Synthesis, anti-microbial and anti-cancer evaluation study of 3-(3-benzofuranyl)-coumarin derivatives

Chougala, Bahubali M.; Shastri, Samundeeswari L.; Holiyachi, Megharaja; More, Sunil S.; Ramesh, K. J.

doi:10.1007/s00044-015-1449-y

Cited by 13 publications

(7 citation statements)

References 40 publications

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“…It also represents the core structure of several molecules of pharmaceutical importance. Coumarin has been reported to serve as anti-cancer [2], anti-microbial [3], anti-inflammatory [4] and anticoagulant [5]. These pharmacological properties of coumarin encouraged us to synthesize some coumarin derivatives.…”

Section: Introductionmentioning

confidence: 99%

Grinding technique for the tandem synthesis of bis coumarinyl methanes using [BDBDMIm]Br-CAN

Nikpassand¹,

Fekri²,

Sahrapeima³

2017

Bull. Chem. Soc. Eth.

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ABSTRACT. 3,3-(Butane-1,4-diyl)bis(1,2-dimethyl-1H-imidazole-3-ium)bromide ([BDBDMIm]Br) is easily used as an efficient and recyclable ionic liquid for the synthesis of bis coumarinyl methanes in the presence of a catalytic amount of ceric ammonium nitrate (CAN) under grinding. All reactions are performed in the absence of solvent in excellent yield during short reaction time. Furthermore, the ionic liquid can be reused and recovered for several times without loss of activity. This method provides several advantages such as simple work-up, environmental friendliness and shorter reaction time along with high yields. All of synthesized compounds were characterized by infrared spectroscopy, 1 H and 13 C nuclear magnetic resonance spectroscopy and elemental analyses.

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Section: Introductionmentioning

confidence: 99%

Grinding technique for the tandem synthesis of bis coumarinyl methanes using [BDBDMIm]Br-CAN

Nikpassand¹,

Fekri²,

Sahrapeima³

2017

Bull. Chem. Soc. Eth.

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“…5 Coumarin and its derivatives are important oxygen containing heterocycles which are found in natural products. Over the past decades, coumarins have attracted great attention because of their interesting biological and pharmacological activities such as anticoagulant, 7 antiinflammatory, 8,9 antioxidant, 10 antiviral, 11 antimicrobial, 12,13 antidepressants, 14 and anti-HIV effects. [15][16][17] Also, they are promising compounds due to their low toxicity, little drug resistance, less side effects, high bioavailability, and ease of chemical synthesis.…”

Section: Introductionmentioning

confidence: 99%

A QSAR Study on the 4-Substituted Coumarins as Potent Tubulin Polymerization Inhibitors

Dinparast

Dastmalchi

2020

Adv Pharm Bull

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Purpose: Despite the discovery and synthesis of several anticancer drugs, cancer is still a major life threatening incident for human beings after cardiovascular diseases. Toxicity, severe side effects, and drug resistance are serious problems of available commercial anticancer drugs. Coumarins are synthetic and natural heterocycles that show promising antiproliferative activities against various tumors. The aim of this research is to computationally study the coumarin derivatives in order to develop reliable quantitative structure-activity relationship (QSAR) models for predicting their anticancer activities. Methods: A data set of thirty one coumarin analogs with significant antiproliferative activities toward HepG2 cells were selected from the literature. The molecular descriptors for these compounds were calculated using Dragon, HyperChem, and ACD/Labs programs. Genetic algorithm (GA) accompanied by multiple linear regression (MLR) for simultaneous feature selection and model development was employed for generating the QSAR models. Results: Based on the obtained results, the developed linear QSAR models with three and four descriptors showed good predictive power with r2 values of 0.670 and 0.692, respectively. Moreover, the calculated validation parameters for the models confirmed the reliability of the QSAR models. Conclusion: The findings of the current study could be useful for the design and synthesis of novel anticancer drugs based on coumarin structure.

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“…[3] Fore xample, Neo-tanshinlactone,afuro [3,2-c]coumarin, was found to be 10-fold more potent and 20-fold more selective against human breast cancer cells than the prescription drug tamoxifen citrate. [5] In view of the therapeutic significance of these two species and the fact that the range of heterocyclic libraries is narrowly defined, the development of efficient and concise synthetic methods that fill the chemical space with diverse heterocyclic structures remains an important task in modern organic chemistry. [5] In view of the therapeutic significance of these two species and the fact that the range of heterocyclic libraries is narrowly defined, the development of efficient and concise synthetic methods that fill the chemical space with diverse heterocyclic structures remains an important task in modern organic chemistry.…”

mentioning

confidence: 99%

“…[4] Benzofuranyl coumarins are another class of coumarins that are known to possess remarkable therapeutic activities,s uch as antibacterial, antianalgesic,a nd even anticancer properties. [5] In view of the therapeutic significance of these two species and the fact that the range of heterocyclic libraries is narrowly defined, the development of efficient and concise synthetic methods that fill the chemical space with diverse heterocyclic structures remains an important task in modern organic chemistry. [6] Earlier,wereported ageneral method for the preparation of an ew type of highly functional phosphorus zwitterions through at andem three-component reaction of functional alkanes,a ldehydes,a nd Bu 3 Pa nd demonstrated the use of these phosphorus zwitterions in the efficient synthesis of furo [3,2-c]coumarins (Scheme 1a).…”

mentioning

confidence: 99%

Diversity‐Oriented Synthesis of Furo[3,2‐c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

et al. 2018

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A highly efficient and chemoselective one-pot protocol for the diversity-oriented synthesis of two types of coumarin-based formal cross-coupling adducts, furo[3,2-c]coumarins and 3-benzofuranyl chromenones, is described. Key attributes of the methodology are an initial chemoselective acylation of functionalized phosphorus zwitterions and a subsequent chemoselective intramolecular Wittig reaction that preferentially resulted in one of the two coumarin derivatives in high yield, depending on relative reactivities and the addition sequence of the acylating agents.

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Synthesis, anti-microbial and anti-cancer evaluation study of 3-(3-benzofuranyl)-coumarin derivatives

Cited by 13 publications

References 40 publications

Grinding technique for the tandem synthesis of bis coumarinyl methanes using [BDBDMIm]Br-CAN

Grinding technique for the tandem synthesis of bis coumarinyl methanes using [BDBDMIm]Br-CAN

A QSAR Study on the 4-Substituted Coumarins as Potent Tubulin Polymerization Inhibitors

Diversity‐Oriented Synthesis of Furo[3,2‐c]coumarins and Benzofuranyl Chromenones through Chemoselective Acylation/Wittig Reaction

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