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Diorganotin(IV) complexes of indole 3‐acetic acid
Author(s) -
Sandhu G K,
Sharma N
Publication year - 1993
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590070104
Subject(s) - chemistry , moiety , deprotonation , acetic acid , ligand (biochemistry) , indole test , substituent , stereochemistry , steric effects , medicinal chemistry , chelation , indole 3 acetic acid , hydrolysis , organic chemistry , ion , biochemistry , receptor , auxin , gene
Alkyl derivatives of indole 3‐acetic acid (IAA) have been prepared and are suitable for investigating steric substituent effects on hormonal activity without major interference from electronic effects. Triorganotin(IV) derivatives of indole 3‐acetic acid and N ‐methylindole 3‐acetic acid have been reported to act as insecticidal, fungicidal and bactericidal agents. Me 3 SnIAA is more active as a biocide than Cy 3 SnIAA. The activity of these two compounds may be due to the fact that four‐coordinated tin monomers or five‐coordinated tin polymers are often more active than chelated five‐coordinated tin species because these readily undergo hydrolysis to give R 3 Sn(H 2 O + ) 2 species. The ligand affects the rate of formation of the ligand‐free active organotin entity. Biocidal activity is expected from diorganotin(IV) pentacoordinated complexes of indole 3‐acetic acid in the present case due to (i) the activity of pentacoordinated organotin species, (ii) the presence of an—NH moiety in the complexes, which is an active site for binding. The NH moiety may be deprotonated and nitrogen may coordinate with metal ions present in the physiological systems and thus destroy the activity of enzymes.