Synthesis, anti-mycobacterial and cytotoxic evaluation of substituted isoindoline-1,3-dione-4-aminoquinolines coupled via alkyl/amide linkers

Abstract

A series of secondary amine-substituted isoindoline-1,3-dione-4-aminoquinolines were prepared via microwave heating and assayed for their anti-mycobacterial activities.

Design and synthesis of 4-Aminoquinoline-isoindoline-dione-isoniazid triads as potential anti-mycobacterials

“…Relating the activity and cytotoxicity data of currently synthesized compounds (6e, 8e, 11) with our earlier report (I-IV) [28][29][30][31], the introduction of INH at C-5 of isoindoline ring not only improved anti-mycobacterial activity but also resulted in the reduction of cytotoxicity (Figure 2). The general anti-TB SAR/cytotoxicity of the synthesized series of 4-aminoquinolineisoindoline-isoniazid triads is elucidated in Figure 3.…”

“…Figure 2: Comparison of activity against mc 2 6230 and cytotoxicity against Vero cells of 6e, 8eand 11 with previously reported scaffolds I-IV[28][29] 31] …”

“…Recently, we introduced a functionalized isoindoline-1,3-diones into the alkyl chain of 4aminoquinolines to access their anti-mycobacterial potency. The compounds were promising candidates with a MIC of 5.9-6.25 µg/mL against the mc 2 6230 strain of M. tuberculosis (Figure 2) [28][29]. Motivated by these results and in continuation [30], the present work is a logical extension and involves the synthesis and anti-mycobacterial evaluation of 4aminoquinoline-isoniazid hybrids linked via isoindoline-1,3-diones.…”

Synthesis of Substituted Phthalimides via Ultrasound-Promoted One-Pot Multicomponent Reaction

“…One of the primary goals of organic and medicinal chemistry is the design and synthesis of scaffolds possessing biological features. Phthalimide core, − in particular, serves as the structural unit in various drugs such as thalidomide, , pomalidomide, apremilast, and batracylin (Figure ). Furthermore, phthalimides have been used as intermediates to produce functionalized natural products and alkaloids, including nuevamine, chilenine, lennoxamine, and magallanesine .…”

Design, Synthesis, Heme Binding and Density Functional Theory Studies of Isoindoline-Dione-4-Aminoquinolines as Potential Antiplasmodials

“…Encouraged with these results and recent disclosures from our lab [26][27][28][29], we envisaged the incorporation of isoindoline-1,3-diones having cycloalkyl amine functionality at C4/C5 position in the side chain of 4aminoquinolines in order to ascertain their structure-antiplasmodial activity relationship. The introduction of a basic amino substituent is generally considered essential for trapping high concentrations of the drug in the acidic food vacuole of the malaria parasite [30].…”