SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL STUDIES OF N-METHYLINDOLE-3-THIOACETIC ACID

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Published: 2017-01-14

Page: 90-114


OWOLABI BODUNDE JOSEPH

Department of Chemistry, Federal University of Technology, P.M.B. 704, Akure, Nigeria

ADEPOJU TAIWO SHOLAGBADE *

Department of Chemistry, Federal University of Technology, P.M.B. 704, Akure, Nigeria

JEMILUYI OYINDAMOLA OLUBUNMI

Department of Chemistry, Federal University of Technology, P.M.B. 704, Akure, Nigeria

*Author to whom correspondence should be addressed.


Abstract

The study aimed at synthesizing compounds with biological activities. N-methylindole-3-isothiouronium iodide was synthesized in two steps but one pot reaction, by reacting N-methyl indole with potassium iodide/iodine mixture followed by addition of thiourea. In another two-step-one-pot reaction, N-methylindole-3-thioacetic acid was synthesized by hydrolyzing N-methylindole-3-isothiouronium iodide in 10% sodium hydroxide solution under hydrogen atmosphere. The reaction mixture was treated with monochloroacetic acid. The structures of the compounds were elucidated by Fourier Transform infra-red spectrophotometer (FT-IR), nuclear magnetic resonance (1D and 2D NMR) and electro-spray ionization mass spectrometer (ESI-MS). The synthesized compounds were screened for antimicrobial activities at 10 mg/L. The results obtained from antibacterial screening showed that the compounds possessed some antibacterial activity against the test bacteria. Herbicidal bioassay was carried out with N-methylindole-3-thioacetic acid at various concentrations (0.5, 1.0, 1.5, 2.0 and 2.5 g/L) against the test weeds (Eleusine indica, Sporobolus pyramidalis, Tridax procumbens and Ageratum conyzoides) for five weeks, using 2, 4-D (2, 4-dichlorophenoxyl acetic acid) as standard. Results obtained revealed that synthesized compound exhibited no herbicidal activity. However, the observation suggested that the compound might have plant growth regulating activity but further work would be needed to ascertain it.

Keywords: Bacteria, fungi, monochloroacetic acid, N-methylindole-3-isothiouronium iodide and N-methylindole-3-thioacetic acid


How to Cite

JOSEPH, O. B., SHOLAGBADE, A. T., & OLUBUNMI, J. O. (2017). SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL STUDIES OF N-METHYLINDOLE-3-THIOACETIC ACID. Journal of Applied Chemical Science International, 7(2), 90–114. Retrieved from https://ikprress.org/index.php/JACSI/article/view/3739

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