Interaction of 5′-Guanosine Monophosphate with Organotin(IV) Moieties: Synthesis, Structural Characterization, and Anti-Inflammatory Activity
Author(s) -
Mala Nath,
Hitendra Singh,
George Eng,
Xueqing Song
Publication year - 2012
Publication title -
isrn organic chemistry
Language(s) - English
Resource type - Journals
eISSN - 2090-5157
pISSN - 2090-5149
DOI - 10.5402/2012/873035
Subject(s) - guanosine , chemistry , cyclic guanosine monophosphate , characterization (materials science) , anti inflammatory , stereochemistry , combinatorial chemistry , biochemistry , pharmacology , organic chemistry , materials science , nanotechnology , medicine , nitric oxide
Reaction(s) of 5′-guanosine monophosphate (5′GMP) with di- and triorganotin(IV) chloride(s) led to formation of organotin(IV) derivatives of general formulae, [R 2 Sn(5′-GMP) · H 2 O] n and [(R′ 3 Sn) 2 (5′-GMP) · H 2 O] n , where R = Me, n -Bu, and Ph; R′ = Me, i -Pr, n -Bu, and Ph; (5′-GMP) 2− = 5′-guanosine monophosphate. An attempt has been made to prove the structures of the resulting derivatives on the basis of FT-IR, multinuclear 1 H, 13 C, and 119 Sn NMR and 119 Sn Mössbauer spectroscopic studies. These investigations suggest that both di- and triorganotin(IV)-5′-guanosine monophosphates are polymeric in which (5′-GMP) 2− is bonded through phosphate group resulting in a distorted trigonal bipyramidal geometry around tin. The ribose conformation in all of the derivatives is C 3′- endo , except diphenyltin(IV) and tri- i -propyltin(IV) derivatives where it is C 2′- endo . All of the studied derivatives exhibited mild-to-moderate anti-inflammatory activity (~15.64–20.63% inhibition) at 40 mg kg −1 dose and LD50 values > 400 mg kg −1 in albino rats.
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