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Synthesis and Antimicrobial Activity of Novel Iminophosphocin Derivatives
Author(s) -
Koteswara rao Valasani,
Subba reddy Sanapalli,
Dada peer Echchukattula,
Janardhan rao Alahari,
Naga raju Chamarthi
Publication year - 2009
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090012
Subject(s) - chemistry , triethylamine , tetrahydrofuran , trichlorosilane , amine gas treating , staudinger reaction , alkyl , medicinal chemistry , antimicrobial , tris , organic chemistry , solvent , silicon , biochemistry
Iminophosphocins 8a – 8e and 9a – 9e were synthesized in four‐step reactions via Staudinger reaction. 3‐(Bromomethyl)‐1,2,3,4,5‐pentahydro‐3 λ 5 ‐naphtho[1,8‐ f , g ][1,5,3]diazaphosphocin‐3‐one ( 3 ) was prepared by reacting tris(bromomethyl)phosphineoxide ( 1 ) with 1,8‐diaminonaphthalene ( 2 ) in the presence of triethylamine (TEA) in dry tetrahydrofuran (THF), and treated with L ‐valine methyl ester ( 4 ) and bis(2‐chloroethyl)amine ( 5 ) in the presence of TEA in dry THF to get 3‐methyl‐2‐[(3‐oxo‐1,2,3,4,5‐pentahydro‐3 λ 5 ‐naphtho[1,8‐ f , g ][1,5,3]diazaphosphocin‐3‐yl)methylamino]butanoate ( 6 ) and 3‐[di(2‐chloroethyl)aminomethyl]‐1,2,3,4,5‐pentahydro‐3 λ 5 ‐ naphtho[1,8‐ f , g ][1,5,3]diazaphosphocin‐3‐one ( 7 ). The compounds 6 and 7 were treated with trichlorosilane (SiCl 3 H) in dry tetrahydrofuran (THF) to form the trivalent P(III) intermediates 8 and 9 , which were further treated with various alkyl azides in dry THF in 55–60°C to afford the title compounds 8a – 8e and 9a – 9e . Their structures were established by multi‐nuclear NMR and mass spectra. All the newly synthesized compounds were found to possess moderate anti‐microbial activity.