58344-62-0

Upstream product

• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1885-35-4 3,4,5-trimethoxybenzonitrile 
• 3086-62-2 3,4,5-trimethoxybenzamide 
• 120-57-0 piperonal 
• 1136-86-3 methyl (3,4,5-trimethoxyphenyl) ketone 

Downstream Products

• 851729-14-1 (3-benzo[1,3]dioxol-5-yl-oxiranyl)-(3,4,5-trimethoxy-phenyl)-methanone 
• 188395-18-8 2-Benzo[1,3]dioxol-5-yl-4-oxo-4-(3,4,5-trimethoxy-phenyl)-butyric acid methyl ester 

Relevant academic research and scientific papers

Synthesis and evaluation of chalcone derivatives as novel sunscreen agent

Ultraviolet (UV) irradiation is a serious problem for skin health thus the interest in the research to develop sunscreen agent has been increasing. Chalcone is a promising compound to be developed as its chromophore absorbs in the UV region. Therefore, in

An environment-friendly synthesis of piperonal chalcones and their cytotoxic and antioxidant evaluation

Background: Grindstone technique has been widely used as an efficient, consistent, more environmentally benign, solvent-free protocol for the preparation of many compounds with higher atom economy. Methods: A series of fourteen piperonal chalcone compound

The synthesis of chalcones as anticancer prodrugs and their bioactivation in CYP1 expressing breast cancer cells

Background: Although the expression levels of many P450s differ between tumour and corresponding normal tissue, CYP1B1 is one of the few CYP subfamilies which is significantly and consistently overexpressed in tumours. CYP1B1 has been shown to be active within tumours and is capable of metabolising a structurally diverse range of anticancer drugs. Because of this, and its role in the activation of procarcinogens, CYP1B1 is seen as an important target for anticancer drug development. Objective: To synthesise a series of chalcone derivatives based on the chemopreventative agent DMU-135 and investigate their antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1. Method: A series of chalcones were synthesised in yields of 43-94% using the Claisen-Schmidt condensation reaction. These were screened using a MTT assay against a panel of breast cancer cell lines which have been characterised for CYP1 expression. Result: A number of derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing significantly lower toxicity towards a non-tumour breast cell line with no CYP expression. Experiments using the CYP1 inhibitors acacetin and α-naphthoflavone provided supporting evidence for the involvement of CYP1 enzymes in the bioactivation of these compounds. Conclusion: Chalcones show promise as anticancer agents with evidence suggesting that CYP1 activation of these compounds may be involved.

NBS-mediated cyclization of trans-cinnamic alcohols

An efficient and straightforward three-step synthetic route toward 2,4-disubstituted-3-bromooxetanes 5 with the trans-trans contiguous stereogenic centers is developed from functionalized chalcones 3 via NaBH 4-mediated reduction of chalcones 3

Combretastatin-like chalcones as inhibitors of microtubule polymerization. Part 1: Synthesis and biological evaluation of antivascular activity

The α-methyl chalcone SD400 is a potent inhibitor of tubulin assembly and possesses potent anticancer activity. Various chalcone analogues were synthesized and evaluated for their cell growth inhibitory properties against the K562 human chronic myelogenous leukemia cell line (SD400, IC50 0.21 nM; combretastatin A4 CA4, IC50 2.0 nM). Cell cycle analysis by flow cytometry indicated that these agents are antimitotic (SD400, 83% of the cells are in G2/M phase; CA4 90%). They inhibit tubulin assembly at low concentration (SD400, IC50 0.46 μM; CA4, 0.10 μM) and compete with [3H]colchicine for binding to tubulin (8% [3H]colchicine remained bound to tubulin after competition with SD400 or CA4). Upon treatment with SD400, remarkable cell shape changes were elicited in HUVEC cells, consistent with vasculature damaging activity.

Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA

In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were ob

Study on the substituents' effects of a series of synthetic chalcones against the yeast Candida albicans

A large series of chalcones were synthesized and studied for activity against Candida albicans. The SAR analysis showed that the antifungal activity was highly dependent on the substitution pattern of the aryl rings and correlated to a large extent with the ability of compounds to interact with sulfhydryl groups. The most active were the hydroxylated chalcones as their activity related to the location of the phenolic group in the aryl ring B as follows: o-OH > p-OH ～ 3,4-di-OH > m-OH. These and other correlations obtained strongly contribute to the knowledge for design of anticandidal chalcones.

The synthesis of indanones related to combretastatin A-4 via microwave-assisted Nazarov cyclization of chalcones

A fast and efficient microwave-assisted synthesis of combretastatin A-4-like indanones has been developed. Microwave irradiation provides a useful alternative to traditional heating techniques to promote the TFA-catalyzed Nazarov cyclization of chalcones.

Synthesis and biological evaluation of chalcones and their derived pyrazoles as potential cytotoxic agents

A series of substituted chalcones and their corresponding pyrazoles were synthesized and evaluated for in vitro cytotoxic activity against a panel of human cancer cell lines. Out of 93 compounds screened, 8 compounds, 1s, 3i,j,n, 4i,j,n and 4s, showed marked activity. Compounds 4j,n and 4s were found to be the most promising in this study. SAR is also discussed.

Potent antimitotic and cell growth inhibitory properties of substituted chalcones

A series of substituted chalcones was synthesised and screened for cytotoxic activity against the K562 human leukaemia cell line. (E)-3-(3'- Hydroxy-4'-methoxyphenyl)-2-methyl-1-(3',4',5'-trimethoxyphenyl)-prop-2-en- 1-one [IC50 (K562) 0.21 nM] was found to be the most active. A relationship between the conformation and cytotoxicity of the chalcones is discussed.