Synthesis of 1-indanones with a broad range of biological activity

Abstract

This comprehensive review describes methods for the preparation of 1-indanones published in original and patent literature from 1926 to 2017. More than 100 synthetic methods utilizing carboxylic acids, esters, diesters, acid chlorides, ketones, alkynes, alcohols etc. as starting materials, have been performed. This review also covers the most important studies on the biological activity of 1-indanones and their derivatives which are potent antiviral, anti-inflammatory, analgesic, antimalarial, antibacterial and anticancer compounds. Moreover, they can be used in the treatment of neurodegenerative diseases and as effective insecticides, fungicides and herbicides.

Design and Synthesis of Fluorinated and/or Hydroxylated 2‐Arylidene‐1‐indanone Derivatives as an Inhibitor of LPS‐stimulated ROS Production in RAW 264.7 Macrophages with Structure–Activity Relationship Study

“…20 1-Indanone and their derivatives have been extensively studied recently and have shown very good biological activity as anti-inflammatory, anti-cancer, antiviral, and antibacterial. 21 Studies carried out on compounds possessing 1-indanone moiety demonstrated a very potent anti-inflammatory activity in RAW 264.7 macrophages and inhibiting NO production up to 61%. 22 Thereafter, in the quest to discover valuable anti-inflammatory compounds, our research groups have performed some synthetic modifications of chalcone to 2-benzylidene-1-indanone ( Figure 1(c)) and 3-benzylidenechroman-4-ones derivatives that inhibited the production of ROS in LPS-stimulated RAW 264.7 macrophages.…”

“…Chalcone derivatives having thiophenyl, furanyl and/or hydroxyphenyl moiety (Figure (b)) illustrating the importance of hydroxyphenyl and thiophenyl moiety for inhibiting the production of ROS stimulated by LPS in RAW 264.7 macrophages was reported by our previous research group . 1‐Indanone and their derivatives have been extensively studied recently and have shown very good biological activity as anti‐inflammatory, anti‐cancer, antiviral, and antibacterial . Studies carried out on compounds possessing 1‐indanone moiety demonstrated a very potent anti‐inflammatory activity in RAW 264.7 macrophages and inhibiting NO production up to 61% .…”

Cp*Co(III)‐Catalyzed C−H Alkenylation of Aromatic Ketones with Alkenes

“…A base mediated intramolecular 1,4‐addition of acetophenone to acrylates produced indanone 6 (Scheme a), a very demanding motif of biological importance . Divinyl sulfone can be modified by incorporating two different arenes using our alkenylation protocol. The best yield was obtained when electron‐rich aromatic ketone was incorporated in the second step (Scheme b).…”

Synthesis and Structure Activity Relationships of Chalcone based Benzocycloalkanone Derivatives as Adenosine A1 and/or A2A Receptor Antagonists

“…1) [16]; which contains the 1-indanone moiety. The 1-indanone moiety is associated with wide-ranging biological activity and considered a privileged scaffold in medicinal chemistry [17,18]. In fact, it is present in therapeutic agents, such as the acetylcholinesterase inhibitor donepezil (Aricept ® ) (1d) (▶Fig.…”