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1.
Horm Mol Biol Clin Investig ; 10(3): 293-9, 2012 Jun.
Article in English | MEDLINE | ID: mdl-25436687

ABSTRACT

Abstract Interest has developed into 7-hydroxylated derivatives of 3ß-hydroxylated C19-steroids, such as dehydroepiandrosterone (DHEA) and epiandrosterone because of their effects on inflammation, immune response, and cell repair. These steroids are not currently available from commercial sources, and it is necessary to produce them for relevant studies. We report here the chemical and biochemical approaches that were used for their production. Simplified chemical approaches lead to the production of 7α-/7ß-hydroxy-DHEA and 7ß-hydroxy-epiandrosterone in gram quantities, which are made available to researchers. Biochemical approaches were used to produce isotope-labeled compounds. Thus, 2H-, 3H-, and 14C-labeled 7α-/7ß-hydroxy-DHEA and 7ß-hydroxy-epiandrosterone could be produced in quantities sufficient for use in investigations into their mode of action.

2.
Horm Mol Biol Clin Investig ; 7(1): 295-301, 2011 Oct 01.
Article in English | MEDLINE | ID: mdl-25961267

ABSTRACT

In order to develop an immunoassay of 7ß-hydroxy-epiandrosterone, a stereoselective synthesis of a specific hapten, 7ß-hydroxy-19-oxo-androstan 19-(O-carboxymethyl)oxime (17), was performed. This synthesis was achieved in 16% overall yield starting from the well-known 3ß-acetoxy-19-hydroxy-5-androsten-17-one (1). After coupling of the alkyl oxime moiety, an allylic oxidation of the C-7 carbon under mild conditions followed by two selective reductions established all the functionalities of the final compound 17.

3.
Steroids ; 76(1-2): 28-30, 2011 Jan.
Article in English | MEDLINE | ID: mdl-20727907

ABSTRACT

The synthesis of 7ß-hydroxy-epiandrosterone (6) possessing strong anti-inflammatory properties was achieved starting from 3ß-acetoxy-17,17-(ethylenedioxy)-5-androsten (1). This approach involved as a main step an allylic oxidation of the C-7 followed by two reduction reactions of the double bond and of the carbonyl group. This stereoselective synthesis in 5 steps gave 7ß-hydroxy-epiandrosterone in 63% overall yield.


Subject(s)
Androsterone/analogs & derivatives , Androsterone/chemical synthesis , Androsterone/chemistry , Molecular Conformation , Stereoisomerism
4.
J Enzyme Inhib Med Chem ; 25(4): 565-71, 2010 Aug.
Article in English | MEDLINE | ID: mdl-20205628

ABSTRACT

The synthesis of a new series of 1-[(benzazole-2-yl)thioacetyl]-3,5-diaryl-2-pyrazoline derivatives was obtained by reacting 1-(chloroacetyl)-3,5-diaryl-pyrazolines with 2-mercaptobenzimidazole/benzoxazole/benzothiazole. The chemical structures of the compounds were elucidated by (1)H-NMR, (13)C-NMR, and FAB(+)-MS spectral data. Their antifungal activities against Candida albicans, Candida glabrata, Candida utilis, Candida tropicalis, Candida krusei, and Candida parapsilosis were investigated. A significant level of activity was observed.


Subject(s)
Antifungal Agents/chemical synthesis , Pyrazoles/chemical synthesis , Antifungal Agents/pharmacology , Fungi/drug effects , Magnetic Resonance Spectroscopy , Mass Spectrometry , Microbial Sensitivity Tests , Molecular Structure , Pyrazoles/pharmacology , Structure-Activity Relationship
5.
J Enzyme Inhib Med Chem ; 23(6): 866-70, 2008 Dec.
Article in English | MEDLINE | ID: mdl-18608774

ABSTRACT

New hydrazide derivatives of imidazo[1,2-a]pyridine have been synthesized and evaluated for anticandidal activity. The reaction of imidazo[1,2-a]pyridine-2-carboxylic acid hydrazides with various benzaldehydes gave N-(benzylidene)imidazo[ 1,2-a]pyridine-2-carboxylic acid hydrazide derivatives. Their anticandidal activities against Candida albicans and Candida glabrata (isolates obtained from Osmangazi University, Faculty of Medicine, Eskisehir, Turkey), Candida albicans (ATCC 90028), Candida utilis (NRLL Y-900), Candida tropicalis (NRLL Y-12968), Candida krusei (NRLL Y-7179), Candida zeylanoides (NRLL Y-1774), and Candida parapsilosis (NRLL Y-12696) were investigated.


Subject(s)
Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Imidazoles/chemistry , Pyridines/chemical synthesis , Pyridines/pharmacology , Antifungal Agents/chemistry , Candida/drug effects , Molecular Structure , Pyridines/chemistry , Structure-Activity Relationship
6.
Eur J Med Chem ; 43(1): 155-9, 2008 Jan.
Article in English | MEDLINE | ID: mdl-17499887

ABSTRACT

Triazole and triazoles fused with six-membered ring systems are found to possess diverse applications in the fields of medicine, agriculture and industry. The new 1,2,4-triazole and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine derivatives were synthesized as novel antimicrobial agents. The reaction of 1H-indol-3-acetic acid with thiocarbohydrazide gave the 4-amino-3-mercapto-5-[(1H-indol-3-yl)methyl]-4H-1,2,4-triazole. The reaction of triazole with arylaldehydes in ethanol gave the 4-arylideneamino-3-mercapto-5-[(1H-indol-3-yl)methyl]-4H-1,2,4-triazoles (I). The 3-[(1H-indol-3-yl)methyl]-6-aryl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines (II) were obtained by condensing triazole with phenacyl bromides in absolute ethanol . The chemical structures of the compounds were elucidated by IR, (1)H NMR and FAB(+)-MS spectral data. Their antimicrobial activities against Micrococcus luteus (NRLL B-4375), Bacillus cereus (NRRL B-3711), Proteus vulgaris (NRRL B-123), Salmonella typhimurium (NRRL B-4420), Staphylococcus aureus (NRRL B-767), Escherichia coli (NRRL B-3704), Candida albicans and Candida glabrata (isolates obtained from Osmangazi University, Faculty of Medicine) were investigated and significant activity was obtained.


Subject(s)
Anti-Infective Agents/chemical synthesis , Anti-Infective Agents/pharmacology , Thiadiazines/chemical synthesis , Thiadiazines/pharmacology , Triazoles/chemical synthesis , Triazoles/pharmacology , Anti-Infective Agents/chemistry , Bacteria/drug effects , Drug Design , Fungi/drug effects , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Thiadiazines/chemistry , Triazoles/chemistry
7.
Eur J Med Chem ; 42(3): 403-9, 2007 Mar.
Article in English | MEDLINE | ID: mdl-17125888

ABSTRACT

Several 1-(4-aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives were synthesized by reacting substituted 3-(2-thienyl)-5-aryl-1-thiocarbamoyl-2-pyrazolines with phenacyl bromides in ethanol. The structures of the synthesized compounds were confirmed by (1)H NMR, (13)C NMR, and EIMS spectral data. Their antimicrobial activities against Escherichia coli (NRRL B-3704), Staphylococcus aureus (NRLL B-767), Salmonella typhimurium (NRRL B-4420), Bacillus cereus (NRRL B-3711), Streptococcus faecalis (NRRL B-14617), Aeromonas hydrophila (Ankara Uni. Fac. of Veterinary), Candida albicans and Candida glabrata (isolates obtained from Osmangazi Uni. Fac. of Medicine) were investigated. A significant level of activity was observed.


Subject(s)
Anti-Bacterial Agents/chemical synthesis , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemical synthesis , Antifungal Agents/pharmacology , Pyrazoles/chemical synthesis , Pyrazoles/pharmacology , Thiazoles/chemical synthesis , Thiazoles/pharmacology , Bacteria/drug effects , Fungi/drug effects , Indicators and Reagents , Magnetic Resonance Spectroscopy , Microbial Sensitivity Tests , Molecular Conformation , Spectrometry, Mass, Electrospray Ionization
8.
Arch Pharm Res ; 27(11): 1081-5, 2004 Nov.
Article in English | MEDLINE | ID: mdl-15595406

ABSTRACT

Several 2-[[(benzoxazole/benzimidazole-2-yl)sulfanyl]acetylamino]thiazoles derivatives were synthesized by reacting 4-substituted-2-(chloroacetylamino)thiazoles with benzoxazole/benzimidazole-2-thioles in acetone and in the presence of K2CO3. The chemical structures of the compounds were elucidated by IR, 1H-NMR, and FAB(+)-MS spectral data. Their antimicrobial activities against Micrococcus luteus (NRLL B-4375), Bacillus cereus (NRRL B-3711), Proteus vulgaris (NRRL B-123), Salmonella typhimurium (NRRL B-4420), Staphylococcus aureus (NRRL B-767), Escherichia coli (NRRL B-3704), Candida albicans and Candida globrata (isolates obtained from Osmangazi Uni. Fac.of Medicine) were investigated and in this investigation, a significant level of activity was illustrated.


Subject(s)
Anti-Bacterial Agents/chemical synthesis , Antifungal Agents/chemical synthesis , Benzimidazoles/pharmacology , Thiazoles/pharmacology , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Antifungal Agents/chemistry , Antifungal Agents/pharmacology , Bacillus cereus/drug effects , Bacillus cereus/growth & development , Benzimidazoles/chemical synthesis , Benzimidazoles/chemistry , Candida albicans/drug effects , Candida albicans/growth & development , Escherichia coli/drug effects , Escherichia coli/growth & development , Microbial Sensitivity Tests , Micrococcus/drug effects , Micrococcus/growth & development , Salmonella typhimurium/drug effects , Salmonella typhimurium/growth & development , Staphylococcus aureus/drug effects , Staphylococcus aureus/growth & development , Structure-Activity Relationship , Thiazoles/chemical synthesis , Thiazoles/chemistry
9.
Arch Biochem Biophys ; 432(2): 167-77, 2004 Dec 15.
Article in English | MEDLINE | ID: mdl-15542055

ABSTRACT

Cultures of hepatocytes and HepG2 cells provide useful in vitro models of liver specific function. In this study, we investigated metabolic and biosynthetic function in 3-D HepG2 spheroid cultures, in particular to characterise changes on prolonged culture. We show that HepG2 cells cultured in spheroids demonstrate a reduction in mitochondrial membrane potential and respiration following 10 days of culture. This coincides with a modest reduction in glycolysis but an increase in glucose uptake where increased glycogen synthesis occurs at the expense of the intracellular ATP pool. Lowered biosynthesis coincides with and is linked to mitochondrial functional decline since low glucose-adapted spheroids, which exhibit extended mitochondrial function, have stable biosynthetic activity during extended culture although biosynthetic function is lower. This indicates that glucose is required for biosynthetic output but sustained mitochondrial function is required for the maintenance of biosynthetic function. Furthermore, we show that cholesterol synthesis is markedly increased in spheroids cf. monolayer culture and that inhibition of cholesterol synthesis by lovastatin extends mitochondrial and biosynthetic function. Therefore, increased cholesterol synthesis and/or its derivatives contributes to mitochondrial functional decline in extended HepG2 spheroid cultures.


Subject(s)
Cell Culture Techniques/methods , Cholesterol/biosynthesis , Hepatocytes/physiology , Mitochondria, Liver/physiology , Mitochondrial Proteins/metabolism , Signal Transduction/physiology , Tissue Engineering/methods , Albumins/metabolism , Cell Respiration/drug effects , Cell Respiration/physiology , Cells, Cultured , Environment , Glucose/metabolism , Hepatocytes/drug effects , Lovastatin/pharmacology , Membrane Potentials/drug effects , Membrane Potentials/physiology , Microspheres , Mitochondria, Liver/drug effects , Oxygen/metabolism
10.
J Org Chem ; 67(7): 2252-6, 2002 Apr 05.
Article in English | MEDLINE | ID: mdl-11925236

ABSTRACT

Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl(3), leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.


Subject(s)
Bufotenin/chemical synthesis , Indoleacetic Acids/chemical synthesis , Indoles/chemical synthesis , Melatonin/chemical synthesis , Serotonin/chemical synthesis , Catalysis , Chemistry, Organic/methods , Chromatography, Thin Layer , Cyclization , Imines/chemistry , Indoleacetic Acids/chemistry , Indoles/chemistry , Molecular Structure , Picrates/chemistry
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