51116-22-4

Basic information

• Product Name: 3-(1,3-benzodioxol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one
• Synonyms: 3-Benzo[1,3]dioxol-5-yl-1-(3,4-dimethoxy-phenyl)-propenone
• CAS NO: 51116-22-4
• Molecular Formula: C₁₈H₁₆O₅
• Molecular Weight: 312.3166
• Mol File: 51116-22-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 487.3°C at 760 mmHg
• Flash Point: 216.6°C
• Density: 1.254g/cm³
• Vapor Pressure: 1.2E-09mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 3-(1,3-benzodioxol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1,3-benzodioxol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one(51116-22-4)
• EPA Substance Registry System: 3-(1,3-benzodioxol-5-yl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one(51116-22-4)

Safety Data

• Hazardous Substances Data: 51116-22-4(Hazardous Substances Data)

Upstream product

• 120-57-0 piperonal 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 1198088-67-3 6-(3,4-dimethoxyphenyl)-4-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one 
• 51116-23-5 2-benzo[1,3]dioxol-5-yl-4-(3,4-dimethoxy-phenyl)-4-oxo-butyronitrile 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 169804-26-6 2-Benzo[1,3]dioxol-5-yl-4-(3,4-dimethoxy-phenyl)-4-oxo-butyric acid methyl ester 
• 142608-93-3 3-(benzo[d][1,3]dioxol-5-yl)-1-(2,4-dimethoxyphenyl)propan-1-one 
• 76934-56-0 (2-Benzo[1,3]dioxol-5-yl-cyclopropyl)-(3,4-dimethoxy-phenyl)-methanone 

Relevant articles and documents

Synthesis of some novel pyrazoline-thiazole hybrids and their antimicrobial activities

A series of novel thiazolyl pyrazolines 7a-h, 9a-f, and 11a-f have been synthesized by the reaction of thioamide derivatives 5a,b with 1-aryl-2-bromoethanones 6a-d, chloroacetones 8a-c, and hydrazonoyl chlorides 10a-c. Additionally, pyrazoles 15a-c and 20 were prepared starting from enaminone 13. These newly synthesized compounds were screened for their in vitro antibacterial activity against four bacterial species. Compound 11b showed a moderate activity against Klebsiella pneumoniae. Compounds 7c and 11c revealed a moderate activity against Pseudomonas aeruginosa. In addition, the antifungal activity of the newly synthesized compounds was determined against five fungal strains. Compounds 7e, 7g, and 11e showed a good activity against Aspergillus flavus and Penicillium expansum.

Synthesis and biological evaluation of new pyrazolebenzene-sulphonamides as potential anticancer agents and hCA I and II inhibitors

Cancer is a disease characterized by the continuous growth of cells without adherence to the rules that healthy normal cells obey. Carbonic anhydrase I and II (CA I and CA II) inhibitors are used for the treatment of some diseases. The available drugs in the market have limitations or side effects, which bring about the need to develop new drug candidate compound(s) to overcome the problems at issue. In this study, new pyrazole-sulphonamide hybrid compounds 4-[5-(1,3-benzodioxol-5-yl)-3-aryl-4,5-dihydro-1Hpyrazol- 1-yl]benzenesulphonamides (4a - 4j) were designed to discover new drug candidate compounds. The compounds 4a - 4j were synthesized and their chemical structures were confirmed using spectral techniques. The hypothesis tested was whether an introduction of methoxy and polymethoxy group(s) lead to an increased potency selectivity expression (PSE) value of the compound, which reflects cytotoxicity and selectivity of the compounds. The cytotoxicity of the compounds towards tumor cell lines were in the range of 6.7 - 400 μM. The compounds 4i (PSE2 = 461.5) and 4g (PSE1 = 193.2) had the highest PSE values in cytotoxicity assays. Ki values of the compounds were in the range of 59.8 ± 3.0 - 12.7 ± 1.7 nM towards hCA I and in the range of 24.1 ± 7.1 - 6.9 ± 1.5 nM towards hCA II. While the compounds 4b, 4f, 4g, and 4i showed promising cytotoxic effects, the compounds 4c and 4g had the inhibitory potency towards hCA I and hCA II, respectively. These compounds can be considered as lead compounds for further research.

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.