Synthesis and antimicrobial activity of 5-chloroindoline-2,3-dione derivatives

Abstract

A series of 3-(5-chloro-2-oxoindolin-3-ylideneamino)-2-arylthiazolidin-4-ones 4a-k and 5-chloro-3-(3-chloro-2-oxo-4-arylazetidin-1-ylimino)indolin-2-ones 5a-k was synthesized. The structures of final compounds were confirmed by analytical (C, H, N) and spectral (FT-IR, 1 H NMR, 13 C NMR and Mass) data. The synthesized compounds were screened for possible antibacterial and antifungal activity. Compounds 4c, 4f, 4g, 4h, 4i, 4j, 5c, 5f, 5g, 5h, 5i and 5j showed substantially significant activity.

New hydrazonoindolin-2-ones: Synthesis, exploration of the possible anti-proliferative mechanism of action and encapsulation into PLGA microspheres

“…The IR spectra of compounds 4a-o displayed absorption bands around 3400 cm -1 for the indolic NH group in addition to the absorption bands of carbonyl groups near 1720 cm -1 which is consistent with the previously reported ones for compounds 4a [26] and 4f [27]. Also, their 1 H NMR spectra revealed a D 2 O-exchangeable signals in the region δ 10.84-11.01 ppm attributable to the NH protons of the indolin-2-one moieties, in addition to the signal of the methine protons (-CH = N-) in the region δ 8.55-8.70 ppm which is in accordance with those previously reported for compounds 4a [26], 4f [27] and 4i [28]. Moreover, the 13 C NMR spectra of compounds 4a-o showed signals resonating around δ 163 ppm, characteristic of C = O carbons.…”

“…All reagents and solvents were purified and dried by standard techniques. Compounds 4a [ 26 ], 4f [ 27 ], 4i [ 28 ] and 6a, b [ 29 ] have been previously reported. The microspheres were prepared with poly (D, L-lactide co-glycolide) PLGA (50:50, mol.…”

A Series of Isatin-Hydrazones with Cytotoxic Activity and CDK2 Kinase Inhibitory Activity: A Potential Type II ATP Competitive Inhibitor

“…Synthesis of 3-((substituted)benzylidene)hydrazono)indolin-2-one ( 4 ) was straightforward, as illustrated in Scheme 1 [ 36 , 52 ]. In the first step, a mixture of isatin ( 1 ) and hydrazine hydrate was refluxed in ethanol and isatin monohydrazone ( 2 ) was obtained in quantitative yields (~99%).…”

“…It has been reported that tryptophan obtained from food sources is usually converted to indole by gastrointestinal bacteria, which is further oxidized in the liver by CYP450 to isatin, therefore, isatin is present as an endogenous molecule in humans [ 19 , 20 ]. Various substituents on the isatin nucleus displayed numerous biological activities [ 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 ], including antimicrobial activity[ 31 , 37 ], topoisomerase inhibitory activity [ 7 , 38 ], epidermal growth factor receptor (EGFR) inhibitory activity [ 39 ], inhibitory activities on histone deacetylase (HDAC) [ 40 , 41 ], carbonic anhydrase [ 42 , 43 , 44 ], tyrosine kinase [ 45 , 46 , 47 ], cyclin-dependent kinases (CDKs) [ 9 , 48 , 49 ], adenylate cyclase inhibition [ 50 ] and protein tyrosine phosphatase (Shp2) [ 51 ]. A number of isatin-based marketed drugs and potential anticancer agents [ 41 ] are illustrated in Figure 1 .…”

Isatin Dual Functional Inhibitors: Modulating the Aggregation State and Enzyme Activity of SARS-3CL Proteinase

“…Isatin (1H-indole-2,3-dione) and its derivatives can be used as the starting material for preparing quinazoline drugs (such as cinchophen). 1,2 These compounds demonstrate a diverse array of biological and pharmacological activities including anticonvulsant, 3 antibacterial, 4,5 antifungal, 6 antiviral, [7][8][9] and anticancer 10,11 properties.…”