Synthesis of new steroidal imidazo [1,2-a] pyridines: DNA binding studies, cleavage activity and in vitro cytotoxicity

Dar, Ayaz Mahmood; Shamsuzzaman, _; Gatoo, Manzoor Ahmad

doi:10.1016/j.steroids.2015.09.010

Cited by 22 publications

(11 citation statements)

References 41 publications

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“…Dar et al designed and reported a series of novel steroidal imidazo[1',2'- a ]pyridine derivatives (conjugates 97–99 ) via an one-pot three-component tandem approach by reacting different steroidal ketones, 2-aminopyridine and isocyanides and simultaneously investigated their DNA binding affinity and in vitro cytotoxicity ( Fig. 17 ) [ 183 ]. UV–vis, fluorescence, gel electrophoresis and molecular docking studies revealed that the primary mode of binding of these conjugates with the minor groove of the DNA is intercalation, although the van der Waals and other types of electrostatic and hydrophobic interactions could also play important roles.…”

Section: Reviewmentioning

confidence: 99%

An overview of recent advances in duplex DNA recognition by small molecules

Bhaduri

Ranjan

Arya

2018

Beilstein J. Org. Chem.

107

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As the carrier of genetic information, the DNA double helix interacts with many natural ligands during the cell cycle, and is amenable to such intervention in diseases such as cancer biogenesis. Proteins bind DNA in a site-specific manner, not only distinguishing between the geometry of the major and minor grooves, but also by making close contacts with individual bases within the local helix architecture. Over the last four decades, much research has been reported on the development of small non-natural ligands as therapeutics to either block, or in some cases, mimic a DNA–protein interaction of interest. This review presents the latest findings in the pursuit of novel synthetic DNA binders. This article provides recent coverage of major strategies (such as groove recognition, intercalation and cross-linking) adopted in the duplex DNA recognition by small molecules, with an emphasis on major works of the past few years.

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Section: Reviewmentioning

confidence: 99%

An overview of recent advances in duplex DNA recognition by small molecules

Bhaduri

Ranjan

Arya

2018

Beilstein J. Org. Chem.

107

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“…Dar et al . [18] reported another example of a diastereoselective MCR between a 6-ketosteroid, 2-aminopyridines and an isocyanide, using propylphosphonic acid anhydride (TP3) as catalyst to afford a steroidal derivative with an imidazole-pyridine moiety attached to ring B. This moiety is present in several compounds displaying biological activities such as antimicrobial, antiviral and anti-inflammatory, among others.…”

Section: Reviewmentioning

confidence: 99%

“…Multicomponent synthesis of a heterocycle–steroid hybrid using a ketosteroid as carbonyl component [18]. …”

Section: Reviewmentioning

confidence: 99%

Steroid diversification by multicomponent reactions

Reguera¹,

Attorresi²,

Ramírez³

et al. 2019

Beilstein J. Org. Chem.

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Reports on structural diversification of steroids by means of multicomponent reactions (MCRs) have significantly increased over the last decade. This review covers the most relevant strategies dealing with the use of steroidal substrates in MCRs, including the synthesis of steroidal heterocycles and macrocycles as well as the conjugation of steroids to amino acids, peptides and carbohydrates. We demonstrate that steroids are available with almost all types of MCR reactive functionalities, e.g., carbonyl, carboxylic acid, alkyne, amine, isocyanide, boronic acid, etc., and that steroids are suitable starting materials for relevant MCRs such as those based on imine and isocyanide. The focus is mainly posed on proving the amenability of MCRs for the diversity-oriented derivatization of naturally occurring steroids and the construction of complex steroid-based platforms for drug discovery, chemical biology and supramolecular chemistry applications.

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“…Another important biologically active heterocyclic compound, namely imidazo[1,2‐ a ]pyridine which was first synthesized by Chichibabin (1925) through a cyclysation reaction between an α‐aminopyridine and α‐halogenatedcarbonyl derivatives . Imidazo[1,2‐ a ]pyridine containing drugs act as antiviral, anti‐inflammatory, anti‐protozoal, anti‐HIV, anti‐malarial, hypnotic, analgesic, tuberculosis, anti‐ulcer, anxiolytic, benzodiazepine receptor agonist and anti‐cancer and also used in materials science, and molecular biology . Among the commercially available imidazo[1,2‐ a ]pyridines, Zolpidem was the first used as a hypnotic and is widely used in the world to treat insomnia .…”

Section: Introductionmentioning

confidence: 99%

“…Zolimidine is sold as an anti‐ulcer and is also useful in the treatment of osteoporosis. Finally, Olprinone, a phosphodiesterase (PDE 3) inhibitor, has been used to treat acute heart failure (Figure ) …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

et al. 2020

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A novel benzimidazole‐imidazo[1,2‐a]pyridine hybrid; 2‐(imidazo[1,2‐a]pyridine‐8‐yl)benzimidazole and its symmetrical bis‐ derivative 2,2′‐bis‐(imidazo[1,2‐a]pyridine‐8‐yl)‐1H,1H′‐[5,5′]‐bisbenzimidazole were synthesized and characterized. It was found that these two compounds have a strong DNA groove binding and peroxide mediated DNA‐cleavage properties. Furthermore, these molecules were screened against three different human cell lines namely HepG2, DLD‐1 and MDA‐MB‐231, and these compounds were found to have high cytotoxic activities.

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Synthesis of new steroidal imidazo [1,2-a] pyridines: DNA binding studies, cleavage activity and in vitro cytotoxicity

Cited by 22 publications

References 41 publications

An overview of recent advances in duplex DNA recognition by small molecules

An overview of recent advances in duplex DNA recognition by small molecules

Steroid diversification by multicomponent reactions

Synthesis, Characterization, and Antiproliferative Activity Studies of Novel Benzimidazole‐Imidazopyridine Hybrids as DNA Groove Binders

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