144309-50-2

Upstream product

• 120-57-0 piperonal 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 144309-63-7 (4S,5R)-4-Benzo[1,3]dioxol-5-yl-5-(4-methoxy-benzoyl)-1-p-tolyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 144309-71-7 (4S,5R)-4-Benzo[1,3]dioxol-5-yl-1-(4-chloro-phenyl)-5-(4-methoxy-benzoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 86380-74-7 5-Benzo[1,3]dioxol-5-yl-1-(4-bromo-phenyl)-4-(4-methoxy-benzoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 86380-77-0 1-[5-Benzo[1,3]dioxol-5-yl-1-(4-bromo-phenyl)-4-(4-methoxy-benzoyl)-4,5-dihydro-1H-pyrazol-3-yl]-ethanone 
• 115665-28-6 (4S,5R)-4-Benzo[1,3]dioxol-5-yl-1-(4-bromo-phenyl)-5-(4-methoxy-benzoyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 
• 162256-48-6 2-(1,3-benzodioxol-5-yl)-1-(4-methoxyphenyl)-4-oxobutyronitrile 
• 162256-49-7 2-benzo<1,3>dioxol-5-yl-4-(4-methoxyphenyl)-4-oxobutyric acid methyl ester 
• 162256-50-0 3-Benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 
• 198271-01-1 3-Benzo[1,3]dioxol-5-yl-4-[3-(2-dimethylamino-ethoxy)-benzyl]-5-hydroxy-5-(4-methoxy-phenyl)-5H-furan-2-one 

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

Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology

Chalcones are bioactive compounds obtained from either natural sources or synthetic procedures and widely used due to their several biological properties. The most common experimental methodology in obtaining these compounds is Claisen–Schmidt reaction, which is a particular type of aldolic condensation. In this work, we have synthesized 23 chalcones and by density functional theory (DFT) calculation, we have studied the difference in reactivity of the several benzaldehydes and their effects on the yield of this reaction. From molecular orbital descriptors were obtained two quantitative structure–reactivity relationship (QSRR) models based on Hansch’s analysis. The results of this study showed that, for the most benzaldehydes (15 of 23 compounds), their reactivity was correlated with LUMO energy and global Electrophilicity Index (ω) values, which are determined in the first step of Claisen–Schmidt condensation mechanism (nucleophilic addition). Likewise, for the smallest group of benzaldehydes, their reactivity was related to their HOMO and ΔL???H (LUMO???HOMO) energies, which were determined in the second step of the mechanism (trans-elimination). This is the first report of a QSRR model analyzing the yield of chalcone synthesis based on DFT methodology.

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.

Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi

The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structureactivity relationship.

Synthesis and cdc25B inhibitory activity evaluation of chalcones

A library of sixty-five chalcones was prepared for screening against the protein phosphatase, cdc25B. From this library, thirteen compounds were found having good inhibitory activity. Two compounds have excellent activity and can be used for the design of

A novel and efficient direct aldol condensation from ketones and aromatic aldehydes catalyzed by proline-TEA through a new pathway

A novel and efficient direct aldol condensation from various ketones and a wide range of aldehydes was catalyzed by l-proline-TEA (triethylamine) in MeOH at room temperature, affording the corresponding (E)-α,β-unsaturated ketones in excellent yields. By

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

Synthesis and biological evaluation of aromatic enones related to curcumin

Curcumin, a natural product isolated from the spice turmeric, has been shown to exhibit a wide range of pharmacological activities including certain anti-cancer properties. It has been specifically shown to be an effective inhibitor of angiogenesis both in vitro and in vivo. Using curcumin as a lead compound for anti-angiogenic analog design, a series of structurally related compounds utilizing a substituted chalcone backbone have been synthesized and tested via an established SVR cell proliferation assay. The results have yielded a wide range of compounds that equal or exceed curcumin's ability to inhibit endothelial cell growth in vitro. Due to both their commercial availability and their fairly straightforward synthetic preparation, these low molecular weight compounds are attractive leads for developing future angiogenic inhibitors.

Butenolide endothelin antagonists with improved aqueous solubility

Continued development around our ET(A)-selective endothelin (ET) antagonist 1 (CI-1020) has led to the synthesis of analogues with improved aqueous solubility profiles. Poor solubility characteristics displayed by 1 required a complex buffered formulation