15875-58-8Relevant 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.
Synthesis of novel spiro-tetrahydroquinoline derivatives and evaluation of their pharmacological effects on wound healing
Liou, Yan-Cheng,Lin, Yan-An,Wang, Ke,Yang, Juan-Cheng,Jang, Yeong-Jiunn,Lin, Wenwei,Wu, Yang-Chang
, (2021/06/14)
A highly diastereoselective method for the synthesis of novel spiro-tetrahydroquinoline derivatives is reported here, using a one-pot reaction method. All compounds were characterized by1 H-nuclear magnetic resonance (NMR) and mass spectroscopy
Rapid and selective synthesis of spiropyrazolines and pyrazolylphthalides employing Seyferth-Gilbert reagent
Gupta, Ashis Kumar,Vaishanv, Narendra Kumar,Kant, Ruchir,Mohanan, Kishor
, p. 6411 - 6415 (2017/08/10)
An unexpected product-selectivity in the reaction of 2-arylideneindane-1,3-dione with dimethyl diazomethylphosphonate leading to the formation of two different types of products is reported. The reaction carried out in acetone in the presence of catalytic amount of cesium fluoride afforded spiropyrazoline phosphonates via 1,3-dipolar cycloaddition reaction, whereas the reaction in methanol yielded an interesting class of pyrazolylphthalides. This strategy provides an efficient alternative method for the construction of pyrazolylphthalides, and moreover, the process is general, works under mild conditions, and exhibits high functional group compatibility.
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
Enantioselective synthesis of spirocyclic cyclopentenes: Asymmetric [3+2] annulation of 2-arylideneindane-1,3-diones with MBH carbonates derivatives catalyzed by multifunctional thiourea-phosphines
Hu, Fangle,Wei, Yin,Shi, Min
supporting information; experimental part, p. 7911 - 7919 (2012/10/08)
The [3+2] annulation reactions of 2-arylideneindane-1,3-diones with Morita-Baylis-Hillman (MBH) carbonates proceeded smoothly in the presence of multifunctional thiourea-phosphines to produce the corresponding quaternary carbon centered spirocyclic cyclop
Unexpected formation of fluorine-containing multiply substituted dispirocyclohexanes from the reaction of ethyl-4,4,4-trifluoro-1,3- dioxobutanoate and 2-arylideneindane-1,3-diones
Dai, Baifan,Song, Liping,Wang, Pengyuan,Yi, Hai,Cao, Weiguo,Jin, Guifang,Zhu, Shizheng,Shao, Min
scheme or table, p. 1842 - 1846 (2009/12/04)
In the presence of a catalytic amount of piperidine (10 mol%), reaction of ethyl 4,4,4-trifluoro-3-oxobutanoate 3 and 2-arylidene-indane-1,3-diones 4 gave the unexpected fluorine-containing multiply substituted dispirocyclohexanes 5 in good yields. The st
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
