33523-62-5Relevant academic research and scientific papers
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.
3-site piperazinylchalcone derivative, and pharmaceutical composition and applications thereof
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Paragraph 0049-0051; 0056; 0057, (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.
Synthesis, anti-phytopathogenic and DPPH radical scavenging activities of C-prenylated acetophenones and benzaldehydes
Osorio, Mauricio E.,Quiroz, Karol A.,Carvajal, Marcela A.,Vergara, Alejandra P.,Sánchez, Elizabeth Y.,González, Cesar E.,Catalán, Karen S.
, p. 3095 - 3101 (2016/11/17)
The syntheses of six prenylated acetophenone and benzaldehyde derivatives and their anti-phytopathogenic and antioxidant activities are reported. These compounds were obtained by electrophilic aromatic substitution (SEAr) of the corresponding arenes and 3-methyl-2-buten-1-ol using ZnCl2 as a Lewis acid catalyst in ethyl acetate. Reasonable to good yields were obtained based on unrecovered aromatic starting material (45-73%). All the synthesized compounds were evaluated against phytopathogenic gram-negative bacteria Agrobacterium tumefaciens, Pseudomonas syringae and Erwinia carotovora and plant fungal pathogens Botrytis cinerea, Phytophthora cinnamomi and Gibberella fujikuroi. The antioxidant activity was evaluated using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay and expressed as half maximal inhibitory concentration (IC50) values in μM concentrations. The antioxidant activity went from 27.20 μM to >100 μM. Compound 11 showed statistically significant inhibition of the growth of Botrytis cinerea, and compounds 13 and 15 showed statistically significant inhibition of the growth of Phytophthora cinnamomi, with respect to negative control fungal growth. All six compounds showed bacteriostatic effects against gram-negative plant pathogenic bacteria with IC50 values between 250 and 3.9 μM.
Towards the synthesis of platachromone b, a bioactive natural prenylated (E)-2-styrychromone
Baptista, Frederico R.,Pinto, Diana C. G. A.,Silva, Artur M. S.
, p. 1116 - 1120 (2014/05/20)
Strategies towards the synthesis of the natural product platachromone B and related compounds have been investigated starting from commercially available phloroacetophenone. Direct C-prenylation of (E)-2-styryl-4H-chromen-4-ones was also studied. Methods
Synthesis of a natural chalcone and its prenyl analogs - Evaluation of tumor cell growth-inhibitory activities, and effects on cell cycle and apoptosis
Neves, Marta P.,Lima, Raquel T.,Choosang, Kanthima,Pakkong, Panee,De Sao Jose Nascimento, Maria,Vasconcelos, M. Helena,Pinto, Madalena,Silva, Artur M. S.,Cidade, Honorina
body text, p. 1133 - 1143 (2012/09/22)
Six prenyl (= 3-methylbut-2-en-1-yl) chalcones (=1,3-diphenylprop-2-en-1- ones), 2-7, and one natural non-prenylated chalcone, 1, have been synthesized and evaluated for their in vitro growthinhibitory activity against three human tumor cell lines. A pron
Natural and non-natural prenylated chalcones: Synthesis, cytotoxicity and anti-oxidative activity
Vogel, Susanne,Ohmayer, Susanne,Brunner, Gabi,Heilmann, Joerg
, p. 4286 - 4293 (2008/12/20)
A general strategy for the synthesis of 3′-prenylated chalcones was established and a series of prenylated hydroxychalcones, including the hop (Humulus lupulus L.) secondary metabolites xanthohumol (1), desmethylxanthohumol (2), xanthogalenol (3), and 4-methylxanthohumol (4) were synthesized. The influence of the A-ring hydroxylation pattern on the cytotoxic activity of the prenylated chalcones was investigated in a HeLa cell line and revealed that non-natural prenylated chalcones, like 2′,3,4′,5-tetrahydroxy-6′-methoxy-3′-prenylchalcone (9, IC50 3.2 ± 0.4 μM) as well as the phase 1 metabolite of xanthohumol (1), 3-hydroxyxanthohumol (8, IC50 2.5 ± 0.5 μM), were more active in comparison to 1 (IC50 9.4 ± 1.4 μM). A comparison of the cytotoxic activity of xanthohumol (1) and 3-hydroxyxanthohumol (8) with the non-prenylated analogs helichrysetin (12, IC50 5.2 ± 0.8) and 3-hydroxyhelichrysetin (13, IC50 14.8 ± 2.1) showed that the prenyl side chain at C-3′ has an influence on the cytotoxicity against HeLa cells only for the dihydroxylated derivative. This offers interesting synthetic possibilities for the development of more potent compounds. The ORAC activity of the synthesized compounds was also investigated and revealed the highest activity for compounds 12, 4′-methylxanthohumol (4), and desmethylxanthohumol (2), with 4.4 ± 0.6, 3.8 ± 0.4, and 3.8 ± 0.5 Trolox equivalents, respectively.
Anti-ulcer agent comprising chalcone derivative as effective ingredient and novel chalcone derivative
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, (2008/06/13)
The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: STR1 wherein X and Y independently stand for a hydrogen atom or together form a single bond, R1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R3 stands for hydroxyl group or a methoxy group, R4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R7 stands for a hydrogen atom or a methoxy group.
Synthesis of Candidone - A New Flavanone Isolated from Tephrosia Candida
Ganguly, A.,Bhattacharyya, P.,Bhattacharyya, Anjan,Adityachaudhury, N.
, p. 462 - 463 (2007/10/02)
Candidone (5,7-dimethoxy-8-prenylflavanone) has been synthesized from 2-hydroxy-4,6-dimethoxyacetophenone via condensation with benzaldehyde followed by prenylation and cyclisation.
A NEW PRENYLATED FLAVANONE FROM TEPHROSIA VILLOSA
Jayaraman, Indrani,Ghanim, A.,Khan, Hamid A.
, p. 1267 - 1268 (2007/10/02)
Key Word Index -- Tephrosia villosa; Leguminosae; a new flavanone; 7-methylglabramin.
