Synthesis and anti-Mycobacterium tuberculosis activity of imide-β-carboline and carbomethoxy-β-carboline derivatives

Lopes-Ortiz, Mariana Aparecida; Panice, Manuela Ribeiro; Melo, Eduardo Borges de; Martins, João Paulo Ataide; Baldin, Vanessa Pietrowski; Pires, Cláudia Terêncio Agostinho; Caleffi-Ferracioli, Katiany Rizzieri; Siqueira, Vera Lúcia Dias; Scodro, Regiane Bertin de Lima; Sarragiotto, María Helena; Cardoso, Rosilene Fressatti

doi:10.1016/j.ejmech.2019.111935

Cited by 20 publications

(13 citation statements)

References 41 publications

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“…All five derivatives were also found to be non‐toxic to various cell lines, determined by toxicity studies. Compounds 95 and 96 (Figure 16) were found to exhibit maximum potency against M. tuberculosis [60] …”

Section: β‐Carboline Derivatives As Anti‐tb Agentsmentioning

confidence: 99%

Anti‐Tubercular Insights of Carbolines – A Decade Critique

et al. 2021

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Tuberculosis is one of the top 10 leading causes of death worldwide and is caused by the bacteria “Mycobacterium tuberculosis.” The medications used to treat tuberculosis have many deficiencies, including long‐term treatment, expensive medications, etc. The continuing emergence of multidrug resistance (MTR) remains a critical health issue that needs to be tackled urgently. Increased HIV/AIDS co‐infection with tuberculosis has also worsened the condition. Carbolines, nitrogen‐containing tricyclic Compounds have a significant role in medicinal chemistry because of their broad pharmacological properties, such as anti‐tubercular, anti‐bacterial, anti‐leishmanial, anti‐cancer, anti‐viral, etc. A brief description of the anti‐tubercular ability of a diverse set of carbolines collected from the past ten years focused on synthetic procedures, structural‐activity relationship studies, and their molecular mechanism of action was clearly described in the current review.

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Section: β‐Carboline Derivatives As Anti‐tb Agentsmentioning

confidence: 99%

Anti‐Tubercular Insights of Carbolines – A Decade Critique

et al. 2021

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“…Cyclic products (6a-i) were confirmed by the singlet peak appeared at 5.32-5.62 ppm and the disappearance of the peaks in the range of 8.41-8.66 ppm. In 13 The cyclic products finally aromatized to obtain titled products (7a-i). The signals disappeared at 5.32-5.62 ppm and the appearance of new signals at 7.64-7.84 ppm in the 1 H NMR spectra and the peaks observed at 144.5-148.0 ppm and110.5-113.4 ppm in 13 C NMR spectra confirmed the formation of products 7a-i.…”

Section: Synthesis Of β-Carboline Derivativesmentioning

confidence: 99%

“…In 13 The cyclic products finally aromatized to obtain titled products (7a-i). The signals disappeared at 5.32-5.62 ppm and the appearance of new signals at 7.64-7.84 ppm in the 1 H NMR spectra and the peaks observed at 144.5-148.0 ppm and110.5-113.4 ppm in 13 C NMR spectra confirmed the formation of products 7a-i. Further, the expected molecular weights observed in mass spectra positively confirm the synthesis of β-carboline derivatives.…”

Section: Synthesis Of β-Carboline Derivativesmentioning

confidence: 99%

“…In an endeavor to develop new βCA derivatives Lopes-Ortiz et al, synthesized imide βCA and carbomethoxy βCA derivatives and their pharmacological properties were studied [13]. In another study, Sireesha et al, synthesized new benzimidazole/benzoxazole linked β-carbolines by joining two different anti-cancer fragments, these hybrid β-carbolines showed high fold cytotoxic activity against MCF-7 cell lines [14].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and characterization of β-carboline fatty alcohol hybrids as potential biological active and antioxidant molecules

Kontham¹,

Ippakayala²,

Madhu³

2020

Preprint

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Nine new β-carboline fatty alcohol hybrids were synthesized from natural amino acid L-tryptophan and hybridized with 10-undecenol via ester linkage. All the synthesized products were characterized in each step by spectral techniques (1H, 13C NMR mass and HRMS). Synthesized β-carboline derivatives (7a-i) were screened for biological activities such as antimicrobial, antifungal, antibio film and anticancer. Compounds 7d and 7f showed most potent antimicrobial activity against B.subtilis MTCC 121, M.luteus MTCC 2470, S.aureus MTCC 96 and C.albicans MTCC 3017 bacterial strains ranged from 2.8 to 28.3 µg/mL. Biofilm inhibition assay showed that the compound 7f exhibited better activity against three bacterial stains with IC50 values from 1.8 to 2.9 µM. All the β-carboline derivatives showed cytotoxic activity, among them compounds 7f and 7h (IC50 values 9.1 and 11.4 µM) were exhibited potential activity. Free radical scavenging activity via DPPH assay revealed that compound 7g acted as good antioxidant molecule than all the tested compounds.

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“…Hydrazinyl derivatives display biological interesting as antioxidant [ 4 , 7 ], anti-inflammatory [ 8 ], anticonvulsant [ 9 ], analgesic [ 10 ], antimicrobial [ 11 , 12 ], anticancer [ 13 ], antiprotozoal [ 14 ], antiparasitic [ 15 , 16 ], cardioprotective [ 17 , 18 ], antitubercular [ 19 ] and anti-HIV [ 20 , 21 ]. Hydrazinyls derivative are used as common drug diseases for malaria [ 22 ], tuberculosis [ 23 ] and mental disorders.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of arylidene hydrazinylpyrido[2,3-d]pyrimidin-4-ones as potent anti-microbial agents

Abdelhameed

Darwesh

El‐Shahat

2020

Heliyon

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Combination of arylidene hydrazinyl moiety with pyrido[2,3- d ]pyrimidin-4-one skeleton in compounds 7‒26 results in the output of unprecedented anti-microbial agents. Arylidene hydrazinyl based on Pyrido[2,3- d ]pyrimidin-4-one analoges 7‒26 prepared by the treatment of [2,3- d ]pyrimidin-4-ones 6a , b with various aromatic aldehydes. The antimicrobial action for recently synthesized compounds was considered towards gram positive bacterial species ( Staphylococcus aurous ATCC- 47077; Bacillus cereus ATCC-12228), gram negative bacterial species ( Escherichia coli ATCC-25922; Salmonella typhi ATCC-15566) and Candida albicans ATCC-10231 as fungal strains. The antimicrobial action expanded by expanding the electron donating group in position 2 and 5 for Pyrido[2,3- d ]pyrimidin-4-one core. Derivatives 13 , 14 , 15 , 16 and 12 ; individually appeared hopeful anti-microbial action towards all strains utilized with inhibition zone higher than that of standard reference drug with lowest MIC.

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Synthesis and anti-Mycobacterium tuberculosis activity of imide-β-carboline and carbomethoxy-β-carboline derivatives

Cited by 20 publications

References 41 publications

Anti‐Tubercular Insights of Carbolines – A Decade Critique

Anti‐Tubercular Insights of Carbolines – A Decade Critique

Synthesis and characterization of β-carboline fatty alcohol hybrids as potential biological active and antioxidant molecules

Synthesis of arylidene hydrazinylpyrido[2,3-d]pyrimidin-4-ones as potent anti-microbial agents

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