Design, synthesis of 4-aminoquinoline-derived thiazolidines and their antimalarial activity and heme polymerization inhibition studies

Solomon, V. Raja; Haq, W.; Srivastava, Kumkum; Puri, Sunil K.; Katti, S. B.

doi:10.3109/14756366.2012.666537

Cited by 12 publications

(7 citation statements)

References 29 publications

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“…In addition, the introduction of an amide bond with a heterocyclic ring system (4-thiazolidine) to the lateral side chain of 4-aminoquinoline (an antimalarial agent) has been shown to improve the antimalarial activity of this compound [43]. In the present study, ve Ag complexes with thiazolidine ligand showed promising in vitro antiplasmodial activities against chloroquine-resistant P. falciparum of K1 strain.…”

Section: Antiplasmodial Activitymentioning

confidence: 66%

New Silver Complexes with Mixed Thiazolidine and Phosphine Ligands as Highly Potent Antimalarial and Anticancer Agents

Sofyan

Nordin

Razak

et al. 2018

Journal of Chemistry

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Five silver(I) complexes containing a mixed ligand system of phosphine and thiazolidine were successfully synthesized. e structural information of the complexes was assembled using various spectroscopic techniques such as CHN elemental analysis, Fourier transformed infrared (FTIR), 1 H, 13 C, and 31 P{ 1 H} NMR spectroscopy, and thermogravimetric analysis (TGA). A bidentate phosphine ligand acted as a chelating agent which bond to the silver in 1 : 2 molar ratios. Meanwhile, thiazolidine was attached to the silver in a 1 : 1 molar ratio. e antiplasmodial properties of all synthesized complexes were investigated on chloroquine-resistant P. falciparum parasite via HRP2 assays and cytotoxicity tests on Vero cells. Of all the synthesized complexes, complex 2 showed the highest SI value (more than 12.4) followed by complex 5 (6.6). e potent properties of compounds 2 and 5 were also noted in the in vitro antiproliferative assays involving MDA-MB-231 and MCF-7 breast cancer cell lines as well as HT-29 colon cancer cell line. Complex 2 was selective for MDA-MB-231 cells (GI 50 � 1.9 ± 0.3 µM), while complex 5 acted predominantly on breast carcinoma cells (GI 50 MDA-MB-231 � 4.7 ± 1.1 µM; MCF-7 � 2.9 ± 0.9 µM) instead of colon carcinoma (HT-29) cells (GI 50 � 15.1 ± 1.9 µM).

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Section: Antiplasmodial Activitymentioning

confidence: 66%

New Silver Complexes with Mixed Thiazolidine and Phosphine Ligands as Highly Potent Antimalarial and Anticancer Agents

Sofyan

Nordin

Razak

et al. 2018

Journal of Chemistry

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“…In the same vein, TCDs are used as, e.g. antimalarial, 18,19 selective Na + /Ca 2+ exchange inhibitors, 20 immunostimulating agents, 21 tyrosinase inhibitors, 22 influenza A neuraminidase inhibitors, 23 antitubercular, 24 HIV-1 protease inhibitors 2,25 and ACE inhibitors. 26 Furthermore, TCDs were introduced as versatile scaffolds in the syntheses of natural products, i.e.…”

Section: Introductionmentioning

confidence: 99%

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Mahdy¹,

Elboray²,

Fandy³

et al. 2017

Arkivoc

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Aromatic aldehydes reacted readily with (R)-cysteine in boiling acidified methanol to give diastereomeric mixtures of the corresponding 2-(aryl substituted) thiazolidine-4-carboxylic acids. 4-Nitrobenzaldehyde under similar conditions afforded one isomer of 2-(4-nitrophenyl)-thiazolidine-4-carboxylic acid, which epimerized in the NMR solvents into a diastereomeric mixture. 2-Nitrobenzaldehyde reacted with (R)-cysteine to afford 3,5-bis-(2-nitrophenyl)-tetrahydro-1H-thiazolo[3,4-c]oxazol-1-one as the sole product, which collapsed in the NMR solvent into a diastereomeric mixture of the thiazolidine-4-carboxylic acids. The thiazolidine derivatives reacted smoothly with phenyl isothiocyanate to give single isomers of the corresponding thiohydantoins.

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“…Design and synthesis of 3-[(7-chloro-1-oxidoquinolin-4-ylamino)alkyl]-1,3-thiazolidin-4-ones as antimalarial agents of P. yoelii in vivo and some of these compounds were indeed more effective than CQ 14,15 . As an obvious extension of this work we turned our attention on the role of quinoline nitrogen atom (pKa1) with doppelganger objective in mind namely, whether basicity of this nitrogen is important for the transportation of 4-aminoquinoline scaffold across the membrane or to form association complex with hematin or both.…”

Section: Research Articlementioning

confidence: 99%

Design and synthesis of 3-[(7-chloro-1-oxidoquinolin-4-ylamino)alkyl]-1,3-thiazolidin-4-ones as antimalarial agents

Solomon

Haq

Srivastava

et al. 2012

Journal of Enzyme Inhibition and Medicinal Chemistry

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Design, synthesis of 4-aminoquinoline-derived thiazolidines and their antimalarial activity and heme polymerization inhibition studies

Cited by 12 publications

References 29 publications

New Silver Complexes with Mixed Thiazolidine and Phosphine Ligands as Highly Potent Antimalarial and Anticancer Agents

New Silver Complexes with Mixed Thiazolidine and Phosphine Ligands as Highly Potent Antimalarial and Anticancer Agents

New aspects of the formation of 2-substituted thiazolidine-4-carboxylic acids and their thiohydantoin derivatives

Design and synthesis of 3-[(7-chloro-1-oxidoquinolin-4-ylamino)alkyl]-1,3-thiazolidin-4-ones as antimalarial agents

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