- Carbon–Carbon Bond Formation for the Synthesis of 5-Aryl-2-Substituted Furans Catalyzed by K3[Fe(CN)6]
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An efficient method for the carbon–carbon bond formation at C-5 position of 2-substituted furans to provide a range of π-diverse 5-aryl-2-substituted furan derivatives in 58–80% yield has been reported. The method employs several advantages such as use of catalytic amount of K3[Fe(CN)6] under mild conditions and short reaction time with high yields. Also, a variety of anilines with a variety of functional groups can be employed for the synthesis of 5-aryl-2-substituted furans. Graphic Abstract: [Figure not available: see fulltext.]
- Ambika,Singh, Pradeep Pratap
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- 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.
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p. 1074 - 1086
(2021/02/26)
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- 5-Aryl-furan derivatives bearing a phenylalanine- or isoleucine-derived rhodanine moiety as potential PTP1B inhibitors
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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
-
-
- 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
-
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- Discovery of novel inhibitors of human phosphoglycerate dehydrogenase by activity-directed combinatorial chemical synthesis strategy
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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
-
-
- Metal-Free Aerobic Oxidative Selective C-C Bond Cleavage in Heteroaryl-Containing Primary and Secondary Alcohols
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A transition-metal-free aerobic oxidative selective C-C bond-cleavage reaction in primary and secondary heteroaryl alcohols is reported. This reaction was highly efficient and tolerated various heteroaryl alcohols, generating a carboxylic acid derivative and a neutral heteroaromatic compound. Experimental studies combined with density functional theory calculations revealed the mechanism underlying the selective C-C bond cleavage. This strategy also provides an alternative simple approach to carboxylation reaction.
- Xia, Anjie,Qi, Xueyu,Mao, Xin,Wu, Xiaoai,Yang, Xin,Zhang, Rong,Xiang, Zhiyu,Lian, Zhong,Chen, Yingchun,Yang, Shengyong
-
supporting information
(2019/05/07)
-
- Preparation method and application of arylpyrazole compound containing structure of aminophosphonate and aryl furan
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The invention discloses a preparation method and application of an arylpyrazole compound containing a structure of aminophosphonate and aryl furan. The compound has a general molecular formula shown in (I). The compound has a small amount of usage, high insecticide efficiency, a simple process method, low cost and a broad market prospect.
- -
-
Paragraph 0030-0033
(2018/07/28)
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- 5-Aryl-2-furaldehydes in the synthesis of tetrahydropyrimidinones by Biginelli reaction
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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.
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p. 545 - 549
(2018/07/05)
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- 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)
-
- Multicomponent one pot synthesis and characterization of novel 4-furyl-1,4-dihydropyridines
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A series of dihydropyridines were prepared from the multi-component reaction of 5-arylfuran-2-carbaldehydes, ethylacetoacetate and ammonium acetate. These compounds were characterized through elemental analysis and various spectroscopic techniques (FTIR, 1H NMR, 13C NMR and mass).
- Zafar, Ansa Madeeha,Aslam, Samina,Khakwani, Samia,Khan, Muhammad Naeem,Munawar, Munawar Ali,Khan, Misbahul Ain
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p. 735 - 741
(2017/02/10)
-
- Discovery of selective protein arginine methyltransferase 5 inhibitors and biological evaluations
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Protein arginine methyltransferase 5 (PRMT5) is an important protein arginine methyltransferase that catalyzes the symmetric dimethylation of arginine resides on histones or non-histone substrate proteins. It has been thought as a promising target for many diseases, particularly cancer. Despite the potential applications of PRMT5 inhibitors in cancer treatment, very few of PRMT5i have been publicly reported. In this investigation, virtual screening and structure–activity relationship studies were carried out to discover novel PRMT5i, which finally led to the identification of a number of new PRMT5i. The most active compound, P5i-6, exhibited a considerable inhibitory potency against PRMT5 with an IC50 value of 0.57?μm, and a high selectivity for PRMT5 against other tested PRMTs. It displayed a very good antiviability activity against two colorectal cancer cell lines, HT-29 and DLD-1, and one hepatic cancer cell line, HepG2, in a sensitivity assay against 36 different cancer cell lines. Western blot assays indicated that P5i-6 selectively inhibited the symmetric dimethylations of H4R3 and H3R8 in DLD-1 cells. Overall, P5i-6 could be used as a chemical probe to investigate new functions of PRMT5 in biology and also served as a good lead compound for the development of new PRMT5-targeting therapeutic agents.
- Ji, Sen,Ma, Shuang,Wang, Wen-Jing,Huang, Shen-Zhen,Wang, Tian-Qi,Xiang, Rong,Hu, Yi-Guo,Chen, Qiang,Li, Lin-Li,Yang, Sheng-Yong
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p. 585 - 598
(2017/04/06)
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- Novel inhibitors of Plasmodium falciparum based on 2,5-disubstituted furans
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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
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supporting information
p. 929 - 936
(2016/12/23)
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- A phenyl [...] hERG potassium ion channel of small molecule fluorescent probe and its application (by machine translation)
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The invention discloses a phenyl furan small molecule fluorescent probe and its application. The general structure of the fluorescent probe shown in formula (I): In the formula, R 1 is halogen, a mono-substituted alkyl or alkoxy substituent base or many ; R 2 to fluorophore; n=1-6 ; ethylene in between with the fluorophore containing 1-6 is connected with the carbon of the alkyl chain. The fluorescence probe molecule can be used to mark hERG potassium ion channel, can be used for hERG the activity of the potassium ion channel inhibitors screening and listing pharmaceutical evaluation of the cardiac toxicity, in addition can also as a tool to medicine hERG potassium ion channel related phannacological, pathology and physiol research. Furthermore, this kind of compound preparation method mild reaction conditions, the raw material is cheap and easy to obtain, operation and after treatment is simple. (by machine translation)
- -
-
Paragraph 0037; 0038; 0057
(2016/11/24)
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- Sliver ion fluorescence sensor molecule as well as synthesis and application thereof
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The invention designs and synthesizes a sliver ion fluorescence sensor molecule-1H-imidazole[4,5-b] phenazine derivative, wherein phenazine in the sensor molecule is a stable system with a rigid structure; the sensor molecule is used as a fluorophore, so that the solution of the main body molecule emits strong fluorescence; imidazole and a furan ring are used as an identifying functional site; and in a water-containing medium, the molecule identifies sliver ions with high selectivity, and the identifying process is not distributed by other positive ions. Besides, when the silver ions are added at the room temperature, the fluorescence intensity of the solution is quickly weakened within 30 seconds, so that a very good naked-eye identifying effect can be achieved. Ag response test paper manufactured by utilizing the sensor molecule also can conveniently and quickly detect the silver irons in an environmental system.
- -
-
Paragraph 0031; 0033
(2016/10/10)
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- Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes
-
In the present work, a series of α-hydroxyimine palladium complexes with bulky substituents (i.e., {[Ar-N=C(R)-C(R)2-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.
- Luo, Bao-Tian,Liu, Huan,Lin, Zhi-Jie,Jiang, Jingxing,Shen, Dong-Sheng,Liu, Rui-Zhi,Ke, Zhuofeng,Liu, Feng-Shou
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p. 4881 - 4894
(2015/11/09)
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- Synthesis and antibacterial evaluation of furan derivatives bearing a rhodanine moiety
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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
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p. 426 - 435
(2014/03/21)
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- Synthesis of novel arylfurfurylchalcones
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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
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p. 7738 - 7742
(2013/09/23)
-
- Synthesis of novel diarylpyrrole-2-carbaldehydes by ring transformations
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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
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p. 9595 - 9600
(2014/01/06)
-
- Synthesis and biological evaluation of nitromethylene neonicotinoids based on the enhanced conjugation
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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
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p. 10858 - 10863
(2014/01/06)
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- Small-molecular inhibitors of Ca2+-induced mitochondrial permeability transition (MPT) derived from muscle relaxant dantrolene
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A structure consisting of substituted hydantoin linked to a 5-(halophenyl)furan-2-yl group via an amide bond was identified as a promising scaffold for development of low-molecular-weight therapeutic agents to treat vascular dysfunction, including ischemia/reperfusion injury. Among the compounds synthesized, 5-(3,5-dichlorophenyl)-N-{2,4-dioxo-3-[(pyridin-3-yl)methyl] imidazolidin-1-yl}-2-furamide (17) possessed the most potent inhibitory activity against Ca2+-induced mitochondrial swelling. The structural development, synthesis and structure-activity relationship of these compounds are described.
- Murasawa, Shinpei,Sato, Shinichi,Noguchi-Yachide, Tomomi,Hashimoto, Yuichi,Iuchi, Katsuya,Sodeoka, Mikiko,Dodo, Kosuke,Yokomatsu, Tsutomu,Aoyama, Hiroshi
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p. 6384 - 6393,10
(2012/12/11)
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- Development of a novel class of B-RafV600E-selective inhibitors through virtual screening and hierarchical hit optimization
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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)
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- Mono- and biscouplings using triarylbismuths for the atom-efficient arylations of functionalized furans under palladium catalysis
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Palladium-catalyzed cross-coupling reactions of functionalized bromofurans with triarylbismuths have been described for the atom-economic synthesis of functionalized arylfuran systems. The coupling reactions using triarylbismuths with various 2-bromofurans and 2,5-dibromofuran underwent smoothly to afford the corresponding 2-arylfurans and 2,5-diarylfurans in high yields in a short reaction time (one hour). Georg Thieme Verlag Stuttgart · New York.
- Rao, Maddali L. N.,Awasthi, Dheeraj K.,Talode, Jalindar B.
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supporting information; experimental part
p. 1907 - 1912
(2012/09/22)
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- New class of potent antitumor acylhydrazone derivatives containing furan
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A pair of chemical isomeric structures of N-acylhydrazone compounds I and II were designed and synthesized. The reaction was carried out with high diastereoselectivity to obtain one configurational isomer in excellent yields. The exact configuration and conformation of IIa and IIe were confirmed by the X-ray single crystal diffraction. The antitumor bioassay revealed that some compounds exhibited excellent activity against the selected cancer cell lines. In particular, IIf (IC50 = 16.4 μM) was better than doxorubicin (IC50 = 53.3 μM) against human promyelocytic leukemic cells (HL-60). Their toxicities were predicted in silico. The results showed that compounds II were safe and eligible to be development candidates. IIf showed great promise as a novel lead compound for further anticancer discovery.
- Cui, Zining,Li, Ying,Ling, Yun,Huang, Juan,Cui, Jingrong,Wang, Ruiqing,Yang, Xinling
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scheme or table
p. 5576 - 5584
(2011/02/22)
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- Synthesis and fungicidal activity of aryl carbamic acid-5-aryl-2- furanmethyl ester
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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
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scheme or table
p. 3037 - 3042
(2011/07/31)
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- A convenient synthesis of 5-aryl- and 5-heteroaryl-2-furaldehydes by the cross-coupling reaction of organozincs
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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.
- Kim, Seung-Hoi,Rieke, Reuben D.
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experimental part
p. 2657 - 2659
(2010/06/19)
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- Mechanism of Meerwein arylation of furan derivatives
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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
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experimental part
p. 1375 - 1381
(2010/01/11)
-
- Discovering potent inhibitors against the β-hydroxyacyl-acyl carrier protein dehydratase (FabZ) of helicobacter pylori: Structure-based design, synthesis, bioassay, and crystal structure determination
-
The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC50 values less than 2 μM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC 50) 0.86 μM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.
- He, Lingyan,Zhang, Liang,Liu, Xiaofeng,Li, Xianghua,Zheng, Mingyue,Li, HongLin,Yu, Kunqian,Chen, Kaixian,Shen, Xu,Jiang, Hualiang,Liu, Hong
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experimental part
p. 2465 - 2481
(2010/03/03)
-
- Toward novel HIV-1 integrase binding inhibitors: Molecular modeling, synthesis, and biological studies
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The identification of a novel hit compound as integrase binding inhibitor has been accomplished by means of virtual screening techniques. A small family of structurally related molecules has been synthesized and biologically evaluated with one of the compounds showing an IC50 = 12 μM.
- Mugnaini, Claudia,Rajamaki, Suvi,Tintori, Cristina,Corelli, Federico,Massa, Silvio,Witvrouw, Myriam,Debyser, Zeger,Veljkovic, Veljko,Botta, Maurizio
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p. 5370 - 5373
(2008/02/13)
-
- Design, synthesis, and evaluation of inhibitors for severe acute respiratory syndrome 3C-like protease based on phthalhydrazide ketones or heteroaromatic esters
-
The 3C-like protease (3CLpro), which controls the severe acute respiratory syndrome (SARS) coronavirus replication, has been identified as a potential target for drug design in the treatment of SARS. A series of tetrapeptide phthalhydrazide ketones, pyridinyl esters, and their analogs have been designed, synthesized, and evaluated as potential SARS 3CLpro inhibitors. Some pyridinyl esters are identified as very potent inhibitors, with IC50 values in the nanomolar range (50-65 nM). Electrospray mass spectrometry indicates a mechanism involving acylation of the active site cysteine thiol for this class of inhibitors.
- Zhang, Jianmin,Pettersson, Hanna I.,Huitema, Carly,Niu, Chunying,Yin, Jiang,James, Michael N. G.,Eltis, Lindsay D.,Vederas, John C.
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p. 1850 - 1864
(2008/02/02)
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- A novel three-component synthesis of triazinothiazolones
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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
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p. 333 - 340
(2007/10/03)
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- Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid
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A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.
- Pfefferkorn, Jeffrey A.,Greene, Meredith L.,Nugent, Richard A.,Gross, Rebecca J.,Mitchell, Mark A.,Finzel, Barry C.,Harris, Melissa S.,Wells, Peter A.,Shelly, John A.,Anstadt, Robert A.,Kilkuskie, Robert E.,Kopta, Laurice A.,Schwende, Francis J.
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p. 2481 - 2486
(2007/10/03)
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- Facile synthesis of 5-aryl-furan-2-aldehyde and 5-aryl-furan-2-carboxylic acid using ceric ammonium nitrate
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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
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p. 625 - 628
(2007/10/03)
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- Structure-activity relationships of novel anti-malarial agents. Part 4: N-(3-Benzoyl-4-tolylacetylaminophenyl)-3-(5-aryl-2-furyl)acrylic acid amides
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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
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p. 2681 - 2683
(2007/10/03)
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- Regioselective palladium-catalyzed arylation of 2-furaldehyde.
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An efficient regioselective method for the direct arylation of 2-furaldehyde to provide a range of pi-diverse 5-aryl-2-formylfuran derivatives is described. The method employs functionalized aryl halides and a catalytic amount of palladium(II) chloride under relatively mild conditions.
- McClure,Glover,McSorley,Millar,Osterhout,Roschangar
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p. 1677 - 1680
(2007/10/03)
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- N-hydroxy-5-phenyl-2-furancarboximidamides useful as cardiotonic agents
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The present invention involves certain N-hydroxy-5-phenyl-2-furancarboximidamides, pharmaceutical compositions containing such compounds, and methods for increasing the contractile force of cardiac muscle of a mammal which comprises systemically administering such compounds to a mammal.
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- AN IMPROVED SYNTHETIC METHOD FOR 5-ARYL-2-FURANCARBALDEHYDE
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An improved synthetic method for the preparation of 5-aryl-2-furancarbaldehyde via a photochemical arylation of 5-iodo-2-furancarbaldehyde is described.
- D'Auria, Maurizio,Antonioletti, Roberto,Mico, Antonella De,Piancatelli, Giovanni
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p. 1575 - 1578
(2007/10/02)
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- 5-Phenyl-2-furamidines: A new chemical class of potential antidepressants
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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.
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p. 1411 - 1416
(2007/10/02)
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