New thiazolidine-2,4-dione derivatives combined with organometallic ferrocene: Synthesis, structure and antiparasitic activity

Oderinlo, Ogunyemi O; Tukulula, Matshawandile; Isaacs, Michelle; Taylor, Dale; Smith, Vincent J; Khanye, Setshaba D; Hoppe, Heinrich C

Title: New thiazolidine-2,4-dione derivatives combined with organometallic ferrocene: Synthesis, structure and antiparasitic activity
Creator: Oderinlo, Ogunyemi O
Creator: Tukulula, Matshawandile
Creator: Isaacs, Michelle
Creator: Taylor, Dale
Creator: Smith, Vincent J
Creator: Khanye, Setshaba D
Creator: Hoppe, Heinrich C
Date Issued: 2018
Date: 2018
Type: text
Type: article
Identifier: http://hdl.handle.net/10962/122978
Identifier: vital:35382
Identifier: https://doi.org/10.1002/aoc.4385
Description: Favourable physicochemical properties of an organometallic ferrocene and antiplasmodial potency of compounds containing the thiazolidine‐2,4‐dione framework (TZD‐4) prompted us to explore compounds containing both the thiazolidine‐2,4‐dione core and the ferrocenyl unit with the primary aim of identifying compounds with promising antiprotozoal activities. Thus, a new series of rationally designed ferrocene‐based thiazolidine‐2,4‐dione derivatives, containing a selection of secondary cyclic amines, was synthesised and fully characterised using standard spectroscopic techniques. The resulting compounds were screened for their antiplasmodial and antitrypanosomal activities against both the chloroquine‐resistant (Dd2) strain of Plasmodium falciparum and the Nagana Trypanosoma brucei brucei 427. The general trend that emerged indicated that the target compounds were more selective towards T. b. brucei compared to the P. falciparum parasite. Moreover, the analogues bearing methylpiperazine (8a) and piperidine (8b) rings were more active against T. b. brucei compared to hit compound TZD‐4. Except compound 8b, which appeared promising, none of the synthesised compounds showed better activity than TZD‐4 against the P. falciparum parasite. All the synthesised compounds were non‐toxic and often showed >90% viability of the HeLa cell line screened.
Format: 9 pages
Format: pdf
Language: English
Relation: Applied Organometallic Chemistry
Relation: Oderinlo, O.O., Tukulula, M., Isaacs, M., Hoppe, H.C., Taylor, D., Smith, V.J. and Khanye, S.D., 2018. New thiazolidine-2, 4-dione derivatives combined with organometallic ferrocene: Synthesis, structure and antiparasitic activity. Applied Organometallic Chemistry, 32(7), p.e4385.
Relation: Applied Organometallic Chemistry number 32 1 9 March 2018 1099-0739
Rights: Applied Organometallic Chemistry
Rights: Use of this resource is governed by the terms and conditions of the Wiley Online Library Terms of Use Statement (https://onlinelibrary.wiley.com/terms-and-conditions)

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Khanye, David Setshaba (Associate Prof)

RU Centre for Chemico- and Biomedicinal Research (CCBR)

Hoppe, Heinrich C (Prof)

Isaacs, Michelle (Mrs)

RU Department of Pharmacy

RU Department of Biochemistry, Microbiology and Bioinformatics

SDG 03. Good Health and Well-Being

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