58344-61-9

Basic information

• Product Name: (E)-1-(2,5-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2- en-1-one
• Synonyms: (E)-1-(2,5-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2- en-1-one
• CAS NO: 58344-61-9
• Molecular Weight: 312.322
• Mol File: 58344-61-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-1-(2,5-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2- en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-(2,5-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2- en-1-one(58344-61-9)
• EPA Substance Registry System: (E)-1-(2,5-dimethoxyphenyl)-3-(3,4-methylenedioxyphenyl)-prop-2- en-1-one(58344-61-9)

Safety Data

• Hazardous Substances Data: 58344-61-9(Hazardous Substances Data)

Upstream product

• 120-57-0 piperonal 
• 1201-38-3 2',5'-dimethoxyacetophenone 

Relevant articles and documents

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.

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