Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity

Gokhale, Nikhila; Dalimba, Udayakumar; Kumsi, Manjunatha

doi:10.1016/j.jscs.2015.09.003

Cited by 20 publications

(7 citation statements)

References 34 publications

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“…[228] Marine indole alkaloids (meridianins) having 2-amino pyrimidine with indole units were naturally extracted from Aplidium meridianum in the pharmaceutical industry. [229] While C-furyl glycosides pyrimidines (88) have been synthesized from earlier prepared chalcone derivatives (85) and thiourea in ethanolic sodium hydroxide reflux to achieve 72%-75% yield of product [230] (Scheme 21). Both 86 and 87 showed moderate to good antimicrobial due to the interaction of active moieties with the target.…”

Section: Heterocyclic Pyrimidinesmentioning

confidence: 99%

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Farooq

Ngaini

2021

Journal of Heterocyclic Chem

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Chalcone-derived pyrimidine is a well-known heterocyclic compound that is commonly present in ribonucleic acid (RNA) and deoxyribonucleic acid (DNA) bio-isosteres. Pyrimidine derivatives are effective in both the electronic industry and drug industries. This review highlights the synthesis of pyrimidines, namely mono-pyrimidine, bis-pyrimidine, fused pyrimidine, symmetric, and asymmetric pyrimidine via one-pot and two-pot methods. The one-pot method is the direct reaction of amino derivatives with aldehydes and acetophenones, whereas the two-pot method is frequently reported for the synthesis of chalcone before the cyclization to a pyrimidine. This review is important in organic synthesis, particularly in the heterocyclic field, regarding pyrimidines and their significance in therapeutic and electronic industries.

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Section: Heterocyclic Pyrimidinesmentioning

confidence: 99%

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Farooq

Ngaini

2021

Journal of Heterocyclic Chem

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“…Furthermore, earlier research has shown that combining two or more active structural moieties might improve the activity. 21 , 22 As a result, combining pyrimidine and indole moieties in a single molecule can dramatically boost biological activity. 23 Several heterocyclic and non-heterocyclic luminogens have recently been described, and their luminescence was regulated by molecular aggregation.…”

Section: Introductionmentioning

confidence: 99%

“…Applications in biology, such as sensors, biomedical imaging, and bacterial imaging, benefit from materials with both luminous and antimicrobial features. , Recently, solid-state luminous compounds with antimicrobial effects containing indole , or pyrimidine , moieties have been produced. Furthermore, earlier research has shown that combining two or more active structural moieties might improve the activity. , As a result, combining pyrimidine and indole moieties in a single molecule can dramatically boost biological activity . Several heterocyclic and non-heterocyclic luminogens have recently been described, and their luminescence was regulated by molecular aggregation. − …”

Section: Introductionmentioning

confidence: 99%

Solid-State Luminescent Materials Containing Both Indole and Pyrimidine Moieties: Design, Synthesis, and Density Functional Theory Calculations

et al. 2022

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Heterocyclic compounds with effective solid-state luminescence offer a wide range of uses. It has been observed that combining pyrimidine and indole moieties in a single molecule can enhance material behavior dramatically. Here, different heterocyclic compounds with indole and pyrimidine moieties have been synthesized effectively, and their structures have been validated using NMR, IR, and mass spectroscopy. The photoluminescence behavior of two substances was investigated in powder form and solutions of varying concentrations. After aggregation, one molecule displayed a redshifted luminescence spectrum, whereas another homolog showed a blueshift. Thus, density functional theory calculations were carried out to establish that introducing a terminal group allows modifying of the luminescence behavior by altering the molecular packing. Because of the non-planarity, intermolecular interactions, and tiny intermolecular distances within the dimers, the materials demonstrated a good emission quantum yield (Φ em ) in the solid state (ex. 25.6%). At high temperatures, the compounds also demonstrated a stable emission characteristic.

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“…Heterocyclic derivatives of chalcone exhibits anticancer potential against numerous cancer cell lines through different mechanisms. Anticancer chalcone derivatives exhibits and improve the anticancer characteristics by adopting different approaches such as structural and functional manipulation along with substitution of aryl rings (Bhadoriya et al, 2016;Galayev et al, 2015;Gokhale et al, 2017;Lv et al, 2011;Saavedra et al, 2015). Molecular hybridization and replacement in their structure with pharmacological important moieties has been useful for development of novel medicinal agent which shows significant anticancer properties with lesser toxicity.…”

Section: Introductionmentioning

confidence: 99%

Molecular docking, synthesis and biological evaluation of some Imidazo-thiadiazole based Chalcone derivatives as potent triple mutant T790M/C797S EGFR inhibitors

Alman¹,

Soni²,

Killedar

2022

ijhs

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In present study, we have designed and developed some imidazo-thiadiazole based chalcone derivatives as potential EGFR inhibitors. The designed derivative were screened through molecular docking studies and subjected for synthesis followed by in vitro anticancer activity. Most interestingly many molecules had formed one Pi-donor hydrogen bond (Pi-sulfur) or conventional hydrogen bond with Cys797 which is mutated amino acid residue for the second generation EGFR inhibitors. Many molecules had formed Pi-sulfur bond with Met790 which is mutated amino acid residue and developed resistance to the third generation EGFR inhibitors. All the interaction results presented here suggest these molecule has potential to be developed as most potent 4th generation EGFR inhibitors which will might have effectiveness against triple mutant T790M/C797S EGFR. From this investigation, it was decided to synthesize all the designed molecules with their biological evaluation. In vitro cytotoxicity of synthesized compounds against MCF-7 (Breast cancer) and A549 (Lung cancer) cells were carried out using MTT assay. All the synthesized compounds induced the cytotoxicity to MCF-7 and A549 and displayed good range of IC50 values in between 4 to 59 µm/mL.

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Facile synthesis of indole-pyrimidine hybrids and evaluation of their anticancer and antimicrobial activity

Cited by 20 publications

References 34 publications

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

One‐potandtwo‐potmethods for chalcone derived pyrimidines synthesis and applications

Solid-State Luminescent Materials Containing Both Indole and Pyrimidine Moieties: Design, Synthesis, and Density Functional Theory Calculations

Molecular docking, synthesis and biological evaluation of some Imidazo-thiadiazole based Chalcone derivatives as potent triple mutant T790M/C797S EGFR inhibitors

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