Functionalization of 3-chloroformylcoumarin to coumarin Schiff bases using reusable catalyst: an approach to molecular docking and biological studies

Abstract

Recently, heterogeneous catalysts have been explored eximiously in the synthesis of heterocyclic compounds. Therefore, here we used solid-supported heterogeneous silica sulfuric acid as a catalyst for the synthesis of Schiff's base of 3-chloroformylcoumarin in view of simplified procedure, reusability and acceptable efficiency, which are required in organic synthesis. An efficient and facile methodology is preferred for synthesis of a class of chromeno-3-substituted derivatives (1a–1l) with good yields. The molecular docking results showed excellent binding interactions with the Mycobacterium tuberculosis InhA-D148G mutant (PDB: 4DQU). The same biomolecules were screened for their in vitro anti-tubercular activity against the M.tb H37Rv strain and antimicrobial studies. Physico-chemistry, toxicity prediction with IC50 value and bioactivity score were also calculated for title compounds. Most active compounds were further tested for cytotoxicity studies and exhibited low-level cytotoxicity against Vero cells. The suggested conjugates are promising lead compounds for the subsequent investigation in search of new anti-tubercular agents. All the conjugates were obtained within the range and followed the Lipinski rule of 5, indicating more ‘drug-like’ nature.

Synthesis and Biological Properties of Coumarin Derivatives. A Review

“…The synthesis of substituted coumarins from substituted resorcinols and substituted β-keto esters in several steps, Scheme 39, was reported by Guan et al [66] Kumbar et al [67] developed a rapid method to synthesize the conjugated coumarin Schiff bases in good to excellent yields by using the silica sulphuric acid as the catalyst at room temperature in EtOH, Scheme 40.…”

“…As a result of this study, these nanocomposites can be good candidates to be used as heterogeneous catalysts to synthesize coumarin scaffolds with potential biological activities. [131] G. Wang et al [132] S.S. Kumbar et al [133] M.H. Shaikh et al [134] Antiviral L. Xian et al [135] M. Trkovnik et al [136] Y. Yuan et al [137] D. Chen et al [138] Inhibition of enzymatic targets J. Joubert et al [139] K. Kita, et al [140] S.Y.…”

“…The synthesis of substituted coumarins from substituted resorcinols and substituted β‐keto esters in several steps, Scheme 39, was reported by Guan et al [66] …”

Schiff Bases and Their Metallic Derivatives: Highly Versatile Molecules with Biological and Abiological Perspective

“…Photovoltaic characteristics of pyridine Schiff bases have been reported by illumination-dependent current-voltage measurements in solar cell applications [22]. Nickel Schiff base complexes have been studied for molecular docking experiments and their interaction with β-lactamase [23]. Schiff bases have successfully employed in vitro as well as in vivo for probing real-time sensing and analysis of Al 3+ in a variety of diseases in human beings [24].…”

Metal-free Catalyzed One-Pot Multicomponent Synthesis of (E)-3-(2-((5-(Benzylideneamino)-1,3,4-thiadiazol-2-yl)thio) Acetyl)-2H-chromen-2-one Derivatives and Their Biological Evaluation

“…ey are also known as azomethine or imine (-C�N-) types of compounds which have demonstrated several important biological properties including antimicrobial [14], anticonvulsant [15], antioxidant [16], anthelmintic [17], antitubercular [18], anticancer [19], and anti-inflammatory [20] properties. A variety of catalysts have been reported for the synthesis of Schiff base containing scaffolds such as dodecatungstosilicic acid/P 2 O 5 [21], Cu(NO 3 ) 2 , 6H 2 O [22], silica sulfuric acid [23], and hydrotalcites [24]. erefore, in this study, we have developed a novel facile methodology for the synthesis of Schiff base containing scaffolds by one-pot multicomponent reaction (MCR) employing metal-free catalyst.…”