Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

Monga, Vikramdeep; Goyal, Kamya; Steindel, Mário; Malhotra, Manav; Rajani, Dhanji P.; Rajani, Smita D.

doi:10.1007/s00044-013-0803-1

Cited by 47 publications

(19 citation statements)

References 30 publications

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“…Anticancer activity (in terms of growth inhibition/decreased cell viability w.r.t. control) of all synthesized α, β-unsaturated-C-glycoside of indoles (9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20), respective pyrazoline bridged C-glycosides 21-32 and isoxazole bridged C-glycosides 33-44 (n = 36) was investigated by MTT assay in MDA-MB-231 (human breast cancer) cell line at different concentrations for 72 h 56,57 . Anticancer drugs YM155 and menadione were used as positive controls and activity are summarised in Table 2.…”

Section: Resultsmentioning

confidence: 99%

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Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents

Kumari

Mishra

Narayana

et al. 2020

Sci Rep

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C-glycosides are important class of molecules exhibit diverse biological activities and present as structural motif in many natural products. Two series of new pyrazoline and isoxazole bridged indole C-glycoside molecular hybrids (n = 36) were efficiently synthesized starting from diverse indole 3-carboxaldehydes derived α, β-unsaturated ketone derivatives of β-D-glucosyl-propan-2-one, β-D-galactosyl-propan-2-one and β-D-mannosyl-propan-2-one, reacting with hydrazine hydrate and hydroxyl amine hydrochloride in shorter reaction time (15 min) under microwave assisted condition. Anticancer activity of these newly synthesized pyrazoline and isoxazole bridged indoles C-glycoside hybrids were determined in details through cellular assays against MCF-7, MDA-MB-453 and MDA-MB-231 cancer cell lines. The selected library members displayed low micromolar (IC 50 = 0.67-4.67 µM) and selective toxicity against breast cancer cell line (MCF-7). Whereas these compounds were nontoxic towards normal cell line (MCF-10A). Mechanistic studies showed that, active compounds inhibit COX-2 enzyme, which was also supported by molecular docking studies. These findings are expected to provide new leads towards anticancer drug discovery.C-Glycosides are stable surrogates of O-glycosides and are often used as investigative tool in chemical biology and medicinal chemistry, in particular C-glycoside analogues are often used as substrate mimics for different enzymes involved in the carbohydrate metabolism 1-10 . The use of glycomimetic in the design of inhibitors has proven to be a successful approach and now constitutes one of the most attractive ways to develop new generations of effective and selective inhibitors 11 . α, β-unsaturated ketone is a central core for many significant biological compounds 12,13 . According to literature α, β-unsaturated ketone derivatives from natural and synthetic analogues exhibit diverse pharmacological activities such as anti-tuberculosis, anti-inflammatory, anticancer, antineoplastic, antibacterial, antifungal, antimalarial, antiviral, antiallergic, estrogenic 12 and COX-2 inhibitor 13 .Pyrazoline derivatives are important biologically active heterocyclic compounds. These derivatives are the subject of many research studies due to their widespread potential biological activities such as anticancer, antioxidant, antibacterial activities 14 and COX-2 inhibitor 15 . The most prominent compounds containing pyrazoline nucleus are ampyrone, phenazone and propyphenzone. Isoxazole heterocycle is well known for its medicinal relevance 16,17 . There are isoxazole nucleus containing drug molecules currently available in market, such as acetylsulfisoxazole, cycloserine, sulfisoxazole, and zonisamide etc. These drugs possess antimicrobial 18 , antioxidant 19,20 tuberculostatic 21 neurotoxic 22 , antiepileptic activities 23,24 and COX-2 inhibitor 25 . The comparable activities are also observed in other isoxazole derivatives, captivates researcher to search for newer bioactive compounds of using this as pharmacophore. α, β-...

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Section: Resultsmentioning

confidence: 99%

“…The crude product was purified by flash column chromatography which furnished the pure products 9 in 80% (378 mg) isolated yield ( Table 1). The similar reaction protocol was adopted for the synthesis of other similar compounds (10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). (9).…”

Section: Discussionmentioning

confidence: 99%

Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents

Kumari

Mishra

Narayana

et al. 2020

Sci Rep

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“…Bichalcophenes were chosen as many studies and patents of synthetic and naturally occurring chalcone derivatives have reported their potential against Leishmania [53, [55][56][57][58][59][60]. In the first work by Tidwell et al…”

Section: Pentamidinementioning

confidence: 99%

New perspectives for leishmaniasis chemotherapy over current anti-leishmanial drugs: a patent landscape

Machado-Silva

Guimarães

Tavares

et al. 2014

Expert Opinion on Therapeutic Patents

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Most patents related to drugs for leishmaniasis have not been produced by the pharmaceutical industry but rather by public research institutes or by universities, and the majority of the inventions disclosed are still in preclinical phase. There is an urgent need to find new ways of funding research for leishmaniasis drugs, incentivizing product development partnerships and pushing forward innovation.

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“…Compound possessing naphthyl ring attached to C‐5 of the pyrazoline ring ( 31 ) showed better anti‐TB activity, having MIC value of 62.5 µg/mL (Fig. ) .…”

Section: Pyrazole Derivatives For Treatment Of Tuberculosismentioning

confidence: 99%

Recent Progress on Pyrazole Scaffold‐Based Antimycobacterial Agents

Keri

Chand

Ramakrishnappa

et al. 2015

Archiv der Pharmazie

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New and reemerging infectious diseases will continue to pose serious global health threats well into the 21st century and according to the World Health Organization report, these are still the leading cause of death among humans worldwide. Among infectious diseases, tuberculosis claims approximately 2 million deaths per year worldwide. Also, agents that reduce the duration and complexity of the current therapy would have a major impact on the overall cure rate. Due to the development of resistance to conventional antibiotics there is a need for new therapeutic strategies to combat Mycobacterium tuberculosis. Subsequently, there is an urgent need for the development of new drug candidates with newer targets and alternative mechanism of action. In this perspective, pyrazole, one of the most important classes of heterocycles, has been the topic of research for thousands of researchers all over the world because of its wide spectrum of biological activities. To pave the way for future research, there is a need to collect the latest information in this promising area. In the present review, we have collated published reports on the pyrazole core to provide an insight so that its full therapeutic potential can be utilized for the treatment of tuberculosis. In this article, the possible structure-activity relationship of pyrazole analogs for designing better antituberculosis (anti-TB) agents has been discussed and is also helpful for new thoughts in the quest for rational designs of more active and less toxic pyrazole-based anti-TB drugs.

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Synthesis and evaluation of new chalcones, derived pyrazoline and cyclohexenone derivatives as potent antimicrobial, antitubercular and antileishmanial agents

Cited by 47 publications

References 30 publications

Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents

Design and efficient synthesis of pyrazoline and isoxazole bridged indole C-glycoside hybrids as potential anticancer agents

New perspectives for leishmaniasis chemotherapy over current anti-leishmanial drugs: a patent landscape

Recent Progress on Pyrazole Scaffold‐Based Antimycobacterial Agents

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