Synthesis, spectral characterization and biological studies of some organotin(IV) complexes of L-proline, trans-hydroxy-L-proline and L-glutamine.
New organotin(IV) complexes of the general formula R3Sn(L) (where R=Me, n-Bu and HL=L-proline; R=Me, Ph and HL=trans-hydroxy-L-proline and L-glutamine) and R2Sn(L)2 (where R=n-Bu, Ph and HL=L-proline; R=Ph, HL=trans-hydroxy-L-proline) have been synthesized by the reaction of RnSnCl(4-n) (where n=2 or 3) with sodium salt of the amino acid (HL). n-Bu2Sn(Pro)2 was synthesized by the reaction of n-Bu2SnO with L-proline under azeotropic removal of water. The bonding and coordination behavior in these complexes have been discussed on the basis of IR and 119Sn Mössbauer spectroscopic studies in the solid-state. Their coordination behavior in solution has been discussed with the help of multinuclear (1H, 13C and 119Sn) NMR spectral studies. The 119Sn Mössbauer and IR studies indicate that L-proline and trans-hydroxy-L-proline show similar coordination behavior towards organotin(IV) compounds. Pentacoordinate trigonal-bipyramidal and hexacoordinate octahedral structures, respectively, have been proposed for the tri- and diorganotin(IV) complexes of L-proline and trans-hydroxy-L-proline, in which the carboxylate group acts as bidentate group. L-glutamine shows different coordination behavior towards organotin(IV) compounds, it acts as monoanionic bidentate ligand coordinating through carboxylate and amino group. The triorganotin(IV) complexes of L-glutamine have been proposed to have trigonal-bipyramidal environment around tin. The newly synthesized complexes have been tested for their antiinflammatory and cardiovascular activities. Their LD50 values are >1000 mg kg-1.
Nath
Mala
M
Department of Chemistry, Indian Institute of Technology-Roorkee, Roorkee 247667, India. malanfcy@iitr.ernet.in
Jairath
Ruchi
R
Eng
George
G
Song
Xueqing
X
Kumar
Ashok
A
D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002317:Cardiovascular Agents; D004285:Dogs; D005973:Glutamine / Q000737:chemistry*; D006909:Hydroxyproline / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D009947:Organotin Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011392:Proline / Q000737:chemistry*; D051381:Rats; D013055:Spectrophotometry, Infrared; D015204:Spectroscopy, Mossbauer; D018675:Toxicity Tests
D000893:Anti-Inflammatory Agents; D002317:Cardiovascular Agents; D009947:Organotin Compounds; D005973:Glutamine; D011392:Proline; D006909:Hydroxyproline