155673-98-6

Basic information

• Product Name: 3-(4-CHLOROPHENYL)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-2-PROPEN-1-ONE
• Synonyms: 3-(4-CHLOROPHENYL)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-2-PROPEN-1-ONE;4-CHLORO-4',6'-DIMETHOXY-2'-HYDROXYCHALCONE
• CAS NO: 155673-98-6
• Molecular Formula: C₁₇H₁₅ClO₄
• Molecular Weight: 318.75
• Mol File: 155673-98-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(4-CHLOROPHENYL)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-2-PROPEN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-CHLOROPHENYL)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-2-PROPEN-1-ONE(155673-98-6)
• EPA Substance Registry System: 3-(4-CHLOROPHENYL)-1-(2-HYDROXY-4,6-DIMETHOXYPHENYL)-2-PROPEN-1-ONE(155673-98-6)

Safety Data

• Hazardous Substances Data: 155673-98-6(Hazardous Substances Data)

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 108-73-6 3,5-dihydroxyphenol 
• 99-91-2 para-chloroacetophenone 

Downstream Products

• 861137-52-2 (E)-1-(3-bromo-2-hydroxyl-4,6-dimethoxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one 
• 350982-88-6 (2Z)-2-(4-chlorobenzylidene)-4,6-dimethoxy-1-benzofuran-3(2H)-one 
• 26207-65-8 4'-chloro-5,7-dihydroxyflavanone 
• 1042741-41-2 C₁₆H₁₃ClO₄ 

Relevant articles and documents

Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

COMPOSITION FOR PROTECTING KIDNEY CONTAINING CHALCONE DERIVATIVES

The present invention relates to a composition for protecting a kidney or a composition for alleviating kidney diseases which contains a chalcone derivative. When the compound according to the present invention is used, the kidney can be protected from nephrotoxicity due to drugs and the like. Therefore, by utilizing the present specification, it is possible to make a great contribution to fields of patient treatment and welfare.COPYRIGHT KIPO 2019

Design, synthesis and docking studies of flavokawain B type chalcones and their cytotoxic effects on MCF-7 and MDA-MB-231 cell lines

Flavokawain B (1) is a natural chalcone extracted from the roots of Piper methysticum, and has been proven to be a potential cytotoxic compound. Using the partial structure of flavokawain B (FKB), about 23 analogs have been synthesized. Among them, compounds 8, 13 and 23 were found in new FKB derivatives. All compounds were evaluated for their cytotoxic properties against two breast cancer cell lines, MCF-7 and MDA-MB-231, thus establishing the structure-activity relationship. The FKB derivatives 16 (IC50 = 6.50 ± 0.40 and 4.12 ± 0.20 μg/mL), 15 (IC50 = 5.50 ± 0.35 and 6.50 ± 1.40 μg/mL) and 13 (IC50 = 7.12 ± 0.80 and 4.04 ± 0.30 μg/mL) exhibited potential cytotoxic effects on the MCF-7 and MDA-MB-231 cell lines. However, the methoxy group substituted in position three and four in compound 2 (IC50 = 8.90 ± 0.60 and 6.80 ± 0.35 μg/mL) and 22 (IC50 = 8.80 ± 0.35 and 14.16 ± 1.10 μg/mL) exhibited good cytotoxicity. The lead compound FKB (1) showed potential cytotoxicity (IC50 = 7.70 ± 0.30 and 5.90 ± 0.30 μg/mL) against two proposed breast cancer cell lines. It is evident that the FKB skeleton is unique for anticancer agents, additionally, the presence of halogens (Cl and F) in position 2 and 3 also improved the cytotoxicity in FKB series. These findings could help to improve the future drug discovery process to treat breast cancer. A molecular dynamics study of active compounds revealed stable interactions within the active site of Janus kinase. The structures of all compounds were determined by 1H-NMR, EI-MS, IR and UV and X-ray crystallographic spectroscopy techniques.

Mechanisms of action and structure-activity relationships of cytotoxic flavokawain derivatives

22 Flavokawain derivatives (FKd) were obtained by one step syntheses in order to conduct a SAR study to understand the structural requirements for optimum and selective cytotoxicity. FKd and natural flavokawains A and B found into kava, a South Pacific traditional beverage, were evaluated against nine cancer and one healthy cell lines. The targeted cell cycle phases as well as the effects on the induction of apoptosis and cell cycle protein levels were investigated. Therapeutic improvements (more activity and selectivity) were achieved with FKd compared to natural flavokawains and notably with the 2′,3,4′,6′-tetramethoxychalcone (FKd 19). FKd induced a G1/S arrest on p53 wild-type cells and an M arrest on p53 mutant-type, via the up-regulation of p21 and cyclin B1 proteins, followed by apoptosis. Moreover, FKd exhibited a 24?h-effect on Akt/mTor normal cells versus a 48?h-effect on Akt/mTor up-regulated cells. The SAR study resulted in the conclusion that trimethoxy A-ring allowed the best compromise between cytotoxicity and selectivity, as well as the substitution of the meta position on the B-ring and the use of halogens substituents.

Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

A series of 2′-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition.

Synthesis of chalcone analogues with increased antileishmanial activity

Eighteen analogues of an active natural chalcone were synthesized using xanthoxyline and some derivatives, and these analogues were tested for selective activity against both promastigotes and intracellular amastigotes of Leishmania amazonensis in vitro. Three analogues (10, 12, and 19) containing nitro, fluorine or bromine groups, respectively, displayed increased selective activity against the parasites as compared with the natural chalcone. The nitrosylated chalcone 10 was also tested intralesionally in infected mice and was found to be as effective as Pentostan reference drug at a dose 100 times higher than that of the chalcone in controlling both the lesion growth and the parasite burden.