P-methoxyphenyl Derivative Research Articles

Heteronuclear gold(I)–silver(I) sulfanylcarboxylates: Synthesis, structure and cytotoxic activity against cancer cell lines

Heteronuclear complexes of the type [AgAu(PPh3)2(xspa)] [H2xspa=3-(aryl)-2-sulfanylpropenoic acids; (x=3-phenyl-; 3-(2-chlorophenyl)-; 3-(o-methoxyphenyl)-; 3-(p-methoxyphenyl)-; 3-(p-hydroxyphenyl)-; 3-(2-furyl)-; 3-(2-thienyl)-; spa=2-sulfanylpropenoate)] were prepared by reacting the appropriate [Au(PPh3)(Hxspa)] precursor with Ag(PPh3)NO3. The compounds were characterized by spectroscopic methods, (IR; 1H, 13C and 31P NMR) and mass spectrometry and the structures of the phenyl and p-methoxyphenyl derivatives were determined by X-ray diffraction. The in vitro antitumor activity against the HeLa-229, A2780 and A2780cis cell lines was determined and compared with that of cisplatin and the equivalent homonuclear gold(I) complexes.

Studies on Lanthanum Complexes of 1-Aryl-2,5-Dithiohydrazodicarbonamides in Paraffin Oil as Extreme Pressure Lubrication Additives

Testing of lanthanum complexes of 1-aryl-2,5-dithiohydrazodicarbonamides of the formula LaL3 [LH=1-phenyl-2,5-dithiohydrazodicarbonamide(PhTHC), 1-methylphenyl-2,5-dithiohydrazodicarbon-amide(p-MePhTHC), 1-methoxyphenyl-2,5-dithiohydrazodicarbonamide(p-MeOPhTHC), 1-phenyl-2,5-dithiohydrazodicarbonamide(p-ClPhTHC)] for their application as extreme pressure lubrication (EPL) additives was performed on four ball tester using steel balls of 12.7 mm diameter and MoS2 as reference additive. The efficiency of the complexes has been evaluated using the tribological parameters, wear scar diameter, friction coefficient, initial seizure load, 2.5 s seizure delay load, weld load, mean Hertz load, flash temperature parameter and pressure wear index. The tested complexes behave as good extreme pressure additives; however, the best performance is shown by the p-methoxyphenyl derivative. The surface morphology of the wear scar on steel ball has been studied by atomic force microscopy and scanning electron microscopy. In presence of this complex, roughness of the worn surface is significantly reduced. The composition of wear scar has been analyzed by energy dispersive X-ray spectroscopy. The presence of lanthanum and sulfur in energy dispersive X-ray spectrum emphasizes role of additive in the tribofilm formed on the surface.

Suspension of molybdenum–sulphur complexes in paraffin oil as extreme pressure lubricants

Molybdenyl aryl thiobiurets were evaluated as extreme pressure lubrication additives in a four ball test using steel balls of 12.7 mm diameter. A comparative account of performance of the tested compounds is presented on the basis of various tribological parameters such as initial seizure load, 2.5 s seizure delay load, weld load, mean Hertz load, flash temperature parameter, pressure wear index, friction coefficient ( μ) and wear scar diameter ( d), etc. All the tested complexes have been found to possess significant Extreme Pressure (EP) efficiency under the experimental conditions of four ball test. The best performance was shown by p-methoxyphenyl and p-chlorophenyl thiobiurets. The surface topography and tribochemistry of wear scar surface of balls in the presence of p-methoxyphenyl derivative at different loads have been studied by scanning electron microscopy and Auger Electron Spectroscopy (AES). The presence of molybdenum, sulphur, oxygen, nitrogen, etc. on the ball surface, detected by AES, suggests that these compounds act as precursors of tribologically active chemical layers formed under extreme pressure conditions.

Application of molybdenum complexes of 1-aryl-2,5-dithiohydrazodicarbonamides as extreme pressure lubricant additives

Some molybdenum complexes of 1-aryl-2,5-dithiohydrazodicarbonamides have been synthesized and evaluated for their extreme pressure (EP) additive properties using a four-ball machine. The test specimens used were steel balls of 12.7 mm diameter. Compatibility of the synthesized additives has been discussed on the basis of various parameters like wear scar diameter, friction coefficient, initial seizure load (ISL), 2.5 s seizure delay load (SDL), weld load (WL), mean specific pressure at contact points, mean Hertz load (MHL), pressure wear index (PWI) and flash temperature parameter (FTP). All the tested molybdenum complexes have been found to show significant E.P. efficiency under the experimental conditions of four ball test, however, the best performance was exhibited by p-methoxyphenyl and p-chlorophenyl derivatives. The topography of wear scar surface of ball at different loads and tribochemistry at just before WL in presence of p-methoxyphenyl derivative has been studied by scanning electron microscopy (SEM) and Auger electron spectroscopy (AES) respectively. Presence of molybdenum, sulfur, nitrogen and oxygen on the ball surface detected by AES provides an evidence in favor of decomposition of the additive leading to formation of tribologically active substances which bear the load up to WL.

Studies on the scope and applications of the catalysed asymmetric addition of organolithium reagents to imines

The sparteine induced asymmetric addition of organolithium reagents to α,β-unsaturated imines has been used to prepare non-racemic α-amino acids and their derivatives. The effect of various protecting groups for the nitrogen atom was investigated and p-methoxyphenyl derivatives were found to give the best enantiomeric excesses whilst trimethylsilyl protected imines were the most versatile for subsequent manipulation.

Detection of new neutral radicals: 2-phenyl- and 2- p-methoxyphenyl-3-oxophenalenoxyl radicals

New neutral radicals, 2-phenyl and 2- p-methoxyphenyl derivatives of 3-oxophenalenoxyl radical, were detected by ESR measurement. The radicals were generated by thermal decomposition of the dimers of the corresponding radicals and by oxidation of 2-phenyl-3-hydroxyphenalenone.

Asymmetric Deprotonation by BuLi/(−)-Sparteine: Convenient and Highly Enantioselective Syntheses of (S)-2-Aryl-Boc-Pyrrolidines

Highly enantioselective syntheses of (S)-2-aryl-Boc-pyrrolidines (Boc = tert-butoxycarbonyl) can be achieved by treatment of the corresponding (arylmethyl)(3-chloropropyl)-Boc-amines with s-BuLi/(−)-sparteine. The reactions are solvent dependent with the phenyl, p-chlorophenyl, p-fluorophenyl, p-methylphenyl, m-methoxyphenyl, 1-naphthyl, and 2-naphthyl derivatives 1−7 providing 11−17 in yields of 46−75% with enantiomeric excesses of 84−96% in toluene. The 2-thienyl and 3-furyl analogs 8 and 9 afford the (S)-2-heteroaryl-Boc-pyrrolidines 18 and 19 in 51 and 21% yields with 93−96% enantiomeric excesses. The p-methoxyphenyl derivative 10 gives 20 as a racemic product in 42% yield under the same conditions. Reactions of n-BuLi/(−)-sparteine with 1 and 8 give results comparable to those with s-BuLi/(−)-sparteine. Illustrative syntheses of (S)-2-phenyl-(S)-5-methyl-Boc-pyrrolidine (22) and 1,2-(bis-(S)-2-phenylpyrrolindyl)ethane (23) are reported. The mechanism of the reaction is shown to be an asymmetric depro...

Comparison of α-chlorohydrin and two aromatic ketal analogues as antifertility agents in male rats

The antifertility activity and toxicity of α-chlorohydrin was compared with that of two ketal analogues (compound 1, a phenyl and compound 2, a p-methoxyphenyl derivative). Each substance was injected subcutaneously into male rats daily for 15 days at a dose equivalent to 5, 2.5 and 1.25 mg α-chlorohydrin per kilogram of body weight. Fertility trials showed that only the highest dose of α-chlorohydrin and analogues abolished fertility in all males. The parent compound was the most effective antifertility agent since at the 2.5 mg/kg dose, the percentage of pregnant rats per rats mated was at least 50% less for α-chlorohydrin than for the analogues. Furthermore, if the rats became pregnant, α-chlorohydrin reduced the litter size. All doses of α-chlorohydrin, and the highest doses of the analogues reduced the motility of sperm recovered from the cauda epididymis. None of the compounds affected libido. All compounds reduced adrenal weight, but none affected body or testis weight.

Studies on the hydrolysis of 3,1-benzoxazin-4-ones

The hydrolysis of 2-methyl-3,1-benzoxazin-4-one (I) obeys the rate law k=(31·6 ± 0·5)aH++(56·2 ± 0·9)[OH–] in dilute buffers at 25° and 0·1M ionic strength. In deuterium oxide solvent the rate law is k=(31·6 ± 1·5)aD++(10·0 ± 0·05)[OD–]. The basic components of the buffers exerted a catalytic effect and the derived second-order rate constants obeyed a Bronsted relationship with exponent 0·67. The term for imidazole was of the same order of magnitude as that for phosphate, indicating general base catalysis by imidazole; the solvent deuterium isotope effect on the hydroxide ion term indicated general base catalysis. The reaction with azide ion was nucleophilic but did not yield hydrolysis products. Hydrolysis under acidic and basic conditions in oxygen-18 enriched water revealed that attack took place at C-2 and C-4, respectively. Hydrolysis of compound (I) in basic deuterium oxide gave product with no deuterium incorporation in the acetyl group, indicating the absence of an E1cB mechanism. Substituted 2-phenyl-3,1-benzoxazin-4-ones (II) showed Hammett ρ values under acidic and basic conditions of hydrolysis (–0·38 and +0·71) consistent with the foregoing cleavage patterns. Strongly acidic media inhibited hydrolysis of the phenyl and p-methoxyphenyl derivatives in accord with extensive protonation of N-1 and a lowering of the water activity with increase in acidity.

Photodehydrocondensation of anisole homologs. Photosynthesis of synestrol

1. When exposed to ultraviolet radiation in presence of aceton, para anisole homologs undergo dehydrodrocondensation with formation of p-methoxyphenyl derivatives of aliphatic hydrocarbons. In particular, synestrol can be obtained by this method from p-propylanisole. 2. When these reactions are carried out in presence of benzophenone, in addition to dehydrocondensation products it is possible to isolate 2-(p-methoxyphenyl)-1,1-diphenyl-1-alkanols, formed by the condensation of the para anisole homologs with the ketone.