31293-75-1Relevant academic research and scientific papers
N-substituted alpha-aminoalkylacrylophenones and some related compounds: a new class of spermicidal agents.
Gupta,Nautiyal,Jhingran,Kamboj,Setty,Anand
, p. 303 - 307 (2007/10/02)
The results of a screening program to test the spermicidal effectiveness of several compounds is presented. The program was initiated after N-substituted 3-aminoacrylophenones were found to have unexpected spermicidal activity. The compounds had been synthesized as possible antiinflammatory agents. This result prompted the synthesis and screening of N-substituted alpha-aminomethylacrylophenones, alpha-(2-aminomethyl)acrylophenones and 3-N-substituted-2-methyleneindan-1-ones. The starting materials, substituted acetophenones, for the synthesis of N-substituted alpha-aminomethylacrylophenones were either commercial products or obtained by standard methods. N-substituted amino-butyrophenone was reacted with paraformaldehyde to yield the alpha-(2 aminoethyl)acrylophenones. A series of reactions was undertaken to synthesize 2-methyleneindan-1-ones. The preparation of each is detailed and molecular formulas are provided. Spermicidal activity was assessed by dissolving the compound in physiological saline at different concentrations. 2 drops of rat sperm suspension or human semen were placed on a slide, followed by 2 drops of a compound solution. Control slides of physiological saline were prepared. The contents were mixed for approximately 5 seconds and examined under a phase contrast microscope. The results were considered positive if 100% of the spermatozoa became immotile instantaneously. Several of the compounds showed marked spermicidal activity.
