Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly(ADP-ribose) polymerase-1 inhibitors

Arumugam, Suyavaran; Ramamurthy, Chitteti; Mareeswaran, Ramachandran; Shanthi, Yagna Viswa; Selvakumar, Jayaraman; Mangalaraj, Selvaraj; Kumar, Mithilesh; Ramanathan, Chinnasamy Ramaraj; Thirunavukkarasu, Chinnasamy

doi:10.1016/j.bmc.2014.12.017

Cited by 59 publications

(33 citation statements)

References 50 publications

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“…Unlike those of mammals, presence of intact but transcriptionally inactive nucleus and other cell organelles are the most persuasive nature of mature chicken erythrocyte 34, 35 . Hence they are considered as animal cell model to monitor the response to the drug 36, 37 .…”

Section: Discussionmentioning

confidence: 99%

Size Dependent Uptake and Hemolytic Effect of Zinc Oxide Nanoparticles on Erythrocytes and Biomedical Potential of ZnO-Ferulic acid Conjugates

Babu

Subastri

Arumugam

et al. 2017

Sci Rep

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Despite zinc oxide nanoparticles (ZnONPs) being increasingly used as carriers in biomedical fields due to their multifaceted properties and therapeutic importance, better understanding of the mechanisms and cellular consequences resulting from their interaction with cells and cellular components has been warranted. In the present study, we investigate the size-dependent interaction of ZnONPs on RBCs, and its impact on cell viability, DNA damage, ROS generation and morphological changes, employing cellular and analytical methods. Size, charge, stability and solubility were confirmed by DLS, zeta potential, ICP-AES and TEM analysis. Further ICP-AES, TEM, spectroscopic observations and cell based assays showed that ZnONPs exhibited a size dependent impact on RBCs and haemoglobin (Hb), particularly size <50 nm. Conversely, ferulic acid (FA) conjugates and serum albumin significantly reduced the adverse effects exhibited by ZnONPs. The extent of DNA damage and ROS generation is comparatively low in ZnONPs-FA than in ZnONPs alone treated cells. Thus our study documents a novel conceptualization delineating the influence of size on the material properties and therapeutic potential of nanoparticle.

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Section: Discussionmentioning

confidence: 99%

Size Dependent Uptake and Hemolytic Effect of Zinc Oxide Nanoparticles on Erythrocytes and Biomedical Potential of ZnO-Ferulic acid Conjugates

Babu

Subastri

Arumugam

et al. 2017

Sci Rep

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“…The isoquinolone 13 probably gets formed by intramolecular cyclization of the initially formed aryl anion 12 which undergo nucleophilic attack on carbonyl group followed by removal of tert ‐butoxide ion. The compound 13 is a member of Berberidaceae plant family, and these are known to show diverse biological activities like inhibition of PARP‐1and anti‐HIV activities and we plan to further investigate this procedure for their synthesis.…”

Section: Resultsmentioning

confidence: 99%

Intermolecular Nucleophilic Addition of N‐Diaminophosphinoyl‐Protected α‐Carbanions Derived from Secondary Amines to Arynes: Synthesis of 1‐Aryl‐1,2,3,4‐tetrahydroisoquinolines

Singh

Kaur

et al. 2017

ChemistrySelect

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Various 1‐aryl‐1,2,3,4‐tetrahydroisoquinolineswere synthesized by coupling α‐amino carbanions, derived from N‐protected secondary amines, with in situ generated arynes. Different N‐protecting/activating groups were investigated and it was found that only the N‐bis(dimethylamino)phosphinoyl group is suitable to obtain the title compounds.This procedure has also been used for an efficient one‐pot synthesis of the drug (±)‐FR115427.

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“…The 3-substituted 3-hydroxyisoindolinone motif is common to a variety of compounds with potent biological activities. They have been established as precursors to anti-ischemic stroke agents [1], MDM2-p53 protein-protein [2][3][4][5][6], HIV-1 integrase [7], and protein-tyrosine phosphatase inhibitors [8], as well as antimicrobial [9] and antitumor [10] agents. In addition, molecules containing the 3substituted isoindolinone core are registered anxiolytic [11], anticonvulsant [12] and antihypertensive [13] drugs ( Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides

Glavač

Dokli

Gredičak

2017

COC

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Background: The 3-substituted 3-hydroxyisoindolinone motif is common to a variety of compounds with potent biological activities. In recent years, they have also been increasingly used as substrates in various asymmetric transformations. Current methods for their preparation either do not tolerate wide range of functional groups, or yield 3-hydroxyisoindolinones as N-substituted products, which makes them inapplicable as substrates for the asymmetric transformations.Objective: Aim of this study was a detailed examination of the synthesis of 3-substituted 3hydroxyisoindolinones comprising various functional groups and unsubstituted phthalimide nitrogen.Method: Grignard and organolithium reagents were employed as nucleophiles for the synthesis of 3substituted 3-hydroxyisoindolinones under various reaction conditions. Results: Phenyl substituents with electron donating groups are easily introduced by employing a Grignard reaction, while electron-poor arenes require a lithium exchange or direct lithiation strategy. The protocols are tolerant of various functional groups on the nucleophile, and a wide range of 3-hydroxyisoindolinones were afforded in good to excellent yields. Conclusion:Simple and inexpensive method for the synthesis of 3-substituted 3-hydroxyisoindolinone has been developed. By tweaking the reaction conditions, described protocols are tolerant of a wide range of functional groups, and yield 3-substituted isoindolinone alcohols with unsubstituted phthalimide nitrogen.

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Synthesis and biological evaluation of isoindoloisoquinolinone, pyroloisoquinolinone and benzoquinazolinone derivatives as poly(ADP-ribose) polymerase-1 inhibitors

Cited by 59 publications

References 50 publications

Size Dependent Uptake and Hemolytic Effect of Zinc Oxide Nanoparticles on Erythrocytes and Biomedical Potential of ZnO-Ferulic acid Conjugates

Size Dependent Uptake and Hemolytic Effect of Zinc Oxide Nanoparticles on Erythrocytes and Biomedical Potential of ZnO-Ferulic acid Conjugates

Intermolecular Nucleophilic Addition of N‐Diaminophosphinoyl‐Protected α‐Carbanions Derived from Secondary Amines to Arynes: Synthesis of 1‐Aryl‐1,2,3,4‐tetrahydroisoquinolines

Synthesis of 3–aryl 3–hydroxyisoindolinones by the Addition of Grignard and Organolithium Reagents to Phthalimides

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