The synthesis of 5-aryl-2-furancarboxylic acids

Krutošíková, A.; Kováč, J.; Sýkora, V.

doi:10.1135/cccc19741892

Cited by 21 publications

(5 citation statements)

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“…7: 4,4′-Bis[2-(5-amidinobenzimidazoyl)]-2,5-diphenylfuran Hydrochloride. 2,5-Bis(4-formylphenyl)furan was prepared by reduction of 2,5-bis(4-cyanophenyl)furan 29,30 (1.12 g, 0.004 mol) using 1 M DIBAL in (CHCl3:ether). 1 H NMR (DMSO-d6): 10.0 (s, 2H), 8.05 (d, 4H, J ) 7.5), 7.97 (d, 4H, J ) 7.5), 7.37 (s, 2H).…”

Section: : 25-bis[2-(5-(n-cyclopentylamidino)benzimidazoyl)mentioning

confidence: 99%

“…A protocol similar to that described above was employed for the condensation of 2,5-bis(4-formylphenyl)furan and 4-amidino-1,2-phenylenediamine 27 to give a 68% yield of a yellowbrown powder, mp 355-7 °C dec. 1 A protocol similar to that described above was employed for the condensation of 2,5-bis(4-formylphenyl)furan and 4-(N-isopropylamidino)-1,2phenylenediamine 27 to give a 75% yield of yellow solid, mp 290-292 °C dec. 1 H NMR (DMSO-d6/D2O): 8.28 (d, 4H, J ) 6.8), 8.1 (s, 2H), 7.95 (d, 4H, J ) 6.8), 7.80 (d, 2H, J ) 8.4), 7.62 (d, 2H, J ) 8.4), 7.2 (s, 2H), 4.09 (septet, 2H, J ) 6.4), 1.32 (d, 12H, J ) 6.4). 13 29,30 (1.88 g, 0.0152 mol), 3,4-diaminobenzonitrile 27 (2 g, 0.0152 mol), and benzoquinone (1.64 g, 0.0152 mol) in ethanol (150 mL) was allowed to reflux under nitrogen for 4 h. After cooling solid was collected by filtration and recrystallized from chloroform, yield 3.75 g (79%) of yellow solid, mp 157-160 °C dec. 1 H NMR (DMSO-d6): 13.65 (brs, 1H), 8.14 (brs, 1H), 8.11 (d, 2H, J ) 8.4), 7.98 (d, 2H, J ) 8.1), 7.76 (d, 1H, J ) 8.4), 7.62 (dd, 1H, J ) 8.4, 1.5), 7.49 (d, 1H, J ) 3.9), 7.46 (d, 1H, J ) 3.9). 13 C NMR (DMSO-d6): 153.0, 145.8, 145.2, 133.1, 132.9, 125.9, 125.9, 124.…”

Section: : 25-bis[2-(5-(n-cyclopentylamidino)benzimidazoyl)mentioning

confidence: 99%

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Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents

Wilson

et al. 1998

J. Med. Chem.

187

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The syntheses of nine new derivatives of 2, 5-bis[4-(N-alkylamidino)phenyl]furans with extended aromatic systems are reported. The interaction of these dicationic furans with poly(dA)poly(dT) and with the duplex oligomers d(CGCGAATTCGCG)2 and d(GCGAATTCGC)2 was determined by Tm measurement, and the effectiveness of these compounds against the immunosuppressed rat model of Pneumocystis carinii was evaluated. At a screening dose of 10 micromol/kg, 4 of the 12 amidino furans described here are more active than the parent compound 1. In general, extension of the aromatic system in the absence of a substitution of the amidino nitrogens resulted in higher affinity for DNA than the parent compound as judged by the larger DeltaTm values and suggests enhanced van der Waals interactions in the amidino furan-DNA complex. Three of the compounds, 3, 5, and 11, yield cysts counts of less than 0.1% of control when administered at a dosage of 10 micromol/kg. Compound 3, which does not have an extended aromatic system, is the most active derivative. Although a direct correlation between anti-P. carinii activity and DNA binding affinity was not observed, all compounds which have significant activity have large DeltaTm values.

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Section: : 25-bis[2-(5-(n-cyclopentylamidino)benzimidazoyl)mentioning

confidence: 99%

Section: : 25-bis[2-(5-(n-cyclopentylamidino)benzimidazoyl)mentioning

confidence: 99%

Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents

Wilson

et al. 1998

J. Med. Chem.

187

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“…5-Substituted phenyl-2-furoic acid 4 was prepared according to the method given in references. 28,31,32 …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Bioactivity of Novel N,N′‐Diacylhydrazine Derivatives Containing Furan (III)

et al. 2010

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The furan ring system possesses electron-rich properties and exhibits various biological activities, which was introduced into diacylhydrazine to create novel leading compounds that may serve as improved pesticides and pharmaceuticals. A series of novel diacylhydrazine derivatives containing a furan ring were synthesized by the reaction of 5-fluorophenyl-2-furoyl chloride with substituted benzoylhydrazide in anhydrous dichloromethane under reflux. The structures of the resultant compounds were confirmed by IR, 1 H NMR, MS and elemental analysis. Insecticidal and anti-tumor activities of these new compounds were evaluated.

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“…4 5-(2-Trifluoromethylphenyl)-2-furoyl chloride was also synthesized in our laboratory according to a literature. 5 To a stirred solution of 1 (0.89 g, 3 mmol) in acetonitrile (10 mL) was slowly added a solution of 4-methylbenzohydrazide (0.45 g, 3 mmol) in dry acetonitrile (10 ml) over a period of 20 min at room temperature. The mixture was stirred for 2 h at room temperature.…”

Section: Synthesis Of the Title Compoundmentioning

confidence: 99%

Synthesis, Crystal Structure and Bioactivities of N‐(4‐Methyl‐ benzamido)‐ N′‐[5‐(2‐trifluoromethylphenyl)‐2‐furoyl]thiourea

et al. 2008

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The title compound N- (4-methylbenzamido)-N'-[5-(2-trifluoromethylphenyl)-2-furoyl]thiourea has been synthesized for the first time and its crystal structure (C 21 H 16 F 3 N 3 O 3 S, M r ＝447.43) has been determined by single-crystal X-ray diffraction analysis. The crystal belongs to monoclinic, space group P-1 with a＝0.9677 (7) (I)]. In the crystal structure, there are some intra-and intermolecular hydrogen bonds and C-H…π interaction between the molecules, which stabilize the crystal structure. The preliminary bioassay shows that the title compound exhibits good fungicidal activities against Fusarium oxysporium, Botrytis cinereapers, and Dothiorella gregaria.

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The synthesis of 5-aryl-2-furancarboxylic acids

Cited by 21 publications

References 0 publications

Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents

Extended Aromatic Furan Amidino Derivatives as Anti-Pneumocystis carinii Agents

Synthesis and Bioactivity of Novel N,N′‐Diacylhydrazine Derivatives Containing Furan (III)

Synthesis, Crystal Structure and Bioactivities of N‐(4‐Methyl‐ benzamido)‐ N′‐[5‐(2‐trifluoromethylphenyl)‐2‐furoyl]thiourea

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