Synthesis, antitubercular and anticancer activity of new Baylis–Hillman adduct-derived N-cinnamyl-substituted isatin derivatives

Kumar, Sanjeev; Ravinder, M.; Golla, Kishore; Rao, V. Jayathirtha; Yogeeswari, Perumal; Sriram, D.

doi:10.1007/s00044-013-0787-x

Cited by 33 publications

(20 citation statements)

References 25 publications

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“…21 The vehicle control was designated as the well containing live cells with the culture medium. 22 The percentage growth inhibition was calculated using the formula depicted below and concentration of test drug needed to inhibit cell growth by 50% i.e., the half maximal cytotoxic inhibitory concentration (CTC 50 values) generated from the dose-response curves for each cell line. 23 The inhibition of cell growth in vehicle control was zero percentage.…”

Section: Assessment Of Cytotoxicity By Mtt Assaymentioning

confidence: 99%

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Sathianarayanan¹,

Chittethu²,

Jose³

et al. 2017

JYP

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Objective: The present study was aimed to determine cytotoxic and apoptotic activity of isatin semicarbazones against mammary carcinoma. Methodology: The preparation of these target compounds involved substitution at the third position of the isatin nucleus along with chemical modification at the nitrogen atom of the scaffold to obtain more potent derivatives. The synthesized analogs were characterized by recording their melting point and R f values along with IR, NMR and mass spectra. An antioxidant study and Cytotoxic Studies were performed by DPPH, Nitric oxide scavenging method and MTT assay methods. Results: The results revealed that all the test compounds (5a-5d) exhibited good anti oxidant activity. The synthesized compounds were then screened for in-vitro cytotoxicity by MTT cell proliferation assay method against breast cancer cell lines including MCF-7 and BT-549 with derivative 5a exhibiting maximum activity in both the cell lines. DNA fragmentation studies further indicated that 5a was involved in apoptotic process. Conclusion: Interestingly, it was observed that while all the synthesized compounds seemed active, 5a exhibited a superior ability to induce apoptosis.

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Section: Assessment Of Cytotoxicity By Mtt Assaymentioning

confidence: 99%

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Sathianarayanan¹,

Chittethu²,

Jose³

et al. 2017

JYP

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“…A one-pot, three-component procedure for the synthesis of novel dispiropyrrolidinebisoxindole derivatives 60 by cycloaddition trapping of azomethine ylides generated in situ from isatin 1 and sarcosine 9, and 3-aroylmethyleneindol-2-ones 59 has been reported in [bmim]PF 6 , as a recyclable solvent in excellent yield without using any catalyst (Scheme 23).…”

Section: Scheme 22mentioning

confidence: 99%

“…Substituted isatin analogues constitute valuable building blocks for potential pharmaceuticals with a wide range of biological properties such as antimicrobial, 4 antitumor, [5][6][7][8] antitubercular, [9][10] antimalaria, 11 anti-HIV, 12 and antibacterial. 13 Furthermore, isatin is a core constituent of many drugs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

Ziarani¹,

Moradi²,

Lashgari³

2015

Arkivoc

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Isatin has been utilized in many heterocyclic preparations and considered as an important building block in organic synthesis. There is a wide range of multi-component reactions that include isatin in the synthesis of heterocyclic compounds. This review highlights the advances in the use of isatin as starting material in the synthesis of various organic compounds and drugs during the period from 2012 to 2015.

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“…Inspired with the biological profile of nitro methylene imidazole group and their increasing importance in pharmaceutical and biological fields, and in continuation of our research towards the exploitation of the Baylis-Hillman reaction in heterocyclic chemistry, design and synthesis of biologically active and pharmacologically important new heterocycles and their derivatives, [30][31][32][33][34][35][36][37] we have synthesized 19 new Baylis-Hillman derived nitro methylene imidazole derivatives by the reaction of Baylis-Hillman acetates and nitro methylene imidazole and screened for their insecticidal activity.…”

Section: Fig 1: Commercialized Neonicotinoid Insecticides and Activementioning

confidence: 99%

Untitled

2015

IJPSR

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ABSTRACT:A series of Baylis-Hillman derived N-cinnamyl substituted nitro methylene imidazole derivatives 4a-swere synthesizedfrom BaylisHillman acetates and nitro methylene imidazole compoundsand characterised by 1 H NMR, IR, Mass and HRMS spectroscopy. Their insecticidal activities were evaluated against T. Castaneum and compared with a standard insecticide Permethrane. Preliminary biological activity tests showed that most of the compounds exhibited good insecticidal activity against T. Castaneum at 100µg/cm 2 especially compounds 4b, 4g, 4i, 4l, 4n and 4r showed good insecticidal activity against T. castaneum, interestingly compound 4b with p-fluoro substitution displayed 75% activity. The structure-activity relationship showed that compounds with electron-with drawing substitutions like -F, -Br, -Cl, -NO 2 , -CF 3 at the para position havinggood insecticidal activity and compounds with electron-with drawing groups like -F, -Br at the meta position have shown moderate activity.This work provides some hints for further structural modifications on the Baylis-Hillman derivatives and the enhancement of insecticidal activity.

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Synthesis, antitubercular and anticancer activity of new Baylis–Hillman adduct-derived N-cinnamyl-substituted isatin derivatives

Cited by 33 publications

References 25 publications

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Utility of Isatin Semicarbazones in Mammary Carcinoma Cells - A Proof of Concept Study

Synthesis of spiro-fused heterocyclic scaffolds through multicomponent reactions involving isatin

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