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At least 199 records · Page 11Linked to original sources
PubMed1991

Formation of an antibacterial metabolite from a new macrolide compound 23-O-benzyl-5-mycaminosyl-tylonolide (TMC-101), by a hepatic microsomal drug-metabolizing enzyme system.

Upon incubation of 23-O-benzyl-5-mycaminosyl-tylonolide (TMC-101) with liver microsomes in the presence of an nicotinamide adenine dinucleotide phosphate-generating system, at least four metabolites were formed: two of them were also formed by an enzyme(s) in rat serum. One of the metabolites formed by liver microsomes possessed antibacterial activity comparable to TMC-101 as examined by bioautography using Micrococcus luteus ATCC 9341 as a tester strain. Incubation of TMC-101 with rat serum degraded most of the parent compound and did not form the active metabolite. The capacity of liver microsomes to produce the active metabolite was increased by pretreatment of rats with 3-methylcholanthrene, phenobarbital and polychlorinated biphenyl. The metabolite with the antibacterial activity was estimated not to be formed by the N-demethylation of TMC-101, and was chemically unstable.

Animals↗
PubMed2005

Computational study of a chiral supramolecular arrangement of organic structure directing molecules for the AFI structure.

Molecular mechanics computational methods have been employed to study the structure directing effect of S-(-)-1-benzyl-2-pyrrolidiniummethanol molecules towards microporous aluminophosphate materials with the AFI structure. These chiral molecules form dimers inside the one-dimensional AFI channel, which are the active structure-directing agents in the synthesis. Four different conformers of the S-(-)-1-benzyl-2-pyrrolidiniummethanol molecule are in principle available; of these, the S,S-trans shows a marked stability in dimeric form. Self-assembly between adjacent dimers generates a helicoidal, and hence chiral arrangement of the organic molecules, which extends with the same direction of rotation through the whole solid, and may thus be employed to introduce chirality in the microporous material.

Aluminum Compounds↗
PubMed2002

Synthesis of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene: a caveat.

During the preparation of 3-C-(6-O-acetyl-2,3,4-tri-O-benzyl-alpha-D-mannopyranosyl)-1-propene, using a published Sakurai-type reaction on the parent methyl glycoside, some observations were made on the sensitivity to reaction conditions that were not previously reported. This Note presents the study of this allylation reaction followed by acetolysis, which ultimately led to the best conditions to obtain the C-glycoside, and on further transformations to yield the corresponding aldehydic and acidic derivatives.

Acetylation↗
PubMed2002

Controlled photochemical release of nitric oxide from O2-benzyl-substituted diazeniumdiolates.

An investigation of potential photosensitive protecting groups for diazeniumdiolates (R2N-N(O)=NO-) has been initiated, and here the effect of meta electron-donating groups on the photochemistry of O2-benzyl-substituted diazeniumdiolates (R2N-N(O)=NOCH2Ar) is reported. Photolysis of the parent benzyl derivative (Ar = Ph) results almost exclusively in undesired photochemistry-the formation of nitrosamine and an oxynitrene intermediate with very little, if any, photorelease of the diazeniumdiolate. We have been able to use meta substitution to tune the photochemistry of these benzylic systems. The desired diazeniumdiolate photorelease has been shown to become more substantial with stronger pi-donating meta substituents. This effect has been verified by direct observation of the photoreleased diazeniumdiolate with 1H NMR spectroscopy and by NO quantification measurements conducted in high- and low-pH solutions. In addition, the observed rates of NO release are consistent with that expected for normal thermal decomposition of the diazeniumdiolate in aqueous solutions and also show the same pH dependence.

Azo Compounds↗
PubMed1995

Synthesis and antiviral activity of 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents.

Several 6-benzyl analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (1; HEPT) were synthesized and evaluated for their anti-HIV-1 activity. LDA (lithium diisopropylamide) lithiation of 5-ethyluracil derivatives 7 and 8 and subsequent reaction with an aryl aldehyde gave 6-(arylhydroxymethyl)-5-ethyluracil derivatives 9-12. 6-(Arylhydroxymethyl)-5-isopropyluracil derivatives 15-18 were prepared from the 5-isopropyl-2-thiouracil derivatives 13 and 14 by the above procedure following oxidative hydrolysis of the thione. Preparation of the target 5-alkyl-1-(alkoxymethyl)-6-benzyluracil derivatives 27-34 was carried out by acetylation of 9-14 followed by Pd-catalyzed hydrogenolysis. The 1-butyl- (37 and 39) and 1-(2-methoxyl)- (38 and 40) 5-alkyl-6-benzyluracils were synthesized by 1-alkylation of the 3-phenacyl derivatives 35 and 36 with alkyl halides followed by deprotection of the 3-phenacyl group. Compounds synthesized in this study inhibited HIV-1 replication in MT-4 cells in the submicromolar to namomolar concentration range. From this series of compounds, 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (33) was selected for clinical evaluation.

Animals↗
PubMed1981

4-Chloromethylbiphenyl (4CMB): a novel mutagen and potential carcinogen.

The bacterial mutagenicity and cell transforming properties of the monocyclic alkylating agent benzyl chloride have been compared with those of its biphenyl analogue, 4-chloromethylbiphenyl (4CMB), and it is apparent that the addition of the second benzene ring greatly enhances biological activity. The possible reasons for this enhancement are discussed in relation to similar effects observed when comparing the activities of aniline with its biphenyl analogue, 4-aminobiphenyl (4AB). The marked activity observed for 4CMB, a stable and crystalline solid, suggests that it could prove useful as a direct-acting positive control test chemical for use in short-term mutagenicity tests.

Aminobiphenyl Compounds↗
PubMed2005

Targeting of mannosylated liposome incorporated benzyl derivative of Penicillium nigricans derived compound MT81 to reticuloendothelial systems for the treatment of visceral leishmaniasis.

The antileishmanial property of a Benzyl derivative of a new antibiotic MT81 (Bz2MT81), isolated and purified from a fungal strain of Penicillium nigricans NRRL 917 was tested in free, liposome intercalated and mannose coated liposome intercalated forms in vivo against visceral leishmaniasis in hamsters. Mannose grafted liposome intercalated Bz2MT81 eliminated intracellular amastigotes of Leishmania donovani within splenic macrophages more efficiently than the liposome intercalated Bz2MT81 or free Bz2MT81. At a dose equivalent to 7.5 microg/Kg body weight when injected subcutaneously (s.c) in mannose grafted liposome intercalated form for 15 days in an interval of three days, the splenic parasitic load decreased to the extent of 79.1% of the total parasite present in infected control animals. Whereas, an identical amount (7.5 mug/Kg body weight) of Bz2MT81 in free or liposome intercalated form was found less effective in controlling the parasite in spleen (in free Bz2MT81 form, suppression of parasitic load is 49.8% and in liposome intercalated form, it is 55.1%). Both mannosylated liposomes and Bz2MT81 were noted non-toxic to the host peritoneal macrophages. Histological examinations of spleen and liver, kidney function tests (SGPT, alkaline phosphatase, creatinine and urea in blood plasma) showed that the toxicity of Bz2MT81 was reduced up to normal level when mannose grafted liposomal Bz2MT81 were administered.

Animals↗
PubMed1983

Bile acids. LXVIII. Allylic and benzylic photo-chemical oxidation of steroids.

To provide 7-oxocholesterol derivatives in yields superior to those obtained by chemical oxidation, the preparation of steroidal allylic or benzylic ketones was studied. Air-induced oxidation was investigated with a highly selective low energy UV lamp in the presence of mercuric bromide. With this procedure cholesterol acetate, 5-cholestene-3 beta, 27-diol diacetate, 24(R)-24-methyl-5-cholesten-2 beta-yl acetate, 24(R)-24-ethyl-5-cholesten-28-yl acetate and 24(R)-24-ethyl-(22E)-cholesta-5,22-dien-3 beta-yl acetate were oxidized to the allylic keto-derivative in good yields; estradiol-17 beta diacetate was similarly converted to the 6-oxo-product in improved yield. This method can be very useful in the synthesis of 7-oxocholesteryl acetate and its analogs and 6-oxo-estratrienes.

Allyl Compounds↗
PubMed1984

[4-[Benzyl-(2-dimethylaminoethyl)amino]pyrimidine compounds with selective antagonistic activity against H1-histamine receptors].

This paper describes the synthesis of 2- and 4-[benzyl-(2-dimethylaminoethyl)amino]pyrimidine compounds and their antihistaminic properties studied on isolated guinea-pig ileum. Calculated pA2 values show that the antihistaminic activity of 4-[p.methoxybenzyl-(2-dimethylaminoethyl)amino]pyrimidine is specific and potent (8-10 times higher than that of thonzylamine).

Acetylcholine↗
PubMedDate not supplied

A century of DDT.

Explore the source record for details and available documents.

Aniline Compounds↗
PubMed1990

Nonpeptide angiotensin II receptor antagonists: N-[(benzyloxy)benzyl]imidazoles and related compounds as potent antihypertensives.

A series of compounds has been synthesized and demonstrated to be antagonists of the angiotensin II (AII) receptor. These compounds are structurally related to the N-(benzamidobenzyl)imidazoles and extend the scope of this new class of nonpeptide AII antagonists. It has been found that the amide linkage (X = NHCO) in the N-(benzamidobenzyl)imidazoles can be replaced successfully by a variety of groups (X = single bond, O, S, CO, OCH2, CH = CH, NHCONH); linkers of 0-1 atoms in length are most effective. When administered intravenously to awake renal hypertensive rats, these compounds are potent antihypertensives.

Adrenal Cortex↗
PubMed1977

Microbial transformation of 8-chloro-10,11-dihydrodibenz(b,f)(1,4)oxazepine by fungi.

The microbial transformation of 8-chloro-10,11-dihydrodibenz(b,f)(1,4)oxazepine (compound I) was undertaken to obtain new derivatives. Compound I was transformed by Hormodendrum sp. (NRRL 8133) to 8-chloro-10,11-dihydrodibenz(b,f)(1,4)oxazepine-11-one (compound II) and 2-(2-amino-4-chlorophenoxy)benzyl alcohol (compound IV). Microbial cleavage of the nonaromatic ring to form compound IV was accomplished by several other fungi. Compound I was transformed to 8-chlorodibenz(b,f)(1,4)oxazepine (compound III) by Hormodendrum cladosporioides (NRRL 8132).

Azepines↗
PubMed1985

Structure-function studies with derivatives of 6-benzyl-1,3-benzodioxole, a new class of synthetic compounds which inhibit tubulin polymerization and mitosis.

A new class of synthetic antineoplastic compounds, derivatives of 6-benzyl-1,3-benzodioxole, has significant antimitotic activity. These compounds inhibit microtubule assembly and are competitive inhibitors of the binding of colchicine to tubulin. Both their structure and their partial inhibition of tubulin-dependent GTP hydrolysis indicate that they are most comparable to podophyllotoxin of all known antimitotic drugs. Maximum activity required an intact dioxole ring, a methoxy or ethoxy substituent at position 5, and, on the benzyl moiety at position 6, a para-methoxy group. Additional methoxy groups on the benzyl substituent, to increase the apparent structural similarity to podophyllotoxin, resulted in major reduction of the antitubulin activity of these drugs.

Animals↗
PubMed1991

Comparison of known and suspected pheromonal constituents in males of African ticks, Amblyomma hebraeum Koch and Amblyomma variegatum (Fabricius).

Three low molecular weight compounds were found in hexane:diethyl ether extracts of fed males of the African ticks, Amblyomma variegatum (tropical bont tick) and A. hebraeum (bont tick), namely, o-nitrophenol, methyl salicylate and 2,6-dichlorophenol. These same compounds were also fond in a rinse of fed A. variegatum males, but were absent or present in only trace amounts in a rinse of fed A. hebraeum males, o-Nitrophenol and methyl salicylate were present in much higher concentrations (i.e., amounts/tick) in A. variegatum than in A. hebraeum. 2,6-Dichlorophenol was also more abundant in A. variegatum than in A. hebraeum, but the differences were not as great as with the former two compounds. Extraction in hexane over a 3-week period revealed four additional compounds, benzaldehyde, benzyl alcohol, benzothiazole and nonanoic acid. The first three compounds were found in males of both species; nonanoic acid was found only in A. hebraeum males. Published reports consistently show strong attraction by o-nitrophenol and methyl salicylate for both sexes of the two bont tick species; 2,6-dichlorophenol and benzaldehyde have been reported to be attractive to both sexes of A. hebraeum. The possible roles of these compounds, as well as others occasionally reported from A. hebraeum and A. variegatum, as components of the aggregation/attachment pheromone or other pheromones is discussed.

Animals↗