5-Nitroisatin-derived thiosemicarbazones: potential antileishmanial agents

Abstract

A series of 29 previously reported N 4 -substituted 5-nitroisatin-3-thiosemicarbazones 2-30 has been screened for leishmanicidal potential. 7,8,[10][11][12][13][15][16][17][18][19]21,23,24,26,28 and 30 exhibited good to excellent antileishmanial activities with IC 50 values ranging from 0.44 AE 0.02 to 32.38 AE 0.66 mg/mL. Of these, 5, 7, 19 and 28 proved to be the most active antileishmanial agents, displaying activities with IC 50 values 1.78 AE 0.35, 0.44 AE 0.02, 1.91 AE 0.04 and 4.28 AE 0.75 mg/mL, respectively, which were even better than the standard drug, pentamidine (IC 50 ¼ 5.09 AE 0.04 mg/mL). This study presents the first example of exhibition of leishmanicidal potential by isatin-thiosemicarbazones and as such furnishes a solid basis for further research on these compounds to develop more potent antileishmanial agents.

Isatin thiosemicarbazones promote honeycomb structure formation in spin-coated polymer films: concentration effect and release studies

“…The fact that the effect of the 100 mM and 500 mM concentration is within the same range suggests that the effect reaches a plateau. It is worth mentioning that this concentration-dependent behaviour resembles the effect on hydrophobicity observed during copolymerisation processes, by either changing the concentration or the type of the lm polymers, 29,30 a fact that indicates the direct and active participation of ITSC in the BF phenomenon.…”

“…1) on polymer lm surface characteristics. ITSC 1 (K) has been shown to have signicant antifungal activity, 27 antiherpetic activity, 28 antileishmanial activity, 29 and antibacterial activity against antibiotic-resistant gram-positive bacterial strains. 30 ITSC 2 (M) has been shown 28 to have signicant antiherpetic activity whereas isatin derivatives 3 (N) and 4 (NM) have not been studied in the literature previously.…”

3-Hydrazinoindolin-2-one derivatives: Chemical classification and investigation of their targets as anticancer agents

“…In phase II clinical trials, SU5614 (6) induced growth arrest and apoptosis in c-kit expressing Kasumi-1, UT-7 and M-07e cells and inhibited the stem cell factor induced tyrosine phosphorylation of c-kit [14]. Derivatives of 3-hydrazinoindolin-2-one (7) (Figure 3) represents a pharmacophore of an important class of biologically active pharmaceutical agents possessing diverse biological activity as anti-microbial [15], anti-viral [16,17], antimycobacterial [18,19], anti-inflammatory [20], anti-leshmanial [21], anti-parasitic [22], anti-convulsant [23,24] and anti-diabetic agents [25].…”

Synthesis and in vitro Bio-activity Evaluation of N4-benzyl Substituted 5-Chloroisatin- 3-thiosemicarbazones as Urease and Glycation Inhibitors

“…SAR studies in the synthesized thiosemicarbazones disclosed that in some cases the nature and location of the substituent on the phenyl ring attached to thiosemicarbazone N 4 and/or the existence of lipophilic/inductively electron-withdrawing functions (Cl, F, F 3 CO, NO 2 ) at position 5 of the isatin moiety played a significant role in inducing and/or increasing certain activities, including urease inhibition. In view of this and as an extension of our earlier studies [36][37][38][39][40][41][42][43][44][45][46][47] aiming to the synthesis of novel isatin derivatives with enhanced or diverse biological activities, we very recently reported the synthesis of a series of N 4 -benzyl substituted 5-nitroisatin-3-thiosemicarbazones (derivatives of thiourea, a substrate-like urease inhibitor) as highly effective urease inhibitors. 48 Interestingly, all these compounds demonstrated either induced or increased urease inhibitory activity in comparison to the respective N 4 -phenyl substituted derivatives tested in our earlier assays.…”

“…Of the isatin derivatives, isatin-thiosemicarbazones have been found to exhibit a range of biological properties, including antiulcer, 1 anticancer, 1,4,7,12,[21][22][23] antimicrobial, [1][2][3]5,7,22,24,25 antituberculosis, [26][27][28] antiviral 1,2,5,7,12,28 and enzyme inhibitory activities. 1,4,11,17 Incited by these findings and as a part of our synthetic work on bioactive isatin derivatives, we have recently reported the synthesis of numerous N 4 -aryl substituted isatin-3-thiosemicarbazones (thiourea derivatives) as antimicrobial, [36][37][38][39] cytotoxic, [38][39][40][41][42] phytotoxic, [38][39][40][41]43 antileishmanial 44 and more importantly antiurease [36][37][38][39][40]…”