Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones

Molecules

Humayun Pervez¹  Naveeda Saira¹  Mohammad Saeed Iqbal¹  Muhammad Yaqub¹ 

[1] ¹Department of Chemistry, Bahauddin Zakariya University, Multan-60800, Pakistan ²Department of Chemistry, FC College, Lahore-54600, Pakistan ³H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan

关键词: isatin;    5-trifluoromethoxyisatin;    thiosemicarbazones;    5-trifluoromethoxyisatin-3-thiosemicarbazones;    toxicity;   

DOI  :  10.3390/molecules16086408

来源: mdpi

【 摘 要 】

A series of twenty one N⁴-aryl substituted 5-trifluoromethoxyisatin-3-thiosemicarbazones 3a-3u was synthesized by the reaction of trifluoromethoxyisatin 1 with different arylthiosemicarbazides 2 in aqueous ethanol (50%), containing a few drops of acetic acid. Their structures were established on the basis of analytical (CHN) and spectral (IR, ¹H-NMR, EIMS) data. All the synthesized compounds were evaluated for their toxicity potential by a brine shrimp lethality bioassay. Ten compounds i.e., 3a, 3e, 3i-3l and 3n-3q proved to be active in this assay, displaying promising toxicity (LD₅₀ = 1.11 × 10⁻⁵ M − 1.80 × 10⁻⁴ M). Amongst these, 3k, 3n and 3o were found to be the most active ones (LD₅₀ = 1.11 × 10⁻⁵ M − 1.43 × 10⁻⁵ M). Compound 3k showed the highest activity with a LD₅₀ value of 1.11 × 10⁻⁵ M and can, therefore, be used as a lead for further studies. Structure-activity relationship (SAR) studies revealed that the presence of strong inductively electron-attracting trifluoromethoxy substituent at position-5 of the isatin moiety played an important role in inducing or enhancing toxic potentiality of some of the synthesized compounds.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.