Synthesis of sildenafil analogues from anacardic acid and their phosphodiesterase-5 inhibition.
Anacardic acid (6-pentadecylsalicylic acid), a major component of cashew nut shell liquid, consists of a heterogeneous mixture of monoenes, dienes, and trienes. The enes mixture of anacardic acid was hydrogenated to a saturated compound. Using saturated anacardic acid as a starting material, analogues of sildenafil [a potent phosphodiesterase-5 (PDE(5)) inhibitor and an orally active drug for the treatment of erectile dysfunction] were synthesized, to observe the effect of the pentadecyl side chain on PDE(5) inhibition. The synthesized compounds were characterized by spectral studies and tested for PDE(5) inhibition, and the results were compared with those obtained with sildenafil.
Paramashivappa
R
R
Vittal Mallya Scientific Research Foundation, PO Box 406, K R Road, Bangalore-560 004, India.
Phani Kumar
P
P
Subba Rao
P V
PV
Srinivasa Rao
A
A
D015106:3',5'-Cyclic-GMP Phosphodiesterases; D048729:Anacardic Acids; D054706:Cyclic Nucleotide Phosphodiesterases, Type 5; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010726:Phosphodiesterase Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D010727:Phosphoric Diester Hydrolases / Q000378:metabolism; D010879:Piperazines / Q000737:chemistry* / Q000494:pharmacology; D011687:Purines; D012459:Salicylates / Q000737:chemistry*; D000068677:Sildenafil Citrate; D013329:Structure-Activity Relationship; D013450:Sulfones
D048729:Anacardic Acids; D010726:Phosphodiesterase Inhibitors; D010879:Piperazines; D011687:Purines; D012459:Salicylates; D013450:Sulfones; C088115:anacardic acid; D000068677:Sildenafil Citrate; D010727:Phosphoric Diester Hydrolases; D015106:3',5'-Cyclic-GMP Phosphodiesterases; D054706:Cyclic Nucleotide Phosphodiesterases, Type 5