Effects of Base for the Efficient Synthesis of 4-Formylcoumarins and 4-Formylcarbostyrils

Holiyachi, Megharaja; Shastri, Samundeeswari L.; Chougala, Bahubali M.

doi:10.1080/00397911.2014.981754

Cited by 22 publications

(5 citation statements)

References 18 publications

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“…The sequence of reactions during the present work (Scheme ) illustrates the application of the Pictet‐Spengler reaction which has been widely employed to construct the β ‐carboline skeleton ,. 4‐Formyl coumarins 1 were reacted with tryptamine 2 in acetic acid at room temperature to obtain the tetrahydro‐ β ‐carboline linked coumarins 3 via an intramolecular C−C bond formation which is characteristic of the Pictet‐Spengler mechanism . The room temperature reaction required 10–12 h, whereas under MW irradiation, the reaction afforded higher yields in 5–7 min.…”

Section: Resultsmentioning

confidence: 96%

Synthesis and Human Anticancer Cell Line Studies on Coumarin‐β‐carboline Hybrids as Possible Antimitotic Agents

Samundeeswari

Kulkarni

Joshi³

et al. 2016

ChemistrySelect

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A series of coumarin tetrahydro‐β‐carboline hybrids 3 have been synthesized by the Pictet‐Spengler reaction. Stoichiometrically controlled DDQ oxidation has led to dihydro 4 and β‐carboline 5. In vitro anticancer activity against 60 cell lines has revealed the potency of 3 f, 4 a and 5 c. In silico studies indicate the binding properties of 5 c with Kinesin spindle protein (KSP) and tubulin protein. Gel electrophoresis studies revealed that compound 3 f partially cleaved the CT‐DNA, whereas the ring C aromatized compound 5 c completely cleaved the CT‐DNA. Structures of the newly synthesized compounds are confirmed by spectroscopic and X‐ray studies.

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Section: Resultsmentioning

confidence: 96%

Synthesis and Human Anticancer Cell Line Studies on Coumarin‐β‐carboline Hybrids as Possible Antimitotic Agents

Samundeeswari

Kulkarni

Joshi³

et al. 2016

ChemistrySelect

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“…We commenced our investigations by targeting an expedient procedure for the synthesis of target compounds phenyl‐pyrazolo[1,5‐ a ]pyridine derivatives 4 ( a–k ) and substituted coumarin‐pyrazolo[1,5‐ a ]pyridine derivatives 7 ( a–e ), synthetic route outlined in Schemes and respectively . The derived substituted pyrazolo[1,5‐ a ]pyridine derivatives 4/7 were synthesized in one step by the reaction of 5 ‐ amino‐4‐cyano‐3‐cyanomethylpyrazole ( 1 ) with substituted aryl aldehydes ( 2 )/substituted 4‐formyl coumarins ( 5 ) and malononitrilein the presence of catalytic amount of DMAP.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Polyfunctionalized Fused Pyrazolo‐Pyridines: Characterization, Anticancer Activity, Protein Binding and Molecular Docking Studies

Naik

Shastri

et al. 2019

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The reaction of a multi-substituted pyrazole 1 with aryl or heteroaryl aldehydes and active methylene compounds afford unexpected pyrazolo[1,5-a]pyridine derivatives 4(a-k). Mechanism for this unexpected reaction involving reactivity of the active methylene moiety with a neighboring endocyclic NH group is proposed and structure has been established by the NMR and single crystal X-ray diffraction studies. Moreover, all the newly synthesized compounds were tested for their anticancer activity against sixty human cell lines at NCI. Among all the compounds, three scaffolds 4d, 4 h and 4k showed enhancement in anticancer activity in comparison with remaining synthesized compounds. Interestingly compound 4k was found to highly active even at a five dose concentration. The IC 50 values were determined against two cell lines MCF-7 and HepG2, the results obtained have shown promising effects against cancer cell lines. Further, the molecular docking studies revealed that substituted pyrazolo[1,5-a]pyridine derivatives are good candidates in the medicinal field.

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“…Zhou and coworkers also prepared compounds 158a-e bearing bis-imidazolyl ethanol groups starting from phloroglucinol (159) (Scheme 29) via a three-step route, but found that these substances did not show appreciable antibacterial activity against the above-mentioned bacterial pathogens [92]. In 2018, Shastri and coworkers [93] synthesised 4-(4,5-diphenyl-1H-imidazol-2-yl)-2H-chromen-2-ones 160a-g in good to excellent yields by cyclocondensation of benzil ( 161) with 4-formylcoumarins 162a-g [94] and AcONH 4 in AcOH using both conventional heating conditions and microwave irradiation (Scheme 30). As expected, the yields of the microwave promoted cyclocondensation reactions were higher than those of the reactions carried out using conventional heating conditions.…”

Section: Scheme 28 Synthesis Of Hybrids 154a-ementioning

confidence: 99%

“…Hybrids 160a-f were then converted to 4-(4,5-diphenyl-1-tosyl-1H-imidazol-2-yl)-2H-chromen-2-ones 163a-f by treatment with 1.5 eq of TsCl in CH 2 Cl 2 at 0-5 • C in the presence of Et 3 N (Scheme 30). In 2018, Shastri and coworkers [93] synthesised 4-(4,5-diphenyl-1H-imidazol-2-yl)-2H-chromen-2-ones 160a-g in good to excellent yields by cyclocondensation of benzil ( 161) with 4-formylcoumarins 162a-g [94] and AcONH4 in AcOH using both conventional heating conditions and microwave irradiation (Scheme 30). As expected, the yields of the microwave promoted cyclocondensation reactions were higher than those of the reactions carried out using conventional heating conditions.…”

Section: Scheme 28 Synthesis Of Hybrids 154a-ementioning

confidence: 99%

An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

Rossi

Ciofalo

2020

Molecules

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The rapid growth of serious infections caused by antibiotic resistant bacteria, especially the nosocomial ESKAPE pathogens, has been acknowledged by Governments and scientists and is one of the world’s major health problems. Various strategies have been and are currently investigated and developed to reduce and/or delay the bacterial resistance. One of these strategies regards the design and development of antimicrobial hybrids and conjugates. This unprecedented critical review, in which our continuing interest in the synthesis and evaluation of the bioactivity of imidazole derivatives is testified, aims to summarise and comment on the results obtained from the end of the 1900s until February 2020 in studies conducted by numerous international research groups on the synthesis and evaluation of the antibacterial properties of imidazole-based molecular hybrids and conjugates in which the pharmacophoric constituents of these compounds are directly covalently linked or connected through a linker or spacer. In this review, significant attention was paid to summarise the strategies used to overcome the antibiotic resistance of pathogens whose infections are difficult to treat with conventional antibiotics. However, it does not include literature data on the synthesis and evaluation of the bioactivity of hybrids and conjugates in which an imidazole moiety is fused with a carbo- or heterocyclic subunit.

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Effects of Base for the Efficient Synthesis of 4-Formylcoumarins and 4-Formylcarbostyrils

Cited by 22 publications

References 18 publications

Synthesis and Human Anticancer Cell Line Studies on Coumarin‐β‐carboline Hybrids as Possible Antimitotic Agents

Synthesis and Human Anticancer Cell Line Studies on Coumarin‐β‐carboline Hybrids as Possible Antimitotic Agents

Synthesis of Polyfunctionalized Fused Pyrazolo‐Pyridines: Characterization, Anticancer Activity, Protein Binding and Molecular Docking Studies

An Updated Review on the Synthesis and Antibacterial Activity of Molecular Hybrids and Conjugates Bearing Imidazole Moiety

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