cas 20005-42-9, 5-(4-Bromophenyl)furfural | Articles data

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Synthesis of novel diarylpyrrole-2-carbaldehydes by ring transformations
Various diarylpyrrole-2-carbaldehydes were prepared by ring transformation of arylfuran-2-carbaldehydes with anilines in the presence of an acid. The synthesized compounds were characterized through elemental analysis and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).
Aslam, Samina,Nazeer, Areesha,Khan, Muhammad Naeem,Parveen, Najma,Khan, Misbahul Ain,Munawar, Munawar Ali
p. 9595 - 9600
(2013)
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Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
Serine, the source of the one-carbon units essential for de novo purine and deoxythymidine synthesis plays a crucial role in the growth of cancer cells. Phosphoglycerate dehydrogenase (PHGDH) which catalyzes the first, rate-limiting step in de novo serine biosynthesis has become a promising target for the cancer treatment. Here we identified H-G6 as a potential PHGDH inhibitor from the screening of an in-house small molecule library based on the enzymatic assay. We adopted activity-directed combinatorial chemical synthesis strategy to optimize this hit compound. Compound b36 was found to be the noncompetitive and the most promising one with IC50 values of 5.96 ± 0.61 μM against PHGDH. Compound b36 inhibited the proliferation of human breast cancer and ovarian cancer cells, reduced intracellular serine synthesis, damaged DNA synthesis, and induced cell cycle arrest. Collectively, our results suggest that b36 is a novel PHGDH inhibitor, which could be a promising modulator to reprogram the serine synthesis pathway and might be a potential anticancer lead worth further exploration.
Gou, Kun,Luo, Youfu,Luo, Yuan,Sun, Qingxiang,Tan, Yuping,Tao, Lei,Zhao, Yinglan,Zhou, Xia,Zhou, Yue,Zuo, Zeping
(2021/07/26)

Synthesis of arylfuran derivatives as potential antibacterial agents
Bacterial infections represent a serious health care problem mainly due to the misuse and overuse of antibiotics, with consequent emergence of multidrug resistant bacterial strains. Then, because the urgent need to find novel and alternative antibacterial agents, the present work focuses on the synthesis of arylfuran derivatives with potential antimicrobial activity. Eighteen arylfuran derivatives were synthesized and evaluated for their antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Among them, seven compounds containing an amino group in their structure showed activity, with compound 24 being the most effective against both Gram-negative (E. coli, MIC = 49 μM) and Gram-positive (S. aureus, MIC = 98 μM) bacteria, besides having exhibited a modest activity against P. aeruginosa (MIC = 770 μM). In addition, based on in silico studies, this is a druglike compound since it does not violate any rules for predicting oral bioavailability. In this context, the significant antibacterial potential and the low similarity with known antibiotics indicate the innovative aspect of compound 24.
Andrade, Marina M. S.,Protti, ícaro F.,Maltarollo, Vinícius G.,da Costa, Ygor F. G.,de Moraes, Wesley G.,Moreira, Nicole F.,Garcia, Giovana G.,Caran, Gabriel F.,Ottoni, Flaviano M.,Alves, Ricardo J.,Moreira, Carolina P. S.,Martins, Helen R.,Alves, Maria Silvana,de Oliveira, Renata B.
p. 1074 - 1086
(2021/02/26)

5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors
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.
Niu, Tianwei,Wang, Peipei,Li, Cheng,Dou, Tong,Piao, Huri,Li, Jia,Sun, Liangpeng
(2020/12/04)

Synthesis of novel benzimidazoles and benzothiazoles via furan-2-carboxaldehydes, o-phenylenediamines, and 2-aminothiophenol using Cu(II) Schiff-base@SiO2 as a nanocatalyst
2-(5-Substituted phenyl)furan-2-carboxaldehyde derivatives were prepared by using an efficient copper(II) complex of tetradentate Schiff-base ligand immobilized onto silica as a heterogeneous nanocatalyst [Cu(II) Schiff-base@SiO2] (5.0?mol%) using anilines, sodium nitrite, and furan-2-carboxaldehyde. Furthermore, attractive di-heteroaryl benzo-fused systems such as benzimidazole and benzothiazole derivatives were synthesized using this nanocatalyst (5.0?mol%) via the reaction of o-phenylenediamines and 2-aminothiophenol with 2-(5-substituted phenyl)furan-2-carboxaldehydes in EtOH. The catalyst was characterized by Fourier transform infrared (FT-IR), field emission scanning electron microscope (FESEM), energy-dispersive X-ray spectroscopy (EDX), X-ray powder diffraction (XRD), and inductively coupled plasma (ICP) techniques. The advantages of the present catalytic system are short reaction times, mild conditions, good to excellent yields, and low amount of nanocatalyst. Moreover, to the best of our knowledge, this is the first time of using the same catalyst in two steps including synthesis of 2-(5-substituted phenyl)furan-2-carboxaldehyde and benzimidazole or benzothiazole derivatives. In addition, the synthesized catalyst was recycled very well and reused several times without significant loss of its catalytic activity.
Sharghi, Hashem,Mashhadi, Elahe,Aberi, Mahdi,Aboonajmi, Jasem
(2021/06/25)

Discovery of (5-Phenylfuran-2-yl)Methanamine derivatives as new human sirtuin 2 Inhibitors
Human sirtuin 2 (SIRT2), a member of the sirtuin family, has been considered as a promising drug target in cancer, neurodegenerative diseases, type II diabetes, and bacterial infections. Thus, SIRT2 inhibitors have been involved in effective treatment strategies for related diseases. Using previously established fluorescence-based assays for SIRT2 activity tests, the authors screened their in-house database and identified a compound, 4-(5-((3-(quinolin-5-yl)ureido)methyl) furan-2-yl)benzoic acid (20), which displayed 63 ± 5% and 35 ± 3% inhibition against SIRT2 at 100 μM and 10 μM, respectively. The structure-activity relationship (SAR) analyses of a series of synthesized (5-phenylfuran-2-yl)methanamine derivatives led to the identification of a potent compound 25 with an IC50 value of 2.47 μM, which is more potent than AGK2 (IC50 = 17.75 μM). Meanwhile, 25 likely possesses better water solubility (cLogP = 1.63 and cLogS = ?3.63). Finally, the molecular docking analyses indicated that 25 fitted well with the induced hydrophobic pocket of SIRT2.
Wang, Lijiao,Li, Chao,Chen, Wei,Song, Chen,Zhang, Xing,Yang, Fan,Wang, Chen,Zhang, Yuanyuan,Qian, Shan,Wang, Zhouyu,Yang, Lingling
(2019/08/07)

Antimalarial agents against both sexual and asexual parasites stages: structure-activity relationships and biological studies of the Malaria Box compound 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine (MMV019918) and analogues
Therapies addressing multiple stages of Plasmodium falciparum life cycle are highly desirable for implementing malaria elimination strategies. MMV019918 (1, 1-[5-(4-bromo-2-chlorophenyl)furan-2-yl]-N-[(piperidin-4-yl)methyl]methanamine) was selected from the MMV Malaria Box for its dual activity against both asexual stages and gametocytes. In-depth structure-activity relationship studies and cytotoxicity evaluation led to the selection of 25 for further biological investigation. The potential transmission blocking activity of 25 versus P. falciparum was confirmed through the standard membrane-feeding assay. Both 1 and 25 significantly prolonged atrioventricular conduction time in Langendorff-isolated rat hearts, and showed inhibitory activity of Ba2+ current through Cav1.2 channels. An in silico target-fishing study suggested the enzyme phosphoethanolamine methyltransferase (PfPMT) as a potential target. However, compound activity against PfPMT did not track with the antiplasmodial activity, suggesting the latter activity relies on a different molecular target. Nevertheless, 25 showed interesting activity against PfPMT, which could be an important starting point for the identification of more potent inhibitors active against both sexual and asexual stages of the parasite.
Vallone, Alessandra,D'Alessandro, Sarah,Brogi, Simone,Brindisi, Margherita,Chemi, Giulia,Alfano, Gloria,Lamponi, Stefania,Lee, Soon Goo,Jez, Joseph M.,Koolen, Karin J.M.,Dechering, Koen J.,Saponara, Simona,Fusi, Fabio,Gorelli, Beatrice,Taramelli, Donatella,Parapini, Silvia,Caldelari, Reto,Campiani, Giuseppe,Gemma, Sandra,Butini, Stefania
p. 698 - 718
(2018/03/24)

Access to Densely Functionalized Chalcone Derivatives with a 2-Pyridone Subunit via Pd/Cu-Catalyzed Oxidative Furan-Yne Cyclization of N -(2-Furanylmethyl) Alkynamides under Air
A protocol for synthesis of chalcone derivatives with a 2-pyridone subunit from N-(2-furanylmethyl) alkynamides is reported. This synthesis involves Pd/Cu-catalyzed oxidative furan-yne cyclization at room temperature in air and may proceed via nucleopalladation of the alkyne to form a vinylpalladium intermediate, with a furan ring acting as the nucleophile.
Yang, Yongjie,Fei, ChengCheng,Wang, Kai,Liu, Bo,Jiang, Dingxin,Yin, Biaolin
supporting information
p. 2273 - 2277
(2018/04/30)

5-Aryl-2-furaldehydes in the synthesis of tetrahydropyrimidinones by Biginelli reaction
5-Aryl-2-furaldehydes, obtained by furfural arylation with arenediazonium salts, react with ethyl acetoacetate or acetylacetone and (thio)- urea in the presence of FeCl3·6H2O as a catalyst. A series of ethyl 4-(5-aryl-2-furyl)-6-methyl-2-oxo(thioxo)-1,2,3,4-tetrahydropyrimidine- 5-carboxylates was obtained.
Vakhula, Andriy R.,Horak, Yuriy I.,Lytvyn, Roman Z.,Lesyuk, Alexandra I.,Kinzhybalo, Vasyl,Zubkov, Fedor I.,Obushak, Mykola D.
p. 545 - 549
(2018/07/05)

Novel inhibitors of Plasmodium falciparum based on 2,5-disubstituted furans
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.
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)

Chemoselective hydrogen peroxide oxidation of primary alcohols to aldehydes by a water-soluble and reusable iron(iii) catalyst in pure water at room temperature
Hydrogen peroxide oxidation of primary alcohols to aldehydes is described, which is catalyzed by a novel, reusable and water-soluble FeCl3 complex in situ-formed with quaternary ammonium salt-functionalized 8-aminoquinoline. This reaction exhibits unique chemoselectivity and broad functional-group tolerance, and it can operate efficiently in pure water at room temperature.
Yan, Qi,Fang, Ye Chen,Jia, Yun Xue,Duan, Xin Hong
p. 2372 - 2377
(2017/03/21)

Antibacterial and antifungal properties of guanylhydrazones
A series of novel guanylhydrazones were designed, synthesized and characterized. All the compounds were screened for their antibacterial and antifungal activity. Compounds 26 and 27 showed excellent antibacterial activities against Staphylococcus aureus A
Ajda?i?, Vladimir,Lazi?, Jelena,Moji?evi?, Marija,?egan, Sandra,Nikodinovic-Runic, Jasmina,Opsenica, Igor M.
p. 641 - 649
(2017/08/09)

Covalently Immobilized Lipases are Efficient Stereoselective Catalysts for the Kinetic Resolution of rac-(5-Phenylfuran-2-yl)-β-alanine Ethyl Ester Hydrochlorides
Lipase-catalyzed enzymatic resolution of several new, exotic and variously substituted rac-(5-phenylfuran-2-yl)-β-alanine ethyl esters was investigated. Given the structural instability of unsubstituted rac-(5-phenylfuran-2-yl)-β-alanine ethyl ester, we u
Nagy, Botond,Galla, Zsolt,Bencze, László Csaba,To?a, Monica Ioana,Paizs, Csaba,Forró, Enik?,Fül?p, Ferenc
supporting information
p. 2878 - 2882
(2017/06/06)

Selective oxidations of activated alcohols in water at room temperature
Allylic and benzylic alcohols can be selectively oxidized to their corresponding aldehydes or ketones in water containing nanoreactors composed of the designer surfactant TPGS-750-M. The oxidation relies on catalytic amounts of CuBr, bpy, and TEMPO, with N-methyl-imidazole; air is the stoichiometric oxidant. the Partner Organisations 2014.
Lipshutz,Hageman,Fennewald,Linstadt,Slack,Voigtritter
supporting information
p. 11378 - 11381
(2014/11/08)

Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety
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.]
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)

Synthesis of 12-hetaryl-9,9-dimethyl-7,8,9,10-tetrahydrobenzo[a]acridin- 11(12H)-ones
Three-component condensation of naphthalen-2-amine with 5-arylfuran(thiophene, N-methylpyrrole)-2-carbaldehyde and 5,5- dimethylcyclohexane-1,3-dione, as well as condensation of N-[(5- arylfuran(thiophen)-2-ylmethylidene]naphthalen-2-amine with 5,5- dimethylcyclohexane-1,3-dione gave the corresponding 12-[5-arylfuran(thiophen, N-methylpyrrol)-2-yl]-7,8,9,10-tetradrobenzo[a]acridin-11(12H)-ones.
Kozlov,Zhikharko,Lytvyn,Gorak,Skakovskii,Baranovskii,Basalaeva,Obushak
p. 833 - 839
(2014/08/18)

Synthesis and biological evaluation of nitromethylene neonicotinoids based on the enhanced conjugation
The neonicotinoids with a nitroconjugated system had excellent bioactivity, which could rival imidacloprid, and has been previously reported. However, the photodegradation and hydrolysis of this series of neonicotinoids was very quick according to our further investigation, which cannot be developed as a pesticide further. The approach to further enhance the conjugation was tried not only to increase the bioactivities but also to improve the stability in water and in the sun. A substituted phenyl group was introduced into the furan ring of compound 3. A total of 13 novel neonicotinoid analogues with a higher conjugation system were designed and synthesized. The target molecular structures have been confirmed on the basis of satisfactory analytical and spectral data. All compounds presented significant insecticidal activities on cowpea aphid (Aphis craccivora), cotton aphid (Aphis gossypii), and brown planthopper (Nilaparvata lugens). The stability test exhibited that the stability of novel analogues in water and under the mercury lamp has been improved significantly in comparison to compound 3.
Lu, Siyuan,Zhuang, Yingying,Wu, Ningbo,Feng, Yue,Cheng, Jiagao,Li, Zhong,Chen, Jie,Yuan, Jing,Xu, Xiaoyong
p. 10858 - 10863
(2014/01/06)

5-substituted-2-furaldehydes: A synthetic protocol utilizing an organozinc route
Facile synthetic routes for the preparation of a wide range of 5-substituted 2-furaldehydes have been revealed. They were accomplished through either Pd-catalyzed cross-coupling reaction of various aryl- and heteroarylzinc halides with 5-bromo-2-furaldehyde or utilization of a new organozinc reagent, 5-(1,3-dioxolan-2-yl)-2-furanylzinc bromide, which was easily prepared by the direct insertion of highly active zinc to 2-(5-bromofuran-2-yl-1,3-dioxolane. Of special note is the uniqueness of using a new organozinc reagent, representing a first example of the direct synthesis of the corresponding organozinc halide. The subsequent coupling reactions in various types of reaction conditions led to the formation of somewhat different furan derivatives. It is also of significance that all of the cross-coupling reactions were carried out under mild conditions.
Kim, Seung-Hoi,Rieke, Reuben D.
p. 1984 - 1993
(2013/04/10)

Synthesis of novel arylfurfurylchalcones
Various aryl furans-2-carbaldehyde chalcones with different acetophenones were prepared and characterized through their elemental analyses and spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass spectra).
Aslam, Samina,Asif, Nadia,Khan, Muhammad Naeem,Khan, Misbahul Ain,Munawar, Munawar Ali,Nasrullah, Muhammad
p. 7738 - 7742
(2013/09/23)

Development of a novel class of B-RafV600E-selective inhibitors through virtual screening and hierarchical hit optimization
Oncogenic mutations in critical nodes of cellular signaling pathways have been associated with tumorigenesis and progression. The B-Raf protein kinase, a key hub in the canonical MAPK signaling cascade, is mutated in a broad range of human cancers and especially in malignant melanoma. The most prevalent B-RafV600E mutant exhibits elevated kinase activity and results in constitutive activation of the MAPK pathway, thus making it a promising drug target for cancer therapy. Herein, we describe the development of novel B-RafV600E selective inhibitors via multi-step virtual screening and hierarchical hit optimization. Nine hit compounds with low micromolar IC 50 values were identified as B-RafV600E inhibitors through virtual screening. Subsequent scaffold-based analogue searching and medicinal chemistry efforts significantly improved both the inhibitor potency and oncogene selectivity. In particular, compounds 22f and 22q possess nanomolar IC 50 values with selectivity for B-RafV600Ein vitro and exclusive cytotoxicity against B-RafV600E harboring cancer cells.
Kong, Xiangqian,Qin, Jie,Li, Zeng,Vultur, Adina,Tong, Linjiang,Feng, Enguang,Rajan, Geena,Liu, Shien,Lu, Junyan,Liang, Zhongjie,Zheng, Mingyue,Zhu, Weiliang,Jiang, Hualiang,Herlyn, Meenhard,Liu, Hong,Marmorstein, Ronen,Luo, Cheng
experimental part
p. 7402 - 7417
(2012/10/08)

5-(1,3-Dioxolan-2-yl)-2-furanylzinc bromide; Direct preparation, and its application for the synthesis of 5-substituted furan derivatives
5-(1,3-Dioxolan-2-yl)-2-furanylzinc bromide was easily prepared by the direct insertion of active zinc to 2-bromo-5-(1,3-dioxolane)furan under mild conditions. Of interest, the resulting organozinc was successfully coupled with aryl halides and acid chlorides affording the corresponding coupling products in good to excellent yields.
Rieke, Reuben D.,Kim, Seung-Hoi
scheme or table
p. 1128 - 1131
(2011/03/22)

Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2- furanmethyl ester
Chitin, a major structural component of insect cuticle and fungus cell wall but absent in plants and vertebrates, is regarded as a safe and selective target for pest control agents. Chitin synthesis inhibitors (CSIs) have been well-known as insect growth regulators (IGRs) but rarely found as fungicides in agriculture. To find novel CSIs with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 26 novel aryl carbamic acid-5-aryl-2-furanmethyl esters were designed by converting the urea linkages of benzoylphenylureas to carbamic acid esters and changing the aniline parts into furanmethyl groups. The title compounds were synthesized and their structures confirmed by IR, 1H NMR, and elemental analysis. Preliminary insecticidal and fungicidal bioassays were carried out. The results indicated that the title compounds had no insecticidal effect on Culex pipiens pallens and Plutella xylostella Linnaeus, but most compounds exhibited good fungicidal activities against Corynespora cassiicola, Thanatephorus cucumeris, Botrytis cinerea, and Fusarium oxysporum. In particular, compounds V-4, V-6, V-7, and V-8 showed better activities against the four strains than those of the commercialized fungicides. The morphologic result suggested that compound V-21 had disturbed the cell wall formation of C. cassiicola. The results indicated that modification on the urea linkage of benzoylphenylurea was an effective way to discover new candidates for fungicides.
Ying,Bao-Ju,Ling,Miao, Hong-Jian,Yan-Xia,Yang, Xin-Ling
scheme or table
p. 3037 - 3042
(2011/07/31)

Mechanism of Meerwein arylation of furan derivatives
Catalytic arylation of furan-2-carbaldehyde with arenediazonium salts was studied. The yields of 5-arylfuran-2-carbaldehydes were found to depend on the solvent, catalyst, and anion in the arenediazonium salt. Redox catalysis and generation of aryl radicals are not sufficient conditions for the reaction to occur. The reaction is successful only under conditions ensuring formation of complex intermediates. A mechanism involving two Cu2+ ? Cu + catalytic series and generation of furan-2-carbaldehyde was proposed.
Obushak,Lesyuk,Gorak, Yu. I.,Matiichuk
experimental part
p. 1375 - 1381
(2010/01/11)

Investigation of N-aryl-3-alkylidenepyrrolinones as potential Niemann-Pick type C disease therapeutics
A five-step synthesis of an array of N-aryl-3-alkylidenepyrrolinones, which are potential Niemann-Pick type C (NPC) disease therapeutics, is described. The synthetic route allows for the production of analogues, including photoaffinity and biotinylated de
Cosner, Casey C.,Markiewicz, John T.,Bourbon, Pauline,Mariani, Christopher J.,Wiest, Olaf,Rujoi, Madalina,Rosenbaum, Anton I.,Huang, Amy Y.,Maxfield, Frederick R.,Helquist, Paul
supporting information; experimental part
p. 6494 - 6498
(2010/03/31)

Gold catalysis: Oxepines from y-alkynylfurans
A ketal group in a furyl position affords arene oxides from y-alkynylfurans even with the simple gold(III) chloride (AuCl3) catalyst. These can either undergo Diels-Alder reactions, isomerise to stable oxepines by an oxygen-walk reaction or by
Hashmi, A. Stephen K.,Kurpejovic, Elzen,Woelfle, Michael,Frey, Wolfgang,Bats, Jan W.
p. 1743 - 1750
(2008/02/11)

Reactions of 1,5-π-cyclization of gem-difluoro-substituted azomethine ylides involving an aromatic ring
Reactions of N-(5-R-furan-2-ylmethylidene)anilines with difluorocarbene proceeds through intermediate azomethine ylides suffering 1,5-π-cyclization to yield 6,6-difluorocyclopropa[b]furo[2,3-c]pyrrole and/or 4,4,6,6- tetrafluorocyclopropa[b]furo[2,3-c]pyr
Voznyi,Novikov,Khlebnikov,Kostikov
p. 689 - 695
(2007/10/03)

A novel three-component synthesis of triazinothiazolones
A series of 4-arylidene-2-methyloxazol-5-ones 1 were condensed with thiosemi-carbazide to yield 6-arylmethyl-3-mercapto-1,2,4-triazin-5-ones 2. The resulting mercapto triazinones 2 were condensed with monochloroacetic acid and 5-aryl-furan-2-carboxaldehydes 3 in a one-pot three-component reaction in the presence of acetic anhydride, acetic acid, and sodium acetate to yield 4-substituted-5-oxo-7-(5-aryl-2-furfurylidene)-1,2,4-triazino[3,4-b] -thiazol-6-ones 4. Some of the newly synthesized compounds were tested for their antibacterial activity against Gram (+)ve and Gram (-)ve bacteria. The results of such studies are discussed in this paper. Copyright Taylor & Francis, Inc.
Holla, Bantval Shivarama,Malini, Kani Veetil,Sarojini, Balladka Kunhanna,Poojary, Boja
p. 333 - 340
(2007/10/03)

Preparation of novel phenylfuran-based cyanohydrin esters: Lipase-catalysed kinetic and dynamic resolution
A series of novel (R)-5-phenylfuran-2-yl cyanomethyl butanoates were prepared by Pseudomonas cepacia lipase-catalysed dynamic kinetic resolution in toluene. The method exploits a basic resin both for the racemization and formation of phenylfuran-based cyanohydrins and for the decomposition of acetone cyanohydrin in one-pot with enzymatic enantioselective acylation using vinyl butanoate. The lipase-catalysed methanolysis of racemic 5-phenylfuran-2-yl cyanomethyl butanoates in toluene with E ?100 was shown to be usable when the corresponding (S)-butanoates are needed. Candida antarctica lipase A provided racemic cyanohydrin butanoates with quantitative chemical yields under mild conditions.
Paizs, Csaba,Taehtinen, Petri,Lundell, Katri,Poppe, Laszlo,Irimie, Florin-Dan,Kanerva, Liisa T.
p. 1895 - 1904
(2007/10/03)

Dantrolene analogues revisited: General synthesis and specific functions capable of discriminating two kinds of Ca2+ release from sarcoplasmic reticulum of mouse skeletal muscle
The general synthesis of dantrolene analogues with various substituents on its phenyl ring has been developed via palladium-catalyzed cross-coupling reactions, the Stille or Suzuki reaction, as the key step. The effects of synthesized analogues have been evaluated by two kinds of Ca2+ release modes from sarcoplasmic reticulum (SR) of mouse skeletal muscle fibers based on: (1) the measurement of twitch contraction caused by the physiological Ca2+ release (PCR) of intact skeletal muscle and (2) the rate of Ca2+-induced Ca2+ release (CICR) in saponin-treated skinned muscle fibers. Although dantrolene, a lead compound, inhibits both twitch contraction and CICR, some structurally modified analogues exhibit one or the other of these effects. The methoxy congener, GIF-0185, potently inhibits the twitch contraction without affecting the CICR, while GIF-0166 and GIF-0248, the ortho-nitro regioisomer and ortho, ortho-dinitro substituted analogues, respectively, doubly potentiate the CICR exclusively.
Hosoya, Takamitsu,Aoyama, Hiroshi,Ikemoto, Takaaki,Kihara, Yasutaka,Hiramatsu, Toshiyuki,Endo, Makoto,Suzuki, Masaaki
p. 663 - 673
(2007/10/03)

Facile synthesis of 5-aryl-furan-2-aldehyde and 5-aryl-furan-2-carboxylic acid using ceric ammonium nitrate
A new method for the synthesis of furan-2-carboxaldehyde and 5-(substituted-phenyl)-furan-2-carboxylic acids using ceric ammonium nitrate (CAN) is reported.
Subrahmanya Bhat,Shivarama Holla
p. 625 - 628
(2007/10/03)

Structure-activity relationships of novel anti-malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides
In a previous report, we have described novel anti-malarial compounds based on a 2,5-diaminobenzophenone scaffold. Here, we have invesigated acryloyl derivatives carrying a biaryl structure consisting of a terminal aryl residue and a central 2-furyl ring. Several compounds were obtained in the series of para-substituted phenylfurylacryloyl derivatives that displayed improved anti-malarial activity in comparison to earlier described derivatives. From the structure-activity relationships it can be deduced that there has to be a lipophilic moiety in the para-position of the terminal phenyl residue. Furthermore, there are indications that, alternatively, activity may benefit from the presence of a polar moiety with hydrogen bond acceptor properties.
Wiesner, Jochen,Mitsch, Andreas,Wissner, Pia,Kraemer, Oliver,Jomaa, Hassan,Schlitzer, Martin
p. 2681 - 2683
(2007/10/03)

Preparation of 5-aryl furfurals and aryl thiophene-2-carboxaldehydes via palladium-catalyzed C-C bond formation in aqueous media
(matrix presented) A series of 5-aryl furfurals and aryl thiophene-2-carboxaldehydes was synthesized. To this end, efficient and effective palladium-catalyzed C-C bond-forming reactions were carried out at room temperature in aqueous media. This mild proc
Bussolari, Jacqueline C.,Rehborn, Diana C.
p. 965 - 967
(2008/02/09)

5-Phenyl-2-furamidines: A new chemical class of potential antidepressants
A series of 5-phenyl-2-furamidines has been synthesized and evaluated for antidepressant activities. Substitution in the phenyl ring with a nitro (4) or an amino (12) group in the ortho-position resulted in an increase in antidepressant activity. Both 4 and 12 antagonized tetrabenazine-induced ptosis in rodents and inhibited norepinephrine (noradrenaline) uptake into crude synaptosomes of whole mouse brain at doses or concentrations comparable to those of the tricyclic antidepressants. However, these compounds did not possess the anticholinergic and antihistaminic activities common to tricyclic antidepressants. In addition, they lacked monoamine oxidase inhibitory activity. The 5-phenyl-2-furamidines represent a new chemical class of antidepressants and may be useful for depressive patients who cannot tolerate the compromising side effects of the tricyclic antidepressants and monoamine oxidase inhibitors.
Pong,Pelosi Jr.,Wessels,Yu,Burns,White,Anthony Jr.,Ellis,Wright,White Jr.
p. 1411 - 1416
(2007/10/02)