Next Article in Journal
Alkylphenol Activity against Candida spp. and Microsporum canis: A Focus on the Antifungal Activity of Thymol, Eugenol and O-Methyl Derivatives
Previous Article in Journal
Substrate Promiscuity of N-Acetylhexosamine 1-Kinases
Article Menu

Export Article

Open AccessArticle
Molecules 2011, 16(8), 6408-6421; https://doi.org/10.3390/molecules16086408

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

1
Department of Chemistry, Bahauddin Zakariya University, Multan-60800, Pakistan
2
Department of Chemistry, FC College, Lahore-54600, Pakistan
3
H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi-75270, Pakistan
*
Author to whom correspondence should be addressed.
Received: 16 June 2011 / Revised: 13 July 2011 / Accepted: 22 July 2011 / Published: 29 July 2011
Full-Text   |   PDF [446 KB, uploaded 18 June 2014]   |  

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. View Full-Text
Keywords: isatin; 5-trifluoromethoxyisatin; thiosemicarbazones; 5-trifluoromethoxyisatin-3-thiosemicarbazones; toxicity isatin; 5-trifluoromethoxyisatin; thiosemicarbazones; 5-trifluoromethoxyisatin-3-thiosemicarbazones; toxicity
Figures

Figure 1

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

SciFeed

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top