Evaluation of new pregnane derivatives as 5alpha-reductase inhibitor

The objective of this study was to synthesize several new pregnane derivatives and evaluate them as antiandrogens. From the commercially available 16-dehydropregnenolone acetate (7), two new steroidal compounds were synthesized: 17alpha-hydroxy-17beta-methyl-16beta-phenyl-D-homoandrosta-1,4,6-triene-3,20-dione (18) and 17alpha-acetoxy-17beta-methyl-16beta-phenyl-D-homoandrosta-1,4,6-triene-3,20-dione (19). The 5alpha-reductase inhibitory effect of the new compounds 18 and 19 together with the previously synthesized intermediates 7, 8, 13, 16, and 17 was determined in three different models: gonadectomized hamster flank organs diameter size, incorporation of [1,2-(14)C]sodium acetate into lipids in flank organs and conversion of [3H]testosterone (T) to [3H]dihydrotestosterone (DHT) by Penicillium crustosum. The evaluation of these steroids was carried out with three different controls: one group was treated with vehicle, the second with T and the third group with T plus finasteride. The pharmacological results from this work demonstrated that T significantly increases the diameter of the pigmented spot on the flank organs (p<0.05) as well as the incorporation of labeled sodium acetate into lipids in gonadectomized hamster flank organs (from 0.125 to 0.255 nmol per gland). In this study we also observed that broth of Penicillium crustosum converted [3H]T to [3H]DHT in a manner comparable to that of the flank organs. All experiments indicated that finasteride as well as steroids 7, 8, 13, 16-19 reduced significantly the conversion of T to DHT in P. crustosum. These compounds also decrease the size of the pigmented spot in the flank organs as well as reducing the incorporation of radiolabeled sodium acetate into lipids; T and the control sample (treated with vehicle only) were used for comparison. Apparently the presence of the 4,6-diene-3,20-dione moiety and also the C-17 ester group produce a higher inhibitory effect on the parameters used. PPThe data from this study indicated also that the three models used for the pharmacological evaluation exhibited comparable results.     

One-Pot Convenient and High Yielding Synthesis of Dithiocarbamates

Summary. A convenient and high yielding method for the synthesis of diverse dithiocarbamates having various substituents including alkyl, aryl, heteroaryl, and alkylaryl at the thiol chain or at the amine chain or at both thiol and amine chains were developed by the one-pot reaction of mercaptans, amines, and bis(benzotriazolyl)methanethione in presence of amidine base under mild reaction conditions.     

Vibrational study of the metal-adsorbate interaction of phenylacetic acid and alpha-phenylglycine on silver surfaces

Raman and SERS spectra of phenylacetic acid and alpha-phenylglycine on silver sols have been recorded at several concentrations and pH values. The alpha-phenylglycine has been also studied in D(2)O. The respective vibrational assignments have been proposed and the analysis of the SERS spectra has made it possible to conclude that phenylacetic acid links to the metal through its carboxylate group only, while alpha-phenylglycine links also through its amino group. In both cases the aromatic ring seems to be almost perpendicular to the metal surface. On the other hand, the contribution of the charge transfer (CT) mechanism to the enhancement of the SERS spectra has been calculated as well and it is found to be very important in both molecules. The band most enhanced by this mechanism is that of vibration 8a, mainly in alpha-phenylglycine.     

A simple and versatile method for the synthesis of acetals from aldehydes and ketones using bismuth triflate

Acetals are obtained in good yields by treatment of aldehydes and ketones with trialkyl orthoformate and the corresponding alcohol in the presence of 0.1 mol % Bi(OTf)3.4H2O. A simple procedure for the formation of acetals of diaryl ketones has also been developed. The conversion of carbonyl compounds to the corresponding 1,3-dioxolane using ethylene glycol is also catalyzed by Bi(OTf)3.4H2O (1 mol %). Two methods, both of which avoid the use of benzene, have been developed.     

Simple and rapid determination of the drug naproxen in pharmaceutical preparations by heavy atom-induced room temperature phosphorescence

A simple, selective and sensitive heavy atom-induced room temperature phosphorimetric method (HAI-RTP) is described for the determination of naproxen (NAP) in pharmaceutical preparations. The phosphorescence signals are a consequence of intermolecular protection when analytes are, exclusively, in presence of a heavy atom salt and sodium sulfite as an oxygen scavenger to minimize RTP quenching. These variables selection constitute the basis of a HAI-RTP method for the determination of naproxen (detection limit 17.6 ng ml(-1); 1.71% relative standard deviation at 250 ng ml(-1)). The method has been applied satisfactorily to the analysis of pharmaceutical preparations.     

Ligand exchange separation of amines on copper (II) sorbed on zinc silicate

Summary Papers impregnated with Cu(II) sorbed on zinc silicate have been used to study the ligand exchange chromatographic behavior of amines. R_F values of 16 amines have been studied in 6 different systems. On the basis of differences in R_F values various analytically important qualitative separations of amines on impregnated papers and quantitative separations on columns of copper(II) sorbed on zinc silicate have been achieved.     

Effect of cooperativity on the O-H stretching force constant in associated water species

CNDO/force calculations have been employed to calculate the O-H stretching force constants for various structures of associated water species such as water-dimethylether, water-acetonitrile, water-lithium fluoride, linear and cyclic water polymers. The variation in the O-H stretching force constant in A_m… O-H… D_n species where A_m and D_n represent, respectively,m number of electron-acceptor andn number of electron-donor molecules, is explained on the basis of the cooperativity effect. With increasing electron-acceptor power of A and electron-donor power of D, the hydrogen-bonded O-H stretching force constant is significantly reduced. The results obtained in these studies are in general agreement with experimental observations reported earlier.     

Derivative spectrophotometric determination of copper(II) in non-ionic micellar medium

A photometric method for trace analysis of Cu(II) with 1-(2-pyridylazo)-2-naphthol (PAN) in presence of a neutral surfactant, Triton X-100, has been reported in normal and derivative modes. The molar absorption coefficient () and Sandell's sensitivity (S) of PAN-Cu(II) complex at 555 nm is 5.21 x 10(4) l mol(-1) cm(-1) and 1.22 ng cm(-2) respectively. The detection limit of Cu(II) is 4.0 ng ml(-1) and Beer's law is obeyed in the range 0.08-4.00 mug ml(-1) of the analyte. Copper content of a number of commercially available alcoholic beverages, biological and standard alloy samples is reported. The results obtained are in excellent agreement with those obtained using AAS.     

Chemometric analysis of groundwater quality data of alluvial aquifer of Gangetic plain, North India

Water quality data set from the alluvial region in the Gangetic plain in northern India, which is known for high fluoride levels in soil and groundwater, has been analysed by chemometric techniques, such as principal component analysis (PCA), discriminant analysis (DA) and partial least squares (PLS) in order to investigate the compositional differences between surface and groundwater samples, spatial variations in groundwater composition and influence of natural and anthropogenic factors. Trilinear plots of major ions showed that the groundwater in this region is mainly of Na/K-bicarbonate type. PCA performed on complete data matrix yielded six significant PCs explaining 65% of the data variance. Although, PCA rendered considerable data reduction, it could not clearly group and distinguish the sample types (dug well, hand-pump and surface water). However, a visible differentiation between the water samples pertaining to two watersheds (Khar and Loni) was obtained. DA identified six discriminating variables between surface and groundwater and also between different types of samples (dug well, hand pump and surface water). Distinct grouping of the surface and groundwater samples was achieved using the PLS technique. It further showed that the groundwater samples are dominated by variables having origin both in natural and anthropogenic sources in the region, whereas, variables of industrial origin dominate the surface water samples. It also suggested that the groundwater sources are contaminated with various industrial contaminants in the region.     

Conductance studies in amide-water mixtures. II. Sodium salts inN,N-dimethylformamide-water mixtures at 35°C

Conductance data for sodium nitrite, chloride, and acetate in water andN,N-dimethylformamide (DMF)-water mixtures (74.82D42.48) for the concentration range 0.001–0.04N, as well as the densities, viscosities, and dielectric constants of the solvent mixtures at 35°C, are reported. The data have been analyzed by the Fuoss (1975) equation. The existence of a maximum in the viscosity at a 13 mole ratio of DMF and water is indicated. The Walden products for all the three salts pass through a maximum while the equivalent conductances show a minimum with increasing DMF content. The maxima in the Walden product are attributed to the dehydration of ions by the cosolvent (DMF).Part I:Indian J. Chem. 14A, 1015 (1976).Deceased.