A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones

Jain, Manish; Sakhuja, Rajeev; Khanna, Pankaj; Bhagat, Sunita; Jain, Subhash C.

doi:10.3998/ark.5550190.0009.f07

Cited by 39 publications

(4 citation statements)

References 5 publications

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“…Motivated by these findings and in conjunction with recent interest on molecular hybridization concept as well as on the chemistry of bis-heterocyclic compounds, [26][27][28][29][30][31][32][33][34][35][36][37][38][39] we report herein on the synthesis of novel bis[thienopyridines] linked to arene or heteroarene spacers.…”

Section: Introductionmentioning

confidence: 93%

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

Salem¹,

Elwahy²,

Darweesh³

2020

Arkivoc

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A series of novel bis (thieno[2,3-b]pyridines) based arenes or heteroarenes have been synthesized from the appropriate bisbromoacetyl derivatives upon treatment with the corresponding 2-mercaptonicotinonitrile derivatives in ethanolic sodium ethoxide at reflux. Attempts to synthesize these compounds via bis-alkylation of the appropriate phenol derivative with the corresponding dibromo compounds using a mild base were unsuccessful.

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Section: Introductionmentioning

confidence: 93%

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

Salem¹,

Elwahy²,

Darweesh³

2020

Arkivoc

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“…185-187 °C, yield 75 % (0.53 g). IR: ν max / cm À General procedure for the synthesis of n-alkylated isatin 7 ac and 8 a-c [56] Dibromoalkane (6) (1.65 g, 6.80 mmol) was added dropwise during 20 min. at À 10 °C to a stirred solution of 1H-Indol-2,3-dione (4 a-c) (1 g, 6.80 mmol) and K 2 CO 3 in 10 ml of DMF under an inert atmosphere of nitrogen.…”

Section: (S)-5-fluoro-3-((1-oxo-3-phenyl-1-(piperidin-1-yl) Propan-2-...mentioning

confidence: 99%

Development of Isatin‐Based Schiff Bases Targeting VEGFR‐2 Inhibition: Synthesis, Characterization, Antiproliferative Properties, and QSAR Studies

Seliem

Panda

Girgis³

et al. 2022

ChemMedChem

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Three sets of isatin-based Schiff bases were synthesized utilizing the molecular hybridization approach. Some of the synthesized Schiff bases show significant to moderate antiproliferative properties against MCF7 (breast), HCT116 (colon), and PaCa2 (pancreatic) cancer cell lines with potency compared to reference drugs 5-fluorouracil (5-FU) and Sunitinib. Among all, compound 17 f-5-methylindolin-2-one) exhibits promising antiproliferative properties against the MCF7 cancer cell line with 2.1-fold more potency than Sunitinib. However, among all the synthesized compounds, three (5-methylisatin derivatives) were the most effective against HCT116 in comparison to 5-FU. Compound 17 f exhibited the highest anti-angiogenic effect on the vasculature as it significantly reduced BV from 43 mm to 2 mm in comparison to 5.7 mm for Sunitinib and flow cytometry supports the arrest of the cell cycle at G1/S phases. In addition, compound 17 f also showed high VEGFR-2 inhibition properties against breast cancer cell lines. Robust 2D-QSAR studies supported the biological data.

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“…[ 14–17 ] Inspired by the importance of bis compounds and SBs, we have reported earlier the synthesis of some novel bis spiro indoles having an alkyl spacer as well as their SBs, in our previous publications. [ 18–20 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis, comparativein vitroantibacterial, antioxidant and UV fluorescence studies of bis indole Schiff bases and molecular docking with ct‐DNA and SARS‐CoV‐2 M^pro

Singhal

Khanna

2021

Luminescence

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In this study, synthesis of 15 novel bis indole‐based Schiff bases (SBs) 4a–4o was conducted by condensation of 2‐(1‐aminobenzyl)benzimidazole with symmetrical bis‐isatins linked via five alkyl chains (n = 2–6). These were subjected to ADME (absorption, distribution, metabolism and excretion), physiochemical properties, molecular docking, in vitro antibacterial and antioxidant studies. The in silico studies indicated lower toxicity with metabolic stability for nearly all the derivatives proving reliability as drug candidates. The comparative antibacterial study against Staphylococcus aureus and Escherichia coli, also showed a superior inhibition than reference drug and their mono counterparts. The increase in linker alkyl chain length and variation of substituents in indole, further predicted increased inhibition, with maximum value for compound 4o at 50 μg/ml. The in vitro calf thymus DNA (ct‐DNA) binding ability of compounds 4c, 4f, 4i, 4l, 4 m, 4n, and 4o was evaluated via ultraviolet‐visible and fluorescence spectroscopy techniques. A hyperchromic effect was observed with no apparent wavelength shift which predicted for the groove binding mode. A moderate binding constant for 4o, in fluorescence results, confirms groove binding. The molecular docking of 4o with ct‐DNA (PDBID:1BNA) and SARS‐CoV‐2 Mpro (3CL protease, PDBID:6LU7) prove its efficacy as potential DNA binder and antiviral agent.

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A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones

Abstract: An elegant synthesis of some novel unsymmetrical bis-indol-2,3-diones (4a-d) has been achieved via 1-(6-bromohexyl)-1H-indol-2,3-diones (3a,b). These compounds have been further used for the synthesis of novel bis-spiroindoles (7a-d) via hitherto unknown bis Schiff's bases (6a-d).

Cited by 39 publications

References 5 publications

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

Development of Isatin‐Based Schiff Bases Targeting VEGFR‐2 Inhibition: Synthesis, Characterization, Antiproliferative Properties, and QSAR Studies

Synthesis, comparativein vitroantibacterial, antioxidant and UV fluorescence studies of bis indole Schiff bases and molecular docking with ct‐DNA and SARS‐CoV‐2 M^pro

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A facile synthesis of novel unsymmetrical bis-spiro[indole-pyrazolinyl-thiazolidine]-2,4'-diones

Abstract: An elegant synthesis of some novel unsymmetrical bis-indol-2,3-diones (4a-d) has been achieved via 1-(6-bromohexyl)-1H-indol-2,3-diones (3a,b). These compounds have been further used for the synthesis of novel bis-spiroindoles (7a-d) via hitherto unknown bis Schiff's bases (6a-d).

Cited by 39 publications

References 5 publications

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

An expedient synthesis of novel bis[thienopyridines] linked to arene or heteroarene core as novel hybrid molecules

Development of Isatin‐Based Schiff Bases Targeting VEGFR‐2 Inhibition: Synthesis, Characterization, Antiproliferative Properties, and QSAR Studies

Synthesis, comparativein vitroantibacterial, antioxidant and UV fluorescence studies of bis indole Schiff bases and molecular docking with ct‐DNA and SARS‐CoV‐2 Mpro

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Product

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About

Synthesis, comparativein vitroantibacterial, antioxidant and UV fluorescence studies of bis indole Schiff bases and molecular docking with ct‐DNA and SARS‐CoV‐2 M^pro