An expedient synthesis of novel spiro[indenoquinoxaline-pyrrolizidine]-pyrazole conjugates with anticancer activity from 1,5-diarylpent-4-ene-1,3-diones through the 1,3-dipolar cycloaddition/cyclocondensation sequence

Abstract

Endo-1,3-dipolar cycloaddition of azomethine ylides generated in situ from 11H-indeno[1,2-b]quinoxalin-11-one and L-proline/thiaproline to (E)-1,5-diarylpent-4-ene-1,3-diones led to the 3-hydroxy-3-aryl-1-(1'-arylspiro[indeno[1,2-b]quinoxaline-11,3'-(thia)pyrrolizidin]-2'-yl)prop-2-en-1-ones containing the 1,3-diketone fragment. Upon processing of these adducts with arylhydrazine hydrochlorides...

Multifunctional Derivatives of Spiropyrrolidine Tethered Indeno-Quinoxaline Heterocyclic Hybrids as Potent Antimicrobial, Antioxidant and Antidiabetic Agents: Design, Synthesis, In Vitro and In Silico Approaches

“…As shown in Scheme 1 , we have chosen as a model the following four components: ninhydrin 1, o-phenylenediamine 2, sarcosine 3 and ( E )-3-arylidene-1-methylpyrrolidine-2,5-dione 4a (Ar = C6H5) [ 49 , 50 ]. The reaction was carried out at different temperatures in acetonitrile and methanol.…”

New multicomponent reactions in water: a facile synthesis of 1,3-dioxo-2-indanilidene-heterocyclic scaffolds and indenoquinoxalines through reaction of ninhydrin-malononitrile adduct with diverse N-binucleophiles

“… 31 They exhibit various biological properties, such as antitumor activity (I), 32 c-Jun N-terminal kinase (JNK) inhibition (II), 33 acetylcholinesterase (AChE) inhibitory activity (III), 34 α-glucosidase inhibition (IV), 35 tryptophan-tRNA synthetase (TrpRS) inhibition (V) 36 and antimicobacterial activity (VI). 37 In addition, substituted spiro indeno[1,2- b ]quinoxaline (VII) can be utilized as a photonic sensor to detect fluorescent dyes in the waste effluents of textiles, dyes, paper, and other industrial products 38 and 11 H -indeno[1,2- b ]quinoxalin-11-one (VIII) shows acid corrosion inhibitory effect on mild steel surfaces. 39 ( Fig.…”

Synthetic small molecule inhibitors of KRAS expression and antiproliferative small molecules isolated from Onnia tomentosa and Sarcodon scabripes

“…Cycloaddition reactions are one of the most important classes of reactions in organic synthesis and have been extensively used over the past 50 years. Within this class, 1,3-dipolar cycloaddition reactions which involved the chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring have been studied widely owing to their ability to form multiple bonds with high regio-and stereochemical selectivity (Akondi et al, 2017;Ang et al, 2013;Boudriga et al, 2020;Bradner, 2001;Kathiravan et al, 2012;Rouatbi et al, 2016;Saravana Mani et al, 2018;Thangamani, 2010;Zimnitskiy et al, 2020). By proceeding the reaction in an intramolecular sense, it can produce two rings and up to four new chiral centers, making it a powerful method for organic synthesis with specific regio-and stereochemical selectivity (Coldham & Hufton, 2005).…”

“…1,3-dipolar cycloadditions are important carbon-carbon bond-forming reactions in organic synthesis for building five-membered heterocycles and have been used for the synthesis of pyrrolidine, pyrrolizidine, pyrrolothiazole, and pyrazolidine derivatives (Boudriga et al, 2020;Gong et al, 2021;Hussein et al, 2017;Saravanan et al, 2013;Suresh Babu et al, 2012). Among all the different types of cycloadduct derivatives formed through the 1,3-dipolar cycloaddition, pyrrolidine and pyrrolizidine are two exciting classes of bioactive compounds which form the central skeleton of various bioactive molecules with a wide range of therapeutic applications (Akondi et al, 2017;Ali et al, 2010;Ang et al, 2013;Bradner, 2001;Kathiravan et al, 2012;Rouatbi et al, 2016;Saravana Mani et al, 2018;Thangamani, 2010;Tumskiy et al, 2019;Zimnitskiy et al, 2020). For instance, several molecules with a pyrrolizidine nucleus have been antimicrobial (Kathiravan et al, 2012), acetylcholinesterase (AChE) inhibitory (Akondi et al, 2017), antifungal (Thangamani, 2010), and antitumor (Bradner, 2001) activities.…”

“…successfully synthesized and shown to have antitubercular(Rouatbi et al, 2016), anticancer(Saravana Mani et al, 2018;Zimnitskiy et al, 2020), antioxidant (Saravana Mani et al, 2018,…”