- 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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- Discovery of a series of 5-phenyl-2-furan derivatives containing 1,3-thiazole moiety as potent Escherichia coli β-glucuronidase inhibitors
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Gut microbial β-glucuronidases have drawn much attention due to their role as a potential therapeutic target to alleviate some drugs or their metabolites-induced gastrointestinal toxicity. In this study, fifteen 5-phenyl-2-furan derivatives containing 1,3
- Zhou, Tao-Shun,He, Lu-Lu,He, Jing,Yang, Zhi-Kun,Zhou, Zhen-Yi,Du, Ao-Qi,Yu, Jin-Biao,Li, Ya-Sheng,Wang, Si-Jia,Wei, Bin,Cui, Zi-Ning,Wang, Hong
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- Thiazolidin-2-cyanamides derivatives as novel potent Escherichia coli β-glucuronidase inhibitors and their structure–inhibitory activity relationships
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Gut microbial β-glucuronidases have the ability to deconjugate glucuronides of some drugs, thus have been considered as an important drug target to alleviate the drug metabolites-induced gastrointestinal toxicity. In this study, thiazolidin-2-cyanamide de
- Chen, Jian-Wei,Cui, Zi-Ning,He, Min,Li, Ya-Sheng,Wang, Hong,Wang, Si-Jia,Wang, Ya-Kun,Wei, Bin,Zhang, Hua-Wei,Zhou, Tao-Shun
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p. 1736 - 1742
(2020/09/18)
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- 2-furoylamide compound and preparation and application thereof
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The invention discloses a 2-furancarboxamide compound and a preparation method and application thereof. The 2-furancarboxamide compound is obtained by reacting a compound as shown in a formula II with9H-pyridino[3,4-b]indole in the presence of an acid-bin
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Paragraph 0036; 0038-0040; 0049
(2020/08/22)
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- Novel S-Thiazol-2-yl-furan-2-carbothioate Derivatives as Potential T3SS Inhibitors against Xanthomonas oryzae on Rice
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Bacterial leaf blight (BLB) caused by Xanthomonas oryzae pv oryzae (Xoo) is considered as the most destructive disease of rice. The use of bactericides is among the most widely used traditional methods to control this destructive disease. The excessive an
- Jiang, Shan,He, Min,Xiang, Xu-Wen,Adnan, Muhammad,Cui, Zi-Ning
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- Synthesis and biological evaluation of 2,5-disubstituted furan derivatives as P-glycoprotein inhibitors for Doxorubicin resistance in MCF-7/ADR cell
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Multidrug resistance (MDR) is a tendency in which cells become resistant to structurally and mechanistically unrelated drugs, which is mediated by P-glycoprotein (P-gp). It is one of the noteworthy problems in cancer therapy. As one of the most important
- Li, Ya-Sheng,Zhao, Dong-Sheng,Liu, Xing-Yu,Liao, Yi-Xian,Jin, Hong-Wei,Song, Gao-Peng,Cui, Zi-Ning
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p. 546 - 556
(2018/04/17)
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- Synthesis and bioactivity of 3,5-dimethylpyrazole derivatives as potential PDE4 inhibitors
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A series of 3,5-dimethylpyrazole derivatives containing 5-phenyl-2-furan moiety were designed and synthesized as phosphodiesterase type 4 (PDE4) inhibitors. Bioassay results showed that the title compounds exhibited considerable inhibitory activity agains
- Hu, De-Kun,Zhao, Dong-Sheng,He, Min,Jin, Hong-Wei,Tang, Yong-Mei,Zhang, Lian-Hui,Song, Gao-Peng,Cui, Zi-Ning
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p. 3276 - 3280
(2018/08/22)
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- Tetrahydroquinoline and tetrahydroisoquinoline derivatives as potential selective PDE4B inhibitors
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Tetrahydroquinoline and tetrahydroisoquinoline derivatives containing 2-phenyl-5-furan moiety were designed and synthesized as phosphodiesterase type 4 (PDE4) inhibitors. The bioassay results showed that title compounds showed good inhibitory activity aga
- Li, Ya-Sheng,Liu, Xing-Yu,Zhao, Dong-Sheng,Liao, Yi-Xian,Zhang, Lian-Hui,Zhang, Feng-Zhi,Song, Gao-Peng,Cui, Zi-Ning
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p. 3271 - 3275
(2018/08/22)
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- Discovery and development of novel salicylate synthase (MbtI) furanic inhibitors as antitubercular agents
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We report on the virtual screening, synthesis, and biological evaluation of new furan derivatives targeting Mycobacterium tuberculosis salicylate synthase (MbtI). A receptor-based virtual screening procedure was applied to screen the Enamine database, identifying two compounds, I and III, endowed with a good enzyme inhibitory activity. Considering the most active compound I as starting point for the development of novel MbtI inhibitors, we obtained new derivatives based on the furan scaffold. Among the SAR performed on this class, compound 1a emerged as the most potent MbtI inhibitor reported to date (Ki = 5.3 μM). Moreover, compound 1a showed a promising antimycobacterial activity (MIC99 = 156 μM), which is conceivably related to mycobactin biosynthesis inhibition.
- Chiarelli, Laurent R.,Mori, Matteo,Barlocco, Daniela,Beretta, Giangiacomo,Gelain, Arianna,Pini, Elena,Porcino, Marianna,Mori, Giorgia,Stelitano, Giovanni,Costantino, Luca,Lapillo, Margherita,Bonanni, Davide,Poli, Giulio,Tuccinardi, Tiziano,Villa, Stefania,Meneghetti, Fiorella
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p. 754 - 763
(2018/06/26)
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- Synthesis and bioactivity of pyrazole and triazole derivatives as potential PDE4 inhibitors
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A series of pyrazole and triazole derivatives containing 5-phenyl-2-furan functionality were designed and synthesized as phosphodiesterase type 4 (PDE4) inhibitors. The bioassay results showed that title compounds exhibited considerable inhibitory activit
- Li, Ya-Sheng,Tian, Hao,Zhao, Dong-Sheng,Hu, De-Kun,Liu, Xing-Yu,Jin, Hong-Wei,Song, Gao-Peng,Cui, Zi-Ning
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p. 3632 - 3635
(2016/07/21)
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- Synthesis and bioactivity of novel carvacrol and thymol derivatives containing 5-phenyl-2-furan
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A series of novel carvacrol and thymol derivatives containing 5-phenyl-2-furan were synthesized. The antitumor tests showed that the title compounds exhibited promising activity against Bel-7402 and KB. The fungicidal tests showed that most of the title c
- Cui, Zining,Li, Xinghai,Nishida, Yoshihiro
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p. 877 - 885
(2014/07/21)
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- Synthesis and bioactivities of novel pyrazole and triazole derivatives containing 5-phenyl-2-furan
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A series of novel pyrazole and triazole derivatives containing 5-phenyl-2-furan functionality were designed and synthesized. Their toxicities were predicted using in silico assays and proven to be less toxic. The antitumor results showed that the activity
- Cui, Zi-Ning,Shi, Yan-Xia,Cui, Jing-Rong,Ling, Yun,Li, Bao-Ju,Yang, Xin-Ling
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scheme or table
p. 121 - 127
(2012/03/27)
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- Synthesis and fungicidal activity of novel 2,5-disubstituted-1,3,4- oxadiazole derivatives
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A novel series of 1,3,4-oxadiazole derivatives containing a 5-phenyl-2-furan moiety were synthesized from the intermediates diacylhydrazine 3 and acylhydrazone 5 via an efficient approach under microwave irradiation in good yields. Their structures were characterized by IR, 1H NMR, and elemental analysis. The antifungal tests indicated that the title compounds showed in vivo fungicidal activity against Botrytis cinerea and Rhizoctonia solanii at 500 μg/mL obviously. Some tested compounds even had a superiority effect over the commercial fungicides 40% Pyrimethanil SC and 3% Validamycin AS. The activity between the title compound and their precursors diacylhydrazine 3 and acylhydrazone 5 was also compared and discussed.
- Cui, Zi-Ning,Shi, Yan-Xia,Zhang, Li,Ling, Yun,Li, Bao-Ju,Nishida, Yoshihiro,Yang, Xin-Ling
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p. 11649 - 11656
(2013/02/22)
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- Synthesis and bioactivity of N-benzoyl-N'-[5-(2'-substituted phenyl)-2-furoyl] semicarbazide derivatives
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In order to find novel chitin synthesis inhibitors (CSIs) with good activity, benzoylphenylurea, a typical kind of CSIs, was chosen as the lead compound and 15 novel derivatives containing furan moieties were designed by converting the urea linkage of benzoylphenylureas into a semicarbazide and changing the aniline part into furoyl groups. The title compounds were synthesized by the reaction of substituted benzoyl isocyanates with 5-(substituted phenyl)-2-furoyl hydrazine, and the structures were confirmed by IR, 1H-NMR, elemental analysis and single crystal X-ray diffraction analyses (compound E2). The bioassay results indicated that the title compounds exhibit good insecticidal activity, especially towards Plutella xylostella L., but had lower fungicidal activity. Inspiringly, the title compounds possessed obvious anticancer activity against human promyelocytic leukemic cell line (HL-60), and some of the title compounds also had activity against human hepatocellular carcinoma cell line (Bel-7402), human gastric carcinoma cell line (BGC-823), and human nasopharyngeal carcinoma cell line (KB). The results indicated that the linkage in the lead compounds was important to the bioactivity and spectra. The modification on the urea linkage is an effective strategy to discover new pesticide and drug candidates.
- Cui, Zining,Ling, Yun,Li, Baoju,Li, Yongqiang,Rui, Changhui,Cui, Jingrong,Shi, Yanxia,Yang, Xinling
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scheme or table
p. 4267 - 4282
(2010/10/03)
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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 of heterocycles from arylation products of unsaturated compounds: XVIII. 5-Arylfuran-2-carboxylic acids and their application in the synthesis of 1,2,4-thiadiazole, 1,3,4-oxadiazole, and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazole derivatives
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Arylation of furan-2-carboxylic acid or its methyl ester with arenediazonium chlorides in the presence of copper(II) chloride gave the corresponding 5-arylfuran-2-carboxylic acids or methyl 5-arylfuran-2- carboxylates. 5-Arylfuran-2-carbonyl chlorides rea
- Gorak,Obushak,Matiichuk,Lytvyn
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experimental part
p. 541 - 550
(2009/08/17)
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- Metalloform-selective inhibition: Synthesis and structure-activity analysis of Mn(II)-form-selective inhibitors of Escherichia coli methionine aminopeptidase
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Methionine aminopeptidase (MetAP) is a promising target for development of novel antibacterial, antifungal and anticancer agents. However, its physiologically relevant metal ion remains to be defined, and its inhibitors need to inhibit the in vivo metallo
- Huang, Qing-Qing,Huang, Min,Nan, Fa-Jun,Ye, Qi-Zhuang
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p. 5386 - 5391
(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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