63815-27-0Relevant academic research and scientific papers
Bi(OTf)3-Mediated (4+1) Annulation of α-Sulfonyl o-Hydroxyacetophenones with α-Hydroxy Arylketones to Access Sulfonyl 2-Aroylbenzofurans
Chang, Meng-Yang,Chen, Kuan-Ting
, p. 2594 - 2609 (2021/03/29)
In this paper, a high-yield, facile route for the scalable synthesis of sulfonyl 2-aroylbenzofurans via a Bi(OTf)3-mediated intermolecular double cyclocondensation of α-sulfonyl o-hydroxyacetophenones with substituted α-hydroxy arylketones under mild open-vessel reaction conditions is described. In the overall reaction, water is generated as the only byproduct. Various metal triflate-promoted reactions and conditions are investigated for the efficient one-pot (4+1) annulation reaction. (Figure presented.).
Chalcone compound containing oxyacetic acid structure, and uses thereof
-
Paragraph 0016, (2020/01/25)
The invention relates to a chalcone compound containing an oxyacetic acid structure, wherein the chalcone compound is artificially synthesized 4-nitro-2'-carboxymethoxy chalcone. According to the invention, the synthesized new compound has a structure sim
4-Hydroxy-3-methylbenzofuran-2-carbohydrazones as novel LSD1 inhibitors
Gao, Yuan,He, Xingrui,Hui, Zi,Shen, Guodong,Wang, Shuo,Xie, Tian,Ye, Xiang-Yang
supporting information, (2020/03/31)
Histone lysine specific demethylase 1 (LSD1 or KDM1A) is a potential therapeutic target in oncology due to its overexpression in various human tumors. We report herein a new class of benzofuran acylhydrazones as potent LSD1 inhibitors. Among the 31 compounds prepared, 14 compounds exhibited excellent LSD1 inhibitory activity with IC50 values ranging from 7.2 to 68.8 nM. In cellular assays, several compounds inhibited the proliferations of various cancer cell lines, including PC-3, MCG-803, U87 MG, PANC-1, HT-29 and MCF-7. This opens up the opportunity for further optimization and investigation of this class compounds for potential cancer treatment.
Rhodium-Catalyzed Intermolecular Cyclopropanation of Benzofurans, Indoles, and Alkenes via Cyclopropene Ring Opening
Jeyaseelan, Rubaishan,Lautens, Mark,Ross, Rachel J.
supporting information, (2020/06/29)
The generation of metal carbenoids via ring opening of cyclopropenes by transition metals offers a simple entry into highly reactive intermediates. Herein, we describe a diastereoselective intermolecular rhodium-catalyzed cyclopropanation of heterocycles and alkenes using cyclopropenes as carbene precursors with a low loading of a commercially available rhodium catalyst. The reported method is scalable and could be performed with catalyst loadings as low as 0.2 mol %, with no impact to the reaction yield or selectivity.
Mercapto-amide boronic acid derivative and application thereof as MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase) inhibitor
-
Paragraph 0090-0093, (2019/09/14)
The invention provides a compound of a formula (I) shown in the specification, or a conformational isomer, or an optical isomer or a pharmaceutically acceptable salt thereof. The compound of the formula (I) shown in the specification has excellent broad-spectrum inhibitory activity on MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase), and can be used for preparing MBL and/or SBL inhibitors. Moreover, the compound disclosed by the invention has excellent antibacterial activity on multiple drug-resistant bacteria and is capable of reversing drug resistance of carbapenem drug-resistant bacteria, and the antibacterial effect of the compound is prior to those of positive control products such as L-captopril and tazobactam. The compound disclosed by the invention has very great potential in preparation of MBL/SBL dual inhibitors and medicines reversing drug resistance of carbapenem drug-resistance bacteria.
Structure-based development of (1-(3′-Mercaptopropanamido)methyl)boronic Acid Derived Broad-Spectrum, Dual-Action Inhibitors of Metallo- And Serine-β-lactamases
Wang, Yao-Ling,Liu, Sha,Yu, Zhu-Jun,Lei, Yuan,Huang, Meng-Yi,Yan, Yu-Hang,Ma, Qiang,Zheng, Yang,Deng, Hui,Sun, Ying,Wu, Chengyong,Yu, Yamei,Chen, Qiang,Wang, Zhenling,Wu, Yong,Li, Guo-Bo
supporting information, p. 7160 - 7184 (2019/08/28)
The emergence and spread of bacterial pathogens acquired metallo-β-lactamase (MBL) and serine-β-lactamase (SBL) medicated β-lactam resistance gives rise to an urgent need for the development of new dual-action MBL/SBL inhibitors. Application of a pharmacophore fusion strategy led to the identification of (2′S)-(1-(3′-mercapto-2′-methylpropanamido)methyl)boronic acid (MS01) as a new dual-action inhibitor, which manifests broad-spectrum inhibition to representative MBL/SBL enzymes, including the widespread VIM-2 and KPC-2. Guided by the VIM-2:MS01 and KPC-2:MS01 complex structures, further structural optimization yielded new, more potent dual-action inhibitors. Selectivity studies indicated that the inhibitors had no apparent inhibition to human angiotensin-converting enzyme-2 and showed selectivity across serine hydrolyases in E. coli and human HEK293T cells labeled by the activity-based probe TAMRA-FP. Moreover, the inhibitors displayed potentiation of meropenem efficacy against MBL- or SBL-positive clinical isolates without apparent cytotoxicity. This work will aid efforts to develop new types of clinically useful dual-action inhibitors targeting MBL/SBL enzymes.
Cinnamoylated chloroquine analogues: A new structural class of antimalarial agents
Gayam, Venkatareddy,Ravi, Subban
, p. 382 - 391 (2017/05/04)
A novel series of cinnamoylated chloroquine hybrid analogues were synthesized and evaluated as antimalarial agents. The trans cinnamic acid derivatives (3–8) were synthesized by utilizing substituted aldehydes and malanoic acid in DMF catalysed by DABCO. The final cinnamoylated chloroquine analogues (9–14) were synthesized by utilizing DCC coupling reagent. The amido chloroquine (17) was prepared from acid (16) and compound 2 in benzene using SOCl2 as chlorinating agent. The corresponding ester (15) was prepared from 2-hydroxy acetophenone and 2-bromoacetates in actonitrile in presence of K2CO3?as?base followed by basic hydrolysis. The preparation of amide based chloroquine-chalcone analogues (18–22), were obtained by the combination of amido chloroquine (17) and aldehydes in 10% aq. KOH in methanol at room temperature. Further we prepared epichlorohydrin based chloroquine-chalcone analogues (25–28), by reacting the epoxide (24a, 24b and 24c) with 2 and methelenedioxy aniline. In?vitro antimalarial activity against chloroquine sensitive strain 3D7, chloroquine resistant strain K1 of P.?falciparum and in?vitro cytotoxicity of compounds using VERO cell line was carried out. The synthesized molecules showed significant in?vitro antimalarial activity especially against CQ resistant strain (K1). Among tested compounds, 13, 9 and 10 were found to be the most potent compounds of the series with IC50 value of 44.06, 48.04 and 59.37?nM against chloroquine resistant K1 strain.
Synthesis and bioactivity evaluation of novel 2-salicyloylbenzofurans as antibacterial agents
Phan, Phuong-Thuy T.,Nguyen, Thu-Trang T.,Nguyen, Hong-Nhung T.,Le, Bao-Khanh N.,Vu, Thao T.,Tran, Dong C.,Pham, Tuan-Anh N.
, (2017/06/08)
In order to discover new antibacterial agents, series of 2-salicyloylbenzofuran derivatives were designed, synthesized and evaluated for their antibacterial activities against three Gram-(+) strains (methicillin-sensitive Staphylococcus aureus (MSSA) ATCC 29213, methicillin-resistant Staphylococcus aureus (MRSA) ATCC 43300, and Streptococcus faecalis (S. faecalis) ATCC 29212) and one Gram-(-) strain (Escherichia coli (E. coli) ATCC 25922). The 2-salicyloylbenzofuran heterocycles were generated by Rap-Stoermer condensation of salicylaldehydes with phenacyl bromides and then converted to diverse O-ether derivatives by Williamson synthesis. The targeted products were screened for in vitro qualitative (zone of inhibition) and quantitative (MIC) antibacterial activities by agar well diffusion assay and agar dilution method. Amongst the compounds, those bearing carboxylic acid functional group were found to exhibit reasonable activity against Gram-(+) bacterial strains including S. faecalis, MSSA and MRSA with the most potent antibacterial agent 8h (MICs = 0.06-0.12 mM). Besides, the 2-salicyloylbenzofurans partly displayed inhibitory activity against MRSA with the best MICs = 0.14 mM (8f) and 0.12 mM (8h). Finally, the antibacterial results preliminarily suggested that the substituent bearing carboxylic acid group at salicyloyl-C2 and the bromine atoms on the benzofuran moiety seem to be the functionality necessary for antibacterial activities.
Synthesis, SAR, molecular docking and antituberculosis study of 3-methyl-1-benzofuran-2-carbohydrazide
Thorat, Bapu R.,Nazirkar, Bhusan,Thorat, Vaishali B.,More, Kishor,Jagtap, Ravindra,Yamgar, Ramesh
, p. 2346 - 2352 (2016/10/12)
3-Methyl-1-benzofuran-2-carbohydrazide was synthesized from 2-hydroxy acetophenone. To deduce the antibacterial and anticancer activity of the 3-methyl-1-benzofuran-2-carbohydrazide, it is docked with different biomarkers of cancer cell and bacteria. The
Substrate-Tuned Catalysis of the Radical S-Adenosyl- L -Methionine Enzyme NosL Involved in Nosiheptide Biosynthesis
Ji, Xinjian,Li, Yongzhen,Ding, Wei,Zhang, Qi
supporting information, p. 9021 - 9024 (2015/08/03)
NosL is a radical S-adenosyl-L-methionine (SAM) enzyme that converts L-Trp to 3-methyl-2-indolic acid, a key intermediate in the biosynthesis of a thiopeptide antibiotic nosiheptide. In this work we investigated NosL catalysis by using a series of Trp analogues as the molecular probes. Using a benzofuran substrate 2-amino-3-(benzofuran-3-yl)propanoic acid (ABPA), we clearly demonstrated that the 5′-deoxyadenosyl (dAdo) radical-mediated hydrogen abstraction in NosL catalysis is not from the indole nitrogen but likely from the amino group of L-Trp. Unexpectedly, the major product of ABPA is a decarboxylated compound, indicating that NosL was transformed to a novel decarboxylase by an unnatural substrate. Furthermore, we showed that, for the first time to our knowledge, the dAdo radical-mediated hydrogen abstraction can occur from an alcohol hydroxy group. Our study demonstrates the intriguing promiscuity of NosL catalysis and highlights the potential of engineering radical SAM enzymes for novel activities.
