178697-87-5Relevant academic research and scientific papers
Indane-1,3-diones: As potential and selective α-glucosidase inhibitors, their synthesis, in vitro and in silico studies
Hameed, Shehryar,Iqbal, Jamshed,Kanwal,Khan, Khalid Mohammed,Khan, Shahid Ullah,Mukhtar, Asma,Perveen, Shahnaz,Shah, Shazia,Zaib, Sumera
, p. 887 - 902 (2021/10/21)
Background: Diabetes mellitus is one of the most chronic metabolic disorders. Since past few years, our research group had synthesized and evaluated libraries of heterocyclic compounds against α and β-glucosidase enzymes and found encouraging results. The current study comprises of evaluation of indane-1,3-dione as antidiabetic agents based on our previously reported results obtained from closely related moiety isatin and its derivatives. Objective: A library of twenty three indane-1,3-dione derivatives (1-23) was synthesized and evaluated for α and β-glucosidase inhibitions. Moreover, in silico docking studies were carried out to in-vestigate the putative binding mode of selected compounds with the target enzyme. Methods: The indane-1,3-dione derivatives (1-23) were synthesized by Knoevenagel condensation of different substituted benzaldehydes with indane-1,3-dione under basic condition. The structures of synthetic molecules were deduced by using different spectroscopic techniques, including1 H-,13 C-NMR, EI-MS, and CHN analysis. Compounds (1-23) were evaluated for α and β-glucosidase inhibitions by adopting the literature protocols. Result: Off twenty three, eleven compounds displayed good to moderate activity against α-glucosidase enzyme, nonetheless, all compounds exhibited less than 50% inhibition against β-glucosidase enzyme. Compounds 1, 14, and 23 displayed good activity against α-glucosidase enzyme with IC50 values of 2.80 ± 0.11, 0.76 ± 0.01, and 2.17 ± 0.18 μM, respectively. The results have shown that these compounds have selectively inhibited the α-glucosidase enzyme. The in silico docking studies also supported the above results and showed different types of interactions of synthetic molecules with the active site of enzyme. Conclusion: The compounds 1, 14, and 23 have shown good inhibition against α-glucosidase and may potentially serve as lead for the development of new therapeutic representatives.
Phosphine-Catalyzed Cascade Michael Addition/[4+2] Cycloaddition Reaction of Allenoates and 2-Arylidene-1,3-indanediones
Shi, Wangyu,Mao, Biming,Xu, Jiaqing,Wang, Qijun,Wang, Wei,Wu, Yongjun,Li, Xuefeng,Guo, Hongchao
supporting information, p. 2675 - 2680 (2020/03/26)
The phosphine-catalyzed cascade Michael addition/[4+2] cycloaddition reaction of tetrahydrobenzofuranone-derived allenoates and 2-arylidene-1,3-indanediones has been reported, affording spirocyclic 1,3-indanedione derivatives in moderate to high yields wi
Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Vinylethylene Carbonates with 2-Arylidene-1,3-Indandiones: Synthesis of Tetrahydrofuran-Fused Spirocyclic 1,3-Indandiones
Gao, Xing,Guo, Hongchao,Jiang, Feng,Shi, Wangyu,Shi, Xueyan,Wang, Wei,Wu, Yongjun,Zhang, Cheng,Zhang, Huihui
supporting information, (2020/08/06)
An asymmetric [3+2] cycloaddition of 2-arylidene-1,3-indandiones with vinylethylene carbonates (VECs) had been achieved in the presence of Pd2dba3·CHCl3 and axially chiral phosphoramidite ligand. The reaction of various su
A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters
Yang, Shu-Mei,Karanam, Praneeth,Wang, Min,Jang, Yeong-Jiunn,Yeh, Yu-Sheng,Tseng, Ping-Yao,Ganapuram, Madhusudhan Reddy,Liou, Yan-Cheng,Lin, Wenwei
supporting information, p. 1398 - 1401 (2019/02/05)
An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene o
Direct β-acylation of 2-arylidene-1,3-indandiones with acyl chlorides catalyzed by organophosphanes
Lee, Chia-Jui,Sheu, Chia-Ning,Tsai, Cheng-Che,Wu, Zong-Ze,Lin, Wenwei
supporting information, p. 5304 - 5306 (2014/05/06)
We have developed an organophosphane-catalyzed direct β-acylation of a series of conjugated systems bearing ketone, amide and ester functionalities using acyl chlorides as trapping reagents. A wide variety of highly functional ketone derivatives were gene
Synthesis and thermal transformations of spiro-fused N- phthalimidoaziridines Dedicated to Professor Armin de Meijere on the occasion of his 75th birthday
Pankova, Alena S.,Kuznetsov, Mikhail A.
supporting information, p. 2499 - 2503 (2014/05/06)
Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3- diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-2,2′-indene]-1′,3′-diones in good yields. Heating these aziridines with stan
Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile
Cao, Ying,Zhang, Song-Chen,Zhang, Min,Shen, Guang-Bin,Zhu, Xiao-Qing
, p. 7154 - 7168 (2013/08/23)
A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.
