Synthesis of coumarin-theophylline hybrids as a new class of anti-tubercular and anti-microbial agents

Mangasuli, Sumitra N.; Hosamani, Kallappa M.; Devarajegowda, H. C.; Kurjogi, Mahantesh; Joshi, Shrinivas D.

doi:10.1016/j.ejmech.2018.01.025

Cited by 73 publications

(42 citation statements)

References 25 publications

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“…Ligands 1 , 2 , and 3 , and their methyl analogues— N ‐methylbenzimidazole and caffeine—were reacted with [AuCl(PPh 3 )] in the presence of the chloride abstractor AgBF 4 to convert them into the corresponding gold(I) complexes 4 – 8 (Scheme ). The formation of the complexes can be easily monitored by 31 P NMR spectroscopy.…”

Section: Resultsmentioning

confidence: 99%

“…Ligands 1, 2, [26] and 3,a nd their methyl analogues-N-methylbenzimidazole and caffeine-were reacted with [AuCl(PPh 3 )] in the presence of the chloride abstractor AgBF 4 to convert them into the corresponding gold(I) complexes 4-8 (Scheme 2). The formation of the complexes can be easily monitored by 31 PNMR spectroscopy.M oreover,i nt he 1 HNMR spectrum,i ti si nterestingt on ote that the imidazole CÀH proton shifts from d % 7.6 to 8.9 ppm, which is close to the Scheme1.Strategyd eveloped herein to combine results from two of our previous studies.…”

Section: Synthesismentioning

confidence: 99%

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Gold(I)–Coumarin–Caffeine‐Based Complexes as New Potential Anti‐Inflammatory and Anticancer Trackable Agents

et al. 2018

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Three new gold(I)-coumarin-based trackable therapeutic complexes and two non-trackable analogues have been synthesised and fully characterised. They all display anti-proliferative properties on several types of cancer cell lines, including those of colon, breast, and prostate. Two complexes displayed significant anti-inflammatory effects; one displayed pro-inflammatory behaviour; this highlights the impact of the position of the fluorophore on the caffeine scaffold. Additionally, the three coumarin derivatives could be visualised in vitro by two-photon microscopy.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesismentioning

confidence: 99%

Gold(I)–Coumarin–Caffeine‐Based Complexes as New Potential Anti‐Inflammatory and Anticancer Trackable Agents

et al. 2018

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“…7-Amino-4-methylcoumarin (7-amino-4-methyl-2H-chromen-2-one; NA5) showed the lowest MIC of 1 mg/L against H37Rv strain. Reddy et al [36] synthesized a series of coumarin-oxime ether using the SN 2 reaction of bromomethyl coumarins with butane-2,3-dione monoxime and the derivatives were tested for in vitro anti-TB activity against MTBH 37 Rv strain. The compound (1 h) was found to be the most active by exhibiting MIC of 0.04 μg/ml which is closer to the MIC value of standard drug isoniazid (0.02 μg/ml).…”

Section: Antitubercular Activitymentioning

confidence: 99%

“…The compound (1 h) was further used to explore the mode of interaction with a model serum protein, bovine serum albumin which displayed excellent interaction without influencing its normal functioning. Mangasuli et al [37] synthesized a series of substituted C-4 bridged coumarin-theophylline hybrids and assayed for their anti-TB activity against M. tuberculosis H 37 Rv, antimicrobial activity against Gram-positive bacteria (S. aureus) and Gram-negative bacterial strains (E. coli, Salmonella typhi) as well as fungal strain (C. albicans). The compound (3a) represented remarkable anti-TB activity with MIC of 0.12 μg/ml.…”

Section: Antitubercular Activitymentioning

confidence: 99%

Coumarins: A Unique Scaffold With Versatile Biological Behavior

Gupta¹,

Kumar²,

Chaudhary³

2019

Asian J Pharm Clin Res

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Benzopyrones are the club of compounds that can be coumarins or flavonoids. The hydroxyl derivatives of coumarins such as 4-hydroxycoumarins and 7-hydroxycoumarins have extensive biological activities which have employed for the synthesis of miscellaneous coumarin derivatives. These derivatives have exhibited impressive pharmacological and physiological activities such as anticoagulant, antibacterial, antiviral, antitumor, bactericidal, fungicidal, anti-inflammatory agents, and anti-HIV activity. This review comprised pharmacokinetic studies, including absorption, distribution, and metabolism of coumarin analogs along with toxicological studies. The studies of coumarins and their derivatives exhibiting immense pharmacological activity are also summarized in the current study.

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“…Coumarins are a group of heterocyclic compounds naturally present in a large variety of plant families especially in fruits, seeds, roots, and leaves . Coumarins as oxygen‐containing heterocycles are obtained from both natural and synthetic sources, and they possess a variety of biological activities including antioxidant, anti‐inflammatory, anticancer, anti‐HIV, antitumor, anticoagulant, antibiotic, antiproliferative, antidepressant, antiasthmatic, antiplasmodial, antiplatelet, antimalarial, antiviral, anti‐influenza, antifungal, antibacterial, antimicrobial, and α‐glucosidase inhibitors . Photochemical, photophysical, fluorescence, optical, and photoluminescence properties of coumarin derivatives were investigated and discussed .…”

Section: Introductionmentioning

confidence: 99%

An efficient synthesis of novel heterocyclic systems incorporating coumarin moiety

El‐Gohary

El-Kazak

Ibrahim

2019

Journal of Heterocyclic Chem

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Polyfunctional 3-chloro-3-(4-chlorocoumarin-3-yl)prop-2-enal (1) used as a precursor for heterocyclic synthesis. Dichloro-aldehyde 1 was allowed to react with variable nucleophilic reagents, and a diversity of heterocyclic systems linked coumarin moiety at position 3 was synthesized. The reaction of compound 1 with guanidine and cyanoguanidine produced 3-(pyrimidin-4-yl)-4chlorocoumarins 2 and 3. Treating compound 1 with 3-amino-1,2,4-triazole and 2-aminobenzimidazole yielded triazolo[4,3-a]pyrimidine 4 and pyrimido [1,2-a]benzimidazole 5. The treatment of compound 1 with cyanoacetamide, N-benzyl-2-cyanoacetamide, and 1H-benzimidazolylacetonitrile gave 2(1H)pyridones 6, 7 and pyrido[1,2-a]benzimidazole 8. The reaction of compound 1 with 5-amino-3-methyl-1H-pyrazole and 6-aminouracil afforded pyrazolo[3,4b]pyridine 9 and pyrido[2,3-d]pyrimidine 10, respectively. Compound 1 reacted with ethylenediamine, o-phenylenediamine, o-aminophenol, and oaminothiophenol leading to 5-(imidazolylmethyl)chromeno[4,3-e] [1,4] diazepine (12), 3-(benzodiazepin/benzoxazepin-2-yl)-4-chlorocoumarins 13, 14, and 6-(benzothiazol-2-ylmethyl)chromeno[4,3-b][1,5]benzothiazepine 16, respectively. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data.

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Synthesis of coumarin-theophylline hybrids as a new class of anti-tubercular and anti-microbial agents

Cited by 73 publications

References 25 publications

Gold(I)–Coumarin–Caffeine‐Based Complexes as New Potential Anti‐Inflammatory and Anticancer Trackable Agents

Gold(I)–Coumarin–Caffeine‐Based Complexes as New Potential Anti‐Inflammatory and Anticancer Trackable Agents

Coumarins: A Unique Scaffold With Versatile Biological Behavior

An efficient synthesis of novel heterocyclic systems incorporating coumarin moiety

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