6240-52-4Relevant 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.
Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides
Huang, Jie,Lee, Kevin,Ma, Ping,Sun, Shaofa,Wang, Gangqiang,Wang, Jian,Wu, Yang,Xing, Yalan
supporting information, p. 18776 - 18780 (2021/10/26)
A highly diastereoselective spiro-cyclopropanation reaction of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides has been developedviabase-induced annulation. This efficient and simple protocol features simple operations, mild conditions and excellent functional group compatibility. A variety of structurally interesting spiro-cyclopropanes were prepared in excellent yields and diastereomeric ratios (up to 97% yield and 20?:?1 dr). Also, ring expansion of the cyclopropanation product to quickly deliver a complex indeno[1,2-c]pyridazine structure showcased an interesting application of this method.
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
Phosphine-catalyzed [4 + 2] annulation of γ-substituent allenoates: Facile access to functionalized spirocyclic skeletons
Li, Erqing,Huang, You,Liang, Ling,Xie, Peizhong
supporting information, p. 3138 - 3141 (2013/07/26)
The first phosphine-catalyzed [4 + 2] annulation of γ-substituted allenoates with 2-arylidene-1H-indene-1,3(2H)-diones is disclosed. In the reaction, the γ-substituted allenoate serves as a new type of 1,4-dipolar synthon; this broadens the application of
Triphenylarsine-catalyzed cyclopropanation: Highly stereoselective synthesis of trans-2,3-dihydro-spiro[cyclopropane-1,2′-indan-1′, 3′-dione] from alkene and phenacyl bromide
Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi,Chen, Jie,Deng, Hongmei,Wu, Danyi
, p. 2200 - 2214 (2008/09/21)
The triphenylarsine-catalyzed approach for the highly stereoselective synthesis of trans-2,3-dihydro-spiro[cyclopropane-1,2′-indan-1′, 3′-dione] with alkenes and phenacyl bromide in organic solvent is described. The triphenylarsine-catalyzed cyclopropanat
Solvent-free synthesis of 2-arylideneindan-1,3-diones in the presence of magnesium oxide or silica gel under grinding
Wu, Danyi,Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi
, p. 3157 - 3162 (2007/10/03)
The solvent-free synthesis of 2-arylideneindan-1,3-diones can be achieved in the presence of MgO or silica gel under grinding. This process is simple, efficient, and environmentally benign. Copyright Taylor & Francis, Inc.
