Synthesis and reactions of substituted benzofuro[3,2-b]pyrrole derivatives

Krutošíková, A.; Kováč, J.; Dandarova, M.; Bobálová, Mária

doi:10.1135/cccc19823288

Cited by 12 publications

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“…One of the rings together with three unsaturations was assigned to a 1,2,3,5-tetrasubstituted phenyl ring on the basis of two proton doublets in the 1 H NMR spectrum at 7.63 and 7.52 ppm, respectively, with characteristic meta-coupling constants of 1.8 Hz (Table 1). Two of the substituents were assigned to be bromine atoms and one as an oxygen atom, the latter on the basis of a typical 13 C chemical shift of 155 ppm for the phenolic carbon atom. The substitution pattern of the benzene ring was suggested by 2D-NMR spectra displaying three-bond HMBC correlations from both aromatic protons to the oxygenated carbon atom resonating at 155.0 ppm.…”

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“…The alternative arrangement of the hydrogen and bromine atoms would have allowed for only one such correlation to be observed. 13 C NMR chemical shift analysis suggested that the oxygen atom was attached to another carbon atom resonating at 149.1 ppm. This required the third proton represented in the 1 H NMR spectrum by a broad singlet resonance at 8.46 ppm (in CDCl 3 ) to be an exchangeable hydrogen atom attached to nitrogen.…”

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“…As only three protons were present in the structure, including a broad NH singlet at 8.46 ppm, 2D-NMR experiments relying on heteronuclear correlations were insufficient to distinguish between these two possible structures. We therefore turned to 13 C NMR shift calculation using the ACD Laboratories C+H NMR predictor program (v. 12.01) and compared the computed chemical shifts for structures a and b (Figure 2) to the recorded values. The results summarized in Table 2 strongly suggested the regiochemistry of 1 to be that of a benzofuro(3,2-b)pyrrole based on an average ∆δ C ) 2.8 for the calculated 13 C NMR shifts.…”

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Highly Brominated Antimicrobial Metabolites from a MarinePseudoalteromonassp.

et al. 2010

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Extracts of a marine Pseudoalteromonas. sp (CMMED 290) isolated from the surface of a nudibranch collected in Kaneohe Bay, Oahu displayed significant antimicrobial activity against methicillin-resistant Staphylococcus aureus. Bioassay-guided fractionation of the lipophilic extract led to the isolation and structure elucidation of two new highly brominated compounds, 2,3,5,7-tetrabromobenzofuro[3,2-b]pyrrole 1 and 4,4′,6-tribromo-2,2′-biphenol 2. In addition, we have identified the known compounds pentabromopseudilin and bromophene. We describe the isolation and structure elucidation of the compounds 1 and 2 together with their antimicrobial activities against methicillin-resistant Staphylococcus aureus.The continuing emergence of antibiotic resistance in clinically relevant pathogens has placed considerable pressure on the pharmaceutical industry to develop novel drug candidates. 1 A prime example of the urgent need for novel antibiotic compounds is the Gram-positive bacterium methicillin-resistant Staphylococcus aureus (MRSA). In recent years, several reports of clinical resistance to traditional drugs of last resort for the treatment of MRSA infections, such as vancomycin and teicoplanin have appeared. 2 The development of MRSA infection from an originally hospital-acquired disease (HA-MRSA) to a communityassociated problem (CA-MRSA) provides additional reason for concern and makes this pathogen a primary target of antibiotic discovery programs. 3 Proteobacteria isolated from diverse marine environments have been shown to be prolific producers of secondary metabolites. 4 As part of our screening program aimed at the discovery of pharmaceutical lead compounds for the treatment of infective and neoplastic diseases we have previously reported on the isolation of metabolites from marine Proteobacteria belonging to the genus Pseudoalteromonas associated with marine invertebrates. 5 Another marine bacterial isolate streaked from the surface of a nudibranch collected in shallow waters of Kaneohe Bay, Oahu and deposited in our collection as CMMED 290 was shown to be a Pseudoalteromonas sp. based on its 16S rDNA gene sequence. The EtOAc extracts of cultures grown in marine broth displayed significant broad-spectrum biological activity against Staphylococcus aureus (ATCC 25923), methicillin-resistant Staphylococcus aureus (ATCC 43300), Escherichia coli (ATCC 25922), and Candida albicans as well as the human ovarian adenocarcinoma cell line SKOV-3 (ATCC HTB-77).* To whom correspondence may be addressed. Phone: 1-808-956-6401; Fax: 1-808-956-5908; hemschei@hawaii.edu. Supporting Information Available: 1 H-NMR and 13 C-NMR spectra of 1 and 2 and spectroscopic data for the known compounds pentabromopseudilin, bromophene, 3,5-dibromosalicylic acid and 3,5-dibromosalicylamide. This material is available free of charge via the Internet at http://pubs.acs.org. Large-scale fermentation, extraction and bioassay-guided fractionation of CMMED 290 led to the identification of two highly brominated compounds, 1 and 2, that...

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Highly Brominated Antimicrobial Metabolites from a MarinePseudoalteromonassp.

et al. 2010

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“…The following starting compounds were prepared according to literature procedures: 1d [21], 1e [22], 2a-d, and 3a,b [24][25][26][27]. Melting points were determined using a Kofler hotplate apparatus and are uncorrected.…”

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Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid

2004

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4-Heteroarylidene-2-phenyl-1,3-oxazol-5(4H)-ones were prepared by reactions of hippuric acid with substituted furan-2-carboxaldehydes or furo [b]pyrrole type aldehydes. The reactivity of various furan-2-carboxaldehyde derivatives in this reaction is discussed. The effect of microwave irradiation on some condensation reactions was compared with "classical" conditions. The results show that microwave irradiation shortens the reaction times while affording comparable yields. Elementary analysis, UV, IR and 1D NMR proved the structure of new synthesised compounds. 2D NMR spectroscopic measurements confirmed that the configuration at the carbon-carbon double bond corresponds to the pure E isomers of the products.

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“…A large number of 1,2,4-triazines fused with one or more heterocycles are known, and a wide variety of synthetic methods for their preparation are available [16,17]. We have been interested [18][19][20][21][22][23]in the chemistry of the 1,2,4-triazine ring fused on its 4-5 bond with furo [3,2-b]pyrrole and the 1,2,4-triazine ring fused on its 1-6 bond with 1,2,4-triazole ring.…”

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confidence: 99%

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

et al. 2005

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Abstract:The synthesis and reactions of methyl 2-[3-(trifluoromethyl)phenyl]-4H-furo[3,2-b]pyrrole-5-carboxylate (1a) are described.Upon reaction with methyl iodide, benzyl chloride, or acetic anhydride, this compound gave N -substituted products 1b-d. By hydrolysis of compounds 1a-c, the corresponding acids 2a-c were formed, or by reaction with hydrazine-hydrate, the corresponding carbohydrazides 3a-c were formed. 5-[3-(trifluoromethyl)phenyl]furan-2-carboxaldehyde. The effect of microwave irradiation on some condensation reactions was compared with "classical" conditions. The results showed that microwave irradiation shortens the reaction time while affording comparable yields.

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Synthesis and reactions of substituted benzofuro[3,2-b]pyrrole derivatives

Cited by 12 publications

References 0 publications

Highly Brominated Antimicrobial Metabolites from a MarinePseudoalteromonassp.

Highly Brominated Antimicrobial Metabolites from a MarinePseudoalteromonassp.

Reaction of Substituted Furan-2-carboxaldehydes and Furo[b]pyrrole Type Aldehydes with Hippuric Acid

2-[3-(Trifluoromethyl)phenyl]furo[3,2-b]pyrroles: synthesis and reactions

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