- Synthesis and Anti-Cholinesterase Activity of Novel Glycosyl Benzofuranylthiazole Derivatives
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Abstract: A new series of glycosyl benzofuranylthiazole derivatives were designed, synthesized, characterized, and evaluated as potential candidates to treat Alzheimer’s disease. The compounds have been synthesized by the cyclocondensation of glycosyl thiourea with a variety of 2-(bromoacetyl)benzofurans. The reaction conditions have been optimized, and good yields (79–95%) have been obtained. The synthesized compounds showed different degrees of cholinesterase inhibitory activity.
- Cao, L.,Cao, Zh.,Chen, Ch.,Jiang, K.,Liu, Sh.,Liu, W.,Lu, X.,Shao, Zh.,Shi, D.,Su, Z.,Wang, L.,Wang, Y.,Wu, Y.
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p. 1513 - 1518
(2021/10/26)
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- PROTEIN KINASE C AGONISTS
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The present disclosure relates generally to certain diacylglycerol lactone compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions dis
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Paragraph 0348
(2020/09/12)
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- Synthesis and biological evaluation of some novel thiobenzimidazole derivatives as anti-renal cancer agents through inhibition of c-MET kinase
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Benzimidazole is an interesting scaffold constituting a main core in many anticancer agents against variable cell lines as Carbendazim (I) and Nocodazole (II). Accordingly, eighteen compounds of 2-((1H-benzoimidazol-2-yl)thio)-1-(aryl/heteroaryl)ethan-1-ones, in their sulfate salt and free forms, were designed and investigated as anticancer agents. In vitro preliminary screening of selected compounds by the National Cancer Institute (NCI) on a panel of 60 cell lines revealed renal cancer cell line (A498) as the most vulnerable cell line; accordingly, IC50 values against A498 cell line were determined for compounds with the best results. The best inhibitory activity was for compound 4a with (IC50 = 6.97 μM) compared to sunitinib as a reference drug (IC50 = 6.99 μM). Compound 4a was further subjected to cell cycle analysis that indicated the decrease in cell population in the G2/M phase when compared to the untreated control cells. In addition, it showed significant increase in the late apoptosis in Annexin-V FTIC study compared to the control cells. An enzymatic inhibitory study on compound 4a against c-Met and MAP kinases revealed its better activity against c-Met kinase with (IC50 = 0.27 μM) compared to sunitinib (IC50 = 0.18 μM). Molecular docking study was conducted to reveal the interactions of compound 4a in the active site of c-Met kinase. Computational ADME study was performed to insure that compound 4a has proper pharmacokinetic and drug-likeness properties.
- Ibrahim, Hany S.,Albakri, Mohamed E.,Mahmoud, Walaa R.,Allam, Heba Abdelrasheed,Reda, Ahmed M.,Abdel-Aziz, Hatem A.
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p. 337 - 348
(2019/01/18)
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- Synthesis and bioactivity of novel C2-glycosyl benzofuranylthiazoles derivatives as acetylcholinesterase inhibitors
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A new series of C2-glycosyl benzofuranylthiazole derivatives was synthesised by the further cyclization of glycosyl thiourea and 2-(bromoacetyl)-benzofuran via Hantzsch’s method. The corresponding 2-(bromoacetyl)-benzofuran derivatives were obtained by the reaction from various salicylaldehydes, and the glycosyl thiourea was prepared through a series of steps from D-Glucosamine. The acetylcholinesterase-inhibitory activities of the products were tested by Ellman’s method. The most active compounds were subsequently evaluated for the 50% inhibitory concentration values. N-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranosyl)-4-(5-methoxy-benzofuran-2-yl)-1,3-thiazole-2-amine possessed the best acetylcholinesterase-inhibition activity with a 50% inhibitory concentration of 2.03 ± 0.26 μM.
- Wang, Lei,Wu, Yu-Ran,Ren, Shu-Ting,Yin, Long,Wang, You-Xian,Liu, Shu-Hao,Liu, Wei-Wei,Shi, Da-Hua,Cao, Zhi-Ling,Sun, Hui-Min
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p. 257 - 261
(2019/09/03)
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- Design, synthesis and biological evaluation of benzofuran appended benzothiazepine derivatives as inhibitors of butyrylcholinesterase and antimicrobial agents
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A series of bezofuran appended 1,5-benzothiazepine compounds 7a–v was designed, synthesized and evaluated as cholinesterase inhibitors. The biological assay experiments showed that most of the compounds displayed a clearly selective inhibition for butyrylcholinesterase (BChE), while a weak or no effect towards acetylcholinesterase (AChE) was detected. All analogs exhibited varied BChE inhibitory activity with IC50 value ranging between 1.0 ± 0.01 and 72 ± 2.8 μM when compared with the standard donepezil (IC50, 2.63 ± 0.28 μM). Among the synthesized derivatives, compounds 7l, 7m and 7k exhibited the highest BChE inhibition with IC50 values of 1.0, 1.0 and 1.8 μM, respectively. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 7l with BChE. In addition, docking studies confirmed the results obtained through in vitro experiments and showed that most potent compounds bind to both the catalytic anionic site (CAS) and peripheral anionic site (PAS) of BChE active site. The synthesized compounds were also evaluated for their in vitro antibacterial and antifungal activities. The results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms and showed high activity against both gram positive and gram negative bacteria and fungi.
- Mostofi, Manizheh,Mohammadi Ziarani, Ghodsi,Lashgari, Negar
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p. 3076 - 3095
(2018/06/06)
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- TBAI/TBHP mediated oxidative cross coupling of ketones with phenols and carboxylic acids: Direct access to benzofurans
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TBAI/TBHP mediated oxidative cross coupling of phenols and carboxylic acids with ketones has been reported under metal-free, base free, solvent free conditions enabling environmentally benign synthesis of aryloxyketones, acyloxy ketones and benzofurans. Phenoxyketones and acyloxylcarbonyl compounds were synthesized in good to high yields, where as benzofurans were synthesized in moderate yields. This method is operationally simple, works under mild conditions, using commercially available as well as inexpensive TBAI and an oxidant TBHP.
- Santhosh Kumar,Ravikumar,Chinna Ashalu,Rajender Reddy
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supporting information
p. 33 - 37
(2017/12/11)
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- Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation
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Cytotoxic and antimicrobial agents structurally based on quinazolinone, benzofuran and imidazole pharmacophores, have been designed and synthesized. Spectral (IR, 1H-NMR) and elemental analysis data established the structures of these novel 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride hybrid derivatives. All the synthesized compounds were evaluated for in?vitro cytotoxicity and antimicrobial activities. Cytotoxic evaluation using MTT assay revealed that compounds 12c, 12g and 12i exhibited significant cytotoxicity with IC50 values 1, 1, and 0.57?μm on this cell line, respectively. Biological activity of the synthesized compounds as antibacterial agent were also evaluated against three Gram-negative (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-positive (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungi (Candida albicans) strains. All compounds 12a?–?12i showed slightly higher activity against Gram-positive bacteria than the Gram-negative one. Among the nine new compounds screened, 3-[1-(5-bromo-1-benzofuran-2-yl)-2-(6-chloro-4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride (12e) has pronounced higher antimicrobial activity against all tested strains. These results demonstrated potential importance of molecular hybridization in the development of new lead molecules with major cytotoxicity and antimicrobial activity.
- Asadi, Parvin,Khodarahmi, Ghadamali,Jahanian-Najafabadi, Ali,Saghaie, Lotfollah,Hassanzadeh, Farshid
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- BICYCLIC COMPOUND
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Provided is a bicyclic compound having an acetyl-CoA carboxylase inhibitory action. A compound represented by the formula: wherein each symbol is as described in the DESCRIPTION, or a salt thereof has an acetyl-CoA carboxylase inhibitory action, is useful for the prophylaxis or treatment of cancer, inflammatory diseases and the like, and has superior efficacy.
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Paragraph 1022; 1161
(2017/12/28)
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- Synthesis, Characterization, and Anticancer Activity of New Benzofuran Substituted Chalcones
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Benzofuran derivatives are of great interest in medicinal chemistry and have drawn considerable attention due to their diverse pharmacological profiles including anticancer activity. Similarly, chalcones, which are common substructures of numerous natural products belonging to the flavonoid class, feature strong anticancer properties. A novel series of chalcones, 3-aryl-1-(5-bromo-1-benzofuran-2-yl)-2-propanones propenones (3a-f), were designed, synthesized, and characterized. In vitro antitumor activities of the newly synthesized (3a-f) and previously synthesized (3g-j) chalcone compounds were determined by using human breast (MCF-7) and prostate (PC-3) cancer cell lines. Antitumor properties of all compounds were determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. Cell viability assay for the tested chalcone compounds was performed and the log I C 50 values of the compounds were calculated after 24-hour treatment. Our results indicate that the tested chalcone compounds show antitumor activity against MCF-7 and PC-3 cell lines (p 0.05).
- Co?kun, Demet,Tekin, Suat,Sandal, Süleyman,Co?kun, Mehmet Fatih
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- Potential of aryl-urea-benzofuranylthiazoles hybrids as multitasking agents in Alzheimer's disease
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New benzofuranylthiazole derivatives containing the aryl-urea moiety were synthesized and evaluated in vitro as dual acetylcholinesterase (AChE)-butyrylcholinesterase (BuChE) inhibitors. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were assayed. The result showed that all the synthesized compounds exhibited inhibitory activity on both AChE and BuChE with 1-(4-(5-bromobenzofuran-2-yl)thiazol-2-yl)-3-(2-fluorophenyl)urea (e25, IC50 value of 3.85 1/4M) and 1-(4-iodophenyl)-3-(4-(5-nitrobenzofuran-2-yl)thiazol-2-yl)urea (e38, IC50 value of 2.03 1/4M) as the strongest inhibitors against AChE and BuChE, respectively. Compound e38 was 8.5-fold more potent than galanthamine. The selectivity index of e25 and e38 was 2.40 and 0.37 against AChE and BuChE, respectively. Compound e2, e4 and e11 (IC50 Combining double low line 0.2, 0.5 and 1.13 1/4M, respectively) showed a better ABTS cation radical scavenging ability than the standard quercetin (IC50 Combining double low line 1.18 1/4M). Best poses of compounds e38 on BuChE and e25 on AChE indicate that the thiazole ring and the amidic moiety are important sites of interaction with both ChEs. In addition, the benzofuran ring and phenyl ring are anchored to the side chains of both enzymes by €-€(pi-pi) interactions.
- Kurt, Belma Zengin,Gazioglu, Isil,Basile, Livia,Sonmez, Fatih,Ginex, Tiziana,Kucukislamoglu, Mustafa,Guccione, Salvatore
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- Synthesis and structure-activity relationship study of benzofuran-based chalconoids bearing benzylpyridinium moiety as potent acetylcholinesterase inhibitors
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A series of benzofuran-based chalconoids 6a-v were designed and synthesized as new potential AChE inhibitors. The in vitro assay of synthesized compounds 6a-v showed that most compounds had significant anti-AChE activity at micromolar or sub-micromolar levels. Among the tested compounds, 3-pyridinium derivative 6m bearing N-(2-bromobenzyl) moiety and 7-methoxy substituent on the benzofuran ring exhibited superior activity. This compound with IC50 value of 0.027 μM was as potent as standard drug donepezil.
- Mostofi, Manizheh,Mohammadi Ziarani, Ghodsi,Mahdavi, Mohammad,Moradi, Alireza,Nadri, Hamid,Emami, Saeed,Alinezhad, Heshmatollah,Foroumadi, Alireza,Shafiee, Abbas
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p. 361 - 369
(2015/09/28)
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- NEW ARYLALKENYLPROPARGYLAMINE DERIVATIVES EXHIBITING NEUROPROTECTIVE ACTION FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
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The invention relates to novel arylalkenylpropargylamine derivatives of general formula (I) or enantiomers or diastereomers thereof or salts, optionally pharmaceutically acceptable salts, or solvates of any of these. The compounds can be used in treating or preventing a disease or condition in a mammal related to monoamine oxidase dysfunction, especially in neurodegenerative diseases, e.g. Parkinson's disease, Alzheimer's disease or Huntington's disease.
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Page/Page column 27; 41
(2015/06/25)
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- Comparative studies of synthesis of symmetric 2,6-di(benzofuran-2-yl)-4-phenyl-pyridine derivatives via pyrylium tetrafluoroborate salt and 1,5-dione derivatives
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A comparative study for the synthesis of symmetric 2,6-di(benzofuran-2-yl)-4-phenyl-pyridine derivatives 4a-h as antibacterial agents, has been reported by two methods. Method A follows nucleophilic substitution reaction of 2,6-di (benzofuran-2-yl)-4-phenyl-pyrilium tetrafluoroborate salt derivatives 3a-h with ammonium acetate in ether at room temperature. Method B follows cyclisation reaction of 1,5-di (benzofuran-2-yl)-3-(4-substituted-aryl)-pentane-1,5-dione derivatives 2a-h with ammonium acetate in acetic acid under reflux. It has been found that method B proceeds under mild reaction condition with short reaction time and high yield when compared to method A. The structures of the newly synthesized compounds have been characterized by spectral studies.
- Kumar, D. B. Aruna,Desai, Nivedita R.,Krishnaswamy,Sreenivasa,Mahadevan
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p. 538 - 544
(2015/04/27)
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- One-pot synthesis of novel symmetric 1,5-di(benzofuran-2-yl)-3-(4- substituted-aryl)-pentane-1,5-dione derivatives
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Salicylaldehyde and its substituted derivatives on reaction with bromoacetone under basic condition in ethanol afford corresponding benzofuran derivatives 1a-d. The compounds 1a-d on treatment with different para substituted aromatic aldehydes in presence of base and minimum amount of acetonitrile upon grinding at room temperature gives corresponding α,β-unsaturated carbonyl compounds by crossed aldol condensation, which further undergo Michael addition with 2-acetyl benzofuran to give a new class of symmetric 1,5-di(benzofuran-2-yl)-3-(4-substituted-aryl)-pentane-1,5- dione derivatives 2a-p in one step. The structures of all the newly synthesized compounds have been established by spectral studies.
- Aruna Kumar,Desai, Nivedita R.,Krishnaswamy,Sreenivasa,Mahadevan
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p. 426 - 430
(2014/05/06)
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- Use of transesterified 1,3-diketoesters in the synthesis of trisubstituted pyrazoles and their biological screening
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Starting from 2-acetylbenzofuran derivatives 1a-d, methyl/ethyl 4-substituted/unsubstituted benzofuran-2-yl)-2,4-dioxobutanoate 2a-d and 3a-d have been synthesized by Claisen's condensation reaction with diethyloxalate. The transesterified product, 1,3-diketoester 2a-d on condensation with phenyl hydrazine undergo cyclization to afford the corresponding methyl 5-(substituted/unsubstituted benzofuran-2-yl)-1-phenyl- 1H-pyrazole-3- carboxylate 4a-d, which upon further condensation with hydrazine hydrate yielded 5- (substituted/unsubstituted benzofuran-2-yl)-1-phenyl-1H-pyrazole-3- carbohydrazide 5a-d. The structures of the newly synthesized compounds 2a-d, 3a-d, 4a-d and 5a-d were characterized by their elemental analysis and spectral studies such as IR, 1H NMR, 13C NMR and MS. All the synthesized compounds were screened for their antimicrobial activity. Most of the synthesized compounds showed high sensitivity against the selected bacteria and fungi at various concentrations.
- Siddiqui, Naqui-Jahan,Idrees, Mohammad,Khati, Niraj T.,Dhonde, Madhukar G.
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- A facile synthesis of bromo-substituted benzofuran containing thiazolidinone nucleus bridged with quinoline derivatives: Potent analgesic and antimicrobial agents
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Treatment of 5-bromo-2-acetyl benzofuran with hydrazine followed by condensation of the resulting hydrazone with different quinoline derivatives gave the corresponding Schiff bases. Reaction of these Schiff bases with thioacetic acid furnished the target thiazolidinone molecule. Some of the newly synthesized compounds show promising analgesic and antimicrobial activity. Supplemental materials are available for this article. Go to the publisher′s online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Bhovi, Venkatesh K.,Bodke, Yadav D.,Biradar,Swamy, B. E. Kumara,Umesh
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scheme or table
p. 110 - 116
(2010/05/02)
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- Synthesis of 2-, 4- And 5-(2-alkylcarbamoyl-l-methylvinyl)-7- alkyloxybenzo[b]furans and their leukotriene 64 receptor antagonistic activity
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Variable benzo[6]furan derivatives having (E)- and (Z)-2-alkylcarbamoyl-l- methylvinyl groups at the 2-, 4- and 5-positions and a carboxylpropoxy or (1-phenyl)ethoxy group at the 7-position were prepared to find novel and selective leukotriene B4 (LTB4) receptor antagonists. (E)-2-(2-Diethylcarbamoyl- l-methylvinyl)-7-(1-phenylethoxy)benzo[b]furan (4v) showed selective inhibition to the human BLT2 receptor (hBLT2). On the other hand, (E)-2-acetyl-4-(2-diethylcarbamoyl-l-methylvinyl)-7-(l-phenylethoxy)benzo[b] furan (7v) inhibited both human BLTi receptor (hBLT1) and hBLT 2. The (E)-2-(2-diethylcarbamoyl-l-methylvinyl) group lay on approximately the same plane as the benzo[e]furan ring, whereas the (E)-4-(2-diethylcarbamoyl-l-methylvinyl) group had the torsion angle (45.7°) from the benzo[e]furan ring plane. However, the (Z)-(2-alkylcarbamoyl-l- methylvinyl)benzo[b]furans were inactive. The inhibitory activity depended on the conformation of the 2-diethylcarbamoyl-l-methylvinyl group. The Royal Society of Chemistry 2005.
- Ando, Kumiko,Tsuji, Eriko,Ando, Yuko,Kunitomo, Jun-Ichi,Kobayashi, Reina,Yokomizo, Takehiko,Shimizu, Takao,Yamashita, Masayuki,Ohta, Shunsaku,Nabe, Takeshi,Kohno, Shigekatsu,Ohishi, Yoshitaka
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p. 2129 - 2139
(2007/10/03)
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- Retinoid x receptor modulators
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The present invention is directed to compounds represented by Structural Formula (I) and pharmaceutically acceptable salts, solvates and hydrates thereof: (I). The invention is also directed to pharmaceutical compositions, methods of use and methods of making compounds represented by Structural Formula (I) and pharmaceutically acceptable salts, solvates and hydrates thereof.
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- Quinoxalines. Part 13: Synthesis and mass spectrometric study of aryloxymethylquinoxalines and benzo[b]furylquinoxalines
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A series of new aryloxymethylquinoxalines, benzo[b]- and naphtho[2,1-b]furylquinoxalines, possessing potential biological activity, was prepared, characterized by IR and NMR spectroscopy and their electron ionization (EI) mass spectra studied in detail. The aryloxymethylquinoxalines were obtained by reacting halogenomethylquinoxalines with bifunctional O-nucleophiles. The benzo[b]furylquinoxalines and naphtho[2,1-b] furylquinoxalines were prepared via two routes, which differed in the order of the two cyclization steps involved in the syntheses. The composition of the ions obtained by EI mass spectrometry were determined by accurate mass measurements and the fragmentation pathways clarified by B/E linked scans and collision induced dissociation. The mass spectrometric behaviour of the compounds studied as to the possible loss of OH· radicals proved to be very characteristic.
- Starke, Ines,Sarodnick, Gerhard,Ovcharenko, Vladimir V.,Pihlaja, Kalevi,Kleinpeter, Erich
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p. 6063 - 6078
(2007/10/03)
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- Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions
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Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee].
- Paizs, Csaba,Tosa, Monica,Majdik, Cornelia,Moldovan, Paula,Novak, Lajos,Kolonits, Pal,Marcovici, Adriana,Irimie, Florin-Dan,Poppe, Laszlo
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p. 1495 - 1501
(2007/10/03)
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- Sulfonamide compounds and medicinal use thereof
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A sulfonamide compound of the formula (I):R 1 --SO 2 NHCO--A--R 2 (I)wherein R 1 is alkyl, alkenyl, alkynyl and the like; A is an optionally substituted heteropolycyclic group except benzimidazolyl, indolyl, 4,7-dihydrobenzimidazolyl and 2,3-dihydrobenzoxazinyl; X is alkylene, oxa, oxa(lower)alkylene and the like; and R 2 is optionally substituted aryl, substituted biphenylyl and the like, a salt thereof and a pharmaceutical composition comprising the same. The sulfonamide compound is effective for the diseases treatable based on their blood sugar level-depressing activity, cGMP-PDE (especially PDE-V)-inhibiting activity, smooth muscle relaxing activity, bronchodilating activity, vasodilating activity, smooth muscle cell suppressing activity, and antiallergic activity.
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Page column 70
(2010/02/04)
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- Antifungal activity of dicationic molecules
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Methods of treating fungal infections comprise administering a therapeutically effective amount of a compound described by Formulas [(I)-(VI)]. Examples of fungal infections include Candida albicans, Cryptococcus neoformans, Aspergillus fumigatus, Fusariu
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