1408316-03-9Relevant academic research and scientific papers
Synthesis, photophysical and electrochemical properties of donor-acceptor type hydrazinyl thiazolyl coumarins
Godugu, Kumar,Gundala, Thrivikram Reddy,Bodapati, Ramakrishna,Yadala, Venkata Divya Sri,Loka, Subramanyam Sarma,Nallagondu, Chinna Gangi Reddy
, p. 7007 - 7016 (2020)
A water-mediated MCR strategy has been developed for the synthesis of donor (D)-acceptor(A) type hydrazinyl thiazolyl coumarins (HTCs) (4) in excellent isolated yields (90-98%) from a three %component reaction of aromatic aldehydes/ketones (1), thiosemicarbazide (2) and 3-(2-bromoacetyl)-2H-chromen-2-one (3) catalyzed by an environmentally compatible montmorillonite (MMT) K10 clay at RT for 20-40 min. The present MCR strategy has several advantages that include its wide-spread substrate scope, eco-compatibility, short reaction times and products that do not require chromatographic purification. Besides, the method is simple to perform, it is easy to construct C-N, C N and C-S bonds in one pot and the reaction can be scaled up to a gram level. Moreover, the catalyst can be reused 7 times without significant change of activity. The photophysical properties of the synthesized D-A type HTCs are also studied and it was noticed that the fluorescence properties can be varied with the position of electron donating group on the aromatic ring of aldehyde/ketone of HTCs. Most of the compounds exhibited bright fluorescence in chloroform (1.0 × 10?5M) with emission maxima ranging from 409 to 511 nm and large Stokes shifts. Further, the HOMO and LUMO energy levels of the HTCs are found in the range from ?5.65 eV to ?5.22 eV and ?2.67 eV to ?2.17 eV, respectively, and in good agreement with the reported hole transporting materials.
Synthesis and Biological Evaluation of 3-thiazolocoumarinyl Schiff-base Derivatives as Cholinesterase Inhibitors
Raza, Rabia,Saeed, Aamer,Arif, Mubeen,Mahmood, Shamsul,Muddassar, Muhammad,Raza, Ahsan,Iqbal, Jamshed
, p. 605 - 615 (2012/10/30)
On the basis of the observed biological activity of the coumarins, a new set of 3-thiazolocoumarinyl Schiff-base derivatives with chlorine, hydroxy and methoxy functional group substitutions were designed and synthesized. These compounds were tested against acetylcholinesterase from Electrophorus electricus and butyrylcholinesterase from horse serum and their structure-activity relationship was established. Studies revealed them as the potential inhibitors of cholinesterase (acetylcholinesterase and butyrylcholinesterase). The 3f was found to be most potent against acetylcholinesterase with Ki value of 1.05±0.3μm and 3l showed excellent inhibitory action against butyrylcholinesterase with Ki value of 0.041±0.002μm. The synthesized compounds were also docked into the active sites of the homology models of acetylcholinesterase and butyrylcholinesterase to predict the binding modes of these compounds. It was predicted that most of the compounds have similar binding modes with reasonable binding affinities. Our docking studies have also shown that these synthesized compounds have better interaction patterns with butyrylcholinesterase over acetylcholinesterase. The main objective of the study was to develop new potent and selective compounds, which might be further optimized to prevent the progression of the Alzheimer's disease and could provide symptomatic treatment.
