Ferrocene‐substituted bis(ethynyl)anthracene compounds as anticancer agents

Singh, Ajeet; Kumari, Pratibha; Raghuvanshi, Abhinav; Mathur, P. C.

doi:10.1002/aoc.4071

Cited by 9 publications

(7 citation statements)

References 49 publications

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“…DNA serves as a primary target for various drugs . DNA binding is also one of the critical steps for the understanding of actual aroyl‐hydrazone based drugs design.…”

Section: Resultsmentioning

confidence: 99%

“…[35] DNA Binding Study of L 1 -L 4 DNA serves as a primary target for various drugs. [40] DNA binding is also one of the critical steps for the understanding of actual aroyl-hydrazone based drugs design. It helps know the proper mechanisms which participate in the site-specific recognition of duplex DNA and synthesis of aroyl-hydrazone based pharmaceutical molecules.…”

Section: Tryptophan Quenching Experimentsmentioning

confidence: 99%

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Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Kumari

Ansari

Kumar

et al. 2019

Chemistry & Biodiversity

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Here, we report the synthesis and characterization of four new aroyl‐hydrazone derivatives L1–L4, and their structural as well as biological activities have been explored. In addition to docking with bovine serum albumin (BSA) and duplex DNA, the experimental results demonstrate the effective binding of L1–L4 with BSA protein and calf thymus DNA (ct‐DNA) which is in agreement with the docking results. Further biological activities of L1–L4 have been examined through molecular docking with different proteins which are involved in the propagation of viral or cancer diseases. L1 shows best binding affinity with influenza A virus polymerase PB2 subunit (2VY7) with binding energy −11.42 kcal/mol and inhibition constant 4.23 nm, whereas L2 strongly bind with the hepatitis C virus NS5B polymerase (2WCX) with binding energy −10.47 kcal/mol and inhibition constant 21.06 nm. Ligand L3 binds strongly with TGF‐beta receptor 1 (3FAA) and L4 with cancer‐related EphA2 protein kinases (1MQB) with binding energy −10.61 kcal/mol, −10.02 kcal/mol and inhibition constant 16.67 nm and 45.41 nm, respectively. The binding energies of L1–L4 are comparable with binding energies of their proven inhibitors. L1, L3 and L4 can be considered as both 3FAA and 1MQB dual targeting anticancer agents, while L1 and L3 are both 2VY7 and 2WCX dual targeting antiviral agents. On the other side, L2 and L4 target only one virus related target (2WCX). Furthermore, the geometry optimizations of L1–L4 were performed via density functional theory (DFT). Moreover, all four ligands (L1–L4) were characterized by NMR, FT‐IR, ESI‐MS, elemental analysis and their molecular structures were validated by single crystal X‐ray diffraction studies.

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“…DNA serves as a primary target for various drugs . DNA binding is also one of the critical steps for the understanding of actual aroyl‐hydrazone based drugs design.…”

Section: Resultsmentioning

confidence: 99%

Section: Tryptophan Quenching Experimentsmentioning

confidence: 99%

Design and Construction of Aroyl‐Hydrazone Derivatives: Synthesis, Crystal Structure, Molecular Docking and Their Biological Activities

Kumari

Ansari

Kumar

et al. 2019

Chemistry & Biodiversity

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“…Based on the binding energy (−10.61 kcal/mol −1 ) and inhibition constant (16.74 nM), it was obvious that compound 2 had the best interaction with cancer-related Aurora A kinase protein of all the analogs in this series. Indeed, both molecular docking and cell cytotoxicity assays revealed that 2 was a more effective anticarcinogen when compared with 1 and 3 as it was capable of binding to DNA strands and triggering apoptosis [29]. Of particular interest was the antimicrobial agent Chloroquinocin 1, which was shown to be active against Gram-positive bacteria, such as methicillin-resistant Staphylococcus aureus (MRSA) [12].…”

Section: Chemical Propertiesmentioning

confidence: 99%

Fundamental and Applied Aspects of the Chemistry of Acetylenylquinones

Vasilevsky¹,

Stepanov²

2020

REFFIT

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In addition to the reported synthetic routes for the acetylene derivatives of quinones, a detailed analysis of the fundamental chemical, physicochemical, and biological properties of this class of compounds is presented herein. The advantages of Pd- and Cu-catalyzed cross-coupling of terminal alkynes with iodarenes via the Sonogashira reaction to produce new acetylenylquinones with predetermined properties are examined. Here, combining quinoid and acetylene residues into one molecule gives the resulting compounds chemical specificity, as demonstrated by several reported examples of non-trivial transformations. In particular, the presence of the quinoid cycle significantly increases the electrophilicity of the triple bond and determines the range of transformation possibilities. Moreover, acetylenylquinones have heightened sensitivity to both external (such as the reaction temperature and the nature of the solvent) and internal (e.g., the structure of substituents in the nucleus and the acetylene fragment) factors. For example, regioselective cleavage of a strong triple bond under the action of amines is possible in the absence of a metal catalyst. Peri-substituted acetylenyl-9,10-anthraquinones are most suited for the synthetic route because of the proximity of the acetylene and carbonyl groups. Mechanisms of reactions of selective alkynylquinones are described.

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“…Singh et al reported a di-Fc anthraquinone with alkyne linkages, which showed cytotoxicity against human melanoma cancer (A375) and cervical carcinoma (HeLa) cell lines. 40 That compound was also found to be relatively inactive against normal human embryonic kidney (HEK) cells, suggesting some selectivity. The mechanism of the observed anticancer activity was linked to interactions with proteins and DNA.…”

Section: Introductionmentioning

confidence: 99%