- Oxidative coupling of enolates using memory of chirality: An original enantioselective synthesis of quaternary α-amino acid derivatives
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We describe here the first enantioselective oxidative heterocoupling of enolates. Our strategy relies on the memory of chirality concept and allows the stereocontrolled formation of quaternary centres on α-amino acid derivatives with an enantiomeric excess of up to 94%.
- Mambrini, Antonin,Gori, Didier,Guillot, Régis,Kouklovsky, Cyrille,Alezra, Valérie
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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, anticancer and antimicrobial evaluation of new benzofuran based derivatives: PI3K inhibition, quorum sensing and molecular modeling study
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A new series of benzofuran derivatives has been designed and synthesized. The structures of the synthesized compounds have been confirmed by the use of 1H NMR, 13C NMR, 2D 1H–1H NOESY NMR, and IR. Anticancer activity is evaluated against Hepatocellular carcinoma (HePG2), mammary gland breast cancer (MCF-7), Epitheliod carcinoma cervix cancer (Hela) and human prostate cancer (PC3). Compounds 8, 9, and 11 showed the highest activity towards the four cell lines with an IC50 range of 8.49–16.72 μM, 6.55–13.14 μM and 4–8.99 μM respectively in comparison to DOX (4.17–8.87 μM). Phosphatidylinositol-3-kinases (PI3K) inhibition was evaluated against the most active anticancer compounds 8, 9 and 11. Compounds 8, 9 and 11 showed good inhibitory activity against PI3Kα with IC50 values 4.1, 7.8, and 20.5 μM, respectively in comparison to 6.18 μM for the reference compound LY294002. In addition, activity of compounds 8 and 9 on cell cycle arrest and induction of apoptosis in different phases of MCF-7 cells were assessed and detected pre-G1 apoptosis and cell growth arrest at G2/M. Also, both extrinsic and intrinsic apoptosis in MCF-7 cells induced by compounds 8 and 9. Molecular docking, binding affinity surface mapping, and contact preference of the synthesized compounds 8, 9 and 11 against PI3K were estimated and studied computationally using molecular operating environment software (MOE) and showed good interaction with essential residues for inhibition Val851. In addition, antimicrobial activity was evaluated against gram positive isolates as Staphylococcus aureus and Bacillus cereus, gram negative isolate as Escherichia coli, Pseudomonas aeruginosa and antifungal potential against Candida albicans. Compound 17 showed outstanding anti Gram-positive activity with MIC values 8 and 256 μg/mL in Staphylococcus aureus and Bacillus cereus respectively. Also, compounds 15, 17, 18 and 21 showed good anti Gram-negative activity with MIC value 512 μg/mL for all compounds. In addition, the state-of-art quorum sensing (QS) inhibiting effects were detected using Chromobacterium violaceum and compounds 7, 9, 10, 11, and 12 showed good QS inhibition (3, 3, 5, 2, and 7 mm).
- El-Khouly, Omar A.,Henen, Morkos A.,El-Sayed, Magda A.-A.,Shabaan, Mona I.,El-Messery, Shahenda M.
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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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- Benzofuranyl esters: Synthesis, crystal structure determination, antimicrobial and antioxidant activities
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A series of five new 2?(1?benzofuran?2?yl)?2?oxoethyl 4-(un/substituted)benzoates 4(a-e), with the general formula of C8H5O(C=O)CH2O(C=O)C6H4X, X = H, Cl, CH3, OCH3 or NO2, was synthesized in high purity and good yield under mild conditions. The synthesized products 4(a-e) were characterized by FTIR, 1H-, 13C- and 1H-13C HMQC NMR spectroscopic analysis and their 3D structures were confirmed by single-crystal X-ray diffraction studies. These compounds were screened for their antimicrobial and antioxidant activities. The tested compounds showed antimicrobial ability in the order of 4b 4a 4c 4d 4e and the highest potency with minimum inhibition concentration (MIC) value of 125 μg/mL was observed for 4e. The results of antioxidant activities revealed the highest activity for compound 4e (32.62% ± 1.34%) in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, 4d (31.01% ± 4.35%) in ferric reducing antioxidant power (FRAP) assay and 4a (27.11% ± 1.06%) in metal chelating (MC) activity.
- Kumar, C.S. Chidan,Then, Li Yee,Chia, Tze Shyang,Chandraju, Siddegowda,Win, Yip-Foo,Sulaiman, Shaida Fariza,Hashim, Nurul Shafiqah,Ooi, Kheng Leong,Quah, Ching Kheng,Fun, Hoong-Kun
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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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- In Vitro antioxidant, antimicrobial and admet study of novel furan/benzofuran C-2 coupled quinoline hybrids
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Objective: Synthesis of novel 2-(benzofuran-2-yl) and 2-(furan-2-yl) quinoline-4-carboxylates and their [2-(1-benzofuran-2-yl) quinolin-4-yl] methanol, [2-(1-furan-2-yl) quinolin-4-yl] methanol and its derivatives for antioxidant, antimicrobial and in silico pharmacokinetic study. Methods: Synthesis was carried with the conventional method and the structures were confirmed by IR, 1H NMR, 13C NMR and mass spectral analysis. The antioxidant activity was performed by DPPH and H2O2 radical scavenging method. The antimicrobial investigation was established by cup plate and food poison technique. The in silico absorption, distribution, metabolism, excretion and toxicity (ADMET) study of the drug was carried out in ACD/lab-2. Results: The antioxidant activity results revealed that compounds 4b-c, 5a-b, 10c and 10f exhibited good DPPH radical and hydrogen peroxide scavenging activity. The antibacterial results revealed that compounds 4c, 5a-b, 10b, 10d and 10f exhibited good activity against Escherichia coli, Klebsiella pneumonia and Salmonella typhimurium. Further, the antifungal activity results showed that compounds 4c, 5c and 10c-e were showing good activity against Aspergillusflavus and Candida neoformans. The mean value of P0.05 were considered to be statistically significant. The ADMET results revealed that compounds emerged as a potential candidate for antioxidant and antimicrobial agents. Conclusion: The study reveals that compounds containing furan/benzofuran coupled heterocycles played the important role for activity as they possess potent antioxidant and antimicrobial agents. The in silico ADME analysis also suggesting the compounds were in acceptable range to obey the pharmacokinetic parameters.
- Rajpurohit, Anantacharya,Satyanarayan, Nayak D.,Patil, Sameer,Mahadevan, Kittappa M.,Adarsha
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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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- Glutathione conjugation and protein adduction derived from oxidative debromination of benzbromarone in mice
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Benzbromarone (BBR), a uricosuric agent, has been known to induce hepatotoxicity, and its toxicity has a close relation to cytochrome P450-mediated metabolic activation. An oxidative debromination metabolite of BBR has been reported in microsomal incubations. The present study attempted to define the oxidative debromination pathway of BBR in vivo. One urinary mercapturic acid (M1) and one glutathione (GSH) conjugate (M2) derived from the oxidative debromination metabolitewere detected in BBR-treated mice after solid phase extraction.M1 andM2 shared the same chromatographic behavior and mass spectral identities as those detected in N-acetylcysteine/GSHand BBR-fortified microsomal incubations. The structure of M1 was characterized by chemical synthesis, along with mass spectrometry analysis. In addition, hepatic protein modification that occurs at cysteine residues (M93) was observed in mice given BBR. The observed protein adduction reached its peak 4 hours after administration and occurred in a dose-dependent manner. A GSH conjugate derived from oxidative debromination of BBR was detected in livers of mice treated with BBR, and the formation of the GSH conjugate apparently took place earlier than the protein adduction. In summary, our in vivo work provided strong evidence for the proposed oxidative debromination pathway of BBR, which facilitates the understanding of the mechanismsof BBR-induced hepatotoxicity. SIGNIFICANCE STATEMENT This study investigated the oxidative debromination pathway of benzbromarone (BBR) in vivo. One urinary mercapturic acid (M1) and one glutathione (GSH) conjugate (M2) derived from the oxidative debromination metabolite were detected in BBR-treated mice. M1 and M2 were also observed in microsomal incubations. The structure of M1 was characterized by chemical synthesis followed by mass spectrometry analyses. More importantly, protein adduction derived fromoxidative debromination ofBBR(M93) was observed in mice given BBR, and occurred in dose- and time-dependent manners. The success in detection of GSH conjugate, urinary N-acetylcysteine conjugate, and hepatic protein adduction in mice given BBR provided solid evidence for in vivo oxidative debromination of BBR. The studies allowed a better understanding of the metabolic activation of BBR.
- Wang, Hui,Wang, Wenbao,Gong, Bowen,Wang, Zedan,Feng, Yukun,Zhang, Weige,Wang, Shaojie,Peng, Ying,Zheng, Jiang
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- New method for the acylation of benzofurans toward the synthesis of 6H-indeno[2,1-b]benzofuran-6-ones and 2,2-bibenzofurans
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We have developed a TFAA-mediated acylation of benzofurans using carboxylic acids as acylating agents. The reaction does not require the aid of Lewis acid catalysts, and lead to the regioselective formation of 2-acyl benzofurans. Among these, 2-bromophenylacyl benzofurans and 2-(2-bromophenyl)acetyl benzofurans could be converted into 6H-indeno[2, 1-b]benzofuran-6-ones and 2, 2'-bibenzofurans, respectively.
- Zheng, Xuebing,Song, Chuanjun,Meng, Yonggang
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- 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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- STRONGLY LEWIS ACIDIC METAL-ORGANIC FRAMEWORKS FOR CONTINUOUS FLOW CATALYSIS
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Lewis acidic metal-organic framework (MOF) materials comprising triflate-coordinated metal nodes are described. The materials can be used as heterogenous catalysts in a wide range of organic group transformations, including Diels-Alder reactions, epoxide-ring opening reactions, Friedel-Crafts acylation reactions and alkene hydroalkoxylation reactions. The MOFs can also be prepared with metallated organic bridging ligands to provide heterogenous catalysts for tandem reactions and/or prepared as composites with support particles for use in columns of continuous flow reactor systems. Methods of preparing and using the MOF materials and their composites are also described.
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Paragraph 0216-0219; 0224; 0239; 0255
(2021/02/26)
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- Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes
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We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.
- Chen, Zi-Yan,Deng, Xue-Zu,Song, Yang,Xue, Fei,Yamane, Motoki,Yue, Yan-Ni
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p. 12693 - 12704
(2021/09/28)
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- Reductive 3-Silylation of Benzofuran Derivatives via Coupling Reaction with Chlorotrialkylsilane
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Reductive silylation of benzofurans with an electron-withdrawing group by a magnesium metal and the subsequent oxidative rearomatization by DDQ gave the selective formation of less reported 3-silylated benzofurans in moderate to good yields under mild reaction conditions with wide substituent scope. The silyl group introduced on the five-membered ring by the reductive coupling could survive with no elimination throughout the oxidation process. The silylated heteroaromatic skeleton is useful as an intermediate in organic synthesis, and its practical utility was also demonstrated by several transformation reactions.
- Zheng, Suhua,Zhang, Tianyuan,Maekawa, Hirofumi
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p. 13965 - 13972
(2020/11/03)
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- Synthesis, biological evaluation and molecular dynamic simulations of novel Benzofuran-tetrazole derivatives as potential agents against Alzheimer's disease
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A series of novel Benzofuran-tetrazole derivatives were successfully synthesised by integrating multicomponent Ugi-azide reaction with the molecular hybridization approach. Interestingly, a number of synthesized derivatives (5c, 5d, 5i, 5l, 5q and 5s) exhibited significant reduction of aggregation of “human” amyloid beta peptide, expressing on transgenic Caenorhabditis elegans (C. elegans) strain CL4176. Further, in silico docking results have evidenced the exquisite interaction of active compounds with the help of TcAChE–E2020 complex. These findings underscore the potential of these hybrids as lead molecules against Alzheimers's disease.
- Kushwaha, Pragati,Fatima, Soobiya,Upadhyay, Akanksha,Gupta, Sampa,Bhagwati, Sudha,Baghel, Tanvi,Siddiqi,Nazir, Aamir,Sashidhara, Koneni V.
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supporting information
p. 66 - 72
(2018/11/23)
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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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- Strongly Lewis Acidic Metal-Organic Frameworks for Continuous Flow Catalysis
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The synthesis of highly acidic metal-organic frameworks (MOFs) has attracted significant research interest in recent years. We report here the design of a strongly Lewis acidic MOF, ZrOTf-BTC, through two-step transformation of MOF-808 (Zr-BTC) secondary building units (SBUs). Zr-BTC was first treated with 1 M hydrochloric acid solution to afford ZrOH-BTC by replacing each bridging formate group with a pair of hydroxide and water groups. The resultant ZrOH-BTC was further treated with trimethylsilyl triflate (Me3SiOTf) to afford ZrOTf-BTC by taking advantage of the oxophilicity of the Me3Si group. Electron paramagnetic resonance spectra of Zr-bound superoxide and fluorescence spectra of Zr-bound N-methylacridone provided a quantitative measurement of Lewis acidity of ZrOTf-BTC with an energy splitting (?E) of 0.99 eV between the ?x? and ?y? orbitals, which is competitive to the homogeneous benchmark Sc(OTf)3. ZrOTf-BTC was shown to be a highly active solid Lewis acid catalyst for a broad range of important organic transformations under mild conditions, including Diels-Alder reaction, epoxide ring-opening reaction, Friedel-Crafts acylation, and alkene hydroalkoxylation reaction. The MOF catalyst outperformed Sc(OTf)3 in terms of both catalytic activity and catalyst lifetime. Moreover, we developed a ZrOTf-BTC?SiO2 composite as an efficient solid Lewis acid catalyst for continuous flow catalysis. The Zr centers in ZrOTf-BTC?SiO2 feature identical coordination environment to ZrOTf-BTC based on spectroscopic evidence. ZrOTf-BTC?SiO2 displayed exceptionally high turnover numbers (TONs) of 1700 for Diels-Alder reaction, 2700 for epoxide ring-opening reaction, and 326 for Friedel-Crafts acylation under flow conditions. We have thus created strongly Lewis acidic sites in MOFs via triflation and constructed the MOF?SiO2 composite for continuous flow catalysis of important organic transformations.
- Ji, Pengfei,Feng, Xuanyu,Oliveres, Pau,Li, Zhe,Murakami, Akiko,Wang, Cheng,Lin, Wenbin
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supporting information
p. 14878 - 14888
(2019/10/02)
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- Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source
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The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.
- Xia, Aiyou,Xie, Xin,Hu, Xiaoping,Xu, Wei,Liu, Yuanhong
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p. 13841 - 13857
(2019/10/17)
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- Catalyst-Free Photodriven Reduction of α-Haloketones with Hantzsch Ester
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Catalyst-free dehalogenation of α-haloketones under visible light irradiation is studied. The reactions were carried out in common organic solvent. The outcomes of dechlorination are excellent in yields up to 92%, and it is also applicable to bromides, which give even higher yields. The reaction is tolerable to a broad spectrum of substrates, especially to aromatic ketones, including various aryl and hetaryl groups. There are two examples of aliphatic ketones presented in the paper, although their reactivities are not as high as that of the aromatic ketones.
- Lu, Zheng,Yang, Yong-Qing
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p. 508 - 515
(2019/01/10)
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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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- Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters
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A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.
- Michel, Nicholas W. M.,Jeanneret, Alexandria D. M.,Kim, Hyehwang,Rousseaux, Sophie A. L.
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p. 11860 - 11872
(2018/10/02)
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- Hydrogen bond donor solvents enabled metal and halogen-free Friedel–Crafts acylations with virtually no waste stream
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We have developed a metal and halogen-free Friedel–Crafts acylation protocol with virtually no waste stream generation. We propose a hydrogen bonding donor solvent will form a hydrogen bonding network and may provide significant rate enhancement for Friedel–Crafts reactions. Trifluoroacetic acid is one of the strongest H-bond donor solvents, which is also volatile and can be easily recovered by distillation without need for reaction workup. Our protocol is a ‘green’ Friedel–Crafts acylation process: 1) the catalyst can be recovered and reused; 2) using halogen free starting material (carboxylic acids anhydride or carboxylic acids); 3) no need for aqueous reaction work-up; 4) minimum or no waste steam generation.
- Liu, Guangchang,Xu, Bo
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supporting information
p. 869 - 872
(2018/02/09)
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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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- 1,3-disubstituted ketene compound and application thereof
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The invention relates to a 1,3-disubstituted ketene compound with a structure as shown in a formula (I) and application thereof. The compound mainly activates a PPAR (Peroxisome Proliferators-Activated Receptor) alpha, and also has excitation activity for PPPA delta and PPPA gamma. The 1,3-disubstituted ketene compound can be used for treating various diseases related to the PPAR regulation abnormality, such as NASH (nonalcoholic steatohepatitis), and particularly treating nonalcoholic hepatitis, also has potentials for treating diabetes, obesity, fibrotic diseases, cardiovascular diseases (comprising a heart failure, atherosclerosis and the like), kidney diseases (comprising chronic nephrosis, a kidney failure and the like), brain degenerative diseases (comprising the alzheimer disease and the like) and the like, and has higher application value. The formula is shown in the description.
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Paragraph 0227; 0228
(2018/11/03)
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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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- Synthesis of new benzofuran-pyrazole hybrids as potential antibiofilm agents
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A new series of 3-aryl/heteroaryl-5-benzofurnyl pyrazoles [5(a-l)] were synthesized from 1,3-β-monothiodiketones through the cyclocondensation reaction with phenyl hydrazine in good yield and characterized by IR, 1H and 13C NMR, Mass and elemental analyses. All compounds were subjected to evaluate antimicrobial activity against various bacteria viz Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Escherichia coli and Klebsiella pneumoniae and fungal strains viz Fusarium oxysporum and Aspergillus flavus. Further, the inhibition of biofilm formation of Pseudomonas aeruginosa was also carried out. The results showed that some of the synthesized compounds displayed significant antimicrobial activity against tested pathogens. Compounds bearing 3,4,5-trimethoxy (5c) and 4-chloro (5j) substituents on phenyl ring of pyrazole showed the prominent activity against all strains except Lactobacillus species. Among the compounds screened for antibiofilm activity, compounds 5b-d recorded good antibiofilm potential with 50% biofilm formation at 100 μM of which 5b recorded MIC as low as 20 μM.
- Lingaraju, Gejjalagere S.,Rakesh, Somashekaraiah,Kumar, Koravangala S. V.,Rao, Kanchepalli P.,Sreenivasa, Marikunte Y.,Sadashiva, Maralinganadoddi P.
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p. 186 - 194
(2018/04/12)
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- Copper(I)-Catalyzed Chemoselective Reduction of Benzofuran-2-yl Ketones to Alcohols with B2pin2 via a Domino-Borylation-Protodeboronation Strategy
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A novel copper(I)-catalyzed chemoselective reduction of the carbonyls of benzofuran-2-yl ketones over furan rings with B2pin2 has been developed. This reaction proceeded under mild conditions. High valuable secondary alcohol derivatives of benzofurans were obtained in good to excellent yields with a broad substrate scope. The mechanistic studies suggested that a domino-borylation-protodeboronation pathway was involved in this reaction.
- Xuan, Qingqing,Kong, Weiguang,Song, Qiuling
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p. 7602 - 7607
(2017/07/26)
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- Synthesis of Novel Benzofuran-Gathered C-2,4,6-substituted Pyrimidine Derivatives Conjugated by Sulfonyl Chlorides: Orally Bioavailable, Selective, Effective Antioxidants and Antimicrobials Drug Candidates
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In the present study, we have made an effort to develop the novel synthetic antioxidants and antimicrobials with improved potency. The novel benzofuran-gathered C-2,4,6-substituted pyrimidine derivatives 5a, 5b, 5c, 5d, 5e, 5f, 6a, 6b, 6c, 6d, 6e, 6f, 7a, 7b, 7c, 7d, 7e, 7f, 8a, 8b, 8c, 8d, 8e, 8f, 9a, 9b, 9c, 9d, 9e, 9f were synthesized by simple and efficient four-step reaction pathway. Initially, o-alkyl derivative of salicylaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, upon the treatment with potassium tertiary butoxide in the presence of molecular sieves. Further, Claisen-Schmidt condensation with aromatic aldehydes via treatment with thiourea followed by coupling reaction with different sulfonyl chlorides afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass, and elemental analysis and further screened for their antioxidant and antimicrobial activities. The results showed that the synthesized compounds 8b, 8e, 9b, and 9e produced significant antioxidant activity with 50% inhibitory concentration higher than that of reference, whereas compounds 7d and 7c produced dominant antimicrobial activity at concentrations 1.0 and 0.5 mg/mL compared with standard Gentamicin and Nystatin, respectively.
- Rangaswamy, Javarappa,Kumar, Honnaiah Vijay,Harini, Salakatte Thammaiah,Naik, Nagaraja
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p. 1349 - 1360
(2015/10/06)
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- Synthesis, characterization and thermal decomposition kinetics of a novel benzofuran ketoxime derived polymer
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A novel benzofuran ketoxime derived polymer, poly(benzofuran-2-yl-methylketoxime-O-methacrylate) [poly(BMK-MA], was firstly synthesized by free radical polymerization method. Its thermal degradation studies were performed by thermogravimetric analysis (TGA) in order to determine the actual reaction mechanisms of the decomposition process. The activation energy of the solid-state process was determined by using Flynn-Wall-Ozawa method, which resulted to be 235.9 kJ/mol. The activation energies of different mechanism models were determined by Coats-Redfern, Madhusudanan and Van Krevelen kinetic methods. Compared with the Ozawa method, the actual reaction mechanism obeyed deceleration type, phase boundary controlled reaction (R1).
- Bolat, Zehra,Kirilmis, Cumhur,Kurt, Adnan
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p. 428 - 436
(2015/06/30)
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- Redox Amination Scope of Benzylic Ketones with Indoline: Synthetic and Mechanistic Insights
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Bi(NO3)3·5H2O-Catalyzed redox amination scope and mechanistic insights of benzylic ketones with indoline are discussed. The experimental results demonstrate that the formation of N-alkyl-substituted indole/indoline derivatives over typically competitive redox and reductive amination processes is depending upon the reaction condition for the benzylic ketones.
- Aydin, Omer,Kilic, Haydar,Bayindir, Sinan,Erdogan, Esra,Saracoglu, Nurullah
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p. 1540 - 1553
(2015/10/06)
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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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- Facile microwave-assisted synthesis of substituted benzofuran derivatives
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A series of benzofuran derivatives have been synthesized by use of a microwave-assisted process. Substituted or unsubstituted ?- hydroxyacetophenone and salicylaldehyde reacted with ethyl bromoacetate, ω-bromoacetophenone, or chloroacetone under the action of potassium carbonate in DMF to yield substituted benzofuran derivatives. Compared with conventional heating, this microwave-assisted synthetic process has the advantages of more convenient operation, shorter reaction time, and higher yield.
- Liu, Junqiang,Mi, Chenggen,Tang, Xuemei,Cao, Yuan,Li, Zicheng,Huang, Wencai
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p. 2083 - 2090
(2014/05/06)
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- Synthesis and in vitro antimicrobial evaluation of novel fluorine-containing 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-1H-pyrazoles and 3-benzofuran-2-yl-5-phenyl-4,5-dihydro-isoxazoles
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In the present study, some novel fluorine-containing heterocycles incorporating benzofuran with dihydropyrazoles and dihydroisoxazoles have been synthesized and evaluated for their in vitro antibacterial and antifungal activities. 2-Acetylbenzofuran on treatment with fluorinated aldehydes afforded corresponding fluorine-containing 1-benzofuran-2-yl-3-phenyl-prop-2-en-1-ones (chalcones 5a-g). The cyclocondensation of chalcones (5a-g) with hydrazine hydrate under basic conditions resulted in formation of corresponding novel fluorine-containing 3-benzofuran-2yl-5-phenyl-4,5-dihydro-1H-pyrazoles (6a-g). Similar reaction with hydroxylamine hydrochloride yielded 3-benzofuran-2yl-5- phenyl-4,5-dihydro-isoxazoles (7a-g). All the synthesized compounds have been characterized on the basis of analytical and spectral data, and were screened for their antibacterial and antifungal activities. Some of the synthesized compounds showed good antibacterial and antifungal activities.
- Chundawat, Tejpal Singh,Sharma, Nutan,Bhagat, Sunita
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p. 1350 - 1359
(2014/03/21)
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- Microwave assisted synthesis and in vitro antimicrobial activities of fluorine containing 4-benzofuran-2-yl-6-phenyl-pyrimidin-2-ylamines
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A series of new analogs fluorine containing heterocyclic system viz. 4-benzofuran-2-yl-6-phenyl-pyrimidin-2-ylamine has been synthesized and evaluated for in vitro antibacterial and antifungal activities. Microwave assisted Claisen-Schmidt condensation of 2-acetylbenzofuran (3) with fluorinated benzaldehydes (4) afforded corresponding fluorinated chalcones (5a-g). The cyclocondensation of chalcones with guanidine hydrochloride in alkaline media under microwave resulted in the formation of corresponding fluorine containing 4-benzofuran-2-yl-6-phenyl-pyrimidin-2-ylamines (6a-g). All the synthesized compounds have been characterized on the basis of analytical and spectral data and were screened for their antibacterial and antifungal activities. Some of the synthesized compounds showed good antimicrobial activities against bacteria and fungi.
- Chundawat, Tejpal Singh,Sharma, Nutan,Bhagat, Sunita
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p. 409 - 417
(2014/05/20)
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- Zinc-acetic acid promoted reductive carbon-nitrogen bond cleavage reaction of α-aminoketones
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Scope and limitation of the reductive cleavage reaction of α-aminoketone systems with zinc-acetic acid are described. The carbon-nitrogen bond cleavage reaction was applicable to a wide range of α-aminoalkyl aryl ketones possessing various substituents on the aromatic ring. In contrast, α-aminoalkyl alkyl ketones with protons at the α'-position or α-aminoesters were sluggish to the carbon-nitrogen cleavage reaction.
- Ishikawa, Kyoko,Tomatsu, Miyuki,Nagase, Hiroshi,Fujii, Hideaki
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p. 1051 - 1063
(2014/01/17)
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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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- Synthesis of β-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity
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A series of β-amino carbonyl compounds containing coumarin (4a-h) and benzofuran (6a-i) moieties was synthesized by a three component Mannich reaction of 3-acetyl-2H-chromen-2-one (1) or 1-(1-benzofuran-2-yl) ethanone (5) with p-substituted aromatic aldehydes (2a-g) and aromatic amines (3a-b) in the presence of cerric ammonium nitrate as a catalyst. The newly synthesized compounds were screened for antimicrobial and antioxidant activities. Compounds 4b, 4e, 4f, 6f, 6g, and 6i showed microbial inhibition with minimal inhibition concentration ranging between 0.040 and 0.500 mg/mL, compounds 4b, 4c, 6c, 6e, and 6i showed promising free radical scavenging activity and compounds 4b, 4f, 6c, 6d, and 6h showed good chelating ability with Fe2+ ions. The synthesized compounds were studied for docking on the enzyme, glucosamine-6-phosphate synthase to predict the binding affinity and orientation at the active site of the receptor.
- Kenchappa,Bodke, Yadav D.,Peethambar,Telkar, Sandeep,Bhovi, Venkatesh K.
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p. 4787 - 4797
(2013/09/23)
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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.
-
-
- Synthesis of benzofuran based 1,3,5-substituted pyrazole derivatives: As a new class of potent antioxidants and antimicrobials-A novel accost to amend biocompatibility
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In search for a new antioxidant and antimicrobial agent with improved potency, we synthesized a series of benzofuran based 1,3,5-substituted pyrazole analogues (5a-l) in five step reaction. Initially, o-alkyl derivative of salicyaldehyde readily furnish corresponding 2-acetyl benzofuran 2 in good yield, on treatment with 1,8-diaza bicyclo[5.4.0]undec-7-ene (DBU) in the presence of molecular sieves. Further, aldol condensation with vanillin, Claisen-Schmidt condensation reaction with hydrazine hydrate followed by coupling of substituted anilines afforded target compounds. The structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR, mass, elemental analysis and further screened for their antioxidant and antimicrobial activities. Among the tested compounds 5d and 5f exhibited good antioxidant property with 50% inhibitory concentration higher than that of reference while compounds 5h and 5l exhibited good antimicrobial activity at concentration 1.0 and 0.5 mg/mL compared with standard, streptomycin and fluconazole respectively.
- Rangaswamy, Javarappa,Vijay Kumar, Honnaiah,Harini, Salakatte Thammaiah,Naik, Nagaraja
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supporting information; experimental part
p. 4773 - 4777
(2012/08/07)
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- Enantioselective synthesis of trans -dihydrobenzofurans via primary amine-thiourea organocatalyzed intramolecular michael addition
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A primary amine-thiourea organocatalyzed intramolecular Michael addition access was developed for the synthesis of trans-dihydrobenzofurans. Under the catalysis of an (R,R)-1,2-diphenylethylamine derived primary amine-thiourea bearing a glucosyl scaffold, the corresponding trans-dihydrobenzofurans were obtained in high yields with excellent level of enantioselectivities (94 to >99% ee). Moreover, an in situ isomerization occurring at high temperature gave good to excellent trans/cis ratios as well (trans/cis: 84/16-96/4).
- Lu, Aidang,Hu, Keling,Wang, Youming,Song, Haibin,Zhou, Zhenghong,Fang, Jianxin,Tang, Chuchi
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p. 6208 - 6214
(2012/09/25)
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- DEVELOPING POTENT URATE TRANSPORTER INHIBITORS: COMPOUNDS DESIGNED FOR THEIR URICOSURIC ACTION
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A compound represented by the general Formula (I): a pharmaceutically acceptable salt or ester thereof, a solvate thereof, a chelate thereof, a non-covalent complex thereof, a pro-drug thereof, a deuterated radio-labeled analog thereof, and mixtures of any of the foregoing, wherein: A - K are individually selected from carbon or nitrogen; X = -O, -NR1,or -S; R1-11 are individually selected from the group consisting of-H, C1-C6 alkyl, C6-C aryl, substituted C6-C14 aryl, C1-C14-alkoxy, halogen, hydroxyl, carboxy, cyano, C1-C6-alkanoyloxy, C1-C6-alkylthio, C1-C6-alkylsulfonyl, trifluoromethyl, hydroxy, C2-C6-alkoxycarbonyl, C2-C6-alkanoylamino, -O-R12, S-R12,-SO2-Ri2, -NHSO2R12 and -NHCO2R12, wherein R12 is phenyl, naphthyl, or phenyl or naphthly substituted with one to three groups selected from C1-C6-alkyl, C6-C10 aryl,C1-C6-alkoxy and halogen, and C4-C20 hydroxyheteroaryl wherein the heteroatoms are selected from the group consisting of sulfur, nitrogen, and oxygen.
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Page/Page column 13
(2012/04/23)
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- Developing potent human uric acid transporter 1 (hURAT1) inhibitors
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The kidneys are a vital organ in the human body. They serve several purposes including homeostatic functions such as regulating extracellular fluid volume and maintaining acid-base and electrolyte balance and are essential regarding the excretion of metabolic waste. Furthermore, the kidneys play an important role in uric acid secretion/reabsorption. Abnormalities associated with kidney transporters have been associated with various diseases, such as gout. The current study utilized Xenopus oocytes expressing human uric acid transporter 1 (hURAT1; SLC22A12) as an in vitro method to investigate novel compounds and their ability to inhibit 14C-uric acid uptake via hURAT1. We have prepared and tested a series of 2-ethyl-benzofuran compounds and probed the hURAT1 in vitro inhibitor structure-activity relationship. As compared to dimethoxy analogues, monophenols formed on the C ring showed the best in vitro inhibitory potential. Compounds with submicromolar (i.e., IC 50 1000 nM) inhibitors were prepared by brominating the corresponding phenols to produce compounds with potent uricosuric activity.
- Wempe, Michael F.,Jutabha, Promsuk,Quade, Bettina,Iwen, Timothy J.,Frick, Morin M.,Ross, Ian R.,Rice, Peter J.,Anzai, Naohiko,Endou, Hitoshi
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experimental part
p. 2701 - 2713
(2011/06/25)
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- Human uric acid transporter 1 (hURAT1): An inhibitor structure-activity relationship (SAR) study
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The current study describes the chemical synthesis of a series of (2-ethylbenzofuran-3-yl)(substituted-phenyl)methanone compounds and their subsequent in vitro testing via oocytes expressing hURAT1. The experimental data support the notion that a potent hURAT1 inhibitor requires an anion (i.e., a formal negative charge) to interact with the positively charged hURAT1 binding pocket. An anion appears to be a primary requirement in order to be a hURAT1 substrate (i.e., urate) or inhibitor. We discuss the inhibitor structure-activity relationship and how electronically donating or withdrawing groups attached to the B-ring can decrease or increase inhibitory potency, respectively. Copyright Taylor and Francis Group, LLC.
- Wempe,Quade,Jutabha,Iwen,Frick,Rice,Wakui,Endou
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p. 1312 - 1323
(2013/01/15)
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- An efficient synthesis of benzofuran derivatives under conventional/non-conventional method
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1-Methyl-3-ethyl imidazolium bromide [meim]Br/basic alumina (Al2O3) has been found to promote the cyclocondensation of chloroacetone/chloroethyl acetate with salicylaldehydes under conventional as well as microwave irradiation to yield benzofuran derivatives.
- Sapkal, Suryakant B.,Shelke, Kiran F.,Shingate, Bapurao B.,Shingare, Murlidhar S.
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experimental part
p. 1439 - 1442
(2011/10/09)
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- DMAP-catalyzed cascade reaction: One-pot synthesis of benzofurans in water
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A series of benzofurans were efficiently synthesized in good to excellent yields using 4-dimethylaminopyridine (DMAP) catalyzed cascade reaction between salicylaldehydes and halogenated ketones in water at 80 °C opened atmosphere.
- Shang, Yongjia,Wang, Cuie,He, Xinwei,Ju, Kai,Zhang, Min,Yu, Shuyan,Wu, Jiaping
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experimental part
p. 9629 - 9633
(2011/01/03)
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- MIF MODULATORS
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The invention provides novel heterocyclic compounds, pharmaceutical compositions and methods of treatment that modulate levels of MIF expression and treat disorders associated with high or low levels of MIF expression
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Page/Page column 39-40
(2010/04/03)
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- Synthesis of 3-[4-(1-benzofuran-2-yl)-1,3-thiazol-2-yl]-2-(4-aryl)-1,3- thiazolidin-4-one derivatives as biological agents
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A protocol for the synthesis of 3-[4-(1-benzofuran-2-yl)-1,3-thiazol-2-yl]- 2-(4-aryl)-1,3-thiazolidin-4-one derivatives (5a-e) has been developed from 1-(1-benzofuran-2-yl)-2-bromoethanone (2),which served as a key intermediate for the synthesis of the title compounds. The reaction of compound 2 with thiourea furnished 4-(1-benzofuran-2-yl)-1,3-thiazol-2-amine 3, which upon further reaction with various aromatic aldehydes, gave Schiff bases 4a-e. These Schiff bases, when treated with thioacetic acid in the presence of catalytic amount of anhydrous ZnCl2, yielded thiazolidinone derivatives 5a-e. All the newly synthesized compounds have been characterized by analytical and spectral data and screened for their antimicrobial and analgesic 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. Copyright
- Venkatesh, Bhovi K.,Bodke, Yadav D.,Biradar
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scheme or table
p. 1926 - 1931
(2010/11/18)
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- A convenient synthesis of 2(2-benzo[b]furo) indoles and benzofuropyrazoles
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A short synthesis of benzo[b]furo indolyls 3a-g from 2-acetylbenzofuran 1 in two steps and corresponding pyrazoles 4a-g is described. An interesting scale-up procedure for the synthesis of 2-acetylbenzofuran is also been reported. Similarly 2-acetylbenzofurohydrazones 2a-g is prepared from 2-acetyl benzofuran and with various phenylhydrazine hydrochlorides in presence of CH3COONa/EtOH at RT in excellent yield (90-95%). These 2-acetyl benzofurohydrazones 2a-g are subjected to Fiseher indole cyelisation in presence of ZnCl2 in acetonitrile as solvent to get 2(2-benzo[b]furo)indolcs 3a-g in good yield.
- Goudarshivannanavar,Jayadevappa,Mahadevan
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experimental part
p. 1419 - 1423
(2010/02/28)
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- Synthesis and antimicrobial investigation of some novel phenyl pyrazole, azetidinone and diazenyl ethanone derivatives of benzofurans
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Salicylaldehyde and 2-hydroxy acetophenone on reaction with chloroacetone afford corresponding benzofurans 2a, 2b respectively. The compounds 2a and 2b on treatment with phenyl hydrazine in ethanol give 3a-d. The products 3a-d on treatment with DMF/POCl3 underwent cyclization to produce substituted pyrazoles 4a-d. The compounds 2a-b on treatment with aromatic amines in ethanol afford the corresponding Schiffs bases 5a-h, which on treatment with chloroacetyl chloride in dioxane produced azetidinones 6a-h. Further, the compounds 2a and 2b on reaction with various diazotized aromatic amines produce phenyl diazenyl benzofurans 7a-h. The structure of all newly synthesized compounds are established by elemental analysis and spectral studies. Their antimicrobial activities have been evaluated.
- Aruna Kumar,Prakash,Kumaraswamy,Nandeshwarappa,Sherigara,Mahadevan
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p. 336 - 343
(2008/02/09)
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