Design and synthesis of thiadiazolo-carboxamide bridged β-carboline-indole hybrids: DNA intercalative topo-IIα inhibition with promising antiproliferative activity

Abstract

Graphical abstract

Application of Transition Metal‐Catalyzed C−H Activation Strategies in the Synthesis and Functionalization of β‐Carbolines

“…Metal-coordination of imine group, followed by cyclometalation via ortho-CÀ H bond activation affords a five-membered rhodacyclic intermediate B. Additionally, the alkyne 15 a coordination to Rh-centre (C), followed by subsequent alkyne insertion into The 3d transition-metals like copper has grave attention toward CÀ H/NH annulations for the synthesis of alkaloids and biologically active molecules. [62] Similarly in 2018, Zhang and his group [63] reported CÀ H/NÀ H annulations mediated by copper to construct tetracyclic indoloquinolines (tetrahydro-β-carbolinones, 21) using CsF and TBAI in the presence of molecular oxygen from indolo-2-carboxamides (19). The electron-donating and withdrawing group containing indole derivatives were participated in the reaction with significant yield.…”

“…[1] Based on pyridine ring saturation, these molecules are categorized as: i) β-carbolines (Cs, unsaturated), ii) dihydro-βcarbolines (DHCs, partially saturated), iii) tetrahydro-β-carbolines (THCs, completely saturated). [4] β-Carboline alkaloids and their derivatives possess a significant array of pharmacological properties, including anti-inflammatory [5][6][7] (Eleagnine), anticonvulsant [8][9] (ZK91296), antiviral [10][11] (Harmine), antimicrobial [12] (Eudistomin W), antidepressant [13] (Harmane), anticancer [14][15][16][17][18][19][20] (Arborescidine C) as depicted in Figure 1. Numerous mechanisms has been displayed by this class of molecules like interaction with DNA, [21] topoisomerase I & II inhibition , [16,22] Mitogen-activated protein kinase inhibition (MAPK), [23] action on CDK's, [24] IĸB kinase (IKK) inhibition, [25] MAO-A and MAO-B inhibition etc.…”

One-pot, microwave-assisted copper(i)-catalysed dithiocarbamation: facile introduction of dithiocarbamate on imidazopyridines

“…Owing to the anticancer potentials of the imidazoheterocycles and DTCs, we performed in vitro cytotoxicity studies 33 for the synthesized analogues on HCT-116 (human colon cancer cells), MCF-7 (human breast cancer cells) and BEAS-2B (normal human lung cells). The priliminary screening revealed that few compounds displayed a percentage inhibition ranging from 50.42-91.10% (see Table S1, ESI †).…”

Brown Seaweed‐Derived Alginic Acid: An Efficient and Reusable Catalyst for Pictet‐Spengler Reaction to Access Tetrahydro‐β‐Carboline and Tetrahydroisoquinoline Frameworks

“…Both THBCs and THIQs are appealing architectures, representing natural and synthetic products with diverse array of biological activities (Figure 1). [9][10][11][12] Besides being molecules of pharmacological interest, [13][14][15][16][17][18][19] these heterocycles have been latently explored in several synthetic transformations, such as oxidative rearrangement, ring-opening and CÀ H functionalization. [20][21] Thus, in its synthetic domain, several variations of PSR were devised to prepare THBCs and THIQs.…”

“…Besides being molecules of pharmacological interest, [13–19] these heterocycles have been latently explored in several synthetic transformations, such as oxidative rearrangement, ring‐opening and C−H functionalization [20–21] . Thus, in its synthetic domain, several variations of PSR were devised to prepare THBCs and THIQs.…”