Synthesis of (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-ones as potential cytotoxic agents

Mani, Ganesh Kumar; Anchi, Pratibha; Sunkari, Satish; Donthiboina, Kavitha; Godugu, Chandraiah; Shankaraiah, Nagula; Kamal, Ähmed

doi:10.1016/j.bmcl.2020.127432

Cited by 7 publications

(5 citation statements)

References 47 publications

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“…A series of imidazopyridine-arylaminopropenone conjugates synthesized by Mani et al were tested for activity against A549, HCT116, B16F10, BT474, and MDA-MB-231 cancer cell lines [ 192 ]. Among these compounds, 231 displayed the greatest potency against the HCT116 cell line (IC 50 = 1.21 μM).…”

Section: Anticancer Activities Shown By Imidazole Derivatives Through Undefined Mechanismsmentioning

confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives as anticancer agents appearing in the peer-reviewed literature from 2018 through 2020. Such molecules have been shown to modulate various targets, including microtubules, tyrosine and serine-threonine kinases, histone deacetylases, p53-Murine Double Minute 2 (MDM2) protein, poly (ADP-ribose) polymerase (PARP), G-quadraplexes, and other targets. Imidazole-containing compounds that display anticancer activity by unknown/undefined mechanisms are also described, as well as key features of structure-activity relationships. This review is intended to provide an overview of recent advances in imidazole-based anticancer drug discovery and development, as well as inspire the design and synthesis of new anticancer molecules.

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Section: Anticancer Activities Shown By Imidazole Derivatives Through Undefined Mechanismsmentioning

confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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“…Because of their unique structural features and electron-rich environment, they are used by the pharmaceutical industry for drug discovery. Due to the numerous pharmacological properties of benzimidazole derivatives, including their antibacterial, antiviral, antioxidant, and anti-cancer activity, benzimidazole derivatives are important in the medical research [1][2][3][4][5][6][7]. In addition to their biological applications, benzimidazole derivatives have drawn a lot of attention in materials science because they may be crystallized to produce materials with remarkable conductivity and ferroelectric characteristics due to hydrogen bonds intra -intermolecular interactions [8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations

Gandhi,

Soni,

Patel

et al. 2024

Preprint

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We describe the synthesis and crystal structure of DBZIW, 1,3-Dimethyl-3H-benzimidazol-1-ium iodide monohydrate, which crystallizes in a monoclinic system with space group P21/c and Z = 4. The asymmetric unit contains a molecule of [C9 H11N2]+, an iodine ion I−, and a water molecule. Water oxygen O1 and iodine ion I− (O-H...I) connection display significant involvement in hydrogen bond interactions in the molecular packing of DBZIW. The network of C-H...O hydrogen bond contacts plays an essential part in the stability. The molecular structures 1, 3-Dimethyl-3H-benzimidazol-1-ium [DBZ], 1, 3-Dimethyl-3H-benzimidazol-1-ium, monohydrate [DBZW], 1, 3-Dimethyl-3H-benzimidazol-1-ium, iodine [DBZI] and 1, 3-dimethyl-3H-benzimidazol-1-ium iodide monohydrate [DBZIW] were optimized at the B3LYP method with 6-311G (d, p) level using Gaussain-09 software. The energy band gap value of HOMO and LUMO of DBZ, DBZW, DBZI and DBZIW have 4.997 eV, 4.786 eV, 3.309 eV and 1.265 eV, respectively. The HOMO-LUMO energy gap, which is useful in determining the molecular electrical transport properties, explains the charge transfer interaction inside the molecule. The molecular docking studies indicated that DBZIW had high binding affinity for thyroid stimulating hormone receptor (TSHR) protein targets (4QT5).

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“…Imidazole fused rings are members of an essential class of heterocycles that have gained significant attention because of their broad spectrum of applications − (Figure ). For example, imidazo[1,5- a ]pyridine derivatives display remarkable potential for biological applications in many disease indications, − such as Alzheimer’s disease, AIDS, and cancer. − Their derivatives have also been employed in N -heterocyclic carbene chemistry and as ligands in coordination chemistry . Because of their unique photophysical properties, their derivatives play versatile roles as fluorescent probes , and in technological applications, such as organic light-emitting diodes, luminescent downshifting layers, and thin-layer field-effect transistors …”

Section: Introductionmentioning

confidence: 99%

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination–Cyclization under Aerobic Conditions

Peng,

Li,

Huang

et al. 2023

J. Org. Chem.

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An iron-catalyzed efficient C−H amination for the construction of imidazole-fused-ring systems was developed under aerobic conditions. Compared to previous studies, this work exhibited green features. The reaction was conducted in the green solvent anisole, with water as the only byproduct. Four C(sp 3 )−H bonds were cleaved and three C−N bonds were formed in this transformation. Imidazo[1,5-a]pyridine-, imidazo[5,1-b]oxazole-, imidazo[5,1-b]thiazole-, imidazo[1,5-a]pyrazine-, and imidazo-[1,5-a]imidazole-related N-heterocycles were obtained in acceptable-to-excellent yield.

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Synthesis of (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-ones as potential cytotoxic agents

Cited by 7 publications

References 47 publications

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination–Cyclization under Aerobic Conditions

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Synthesis of (Z)-3-(arylamino)-1-(3-phenylimidazo[1,5-a]pyridin-1-yl)prop-2-en-1-ones as potential cytotoxic agents

Cited by 7 publications

References 47 publications

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

The role of water and iodine in supramolecular assembly of a 2D coordination of benzimidazole derivate: X-ray crystallography and DFT calculations

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp3)-H Amination–Cyclization under Aerobic Conditions

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Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination–Cyclization under Aerobic Conditions