- Simple indole-based colorimetric sensors with electron-withdrawing chromophores: Tuning selectivity in anion sensing
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Three simple colorimetric anion sensors (1, 2, and 3) containing anthrone, 1,3-indanedione, and malononitrile as signaling chromophores and an indole binding site have been designed and synthesized. The introduction of electron-withdrawing groups can not only provide chromogenic signal output, but also tune the sensitivity and selectivity of indole-based anion sensors by electron push-pull features. Their anion binding and sensing properties were investigated in detail by dramatic color changes, UV-vis absorption, and 1H NMR. As results revealed, sensor 1 showed high selectivity for F- over AcO- and H2PO4- with a distinct change in color due to the deprotonation of indole NH group. The excellent selectivity of 1 for F- can be attributed to the fitness in the acidity of its NH-group, which is tuned to be able to distinguish the subtle difference in the affinity of F-, AcO-, and H 2PO4- to NH proton.
- Lv, Yongjun,Guo, Yong,Xu, Jian,Shao, Shijun
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- 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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- 2-Arylidene-1-indandiones as Pleiotropic Agents with Antioxidant and Inhibitory Enzymes Activities ?
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Indandiones are a relatively new group of compounds presenting a wide range of biological activities. The synthesis of these compounds was performed via a Knoevenagel reaction between an aldehyde and 1,3-indandione and were obtained with a yield up to 54%
- Kouzi, Olympia,Pontiki, Eleni,Hadjipavlou-Litina, Dimitra
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- Synthesis and molluscicidal activity of new chromene and pyrano[2,3-c]pyrazole derivatives
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The chromene derivative 4 reacts with acetic anhydride, phenylisothiocyanate and ethyl orthoformate to afford the N-acetyl derivative 6, the chromenopyrimidine 8 and the formimidate 9, respectively. 2-(1H-Indol-3-ylmethylene)-malononitrile 10b reacts with
- Abdelrazek, Fathy M.,Metz, Peter,Kataeva, Olga,Jaeger, Anne,El-Mahrouky, Sherif F.
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p. 543 - 548
(2008/12/21)
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- REACTION PRODUCTS OF 1,3-INDANONE WITH HETEROAROMATIC CARBALDEHYDES: SYNTHESIS, STRUCTURE AND NMR-INVESTIGATIONS
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The synthesis of 1:1 condensation products from 1,3-indadione and various heteroatomic carbaldehydes is described.Employment of aldehydes derived from ?-deficient N-heteroaromatics was found to lead also to 2:1 adducts via Michael-addition of the 1,3-dike
- Franz, Claudia,Heinisch, Gottfried,Holzer, Wolfgang,Mereiter, Kurt,Strobl, Barbara,et al.
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p. 2527 - 2552
(2007/10/03)
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- Reaction of indan-1,3-dione with indole, indole derivatives and other heterocycles
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Reaction of indan-1,3-dione (1) with indole, 2-phenylindole, antipyrine, 4-aminoantipyrine and 3-amino-1-phenylpyrazol-2-in-5-one afford 2a,b,3 and 4a,b, respectively.Treatment of 2a, 3 and 4a with hydrazoic acid under Schmidt reaction conditions, give the 4-substituted carbostyriles 5a,b and 6 respectively.Alkylation of 1 with gramine methosulfate and skatyl bromide afford 8 and 10, respectively.Condensation of 1 with 3-formylindole afford 11 which on treatment with dimethylamine furnish the gramine derivative (12).
- Hammouda, M.
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p. 1181 - 1184
(2007/10/02)
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- ELECTROCHEMISTRY OF AUTOCOMPLEX COMPOUNDS. III. ELECTROCHEMICAL AND SPECTRAL PROPERTIES OF 2-METHYLENE-1,3-INDANDIONE DERIVATIVES
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By reactions of indan-1,3-dione with a number of aromatic, heterocyclic, and ferrocenyl-containing aldehydes a series of autocomplexes, derivatives of 2-methyleneindan-1,3-dione, was synthesized.By electrochemical and spectral methods the mechanisms of in
- Butin, K. P.,Il'ina, I. G.,Moiseeva, A. A.,Reutov. O. A.
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p. 1465 - 1470
(2007/10/02)
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- Indanediones-1,3 VIII. Hydroxy-2 indolyl-2 indanediones-1,3, (indolyl-3 methylene)-2 indanediones-1,3 et derives: recherche d'une activite anti-inflammatoire
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1,3-Indandiones VIII. 2-Hydroxy-2-indolyl-1,3-indandiones, 2-(indol-3-ylmethylene indandione and derivatives: search for anti-inflammatory activity.A series of 2-hydroxy-2-indolyl-1,3-indandiones, diversely substituted on the heterocycle were synthetized in order to study their anti-inflammatory activity.Catalytic hydrogenation gave 2,3-dihydroxy-1 indanones 6 and NaBH4 reduction of 3i led to the corresponding indanetriol 7i.Base-catalyzed isomerization of hydroxy-β-diketones 3 furnished 3-indololylcarbonyl phthalides 9.Only compound 3d exhibited a significant inhibition of mouse paw edema.Experimentation in the rat paw edema test confirmed the anti-inflammatory effect of 3d, but it was associated with an anti-coagulant activity. ω-Amino-alkylation of the indole nitrogen of 3d led to loss of anti-inflammatory activity.Introduction of a double bond between the indandione and indole nuclei, leading to 2-(indol-3-ylmethylene)-1,3 indandiones 12, proved ineffective in raising this activity. 2-hydroxy-2-indolyl-1,3-indandiones/ 2,3-dihydroxyindanones/ 1,2,3-indantriols/ 3-indolylcarbonyl-phthalides/ 2-(indol-3-ylmethylene)-1,3-indandiones/ anti-inflammatory activity/ anti-coagulant activity
- Courant, Jacqueline,Leblois, Danielle,Tandon, Manju,Robert-Piessard, Sylvie,le Baut, Guillaume,et al.
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p. 145 - 154
(2007/10/02)
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