Intramolecular nonbonded S...N interaction in rabeprazole.
Intramolecular nonbonded S...N interactions in the crystal structures of the derivatives (7a-d) of sodium rabeprazole (1) and an intermolecular nonbonded S...N interaction between ethylmethylsulfoxide and pyridine in a solution were recognized. These results made us estimate that the intramolecular nonbonded S...N interaction existed in 1 and its derivatives in a solution, and formed the 4-membered quasi-ring in 2 (Fig. 1) followed by the increase of the reactivity of 2 to give the putative spiro sulfoxide 3, which is the key intermediate in the reaction cascade of 1 (Chart 1).
Hayashi
Kazuhiko
K
College of Pharmacy, Kinjo Gakuin University, Nagoya, Japan. hayashi@kinjo-u.ac.jp
Ogawa
Shiho
S
Sano
Shigeki
S
Shiro
Motoo
M
Yamaguchi
Kentaro
K
Sei
Yoshihisa
Y
Nagao
Yoshimitsu
Y
D053799:2-Pyridinylmethylsulfinylbenzimidazoles / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003545:Cysteine / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008968:Molecular Conformation; D054328:Proton Pump Inhibitors / Q000737:chemistry*; D011725:Pyridines; D064750:Rabeprazole; D012996:Solutions; D021241:Spectrometry, Mass, Electrospray Ionization; D016339:Spectrometry, Mass, Fast Atom Bombardment; D017550:Spectroscopy, Fourier Transform Infrared; D013416:Sulfamerazine / Q000737:chemistry
D053799:2-Pyridinylmethylsulfinylbenzimidazoles; D007202:Indicators and Reagents; D054328:Proton Pump Inhibitors; D011725:Pyridines; D012996:Solutions; C471392:sulfenamide; D064750:Rabeprazole; D003545:Cysteine; C023666:pyridine; D013416:Sulfamerazine