A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of new-fangled dispiropyrrolothiazoles as antimycobacterial agents

Almansour, Abdulrahman I.; Ali, Sadath; Ali, Mohamed Ashraf; Ismail, Rusli; Choon, Tan Soo; Velmurugan, Sellappan; Elumalai, Karthikeyan; Pandian, Suresh

doi:10.1016/j.bmcl.2012.10.059

Cited by 22 publications

(7 citation statements)

References 24 publications

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“…The indanone derivatives beneficial pharmacological properties and it's useful for Alzheimer's disease treatment [57]. Apolipoprotein E (apoE) is a plasma protein and found to be an important lipid-transport protein in human plasma and brain.…”

Section: Molecular Docking Studymentioning

confidence: 99%

Conformational analysis, molecular structure, spectroscopic, NBO, reactivity descriptors, wavefunction and molecular docking investigations of 5,6-dimethoxy-1-indanone: A potential anti Alzheimer's agent

Sebastian¹,

Sylvestre

Sundaraganesan

et al. 2022

Heliyon

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The objective of the present study is focused to elucidate the structure of potential anti-Alzheimer's compound 5,6-Dimethoxy-1-indanone (5,6-DMI) and study its binding interaction towards the active site by molecular docking studies. The structural and various spectroscopic tools are used to understand the various interaction behaviors of the title compound. The theoretical calculation of 5,6-DMI molecule is computed by Gaussian 09W software with Density functional B3LYP and CAM-B3LYP method utilizing 6-311G(d,p) as basis set. The Natural Bond Orbital (NBO) analysis has been performed to find all possible transition was correlate with electronic transition. The Non covalent interaction of 5,6-DMI molecule was examined by adopt Reduced Density Gradient (RDG) analysis and colour filled ELF diagram. Molecular docking results suggest that 5,6-DMI may exhibit inhibitory activity against apoE protein and may act as potential against Alzheimer's disease.

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Section: Molecular Docking Studymentioning

confidence: 99%

Conformational analysis, molecular structure, spectroscopic, NBO, reactivity descriptors, wavefunction and molecular docking investigations of 5,6-dimethoxy-1-indanone: A potential anti Alzheimer's agent

Sebastian¹,

Sylvestre

Sundaraganesan

et al. 2022

Heliyon

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“…In this study, four novel indane derivatives ( 1 – 4 ) were isolated ( Figure 1 ). Indanes are generally characterized by anti-tumor [ 12 ], anti-microbial [ 13 , 14 , 15 ], anti-inflammatory [ 16 , 17 ], neuroprotective [ 18 ], and antioxidant activities [ 19 ], and, thus, they have been used to develop various drugs, such as indacaterol, aprindine, and donepezil. Knowing that indanes have significant free radical scavenging activity [ 19 ], the scavenging activity of compounds 1 – 4 is analyzed herein using ABTS •+ and DPPH •+ assays.…”

Section: Introductionmentioning

confidence: 99%

Novel Indane Derivatives with Antioxidant Activity from the Roots of Anisodus tanguticus

et al. 2023

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Four novel indane derivatives, anisotindans A–D (1–4), were isolated from the roots of Anisodus tanguticus. Their structures were established using comprehensive spectroscopic analyses, and their absolute configurations were determined by electronic circular dichroism (ECD) calculations and single-crystal X-ray diffraction analyses. Anisotindans C and D (3 and 4) are two unusual indenofuran analogs. ABTS•+ and DPPH•+ assays of radical scavenging activity reveal that all compounds (1–4) are active. Specifically, the ABTS•+ assay results show that anisotindan A (1) exhibits the best antioxidant activity with an IC50 value of 15.62 ± 1.85 μM (vitamin C, IC50 = 22.54 ± 5.18 μM).

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“…Spiro heterocycles are frequently encountered in natural products and pharmaceutics, attributable to their interesting conformational features and their structural implications for biological systems and they show greater three‐dimensionality than flat aromatic molecules. The spiro heterocycles containing pyrrolidine/pyrrolothiazole rings are of interest in organic synthesis due to their pronounced biological activities . In particular, spiropyrrolothiazoles are seen to be promising candidates for drug discovery as they display a wide range of biological activities, including anticancer, hepatoprotective, antimicrobial, antidiabetic, anticonvulsant and acetylcholinesterase inhibitory properties .…”

Section: Introductionmentioning

confidence: 99%

A Regioselective Synthesis of Carbazole‐Appended Dispiropyrrolothiazoles/Pyrrolidines: Synthesis, Computational Studies and In Vitro Anticancer Activity

et al. 2019

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Anti‐oncological active carbazole appended dispiroindenoquinoxalinepyrrolothiazoles and dispiroacenaphthylenepyrrolidines were synthesized regioselectively via 1,3‐dipolar cycloaddition reaction of azomethine ylide to exocyclic linkage of dipolarophile. The synthesized spiranic compounds are fully characterized by means of spectral, X‐ray crystallography and elemental analysis. Computational details of theoretical calculations have been discussed for compound 4 g (p‐Cl‐phenyl substituted pyrrolothiazole‐carbazole system) using DFT (Density Functional Theory) approach at the M06‐2X/LANL2DZ level of theory. The cytotoxic effects of the dispiro compounds were examined on cancerous cell lines such as lung cancer (A549) and breast cancer (MCF‐7) cell lines. Compound 4 g was found to be the most promising derivative against A549 (20±1.0 μg/ml) and MCF‐7 (21±1.5 μg/ml) cells. Furthermore, the morphological changes and apoptotic induction of the promising candidates have been studied by AO/EB (Acridine Orange/Ethidium Bromide) and DAPI (4′,6‐diamidino‐2‐phenylindole) staining methods.

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A regio- and stereoselective 1,3-dipolar cycloaddition for the synthesis of new-fangled dispiropyrrolothiazoles as antimycobacterial agents

Cited by 22 publications

References 24 publications

Conformational analysis, molecular structure, spectroscopic, NBO, reactivity descriptors, wavefunction and molecular docking investigations of 5,6-dimethoxy-1-indanone: A potential anti Alzheimer's agent

Conformational analysis, molecular structure, spectroscopic, NBO, reactivity descriptors, wavefunction and molecular docking investigations of 5,6-dimethoxy-1-indanone: A potential anti Alzheimer's agent

Novel Indane Derivatives with Antioxidant Activity from the Roots of Anisodus tanguticus

A Regioselective Synthesis of Carbazole‐Appended Dispiropyrrolothiazoles/Pyrrolidines: Synthesis, Computational Studies and In Vitro Anticancer Activity

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