- Indane-1,3-diones: As potential and selective α-glucosidase inhibitors, their synthesis, in vitro and in silico studies
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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.
- Hameed, Shehryar,Iqbal, Jamshed,Kanwal,Khan, Khalid Mohammed,Khan, Shahid Ullah,Mukhtar, Asma,Perveen, Shahnaz,Shah, Shazia,Zaib, Sumera
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p. 887 - 902
(2021/10/21)
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- Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides
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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.
- Huang, Jie,Lee, Kevin,Ma, Ping,Sun, Shaofa,Wang, Gangqiang,Wang, Jian,Wu, Yang,Xing, Yalan
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supporting information
p. 18776 - 18780
(2021/10/26)
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- Chemo- and Diastereoselective Construction of Indenopyrazolines via a Cascade aza-Michael/Aldol Annulation of Huisgen Zwitterions with 2-Arylideneindane-1,3-diones
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A cascade aza-Michael/Aldol annulation of 2-arylideneindane-1,3-diones with in situ generated Huisgen zwitterions has been developed. This reaction afforded the desired products in moderate to good yields (up to 87%) with excellent chemo- and diastereoselectivity (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important indenopyrazoline derivatives containing two contiguous chiral centers including a quaternary stereogenic center. (Figure presented.).
- Li, Yuming,Zhang, Haikun,Wei, Rong,Miao, Zhiwei
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supporting information
p. 4158 - 4164
(2017/10/11)
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- Styryl and functionalized aryl derivatives of lawsone through metal-free cross-coupling of its BF3-activated phenyliodonium ylide with cinnamaldehydes and arylaldehydes
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Phenyliodonium ylide of lawsone activated with BF3?Et2O reacts with cinnamaldehydes to afford 2-hydroxy-3-styryl-1,4-naphthoquinones in good to excellent yields and relatively high level of stereospecificity through deformylation of the aldehydes. The product yield is diminished with a methoxy substituted cinnamaldehyde and becomes zero with a dimethoxy substituted substrate giving rise to another product, 2-hydroxy-3-aryl-1,4-naphthoquinone. The reaction of the same ylide with salicylic aldehydes forms 2-hydroxy-3-(2-hydroxyaryl)-1,4-naphthoquinones and/or benzo[d]naphtha[2,1-b]furano-5,6-diones, depending on the reaction conditions applied. Plausible reaction mechanisms explaining the formation of these products are proposed. The products showed potent antioxidant activity and inhibited lipoxygenase.
- Malamidou-Xenikaki, Elizabeth,Tsanakopoulou, Maria,Chatzistefanou, Maria,Hadjipavlou-Litina, Dimitra
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p. 5650 - 5661
(2015/08/03)
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- Synthesis and antimicrobial study of novel 1-aryl-2-oxo-indano[3,2-d] pyrido/pyrimido[1,2-b]pyrimidines
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A series of 2-(arylidene)-indan-1, 3-diones 1 were prepared by Knoevenagel reaction between indane-1,3-dione and the appropriate araldehydes. The α,β-enones 1 have been used as a component of Michael addition with equimolar amounts of 2-aminopyridine/2-am
- Sarvesh, Pandey K.,Nizamuddin, Khan
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experimental part
p. 418 - 423
(2009/04/04)
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- Triphenylarsine-catalyzed cyclopropanation: Highly stereoselective synthesis of trans-2,3-dihydro-spiro[cyclopropane-1,2′-indan-1′, 3′-dione] from alkene and phenacyl bromide
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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
- Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi,Chen, Jie,Deng, Hongmei,Wu, Danyi
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p. 2200 - 2214
(2008/09/21)
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- Solvent-free synthesis of 2-arylideneindan-1,3-diones in the presence of magnesium oxide or silica gel under grinding
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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.
- Wu, Danyi,Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi
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p. 3157 - 3162
(2007/10/03)
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- Discovery of the first series of inhibitors of human papillomavirus type 11: Inhibition of the assembly of the E1-E2-Origin DNA complex
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We have discovered a series of inhibitors of the assembly of the HPV11 E1-E2-origin DNA complex, which incorporate an indandione fused to a substituted tetrahydrofuran.
- Yoakim, Christiane,Ogilvie, William W.,Goudreau, Nathalie,Naud, Julie,Hache, Bruno,O'Meara, Jeff A.,Cordingley, Michael G.,Archambault, Jacques,White, Peter W.
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p. 2539 - 2541
(2007/10/03)
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