Acylation of a substituted benzofuran over an HY zeolite and its subsequent deacylation and reacylation

The acylation reaction of 2-butylbenzofuran withp-anisoyl chloride andp-anisic acid in the presence of faujasite type zeolites, in the liquid phase, is reported. A good initial selectivity to the 3-acylated derivative is obtained, but the selectivity decreases with time. This result is explained by the involvement of a deacylation-reacylation process.     

钯催化一锅法合成2-(3,3-二甲基)丁炔基苯并呋喃的研究

在三乙胺与四氢呋喃混合溶剂中,邻乙炔基苯酚与(E)-1,2-二碘-3,3-二甲基-1-丁烯在醋酸钯及碘化亚铜的作用下,在氩气保护下,首先在室温下反应15 h,然后在100°C下再反应13 h,一锅法合成2-(3,3-二甲基)丁炔基苯并呋喃,该方法操作简便,反应产率较好,产物结构经由NMR和MS确证。     

苯酚精制过程中微量杂质的成因及脱除方法

异丙苯法是目前广泛应用的苯酚生产方法.使用异丙苯法生产苯酚时易产生多种有机杂质,这些杂质会影响苯酚色泽的稳定性,使用一般的精馏方法很难将其脱除.采用已工业化的苯酚精制工艺可以使产品质量满足工业生产要求.针对苯酚精制过程中成品含有微量杂质的问题,对苯酚成品进行了分析,验证了苯酚精制塔中存在2-甲基苯并呋喃与其他溶剂共沸的...     

THE SYNTHESES OF BENZOFURAN DERIVATIVES

Two benzofuran derivatives were synthesized from 3,4-bis(trimethylsilyl)furan after a series of reactions. Their structures were identified by 1H NMR, 13C NMR, MS and EA.     

Bis(Benzofuran–1,3-N,N-heterocycle)s as Symmetric and Synthetic Drug Leads against Yellow Fever Virus

The yellow fever virus (YFV) is an emerging RNA virus and has caused large outbreaks in Africa and Central and South America. The virus is often transmitted through infected mosquitoes and spreads from area to area because of international travel. Being an acute viral hemorrhagic disease, yellow fever can be prevented by an effective, safe, and reliable vaccine, but not be eliminated. Currently, there is no antiviral drug available for its cure. Thus, two series of novel bis(benzofuran–1,3-imidazolidin-4-one)s and bis(benzofuran–1,3-benzimidazole)s were designed and synthesized for the development of anti-YFV lead candidates. Among 23 new bis-conjugated compounds, 4 of them inhibited YFV strain 17D (Stamaril) on Huh-7 cells in the cytopathic effect reduction assays. These conjugates exhibited the most compelling efficacy and selectivity with an EC₅₀ of <3.54 μM and SI of >15.3. The results are valuable for the development of novel antiviral drug leads against emerging diseases.     

一种新型共轭蓝光高分子的合成及表征

苯并呋喃衍生物是一种具有高荧光效率、高热及光稳定性和优良空穴传输能力的蓝光发光材料。采用二(溴甲基)苯与溴代邻羟基苯甲醛发生Knoevenagel反应制备出了二溴代苯并呋喃衍生物,再通过与苯二硼酸发生Suzuki偶合,合成出了一种苯并呋喃基新型蓝光高分子材料(PBF)。利用荧光光谱仪(PL)、紫外光谱仪(UV)、差示扫描量热仪(DSC),研究了其相应的光学和热物理学性质。所得聚合物在膜状态下的PL分析表明,其最大荧光发射波长为444 nm,是一种典型的蓝光发光材料;DSC研究表明,聚合物在50~200℃温度范围内无明显的玻璃化转变和晶体熔融现象,表现出优良的热稳定性。该聚合物易溶于CHCl3、THF等有机溶剂,可旋涂成膜,易于加工,是一种具有应用价值的蓝光发光材料。     

4-氨基-7-氯-5-氟-2,3-二氢-2-甲基苯并呋喃的合成研究

4-氨基-7-氯-5-氟-2,3-二氢-2-甲基苯并呋喃是合成除草剂的中间体。它通过以下途径制得:4-氯-2-氟-5-羟基-苯基氨基羧酸乙酯经醚化、水解、转位、闭环制得产品,总收率为21.7%,产品结构经核磁共振氢谱确认。     

Catalytic hydrotreating of indole,benzothiophene, and benzofuran over Mo2N

The activity of -Mo₂N for heteroatom removal from benzofuran, benzothiophene, and indole has been investigated. -Mo₂N is found to be an effective catalyst in all three cases. The distribution of products observed as a function of temperature suggests that the reaction mechanism is similar for all three reactants. Rapid hydrogenation of the heterocyclic ring is followed by hydrogenolysis of the X-C bond in the saturated ring and release of the heteroatom as XH _n (X = O, S, N). The product formed in the last step of the sequence is ethylbenzene. Hydrogenation of the benzene ring in ethylbenzene is not observed, but evidence is found for hydrogenolysis and dealkylation of the alkyl group.     

2,3‐Dihydro‐1‐Benzofuran Derivatives as a Series of Potent Selective Cannabinoid Receptor 2 Agonists: Design,Synthesis, and Binding Mode Prediction through Ligand‐Steered Modeling

We recently discovered and reported a series of N‐alkyl‐isatin acylhydrazone derivatives that are potent cannabinoid receptor 2 (CB₂) agonists. In an effort to improve the druglike properties of these compounds and to better understand and improve the treatment of neuropathic pain, we designed and synthesized a new series of 2,3‐dihydro‐1‐benzofuran derivatives bearing an asymmetric carbon atom that behave as potent selective CB₂ agonists. We used a multidisciplinary medicinal chemistry approach with binding mode prediction through ligand‐steered modeling. Enantiomer separation and configuration assignment were carried out for the racemic mixture for the most selective compound, MDA7 (compound 18 ). It appeared that the S enantiomer, compound MDA104 (compound 33 ), was the active enantiomer. Compounds MDA42 (compound 19 ) and MDA39 (compound 30 ) were the most potent at CB₂. MDA42 was tested in a model of neuropathic pain and exhibited activity in the same range as that of MDA7. Preliminary ADMET studies for MDA7 were performed and did not reveal any problems.     

The Potential Role of Phenolic Acids from Salvia miltiorrhiza and Cynara scolymus and Their Derivatives as JAK Inhibitors: An In Silico Study

JAK inhibition is a new strategy for treating autoimmune and inflammatory diseases. Previous studies have shown the immunoregulatory and anti-inflammatory effects of Salvia miltiorrhiza and Cynara scolymus and suggest that the bioactivity of their phenolic acids involves the JAK-STAT pathway, but it is unclear whether these effects occur through JAK inhibition. The JAK binding affinities obtained by docking Rosmarinic acid (RosA), Salvianolic acid A (SalA), Salvianolic acid C (SalC), Lithospermic acid, Salvianolic acid B and Cynarin (CY) to JAK (PDB: 6DBN) with AutoDock Vina are −8.8, −9.8, −10.7, −10.0, −10.3 and −9.7 kcal/mol, respectively. Their predicted configurations enable hydrogen bonding with the hinge region and N- and C-terminal lobes of the JAK kinase domain. The benzofuran core of SalC, the compound with the greatest binding affinity, sits near Leu959, such as Tofacitinib’s pyrrolopyrimidine. A SalC derivative with a binding affinity of −12.2 kcal/mol was designed while maintaining this relationship. The docking results show follow-up studies of these phenolic acids as JAK inhibitors may be indicated. Furthermore, derivatives of SalC, RosA, CY and SalA can yield better binding affinity or bioavailability scores, indicating that their structures may be suitable as scaffolds for the design of new JAK inhibitors.