27364-71-2Relevant articles and documents
Efficient synthesis of polycycles bearing prenylated, geranylated, and farnesylated citrans: Application to 3′-prenylrubranine and petiolin D regioisomer
Wang, Xue,Lee, Yong Rok
, p. 9179 - 9184 (2011)
Efficient synthetic routes for biologically interesting polycycles with prenylated, geranylated, and farnesylated citrans were developed from several trihydroxybenzenes with prenyl, geranyl, and farnesyl groups on the benzene rings. Ethylenediamine diacet
Magnesium dicarboxylates promote the prenylation of phenolics that is extended to the total synthesis of icaritin
Fu, Xuewen,Lu, Xiaoxia,Wang, Chun,Wen, Yongju,Xiong, Wei,Zhang, Guolin,Zhang, Jichao
, p. 1117 - 1124 (2022/02/16)
The prenylation of phenolic substrates promoted by magnesium dicarboxylates was developed. An investigation of the scope demonstrated that substrates with electron-donating group(s) gave better yields than those with electron-withdrawing group(s). Althoug
PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS
-
Paragraph 00348; 00372, (2021/12/08)
The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).
Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones
Escobar, Gustavo,González, Luis A.,Qui?ones, Wiston,Robledo, Sara,Upegui, Yulieth
, (2021/12/02)
American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.
Convenient and efficient total synthesis method for icaritin and derivatives of icaritin
-
Paragraph 0063; 0069-0073, (2020/02/06)
The invention belongs to the field of natural medicine synthesis and particularly relates to a convenient and efficient total synthesis method for icaritin and derivatives of icaritin. The specific technical scheme is as follows: 2'-hydroxyacetophenone and benzaldehyde are used as raw materials, firstly, isopentene groups are introduced in aromatic rings of raw materials under the catalysis of anorganic polyacid metal ion complex, a flavonol framework is constructed under mild and green conditions, and an isopentenyl flavone compound comprising the icaritin and derivatives of icaritin is further synthesized. The method effectively overcomes the limitation of poor substrate solubility and poor regioselectivity when flavone is constructed firstly and then isopentene groups are introduced, the problems of frequent introduction and removal of protecting groups in a conventional isopentenylation method are solved, and the synthesis route is greatly simplified; and meanwhile, the problems of complex products and more byproducts in an isopentene group rearrangement method are solved. The total synthesis method provided by the invention is mild in condition, convenient to operate, high intotal yield and suitable for mass production of the isopentenyl flavone compound.
3-site piperazinylchalcone derivative, and pharmaceutical composition and applications thereof
-
Paragraph 0049-0051; 0054; 0055, (2019/02/04)
The present invention relates to a 3-site piperazinylchalcone derivative, which has a structure formula represented by a general formula (I) defined in the specification, wherein R is one selected from a substituted or unsubstituted phenyl group, a fused ring group and substituted or a unsubstituted heterocyclic group. The present invention further provides a pharmaceutical composition of the3-site piperazinylchalcone derivative, and applications thereof. According to the present invention, the results of the activity test based on P-gp target show that the 3-site piperazinylchalcone derivative and the pharmaceutical composition have good activity, can provide practical value in the treatment of the multidrug resistance of tumors, can solve the technical problems of difficult synthesis and high cost in the synthesis of the reversing agent used in the prior art, and is meaningful.
Design, synthesis and biological evaluation of chalcones as reversers of P-glycoprotein-mediated multidrug resistance
Yin, Huanhuan,Dong, Jingjing,Cai, Yingchun,Shi, Ximeng,Wang, Hao,Liu, Guixia,Tang, Yun,Liu, Jianwen,Ma, Lei
, p. 350 - 366 (2019/07/19)
Overexpression of P-glycoprotein (P-gp) is one of the major causes for multidrug resistance (MDR), which has become a major obstacle in cancer therapy. One hopeful approach to reverse the MDR is to develop inhibitors of P-gp in expression and/or function. Here, we designed and synthesized a series of chalcone derivatives as P-gp inhibitors and evaluated their potential reversal activities against MDR. Among them, the most active compound MY3 had little intrinsic cytotoxicity and showed the highest activity (RF = 50.19) in reversing DOX resistance in MCF-7/DOX cells. Further studies demonstrated that MY3 could increase intracellular accumulation of DOX and inhibit expression of P-gp at mRNA and protein levels. More importantly, MY3 significantly enhanced the efficacy of DOX against the tumor xenografts bearing MCF-7/DOX cells with the precondition of unchanged body weight. Therefore, MY3 might represent a promising lead to develop MDR reversal agents for cancer chemotherapy.
Hits-to-lead optimization of the natural compound 2,4,6-trihydroxy-3-geranyl-acetophenone (thga) as a potent lox inhibitor: Synthesis, structure-activity relationship (sar) study, and computational assignment
Ng, Chean Hui,Rullah, Kamal,Abas, Faridah,Lam, Kok Wai,Ismail, Intan Safinar,Jamaludin, Fadzureena,Shaari, Khozirah
, (2018/10/15)
A new series of 2,4,6-trihydroxy-3-geranyl-acetophenone (tHGA) analogues were synthesized and evaluated for their lipoxygenase (LOX) inhibitory activity. Prenylated analogues 4a-g (half maximal inhibitory concentration (IC50) values ranging from 35 μM to 95 μM) did not exhibit better inhibitory activity than tHGA (3a) (IC50 value: 23.6 μM) due to the reduction in hydrophobic interaction when the alkyl chain length was reduced. One geranylated analogue, 3d, with an IC50 value of 15.3 μM, exhibited better LOX inhibitory activity when compared to tHGA (3a), which was in agreement with our previous findings. Kinetics study showed that the most active analogue (3e) and tHGA (3a) acted as competitive inhibitors. The combination of in silico approaches of molecular docking and molecular dynamic simulation revealed that the lipophilic nature of these analogues further enhanced the LOX inhibitory activity. Based on absorption, distribution, metabolism, excretion, and toxicity (ADMET) and toxicity prediction by komputer assisted technology (TOPKAT) analyses, all geranylated analogues (3a-g) showed no hepatotoxicity effect and were biodegradable, which indicated that they could be potentially safe drugs for treating inflammation.
Cnidimonins A-C, Three Types of Hybrid Dimer from Cnidium monnieri: Structural Elucidation and Semisynthesis
Su, Fangyi,Zhao, Zheng,Ma, Shuanggang,Wang, Rubing,Li, Yong,Liu, Yunbao,Li, Yuhuan,Li, Li,Qu, Jing,Yu, Shishan
supporting information, p. 4920 - 4923 (2017/09/23)
Three pairs of racemic dimers, (±)-cnidimonins A-C (1-3), were isolated from the fruits of Cnidium monnieri. They represent novel hybrid-dimerization patterns of coumarin skeleton with structurally diverse units (flavonol, benzofuran, and chromone) via an
Evaluation of Dual 5-Lipoxygenase/Microsomal Prostaglandin E2 Synthase-1 Inhibitory Effect of Natural and Synthetic Acronychia-Type Isoprenylated Acetophenones
Svouraki, Alexandra,Garscha, Ulrike,Kouloura, Eirini,Pace, Simona,Pergola, Carlo,Krauth, Verena,Rossi, Antonietta,Sautebin, Lidia,Halabalaki, Maria,Werz, Oliver,Gaboriaud-Kolar, Nicolas,Skaltsounis, Alexios-Leandros
, p. 699 - 706 (2017/04/01)
Among the pathways responsible for the development of inflammatory responses, the cyclooxygenase and lipoxygenase pathways are among the most important ones. Two key enzymes, namely, 5-LO and mPGES-1, are involved in the biosynthesis of leukotrienes and prostaglandins, respectively, which are considered attractive therapeutic targets, so their dual inhibition might be an effective strategy to control inflammatory deregulation. Several natural products have been identified as 5-LO inhibitors, with some also being dual 5-LO/mPGES-1 inhibitors. Here, some prenylated acetophenone dimers from Acronychia pedunculata have been identified for their dual inhibitory potency toward 5-LO and mPGES-1. To gain insight into the SAR of this family of natural products, the synthesis and biological evaluation of analogues are presented. The results show the ability of the natural and synthetic molecules to potently inhibit 5-LO and mPEGS-1 in vitro. The potency of the most active compound (10) has been evaluated in vivo in an acute inflammatory mouse model and displayed potent anti-inflammatory activity comparable in potency to the drug zileuton used as a positive control.
