Structure–activity delineation of quinones related to the biologically active Calothrixin B

Bernardo, Paul H.; Chai, Christina L. L.; Guen, Maurice Le; Smith, Geoffrey D.; Waring, Paul

doi:10.1016/j.bmcl.2006.09.090

Cited by 61 publications

(9 citation statements)

References 18 publications

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“…It is well known that quinones possess a remarkable range of biological activity. They are essential for many cellular processes including respiration and photosynthesis (1), and there are many naturally occurring quinones that possess antioxidant (2), antiinflammatory (3) and antitumour properties (4,5). They have the ability to act as toxic metabolites and are therefore potentially effective anticancer drugs (6).…”

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confidence: 99%

Design, Synthesis and Structure of Novel Para‐Quinones and their Antibacterial Activity

et al. 2011

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Eight new para-quinones and one known analogue have been synthesized from p-chloranil. Five have been structurally characterized by single crystal diffraction, and a range of ligand folding is observed. All nine have been tested for their potency towards Gram(+) S. aureus and Gram(-) E. coli. Quinones 3, 6, 7 and 8 have shown activity towards S. aureus and quinones 3 and 8 also show good activity towards E. coli.

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confidence: 99%

Design, Synthesis and Structure of Novel Para‐Quinones and their Antibacterial Activity

et al. 2011

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“…To study the involvement of the ring structure and the mechanism of action in the inhibitory effects, the same group [ 58 ] synthesized and analyzed the activity of various simple quinone analogs of calothrixin B ( Table 5 ) in 2007. The compounds were evaluated for their selectivity and antiproliferative activity, using an MTT assay, against three different cell lines: human cervical cancer (HeLa) cells, murine P388 macrophage cancer cells, and simian non-cancerous CV-1 cells.…”

Section: Bioactivities Of Calothrixinsmentioning

confidence: 99%

Cyanobacterial Metabolite Calothrixins: Recent Advances in Synthesis and Biological Evaluation

Nijampatnam

Dutta

et al. 2016

Marine Drugs

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The marine environment is host to unparalleled biological and chemical diversity, making it an attractive resource for the discovery of new therapeutics for a plethora of diseases. Compounds that are extracted from cyanobacteria are of special interest due to their unique structural scaffolds and capacity to produce potent pharmaceutical and biotechnological traits. Calothrixins A and B are two cyanobacterial metabolites with a structural assembly of quinoline, quinone, and indole pharmacophores. This review surveys recent advances in the synthesis and evaluation of the biological activities of calothrixins. Due to the low isolation yields from the marine source and the promise this scaffold holds for anticancer and antimicrobial drugs, organic and medicinal chemists around the world have embarked on developing efficient synthetic routes to produce calothrixins. Since the first review appeared in 2009, 11 novel syntheses of calothrixins have been published in the efforts to develop methods that contain fewer steps and higher-yielding reactions. Calothrixins have shown their potential as topoisomerase I poisons for their cytotoxicity in cancer. They have also been observed to target various aspects of RNA synthesis in bacteria. Further investigation into the exact mechanism for their bioactivity is still required for many of its analogs.

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“…Red-brown solid; reaction time-30 min (0.589 g, 98 %); mp>300°C; UV-Vis (acetone)-446.12 nm; IR (KBr)-1,271, 1,346, 1,541, 1,624, 1,691, 3,334, and 3,400 cm General procedure for synthesis of 2-(4-amino-phenylsulfonyl) -5H-benzo [b]carbazole-6,11-diones (1a-7a) Method C [14,15] A mixture of 1-7 (0.5 mmol) in glacial acetic acid (60 mL) and palladium (II) acetate (0.112 g, 0.5 mmol) were refluxed for 2 h, and the reaction mixture was cooled at room temperature and poured into ice-cold water. The precipitate was filtered, dried at 60°C and crystallized from acetone to give 1a-7a.…”

Section: Methods B [13]mentioning

confidence: 99%

Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

2014

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A new series of new 1,4-naphthoquinone derivatives containing carbazole-6,11-dione moiety, which has not been reported yet, has been synthesized from 1,4-naphthoquinone and 4-aminophenylsulfone involving a Michael addition, benzoylation, and Pd-catalyzed coupling. This set of compounds has been evaluated for in vitro antibacterial studies against different Gram-positive and Gramnegative bacteria, and most of the synthesized compounds exhibited good antibacterial activity and the minimum inhibitory concentrations (MICs) are compared with the standard drugs used. Compound 7 exhibited good antibacterial activity among all the molecules studied with the best MIC of 2.1 μg/ mL against Bacillus subtilis. To understand the molecular interactions with targeted proteins, the molecular docking of all the synthesized compounds were carried out; between 14 molecules docked, compound 7 was the one with the best glide and E model score of −7.73 and −95.37, respectively. In all docked molecules, compound 5 exhibited least glide and E model score of −4.55 and −101.56, respectively.

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Structure–activity delineation of quinones related to the biologically active Calothrixin B

Cited by 61 publications

References 18 publications

Design, Synthesis and Structure of Novel Para‐Quinones and their Antibacterial Activity

Design, Synthesis and Structure of Novel Para‐Quinones and their Antibacterial Activity

Cyanobacterial Metabolite Calothrixins: Recent Advances in Synthesis and Biological Evaluation

Synthesis, molecular docking and antibacterial evaluation of new 1,4-naphthoquinone derivatives contains carbazole-6,11-dione moiety

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