Isatin Hybrids Research Articles

Cu(I)Cl-promoted synthesis of novel N-alkylated isatin analogs with an extension toward isatin-4-aminoquinoline conjugates: in vitro analysis against Trichomonas vaginalis

Trichomonas vaginalis, the causative agent of trichomonosis, is the most common non-viral sexually transmitted disease. Infection with this protozoan may have serious consequences, especially for women. Currently, 5-nitroimidazole drugs are the treatment of choice for trichomonosis, but the emergence of drug resistant isolates has limited the effectiveness of this therapy. In this context, a library of isatin-mannich adducts and 4-aminoquinoline-isatin mannich conjugates was synthesized following the Cu-promoted Mannich reaction and evaluated for their preliminary in vitro analysis against T. vaginalis at 50 μM. The preliminary evaluation data revealed that the introduction of 4-aminoquinoline ring enhanced the activity profiles with compounds viz. 6a and 6c exhibiting percentage growth inhibition of 92.13 and 100 %, respectively. Compounds with high levels of potency were further analyzed to determine their IC50 values as well as cytotoxicity profiles against mammalian cells. The most active compound in the synthesized conjugates displayed an IC50 value of 23 μM against cultured G3 strain in TYM Diamond’s media of T. vaginalis and was non-toxic to cultured mammalian HeLa cells at the same concentration. Synthesis of N-alkylated isatin analogs, 4-aminoquinoline isatin hybrids, in vitro evaluation against trichomoniasis and cytotoxicities against HeLa cells.

Synthesis of novel 1H-1,2,3-triazole tethered C-5 substituted uracil–isatin conjugates and their cytotoxic evaluation

The present manuscript describes the synthesis of uracil–isatin hybrids via azide–alkyne cycloadditions and their cytotoxic evaluation against three human cancer cell lines viz. HeLa (cervix), MCF-7 (breast) and DU145 (prostate) using MTT assay. The evaluation studies revealed the dependence of cytotoxicity on C-5 substituents of both uracil and isatin as well as the alkyl chain length with compounds 6g and 6k showing IC50 values 18.21 and 13.90 μM respectively against DU145 cell lines. Most of the synthesized conjugates exhibited considerable selectivity against MCF-7 and DU145 cell lines.

Design, synthesis and in vitro evaluation of tetrahydropyrimidine–isatin hybrids as potential antitubercular and antimalarial agents

A series of 5-substituted-3-[{5-(6-methyl-2-oxo/thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-oxadiazol-2-yl}-imino]-1,3-dihydro-2H-indol-2-one were synthesized, characterized and screened for their anti-tubercular and antimalarial activity.

Design, synthesis, in vitro evaluation of tetrahydropyrimidine–isatin hybrids as potential antibacterial, antifungal and anti-tubercular agents

Abstract A series of 5-substitued-3-(5-(4-(furan-2-yl)-6-methyl-2-oxo/thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-1,3,4-thiadiazol-2-ylimino)indolin-2-one derivatives were synthesized, characterized and were screened for anti-bacterial, anti-fungal and anti-tubercular activity.

Novel thiolactone–isatin hybrids as potential antimalarial and antitubercular agents

The synthesis of a novel series of thiolactone-isatin hybrids led to the discovery of tetracyclic by-products which displayed superior antiplasmodial activity. The tetracycles thus formed the basis of a more focused SAR study. Identified from this series is a compound with an IC(50) of 6.92 μM against the chloroquine-resistant (W2) strain of Plasmodium falciparum. Useful antimalarial SARs delineated include the need for substitution at C-5 of the isatin scaffold and the enhancement of activity by increasing the linker length. In contrast to their antimalarial activity, the tetracycles were devoid of antitubercular activity whereas the advanced intermediates displayed growth inhibitory activity against the H(37)Rv strain of Mycobacterium tuberculosis as revealed by BACTEC, MABA and LORA assays.