- Furan-2-carboxamide derivative, a novel microtubule stabilizing agent induces mitotic arrest and potentiates apoptosis in cancer cells
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The vital role played by microtubules in the cell division process, marks them as a potential druggable target to decimate cancer. A novel furan-2-carboxamide based small molecule, is a selective microtubule stabilizing agent (MSA) with IC50 ranging from 4 μM to 8 μM in different cancer cell lines. Inhibition of tubulin polymerization or stabilization of tubulin polymers abrogates chromosomal segregation during cell division, results in cell cycle arrest and leads to cell death due to the delayed repair mechanism. A novel furan-2-carboxamide based small molecule exhibited potent anti-proliferative and anti-metastatic property In-Vitro against the panel of cancer cells. Annexin V-FITC/PI, double staining reveals potent cytotoxic effect of SH09 against HeLa cells. FACS analysis displays induction of G2/M arrest and accumulation of subG1 population of cells upon treatment with SH09. Molecular docking study unveils SH09 binding affinity to the Taxol binding pocket of tubulin proteins and MM-GBSA also confirms strong binding energies of SH09 with tubulin proteins.
- Shwetha,Sudhanva, M. Srinivasa,Jagadeesha,Thimmegowda,Hamse, Vivek K.,Sridhar,Thimmaiah,Ananda Kumar,Shobith, Rangappa,Rangappa
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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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- Design, synthesis, and electrophysiological evaluation of NS6740 derivatives: Exploration of the structure-activity relationship for alpha7 nicotinic acetylcholine receptor silent activation
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The α7 nicotinic acetylcholine receptor (nAChR) silent agonists, able to induce receptor desensitization and promote the α7 metabotropic function, are emerging as new promising therapeutic anti-inflammatory agents. Herein, we report the structure–activity
- Pismataro, Maria Chiara,Horenstein, Nicole A.,Stokes, Clare,Quadri, Marta,De Amici, Marco,Papke, Roger L.,Dallanoce, Clelia
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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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- Synthesis and bioactivity of phenyl substituted furan and oxazole carboxylic acid derivatives as potential PDE4 inhibitors
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In this present study, a series of 5-phenyl-2-furan and 4-phenyl-2-oxazole derivatives were designed and synthesized as phosphodiesterase type 4 (PDE4) inhibitors. In vitro results showed that the synthesized compounds exhibited considerable inhibitory ac
- Lin, Yinuo,Ahmed, Wasim,He, Min,Xiang, Xuwen,Tang, Riyuan,Cui, Zi-Ning
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- Synthesis and SAR of 5-aryl-furan-2-carboxamide derivatives as potent urotensin-II receptor antagonists
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The synthesis and biological evaluation as potential urotensin-II receptor antagonists of a series of 5-arylfuran-2-carboxamide derivatives 1, bearing a 4-(3-chloro-4-(piperidin-4-yloxy)benzyl)piperazin-1-yl group, are described. The results of a systemat
- Lim, Chae Jo,Kim, Nam Hui,Park, Hye Jin,Lee, Byung Ho,Oh, Kwang-Seok,Yi, Kyu Yang
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p. 577 - 580
(2019/01/05)
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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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- 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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supporting information
p. 754 - 763
(2018/06/26)
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- Furan- and thiophene-2-carbonyl amino acid derivatives activate hypoxia-inducible factor via inhibition of factor inhibiting hypoxia-inducible factor-1
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Induction of a series of anti-hypoxic proteins protects cells during exposure to hypoxic conditions. Hypoxia-inducible factor-α (HIF-α) is a major transcription factor that orchestrates this protective effect. To activate HIF exogenously, without exposing
- Kawaguchi, Shin-ichi,Gonda, Yuhei,Yamamoto, Takuya,Sato, Yuki,Shinohara, Hiroyuki,Kobiki, Yohsuke,Ichimura, Atsuhiko,Dan, Takashi,Sonoda, Motohiro,Miyata, Toshio,Ogawa, Akiya,Tsujita, Tadayuki
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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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- Synthesis of carbohydrazides and carboxamides as anti-tubercular agents
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A novel series of furan/thiophene carbohydrazides and carboxamides were synthesized and evaluated for anti-TB and cytotoxic activities. All the synthesized compounds were characterized using 1H and 13C NMR and mass spectral technique
- Kumar, Gautam,Krishna, Vagolu Siva,Sriram, Dharmarajan,Jachak, Sanjay M.
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p. 871 - 884
(2018/07/31)
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- Design, synthesis and evaluation of aromatic heterocyclic derivatives as potent antifungal agents
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To further enhance the anti-Aspergillus efficacy of our previously discovered antifungal lead compounds (1), a series of aromatic heterocyclic derivatives were designed, synthesized and evaluated for in vitro antifungal activity. Many of the target compounds showed good inhibitory activity against Candida albicans and Cryptococcus neoformans. In particular, the isoxazole nuclei were more suited for improving the activity against Aspergillus spp. Among these compounds, 2-F substituted analogues 23g and 23h displayed the most remarkable in vitro activity against Candida spp., C. neoformans, A. fumigatus and fluconazole-resistant C.alb. strains, which is superior or comparable to the activity of the reference drugs fluconazole and voriconazole. Notably, the compounds 23g and 23h exhibited low inhibition profiles for various isoforms of human cytochrome P450 and excellent blood plasma stability.
- Zhao, Shizhen,Zhang, Xiangqian,Wei, Peng,Su, Xin,Zhao, Liyu,Wu, Mengya,Hao, Chenzhou,Liu, Chunchi,Zhao, Dongmei,Cheng, Maosheng
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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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- Fragment-Based de Novo Design Reveals a Small-Molecule Inhibitor of Helicobacter Pylori HtrA
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Sustained identification of innovative chemical entities is key for the success of chemical biology and drug discovery. We report the fragment-based, computer-assisted de novo design of a small molecule inhibiting Helicobacter pylori HtrA protease. Molecu
- Perna, Anna M.,Rodrigues, Tiago,Schmidt, Thomas P.,B?hm, Manja,Stutz, Katharina,Reker, Daniel,Pfeiffer, Bernhard,Altmann, Karl-Heinz,Backert, Steffen,Wessler, Silja,Schneider, Gisbert
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supporting information
p. 10244 - 10248
(2015/09/01)
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- Identification, synthesis and photo-protection evaluation of arylthiazole derivatives as a novel series of sunscreens
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A novel series of arylthiazole derivatives have been designed, synthesized and evaluated in preventing keratinocytes cell (HaCaT) from UVB exposure induced cellar damage. The structure-activity relationship (SAR) was discussed. More importantly, compound 5a significantly protected the dorsal skin of BALB/c-nu mice against UVB-induced decrustation in vivo. The in vitro and in vivo data for these arylthiazole derivatives suggest further studies for their potential use as photo-protection agents as well as sunscreen candidates.
- Li, Guoliang,He, Yundong,Zhou, Wenbo,Wang, Peng,Zhang, Yong,Tong, Weiguang,Wu, Haigang,Liu, Mingyao,Ye, Xiyun,Chen, Yihua
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p. 453 - 464
(2014/03/21)
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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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- 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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- 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 Antimicrobial Evaluation of Nitazoxanide-Based Analogues: Identification of Selective and Broad Spectrum Activity
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A library composed of nitazoxanide-based analogues was synthesized and assayed for increased antibacterial efficacy against the pyruvate-ferredoxin oxidoreductase (PFOR) using microorganisms Helicobacter pylori, Campylobacter jejuni and Clostridium difficile. Derivatives were found to recapitulate and improve activity against these organisms and select analogues were tested for their ability to disrupt the PFOR enzyme directly. The library was also screened for activity against staphylococci and resulted in the identification of analogues capable of inhibiting both staphylococci and all PFOR organisms at low micromolar minimum inhibitory concentrations with low toxicity to human foreskin cells. Hitting them where it hurts! A library of nitazoxanide-based analogues was synthesized and assayed for antibacterial efficacy against pyruvate-ferredoxin oxidoreductase (PFOR) utilizing microorganisms. Derivatives were found to recapitulate and improve activity against these organisms, and select analogues were screened for activity against staphylococci resulting in the identification of analogues capable of inhibiting both staphylococci and all PFOR organisms at low micromolar minimum inhibitory concentrations.
- Ballard, T. Eric,Wang, Xia,Olekhnovich, Igor,Koerner, Taylor,Seymour, Craig,Salamoun, Joseph,Warthan, Michelle,Hoffman, Paul S.,Macdonald, Timothy L.
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experimental part
p. 362 - 377
(2012/01/11)
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- EP2 RECEPTOR AGONISTS
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A compound of formula (III): or a salt, solvate and chemically protected form thereof, wherein: R5 is an optionally substituted C5-20 aryl or C4-20alkyl group; L′ is a single bond, —O— or —C(═O)—; A is selected from the group consisting of: formulae (i) (ii) (iii) wherein X and Y are selected from the group consisting of: O and CR3; S and CR3; NH and CR3; NH and N; O and N; S and N; N and S; and N and O, and where the dotted lines indicate a double bond in the appropriate location, and where Q is either N or CH; D is selected from: formulae (i) (ii) (iii) (iv) (v) (vii) (viii) (ix) B is selected from the group consisting of: formulae (A) (B) where RP6 is selected from fluoro and chloro; and R2 is either: (i) —CO2H; (ii) —CONH2; (iii) —CH2—OH; or (iv) tetrazol-5-yl.
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Page/Page column 25
(2010/06/14)
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- Ligand-free, atom-efficient Suzuki-Miyaura type cross-coupling reactions at room temperature
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The atom-efficient cross-coupling reaction of sodium tetraarylborates with aryl iodides and bromides was reported. The reaction can be performed directly using a catalytic system composed of palladium chloride, sodium carbonate and methanol (PdCl2/Na2CO3/MeOH) under heat-free conditions at room temperature in an open air conditions. The reactions carried out in an atom-efficient way as 4 equiv of aryl halides coupled effectively with 1 equiv of sodium tetraarylborates to furnish 4 equiv of the corresponding functionalized biaryls in good to excellent yields.
- Zhou, Wen-Jun,Wang, Ke-Hu,Wang, Jin-Xian,Gao, Zhi-Rong
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experimental part
p. 7633 - 7641
(2010/12/19)
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- Atom-efficient, palladium-catalyzed stille coupling reactions of tetraphenylstannane with aryl iodides or aryl bromides in polyethylene glycol 400 (PEG-400)
-
The Stille coupling of tetraphenylstannane with aryl iodides or aryl bromides using the bis(triphenylphosphine)palladium dichloride/sodium acetate/polyethylene glycol 400 [PdCl2(PPh3) 2/NaOAc/ PEG-400] catalytic system at
- Zhou, Wen-Jun,Wang, Ke-Hu,Wang, Jin-Xian
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experimental part
p. 1378 - 1382
(2009/12/24)
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- Pd(PPh3)4-PEG 400 catalyzed protocol for the atom-efficient stille cross-coupling reaction of organotin with aryl bromides
-
(Chemical Equation Presented) Aryl bromides (4 equiv) were coupled efficiently with organotin (1 equiv) in an atom-efficient way using the tetra(triphenylphosphine)palladium/polyethylene glycol 400 (Pd(PPh 3)4/PEG 400) catalytic syst
- Zhou, Wen-Jun,Wang, Ke-Hu,Wang, Jin-Xian
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supporting information; experimental part
p. 5599 - 5602
(2009/12/03)
-
- Suzuki-Miyaura coupling reactions in aqueous microdroplets with catalytically active fluorous interfaces
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Using microfluidic techniques and a novel fluorous-tagged palladium catalyst, we generated droplet reactors with catalytically active walls and used these compartments for small molecule synthesis.
- Theberge, Ashleigh B.,Whyte, Graeme,Frenzel, Max,Fidalgo, Luis M.,Wootton, Robert C. R.,Huck, Wilhelm T. S.
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supporting information; experimental part
p. 6225 - 6227
(2010/02/16)
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- Reusable, polymer-supported, palladium-catalyzed, atom-efficient coupling reaction of aryl halides with sodium tetraphenylborate in water by focused microwave irradiation
-
A rapid and efficient cross-coupling reaction of sodium tetraphenylborate with aryl bromides was carried out in water at 120°C in the presence of a polymer-supported palladium catalyst and potassium carbonate under focused microwave irradiation. All four phenyl groups of sodium tetraphenylborate participated in the reaction and produced polyfunctional biaryls in excellent yields. The polymeric catalyst can be easily separated from the reaction mixture and reused more than 10 times without showing any decrease in activity.
- Bai, Lin,Wang, Jin-Xian
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supporting information; experimental part
p. 315 - 320
(2009/04/08)
-
- EP2 RECEPTOR AGONISTS
-
A compound of Formula (I) or a salt, solvate and chemically protected form thereof, wherein: R5 is an optionally substituted C5-20 aryl or C4-20 alkyl group; A is selected from the group consisting of Formulae (Ai), (Aii), (Aiii) D is selected from Formulae (Di), (Dii), (Diii), (Div), (Dv) B is selected from the group consisting of Formulae (Bi), (Bii), (Biii), (Biv) (Bv).
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Page/Page column 111
(2008/06/13)
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- Cyclic derivatives as modulators of chemokine receptor activity
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The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the treatment of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma.
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Page/Page column 44
(2008/06/13)
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- Substituted cycloalkylamine derivatives as modulators of chemokine receptor activity
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The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the prevention of asthma, multiple sclerosis, artherosclerosis, and rheumatoid arthritis.
- -
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Page/Page column 42
(2010/02/11)
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- The identification and optimization of 2,4-diketobutyric acids as flap endonuclease 1 inhibitors
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Flap endonuclease 1 (FEN1) is a key enzyme involved in base excision repair (BER), a primary pathway utilized by mammalian cells to repair DNA damage. In this report, we describe the identification and SAR of a series of 2,4-diketobutyric acid FEN1 inhibi
- Tumey, L. Nathan,Huck, Bayard,Gleason, Elizabeth,Wang, Jianmin,Silver, Daniel,Brunden, Kurt,Boozer, Sherry,Rundlett, Stephen,Sherf, Bruce,Murphy, Steven,Bailey, Andrew,Dent, Tom,Leventhal, Christina,Harrington, John,Bennani, Youssef L.
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p. 4915 - 4918
(2007/10/03)
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- Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of potassium aryl- and heteroaryltrifluoroborates
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An extended study of the reactivity of potassium aryl- and heteroaryltrifluoroborates in Suzuki-Miyaura cross-coupling reactions is presented. The coupling of aryl- and electron-rich heteroaryltrifluoroborates with aryl and activated heteroaryl bromides proceeds readily under ligandless conditions. When deactivated aryl- and heteroaryltrifluoroborates are coupled with aryl and heteroaryl bromides and chlorides, a low loading (0.5-2%) of PdCl2(dppf)·CH2Cl2 efficiently catalyzes the reactions. Under either condition, reactions can generally be carried out in an open atmosphere.
- Molander, Gary A.,Biolatto, Betina
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p. 4302 - 4314
(2007/10/03)
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- The stille cross coupling reactions on solid support. Link to solution phase directed ortho metalation. An ester linker approach to styryl, biaryl and heterobiaryl carboxylic acids
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The synthesis of the titled compounds by Stille cross coupling on Merrifield resin - linked halo benzoates with stannanes followed by LiOH hydrolysis is reported.
- Chamoin, Sylvie,Houldsworth, Stephen,Snieckus, Victor
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p. 4175 - 4178
(2007/10/03)
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- Biaryl substituted alkylboronate esters as thrombin inhibitors
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Thrombin is a serine protease that plays an important role in the blood coagulation cascade, and is a target enzyme for new therapeutic agents. Ac- (D)-Phe-Pro-boroArg-OH (DuP 714) was found to be a highly effective thrombin inhibitor. In order to reduce the peptidic nature of DuP 714, we have designed a series of novel biaryl substituted alkylboronate esters as potent thrombin inhibitors. The most potent compounds have subnanomolar affinity for thrombin.
- Quan,Wityak,Dominguez,Duncia,Kettner,Ellis,Liauw,Park,Santella,Knabb,Thoolen,Weber,Wexler
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p. 1595 - 1600
(2007/10/03)
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- Palladium-Catalyzed Stille Couplings of Aryl, Vinyl-, and Alkyltrichlorostannanes in Aqueous Solution
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Stille Coupling of water-soluble aryl and vinyl halides with alkyl, aryl-, and vinyltrichlorostannane derivatives (RSnCl3) are effected in aqueous solution using a catalyst generated in situ from PdCl2 and KOH both with and without added PhP(mC6H4SO3Na)2.The yields are generally good to excellent, although some limitations of the protocol are described.
- Rai, Roopa,Aubrecht, Katherine B.,Collum, David B.
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p. 3111 - 3114
(2007/10/02)
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