- 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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Read Online
- Synthesis of arylfuran derivatives as potential antibacterial agents
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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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- 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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- 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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- 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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- 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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- 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 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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- 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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- A drug treating pain neuropathy rational synthesis of intermediates
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The invention relates to a synthetic method of a drug intermediate for treating neuropathic pain and in particular relates to a catalytic synthesis method of 5-(4-chlorphenyl)-furan-2-formic acid. The method comprises the following steps: reacting 4-chlor
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Paragraph 0028; 0029
(2017/02/24)
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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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- An efficient synthesis of N,N-Dialkyl-5-(chlorophenyl)-2-furancarbothioamides from 2-furoic acid
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An efficient synthesis of N,N-dialkyl-5-(chlorophenyl)-2-furancarbothioamides from 2-furoic acid was performed under mild conditions as inhibitor candidates of plant growth. 5-(Chlorophenyl)-2-furoic acids (3a-d) were prepared by treating 2-furoic acid wi
- Lee, Hee Ju,Lee, Jae In
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p. 457 - 461
(2016/12/14)
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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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- 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 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 and antimicrobial activities of some new triazolothiadiazoles bearing 4-methylthiobenzyl moiety
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A series of substituted triazolothiadiazoles (6a-j and 7a-j) have been synthesized by condensing 4-amino-3-[4-methylthiobenzyl]-4H-1,2,4-triazole-5-thiol (5) with substituted aryl furoic acids/aromatic acids in the presence of POCl3. The triazole (5) was obtained by the fusion of 4-methylthiophenyl acetic acid (4) with thiocarbohydrazide. The structures of newly synthesized compounds are characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies and were screened for their antimicrobial activities. The preliminary results revealed that some of the compounds exhibited promising antimicrobial activities.
- Prasad, D. Jagadeesh,Ashok, Mithun,Karegoudar, Prakash,Poojary, Boja,Holla, B. Shivarama,Kumari, Nalilu Sucheta
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experimental part
p. 551 - 557
(2009/09/08)
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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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- EP2 RECEPTOR AGONISTS
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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 190
(2008/06/13)
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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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- AMIDE DERIVATIVES
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The invention concerns amide derivatives of Formula (Ia) wherein X is -NHCO- or -CONH-; m is 0-3; R1 is a group such as hydroxy, halogeno, trifluoromethyl, cyano, mercapto, nitro, amino, carboxy and carbamoyl; n is 0-2; R2 is a group
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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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- 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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- Synthetic and biological studies on 5-(p-chlorophenyl)furan-2-carboxyl peptides and 4-[2′-(5′-formyl)furyl]benzoyl peptides
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Substituted anilines are coupled with furoic acid and furfural at the position-5 to get 5-(p-chlorophenyl)furan-2-carboxylic acid and 4-[2′-(5′-formyl) furyl]benzoic acid which on further coupling with amino acid esters, di-, tetra- and hexapeptides yield
- Belagali,Harish Kumar,Boja, Poojary,Himaja
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p. 370 - 375
(2007/10/03)
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