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Molecules 2011, 16(8), 6408-6421; doi:10.3390/molecules16086408
Article

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

1,* , 1, 2, 1 and 3
Received: 16 June 2011; in revised form: 13 July 2011 / Accepted: 22 July 2011 / Published: 29 July 2011
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Abstract: 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.
Keywords: isatin; 5-trifluoromethoxyisatin; thiosemicarbazones; 5-trifluoromethoxyisatin-3-thiosemicarbazones; toxicity isatin; 5-trifluoromethoxyisatin; thiosemicarbazones; 5-trifluoromethoxyisatin-3-thiosemicarbazones; toxicity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Pervez, H.; Saira, N.; Iqbal, M.S.; Yaqub, M.; Khan, K.M. Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones. Molecules 2011, 16, 6408-6421.

AMA Style

Pervez H, Saira N, Iqbal MS, Yaqub M, Khan KM. Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones. Molecules. 2011; 16(8):6408-6421.

Chicago/Turabian Style

Pervez, Humayun; Saira, Naveeda; Iqbal, Mohammad Saeed; Yaqub, Muhammad; Khan, Khalid Mohammed. 2011. "Synthesis and Toxicity Evaluation of Some N4-Aryl Substituted 5-Trifluoromethoxyisatin-3-thiosemicarbazones." Molecules 16, no. 8: 6408-6421.


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