310459-43-9Relevant academic research and scientific papers
5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors
Niu, Tianwei,Wang, Peipei,Li, Cheng,Dou, Tong,Piao, Huri,Li, Jia,Sun, Liangpeng
, (2020/12/04)
Two series of 5-aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety were identified as competitive protein tyrosine phosphatase 1B (PTP1B) inhibitors. Among the compounds studied, 5g was found to have the best PTP1B inhibitory potency (IC50 = 2.66 ± 0.16 μM) and the best cell division cycle 25 homolog B (CDC25B) inhibitory potency (IC50 = 0.25 ± 0.02 μM). Enzymatic data together with molecular modeling results demonstrated that the introduction of a sec-butyl group at the 2-position of the carboxyl group remarkably improved the PTP1B inhibitory activity.
Novel inhibitors of Plasmodium falciparum based on 2,5-disubstituted furans
Krake, Susann H.,Martinez, Pablo David G.,McLaren, Jenna,Ryan, Eileen,Chen, Gong,White, Karen,Charman, Susan A.,Campbell, Simon,Willis, Paul,Dias, Luiz Carlos
supporting information, p. 929 - 936 (2016/12/23)
Phenotypic HTS campaigns with a blood stage malaria assay have been used to discover novel chemotypes for malaria treatment with potential alternative mechanisms of action compared to existing agents. N1-(5-(3-Chloro-4-fluorophenyl)furan-2-yl)-N3,N3-dimethylpropane-1,3-diamine, 1 was identified as a modest inhibitor of P. falciparum NF54 (IC50= 875 nM) with an apparent long plasma half-life after high dose oral administration to mice, although the compound later showed poor metabolic stability in liver microsomes through ring- and side chain-oxidation and N-dealkylation. We describe here the synthesis of derivatives of 1, exploring the influence of substitution patterns around the aromatic ring, variations on the alkyl chain and modifications in the core heterocycle, in order to probe potency and metabolic stability, where 4k showed a long half-life in rats.
Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety
Che, Jian,Zheng, Chang-Ji,Song, Ming-Xia,Bi, Ya-Jing,Liu, Yi,Li, Yin-Jing,Wu, Yan,Sun, Liang-Peng,Piao, Hu-Ri
, p. 426 - 435 (2014/03/21)
Two series of furan derivatives bearing a rhodanine moiety (4a-l and 5a-l) have been synthesized, characterized, and evaluated for their antibacterial activity. The majority of these compounds showed potent levels of inhibitory activity against a variety of different Gram-positive bacteria, including multidrug-resistant clinical isolates, with minimum inhibitory concentration (MIC) values in the range of 2-16 μg/mL. In particular, compound 4l was found to be the most potent of the synthesized compounds against the multidrug-resistant strains, with a MIC value of 2 or 4 μg/mL. None of the compounds exhibited any activity against the Gram-negative bacteria Escherichia coli 1356 at 64 μg/mL. An examination of the cytotoxicities of these agents revealed that they displayed low levels of toxicity toward HeLa cells. All of the compounds synthesized in the current paper were characterized by 1H and 13C NMR, infrared, and mass spectroscopy. Graphical Abstract: Two novel series of furan derivatives bearing a rhodanine moiety were synthesized, and evaluated for their antibacterial activity. Compounds 4l and 5a presented high potency against several multidrug-resistant clinical isolates.[Figure not available: see fulltext.]
A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
Kim, Seung-Hoi,Rieke, Reuben D.
experimental part, p. 2657 - 2659 (2010/06/19)
An efficient synthetic route for the preparation of 5-heteroaryl- and 5-aryl-2-furaldehydes has been developed. It has been accomplished by the palladium(0)-catalyzed cross-coupling reaction of heteroarylzinc and arylzinc reagents with 5-bromo-2-furaldehyde under very mild conditions.
Synthesis, antitubercular and antimicrobial activity of some new N-aryl-1,4-dihydropyridines containing furan nucleus
Rokad,Tala,Akbari,Dhaduk,Joshi
experimental part, p. 186 - 191 (2010/02/28)
A wide range of biological activities are associated with 1,4-dihydropyridines individually or in combination. The synthesis of N-aryl-2,6-dimethyl-3,5-dicarbmethoxy-4-[5′-(m-chloro-p-flourophenyl) -2′-furyl]-1,4-dihydropyridines (6a-j) and N-aryl-2,6-dimethyl-3,5- dicarbmethoxy-4-[57prime;-(m-chloro-p-flourophenyl)-2′-furyl]-1, 4-dihydropyridines (7a-j) was under-taken with hope that they may be biologically active molecules with improved activity, less toxicity and undesirable side effects. The newly synthesized compounds were characterized on the basis of elemental analysis, IR, 1H NMR and mass spectral data. All newly synthesized compounds were tested for their antitubercular activity against Mycobacterium tuberculosis H37RV ATCC 27294, antibacterial activity against different Gram +ve and Gram -ve bacteria and antifungal activity.
