Synthesis and biological evaluation of pyrrole-2-carboxamide derivatives: oroidin analogues

Takale, Balaram S.; Desai, Neha V.; Siddiki, Afsar Ali; Chaudhari, Hemchandra K.; Telvekar, Vikas N.

doi:10.1007/s00044-013-0743-9

Cited by 9 publications

(2 citation statements)

References 20 publications

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“…Some reduction products of the methyl esters and an amine derivative are represented by compounds 44 – 46 , of which 45 occurs in both sponges, whereas 44 and 46 were exclusively isolated from the Nemoechinata sp. [ 68 , 69 , 76 , 77 ]. The carboxamide 47 is a debromo analog of mukanadin B and is present in Agelas nakamurai [ 68 , 78 , 79 ].…”

Section: Non-halogenated Marine Pyrrole Alkaloidsmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

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Nitrogen heterocycles are essential parts of the chemical machinery of life and often reveal intriguing structures. They are not only widespread in terrestrial habitats but can also frequently be found as natural products in the marine environment. This review highlights the important class of marine pyrrole alkaloids, well-known for their diverse biological activities. A broad overview of the marine pyrrole alkaloids with a focus on their isolation, biological activities, chemical synthesis, and derivatization covering the decade from 2010 to 2020 is provided. With relevant structural subclasses categorized, this review shall provide a clear and timely synopsis of this area.

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Section: Non-halogenated Marine Pyrrole Alkaloidsmentioning

confidence: 99%

Marine Pyrrole Alkaloids

2021

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“…Pyrrole compounds have been shown to exhibit significant activity against some pathogens and insects (Xu and Jiang ). Its structure includes a unit which is indispensable for many antimicrobial substances (Rane and Telvekar ; Takale et al ). In recent research, 1H‐pyrrole‐2‐carboxylic acid showed the significant activity of Pseudomonas by inhibiting QS and virulence determinants of P. aeruginosa PAO1 at the molecular level, which provides a useful scaffold for synthesis and construction of novel anti‐virulence drugs derived from natural sources (Ramadan et al ).…”

Section: Discussionmentioning

confidence: 99%

Identification of antimicrobial metabolites produced by a potential biocontrol Actinomycete strain A217

Hao

Zhou

et al. 2020

J Appl Microbiol

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Aims To extract and identify the metabolites of strain A217 as well as its antifungal spectrum and control effect on various plant pathogens. Methods and Results Strain A217 was identified as a Streptomyces sp. which was most similar to Streptomyces lienomycini. An antimicrobial spectrum test indicated that strain A217 inhibited several plant pathogenic fungi and strong antibacterial effect such as Phytophthora capsici, Botrytis cinerea, Sclerotinia sclerotiorum, Fusarium oxysporum, Pseudomonas syringae and Xanthomonas campestris. An in vivo tissue test demonstrated that the fermentation broth of strain A217 exerted therapeutic and protective effects of 49·47 and 61·60% respectively, on S. sclerotiorum. Additionally, the fermentation broth of A217 exerted control effects on walnut black spot disease in walnut leaves and branches amounting to 79·33 and 81·52% respectively. In a pot experiment, the fermentation broth exhibited a stronger protective and control effect (68·29%), as well as better bacteriostatic and disease control effects on Phytophthora blight of pepper, compared with Metalaxyl. Compounds possessing antifungal and antibacterial activities were obtained from the fermentation broth of strain A217, using column chromatography and HPLC. Chemical and structural analyses conducted using MS and nuclear magnetic resonance confirmed that these compounds were 1H‐pyrrole‐2‐carboxylic acid and 1H‐pyrrole‐2‐carboxamide. The EC50 values of compound 1H‐pyrrole‐2‐carboxylic acid1 for S. sclerotiorum and P. capsici were 20·13 and 50·36 μg ml−1 respectively. Compound 1H‐pyrrole‐2‐carboxamide2 showed significant antibacterial activity against different plant pathogenic bacteria. The MIC values of P. syringae, X. campestris and X. campestris pv. jugiandis were 7·5, 30 and 15·0 μg ml−1 respectively. Conclusions Actinomyces A217 fermentation products have a broad spectrum of bacteriostasis, and have good bacteriostasis activity to many plant pathogenic fungi and bacteria. Significance and Impact of the Study The present study revealed a new antimicrobial producing strain of Streptomyces and its potential application as a biological control agent for plant diseases.

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Concentrated Solar Radiation Aided Green Approach for Preparative Scale and Solvent‐Free Synthesis of 3‐Methyl‐4‐(hetero)arylmethylene Isoxazole‐5(4H)‐ones

Gadkari

Jadhav

Hatvate³

et al. 2020

ChemistrySelect

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An efficient, clean, and environmentally benign approach for the synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones has been developed using concentrated solar radiations (CSR). One pot, multicomponent synthesis from aromatic / heteroaromatic aldehydes, ethyl acetoacetate and hydroxylamine hydrochloride leads to title compounds in high yields. Notably the reaction has been carried out in under solvent and catalystfree conditions within a very short time (3 min). Further, the reaction was scaled up to 50 mmol. The present method is also energy efficient and saves almost more than 87 % of energy as compared to the conventional method.

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Synthesis and biological evaluation of pyrrole-2-carboxamide derivatives: oroidin analogues

Cited by 9 publications

References 20 publications

Marine Pyrrole Alkaloids

Marine Pyrrole Alkaloids

Identification of antimicrobial metabolites produced by a potential biocontrol Actinomycete strain A217

Concentrated Solar Radiation Aided Green Approach for Preparative Scale and Solvent‐Free Synthesis of 3‐Methyl‐4‐(hetero)arylmethylene Isoxazole‐5(4H)‐ones

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