Medicinal Chemistry of Indane and Its Analogues: A Mini Review

Abstract

‘Indane′ and its analogues indene, 1‐indenone, and 1,3‐indandione present an attractive biological profile for the rational development of therapeutic molecules. The indane/ indene moieties contain aromatic benzene ring fused with an aliphatic cyclopentane/ cyclopentene ring, which provides a rigid bicyclic ring‐framework enriched with diverse chemical properties. The multifarious possibilities for varying the substituent pattern on these fused ring systems enable the extensive appraisal of structure‐activity relationship analysis of rationally designed therapeutic molecules deliberated at their molecular targets. Indane analogues serve as useful scaffolds for the development of efficacious pharmaceuticals and commercial drugs, including Indinavir, Sulindac, and donepezil; whereas the pharmacophores based on indane moiety such as Aminoindanes and Indanedione contribute towards the development of neuroleptics and neuroprotective molecules. Similarly, the Indane‐carboxamide derivatives present a robust candidature as CGRP receptor antagonists, while substituted Indane and its analogue Indene present a privileged profile for the development of anticancer therapeutics by targeting the multifaceted oncologic pathways. Besides, the indane natural product scaffolds serve as perspective drug candidates with marked therapeutic properties. The present review summarizes the medicinal chemistry aspects of indane nucleus and its analogues as anticancer, anti‐inflammatory, and neuroprotective agents for the coherent development of impending therapeutics.

Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins

“…Therefore, this structural motif has attracted great attention of researchers in the field of synthetic organic chemistry and pharmaceutical chemistry all over the world. In the previous few decades, a large number of strategies emerged to construct heterocyclic compounds with this skeleton or similar ones [6][7][8][9][10], aiming to explore biological activity and medicinal value conveniently and comprehensively. However, as we know, the construction of these compounds is mostly carried out through transition-metal-catalyzed cyclization reactions [11][12][13][14], whereas strategies using bifunctional chiral thiourea catalysts are rarely reported.…”

IntramolecularAnti‐Carbolithiation of Alkynes: Stereo‐Directing Effect of Lithium‐Coordinating Substituents

“…In the course of our ongoing studies on the formation of carbocycles via intramolecular carbolithiation, [22,23] we took an interest in the 5‐ exo ‐ dig cyclization of o ‐homopropargyl aryllithiums. Such reaction provides an access to functionalized indans, which are useful scaffolds for the development of pharmaceuticals [24] . We were particularly concerned by the influence of oxygen‐based propargylic substituents on the stereochemical course of the carbolithiation and envisioned investigating substituents with varying Li‐coordinating abilities (OH, OMe, OMOM, OCONEt 2 and OSiR 3 ) [25] …”

“…Such reaction provides an access to functionalized indans, which are useful scaffolds for the development of pharmaceuticals. [24] We were particularly concerned by the influence of oxygen-based propargylic substituents on the stereochemical course of the carbolithiation and envisioned investigating substituents with varying Li-coordinating abilities (OH, OMe, OMOM, OCONEt 2 and OSiR 3 ). [25] Herein we present our combined experimental and theoretical results.…”

Synthesis of 1-Trifluorometylindanes and Close Structures: A Mini Review

“…One of the most important types of organic compounds is indanes, which possess various valuable practical properties including biological activity. There are several reviews on the synthesis and use of indanes [14][15][16][17][18]. The introduction of a trifluorometyl group CF 3 in the indane core may bring new, important properties for these compounds.…”