Ammonium chloride catalyzed synthesis of novel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles and evaluation of their antimicrobial and anti-breast cancer activities

Abstract

BackgroundIndolinone and spiro-indoline derivatives have been employed in the preparation of different important therapeutic compounds required for treatment of anticonvulsants, antibacterial, Antitubercular, and anticancer activities. Schiff bases have been found to possess various pharmacological activities such as antitubercular, plant growth inhibiting, insecticsidal, central nerve system depressant, antibacterial, anticancer, anti-inflammatory, and antimicrobial. Mannich bases have a variety of biological activities such as antibacterial and antifungal activities.ResultsIn this study, a green, rapid and efficient protocol for the synthesis of a new series of Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitrile derivatives using ammonium chloride as a very inexpensive and readily available reagent. The prepared compounds were assessed in vitro for their antimicrobial activity. Also, the cytotoxic activity of the prepared compounds was assessed in vitro against human cells line MCF7 breast cancer.ConclusionGood activity was distinguished for Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles, with some members recorded higher antimicrobial and anti-breast cancer activities.Graphical abstractNovel Schiff bases from spiro[indoline-3,4′-pyran]-3′-carbonitriles

Design, synthesis, and biological evaluation of novel N4-substituted sulfonamides: acetamides derivatives as dihydrofolate reductase (DHFR) inhibitors

“…Based on these prior observations relating to the synthesis of sulfonamide derivatives [42, 43] and bioactive nitrogen-containing heterocyclic agents [44–48] we envisaged that sulfonamides bearing acetamide pharmacophores could be very efficient for antimicrobial and anticancer activity. In the present work, we report the synthesis of some novel sulfonamide- N 4 -acetamide derivatives and their evaluation of their cytotoxic activity against human lung carcinoma (A-549) and human breast carcinoma (MCF-7) cell lines.…”

1,3-Dipolar cycloaddition approach to novel dispiro[pyrazolidine-4,3′-pyrrolizidine-2′,3″-indoline]-2″,3,5-triones

“…16,17 Pyrrolidine, pyrrolizine, and pyrrolothiazole derivatives are important bioactive heterocyclic compounds which have antimicrobial, antiviral, anti-inflammatory, antitubercular, anticancer, and antidiabetic activities. [18][19][20][21] In the present paper, we extend our previous studies on the synthesis of bioactive spiroheterocycles, [22][23][24][25][26] and now report a 1,3-dipolar cycloaddition reaction involving the exocyclic olefinic linkage derived from 1-phenylpyrazolidine-3,5-dione 2a-e 5 to synthesise a series of novel dispiro[pyrazolidine-4,3'-pyrrolizine-2',3''-indoline]-2'',3,5-triones 5a-j regioselectively in good to excellent yields through 1,3-dipolar cycloaddition reaction of azomethine ylides produced in situ via decarboxylative condensation of L-proline 3 and isatins 4a and 4b (Scheme 2).…”

Anticancer Activity of Mannich Bases: A Review of Recent Literature

“…Mannich bases of isatin 164 (X=O) and two Mannich bases 164 (X=NC 6 H 5 ) of the aniline Schiff base of isatin (Figure 20) was shown to be in the range of 22 % to 70 % at 100 μM [159] . Also, anticancer activity in two series of Mannich bases 165 (R=NH 2 or N=CH−Ar) with a spiro‐isatin scaffold (Figure 20) was investigated, but the compounds had moderate to poor activity against MCF‐7 breast cancer cell line [160] . In relation to the anticancer activity of isatins, it is worth mentioning the discovery of Mannich bases 166 (Figure 20) as activators of protein p53 through its stabilization [161] .…”

“…[159] Also, anticancer activity in two series of Mannich bases 165 (R = NH 2 or N=CHÀ Ar) with a spiro-isatin scaffold (Figure 20) was investigated, but the compounds had moderate to poor activity against MCF-7 breast cancer cell line. [160] In relation to the anticancer activity of isatins, it is worth mentioning the discovery of Mannich bases 166 (Figure 20) as activators of protein p53 through its stabilization. [161] These compounds are ChemMedChem able to disrupt protein-protein interaction of p53 with mouse double minute 2 (MDM2, which is a protein that effects the ubiquitination of p53), a process that leads to the latter's degradation and is ultimately responsible for p53's inability to play its crucial role in anticancer responses.…”