the following sequence of reactions: (a) benzoylation of sphingenine to the tribenzoyl derivative; (b) osmylation followed by resolution of the mixture of threo-4,5-dihydroxy tribenzoyl (DHTBS) diastereomers; and (c) alkaline hydrolysis to yield the threo-4,5-dihydroxysphinganines (DHS). Carbon atoms 4 and 5 of the high and low melting threo-4,5-DHTBS diastereomers and the compounds derived from them were tentatively assigned 4R, 5S and 5R configurations, respectively;

Amino Alcohols↗
PubMed2005

[Studies on chemical constituents of Patrinia villosa Juss].

Nine compounds including n-dotriacontanoic acid (I), n-dotriacontanol (II), Palmic acid (III), oleanolic acid (IV) aurentiamide acetate (V), daucosterol (VI), beta-sitosterol (VII), 7beta-hydroxysitosterol (VIII) and stigmasterol (IX) were isolated from petroleum ether and chloroform extract of Patrinia villosa Juss. Among them, compounds I, II, V, VIII were obtained from the plant of Patrinia for the first time and compounds VI, VII ,IX were separated from Patrinia villosa Juss for the first time.

Acetates↗
PubMed1989

Effect of some 4-alkyl-5-dimethylamino-1-phenyl-1-penten-3-one hydrochlorides and related compounds on respiration in mouse liver mitochondria.

5-Dimethylamino-1-phenyl-1-penten-3-one hydrochloride (1a) has high inhibiting properties in mitochondria isolated from mice liver. Substitution at the 4-methylene group of 1a by different alkyl substituents lead to compounds with wide variation in respiration-inhibiting properties. No correlations were found between either the Charton steric parameter (v), Taft inductive value (f*) or fragmental constant (f) of the substituents at position 4 of the Mannich bases with inhibition of respiration. However the biological results suggested two receptor sites were present in the mitochondria which may interact with the Mannich bases namely a common receptor for all compounds and in addition a narrow hydrophobic binding area which can accommodate a n-butyl or higher alkyl groups which are present in some of the compounds.

Animals↗
PubMed1994

A nonradioactive assay for microsomal cysteine-S-conjugate N-acetyltransferase activity by high-pressure liquid chromatography.

Microsomal cysteine-S-conjugate N-acetyltransferase, an enzyme specific for S-substituted cysteines, plays an important role in the detoxicative metabolism of xenobiotics by catalyzing the N-acetylation of cysteine-S-conjugates. Cysteine-S-conjugate N-acetyl-transferase activity is generally assayed by measuring the amount of N-[14C]acetyl-S-benzyl-L-cysteine generated from the model compound S-benzyl-L-cysteine and [14C]acetyl-CoA and subsequent extraction of the product. Although sensitive, this method is costly and time consuming. For safety and environmental reasons we developed a nonradioactive assay for cysteine-S-conjugate N-acetyltransferase activity. Our method depends upon the acetylation of the uv-sensitive model compound 4-nitro-S-benzyl-L-cysteine. The test mixture is separated by HPLC, guaranteeing that no by-products interfere with the determination of product formation. Radioactive and nonradioactive methods were compared using different porcine kidney samples. With the nonradioactive test we determined values of Km and Vmax of both 4-nitro-S-benzyl-L-cysteine and acetyl-CoA. In summary, this new nonradioactive assay is sensitive, less costly, safer, less time-consuming, and less laborious than radioactive assays for cysteine-S-conjugate N-acetyltransferase.

Acetyl Coenzyme A↗
PubMedDate not supplied

Quantitative structure-activity relationship of phenoxy and benzyloxy acid derivatives as antisickling agents.

Quantitative structure activity relationship of Hansch-type has been applied to develop correlation between the calculated physicochemical properties and the in vitro activities of phenoxy and benzyloxyacetic acid derivatives as antisickling agents. The antisickling effect of these compounds was first reported by Abraham et al., and is used as a database of this study. QSAR for these compounds was generated in order to provide more information about the structure requirements for the design of more active antisickling analogs. The solubility ratio A/Ao for 22 phenoxyacetic acids and 15 benzyloxyacetic acids were used to develop equations using hydrophobic (pi), electronic (sigma) and molar refraction (MR) parameters. Equations 1 and 2 with correlation coefficients of 0.872 and 0.894 respectively, were obtained for phenoxy and benzyloxy acetic. Potencies were correlated positively with pi values of ortho, meta and/or para substituents. Positive correlations were also obtained for sigma constants of para and/or meta substituents. Negative correlations, on the other hand, were obtained with the MR values of para substituents in the benzenic ring of the benzyloxy acid series. Using the generated correlation equation 2, three potent antigelling benzyloxyacetic acid derivatives were proposed and reported. These compounds are expected to be very promising antisickling agents having A/A. values of 1.016, 1.124 and 1.138.

Antisickling Agents↗
PubMed2003

Synthesis of benzylamides of dipeptides as potential inhibitors of plasmin.

Four benzylamides of dipeptides with the general formula: X-L-Lys-NH-CH2-C6H5, where X = L-or D-Leu and L-or D-Phe were prepared as potential inhibitors of plasmin. All of them influenced on the fibrynolytic activity of plasmin, but only D-Leu-L-Lys-NH-CH2-C6H5 inhibited the amidolytic activity of this enzyme. None of the tested compounds was an inhibitor of thrombin in an amidolytic test.

Benzyl Compounds↗
PubMed2006

Alkylalanes and methyl furanosides: regioselective O-debenzylation or acetal cleavage.

Perbenzylated methyl pentofuranosides were submitted to the action of three alkylalanes and regioselective debenzylation at O-2 of the four pentoses was observed when choosing the right match between anomeric configuration and aluminium reagent. Diisobutylalane (DIBAL-H) allowed an easy access to reduced open-chain compounds, whereas trimethylalane (TMAL) stereoselectively produced methylated open chain derivatives.

Acetals↗
PubMedDate not supplied

Sedative action of some substituted benzylamides.

Substituted benzylamide derivatives of amino acylamide (compound A,B,C, & D) were found to be less potent local anaesthetics than lignocaine and procaine. However, the four compounds exhibited sedation without ptosis and reduced spontaneous locomotor activity better than methaqualone. Compound A alone antagonised methylamphetamine induced hypermotor activity. The test compounds potentiated hexobarbitone induced hypnosis. Three compounds antagonised calcium induced stoppage of isolated heart of frog. Except compound C all caused a transitory fall of blood pressure in dog which was not blocked either by atropine or propranolol. These compounds showed neuromuscular blockade and possessed slight analgesic activity but were devoid of anticonvulsant and tranquillizing activity. LD 50 values were calculated to be 164.1 +/- 23.0, 229.1 +/- 51.0, 181.6 +/- 28.18 and 416+/-38.2 mg/kg for compounds A,B,C & D respectively.

Amides↗
PubMed1987

Regiospecific oxygenations during ring cleavage of a secondary metabolite, 3,4-dimethoxybenzyl alcohol catalyzed by lignin peroxidase.

Enzymatic oxidation of veratryl alcohol yielded a new ring cleavage product (delta-lactone) in addition to the two known gamma-lactone products. The experiment with 18O-enriched water and dioxygen clearly showed that one oxygen atom each from water and dioxygen is specifically incorporated into the cleavage product at the original C3 or C4 position of 3,4-dimethoxybenzyl alcohol. A new type of reaction mechanism proposed for the ring cleavage of this compound is rationally explained in good accord with the one-electron transfer mechanism.

Benzyl Alcohols↗
PubMed1982

5-benzylacyclouridine and 5-benzyloxybenzylacyclouridine, potent inhibitors of uridine phosphorylase.

Various pyrimidine acyclonucleosides (1-(2'-hydroxyethoxymethyl)uracils) are specific inhibitors of uridine phosphorylase[Niedzwicki et al., Biochem. Pharmac. 30, 2097 (1981) )). 5-Benzyluracils have also been shown to inhibit this enzyme[Baker and Kelley, J. med. Chem. 13, 461 (1970); Woodman et al., Biochem. Pharmac. 29, 1059 (1980) )). We have synthesized the acyclonucleoside analogs of 5-benzyluracil (BU) and 5-benzyloxybenzyluracil (BBU). These compounds, 5-benzyl-1-(2'-hydroxyethoxymethyl)uracil (BAU) and 5-(m-benzyloxybenzyl)-1-(2'-hydroxyethoxymethyl)uracil (BBAU), are potent inhibitors of uridine phosphorylase. K1 values of 98 and 32 nM were estimated for BAU and BBAU respectively. These compounds are better inhibitors of uridine phosphorylase than BU (K1= 1575 nM), BBU (K1=270 nM), and all other compounds previously tested, and they have no effect on thymidine phosphorylase, uridine-cytidine kinase, or thymidine kinase. Potential chemotherapeutic applications of BAU and BBAU are discussed.

Animals↗
PubMed2002

Indazole carboxylic acids in male contraception.

Two new chemical entities, 1-(2,4-dichlorobenzyl)-indazole-3-carbohydrazide and 1-(2,4-dichlorobenzyl)-indazole-3-acrylic acid, were synthesized based on the core structure of lonidamine (1-(2,4-dichlorobenzyl)-indazole-3-carboxylic acid). These compounds apparently exert their effects in the testis by perturbing the Sertoli-germ cell adherens junctions causing germ cell loss from the seminiferous epithelium. Recently completed studies in the rat have demonstrated the efficacy, reversibility, and potential use of these two compounds as oral contraceptives for men. Neither compound affected the hypothalamus-pituitary-testicular axis, and both compounds were neither hepatotoxic nor nephrotoxic. These results suggest that these two compounds are safe for further development.

Animals↗
PubMed1986

Photolabile protecting groups for an acetylcholine receptor ligand. Synthesis and photochemistry of a new class of o-nitrobenzyl derivatives and their effects on receptor function.

Two compounds have been synthesized that feature a photosensitive o-nitrobenzyl moiety attached directly to the carbamate nitrogen of carbamoylcholine. The well-characterized acetylcholine analogue, carbamoylcholine, was released from these derivatives in response to laser light pulses at wavelengths between 300 and 355 nm. Photolysis products were isolated by high-performance liquid chromatography and identified by chemical and spectroscopic analysis. The yield of carbamoylcholine molecules per photon absorbed was 0.25. A short-lived photochromic intermediate in the photolysis reaction was detected by laser flash photolysis. A single laser flash induced an instantaneous increase in absorbance at 406 nm, followed by a first-order decay to products, with a half-time of 0.07 ms for one of the compounds [N-[1-(2-nitrophenyl)ethyl]carbamoylcholine iodide] in aqueous buffers at pH 7 and 23 degrees C. Decay rates and quantum yields depended on the nature of the substituent on the protecting group. Evidence is presented in support of the conclusion that the transient species is an aci-nitro intermediate that decays directly to carbamoylcholine and therefore determines its rate of release. The photosensitive carbamoylcholine derivatives activated the nicotinic acetylcholine receptor only after photolysis, as determined by 86Rb+ flux measurements with membrane vesicles prepared from Torpedo californica and Electrophorus electricus. Before photolysis, the compounds interacted weakly with the acetylcholine-binding sites as shown by competitive inhibition of acetylcholine-stimulated flux at high concentrations. The compounds did not induce receptor desensitization at a significant rate. The new compounds afford several major advantages over other photoactivatable acetylcholine analogues.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2006

Synthesis and evaluation as NOP ligands of some spiro[piperidine-4,2'(1'H)-quinazolin]-4'(3'H)-ones and spiro[piperidine-4,5'(6'H)-[1,2,4]triazolo[1,5-c]quinazolines].

Some spiro[piperidine-4,2'(1'H)-quinazolin]-4'(3'H)-ones 3 and spiro[piperidine-4,5'(6'H)-[1,2,4]triazolo[1,5-c]quinazolines] 4 were synthesized and evaluated as ligands of the nociceptin receptor. The examined compounds showed partial agonistic activity, except compounds 3, 4n that proved to be pure antagonists.

Benzyl Compounds↗
PubMed1975

The chemistry of local anaesthetic agents: classification of blocking agents.

Compounds with local anaesthetic properties may be classified according to their action upon the nerve membrane. Four classes of agent are recognized: A. Compounds acting at the exterior of the sodium channels; B. Compounds acting at the axoplasmic part of the sodium channels; C. Compounds acting through a physicochemical mechanism; BC. Compounds acting by a combination of B and C mechanisms. The chemical basis for these different mechanisms is discussed.

Anesthetics, Local↗
PubMed2004

In vitro anti-proliferation/cytotoxic activity of sixty natural products on the human SH-SY5Y neuroblastoma cells with specific reference to dibenzyl trisulphide.

Sixty natural products belonging to the following structural classes: artemisinins, coumarins, flavonoids, tannins, tetrahydroberberine alkaloids, tetracyclic triterpenes, tetranortriterpenoids and polysulphides were screened against the human SH-SY5Y neuroblastoma cell line revealing differences in their effects on cell morphology and in anti-proliferation/cytotoxic activity. Based on the data obtained, dibenzyl trisulphide is the most effective anti-proliferative/cytotoxic compound. In addition, we hereby propose the human SH-SY5Y cell line as a sensitive and uncomplicated in vitro test system for detecting compounds with potential anti-proliferation/cytotoxic activity.

Antineoplastic Agents↗
PubMed1990

[Effects of processing methods on the amounts of volatile oil of nutmeg and on isolation and characterization of the volatile oil constituents].

In this paper, the authors investigated the effects of various processing methods, i.e., scalding in hot purified talc, simmering wrapped in flour in hot purified talc and stir-frying in smoking wheat bran, on nutmeg (Semen Myristicae) in terms of the quantities of the volatile oil. The experimental results revealed that the amounts of volatile oil contained in nutmeg vary remarkably with the lengths of cooking time and the fluctuation of temperature. Detected by GC-MS-computer, 32 compounds of nutmeg were characterized, and their contents were determined by GC respectively.

Allylbenzene Derivatives↗