7-Azaindole Analogues as Bioactive Agents and Recent Results

Abstract

Azaindoles have been accepted as important structures having various biological activities in medicinal chemistry in novel drug discovery. Various azaindole derivatives have been used commercially and newer analogues are synthesized continuously. As in literature, azaindole is a very potent moiety, its derivatives displayed a number of biological activities such as kinase inhibitors, cytotoxic agents, anti-angiogenic activity, CRTh2 receptor antagonists, melanin agonists, nicotine agonists, effectiveness in alzheimer disease, cytokinin analogs, Orai inhibitors in asthma and chemokine receptor- 2 (CCR2) antagonists. This review consists of biological activities of various azaindole analogs, reported so far, and their structure activity relations, along with future perspectives in this field.

Ligand-Controlled Selectivity in the Pd-Catalyzed C–H/C–H Cross-Coupling of Indoles with Molecular Oxygen

“…These 7-azaindoles are highly interesting heterocycles in medicinal chemistry. 27 Moreover, the reaction could be used successfully for the coupling of 5,6dihydro-4H-pyrrolo[3,2,1-ij]quinoline, which forms the basic carbon skeleton of the lilolidine alkaloids (17, 76%). The reaction was found to be ineffective in the coupling of other heteroaromatics, such as benzofuran and benzothiophene.…”

“…Remarkably, 1-methyl-7-azaindole ( 16 , 53%) could be successfully coupled despite the presence of a coordinating, pyridine-like N -heteroatom. These 7-azaindoles are highly interesting heterocycles in medicinal chemistry . Moreover, the reaction could be used successfully for the coupling of 5,6-dihydro-4H-pyrrolo­[3,2,1- ij ]­quinoline, which forms the basic carbon skeleton of the lilolidine alkaloids ( 17 , 76%).…”

Oxidatively induced reactivity in Rh(iii)-catalyzed 7-azaindole synthesis: insights into the role of the silver additive

“…7-Azaindoles are an important class of fused hetero-carbocycles that are key scaffolds of cancer therapeutics and many other drugs for life-threatening conditions. [1][2][3][4][5][6] The synthesis of 7azaindoles can be achieved from either a ve-membered pyrrole ring or a six-membered pyridine ring precursor subjected to appropriate cyclization mediated by transition metal catalysts (Scheme 1). 7 The major caveat in these synthetic schemes is the ability of the pyrrole and pyridine precursors to strongly coordinate to transition metal catalysts and deactivate them.…”

Recent Developments in the Cyclization of Alkynes and Nitrogen Compounds for the Synthesis of Indole Derivatives

“…[5] Indoles have been studied for over one hundred years and these studies delivered to the scientific community impressive advances in biological properties [6] and synthetic applications of this class of compounds. [7] Although less studied, its derivatives azaindole, [8] carbazole, [9] carboline, [10] indazole, [11] 3H-indole, [12] indoline, [13] indolizine, [14] isoindole, [15] and isoindoline [16] have gained prominence in organic synthesis, medicinal chemistry, materials science, and industry. Because of such an application, the synthesis of indole derivatives has been a subject of several approaches.…”