36716-01-5

Usage

Uses

Used in Research and Development:
(E)-3-benzo[1,3]dioxol-5-yl-1-(4-bromophenyl)prop-2-en-1-one is used as a research reagent for the synthesis of various organic compounds. Its unique structural properties make it a valuable tool in the development of new chemical entities.
Used in Pharmaceutical and Medical Research:
(E)-3-benzo[1,3]dioxol-5-yl-1-(4-bromophenyl)prop-2-en-1-one is used as a compound in pharmaceutical and medical research. Its potential applications in these fields are currently under investigation, and its structural properties may contribute to the development of new drugs or therapies.

InChI:InChI=1/C16H11BrO3/c17-13-5-3-12(4-6-13)14(18)7-1-11-2-8-15-16(9-11)20-10-19-15/h1-9H,10H2/b7-1+

Upstream product

• 120-57-0 piperonal 
• 99-90-1 para-bromoacetophenone 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 29668-44-8 2,3-dihydro-benzo[1,4]dioxin-6-carbaldehyde 
• 64376-20-1 3-(2,3-dihydro-benzo[1,4]dioxin-6-yl)-1-(4-methoxy-phenyl)-propenone 
• 1417658-61-7 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 

Downstream Products

• 750604-86-5 1-(5-(benzo[d][1,3]dioxol-6-yl)-3-(4-bromophenyl)-4,5-dihydropyrazol-1-yl)ethanone 
• 1417658-40-2 C₂₆H₂₀BrN₃O₃S 
• 1417658-41-3 C₂₅H₁₇Br₂N₃O₂S 
• 1417658-56-0 5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide 
• 62953-33-7 4-benzo[1,3]dioxol-5-yl-2-(4-bromo-phenyl)-6-phenanthren-3-yl-pyridine 
• 54347-72-7 4-benzo[1,3]dioxol-5-yl-2-(4-bromo-phenyl)-6-phenyl-pyridine 
• 74918-95-9 4-Benzo[1,3]dioxol-5-yl-2-(4-bromo-phenyl)-6-(4-chloro-phenyl)-pyridine 
• 54044-44-9 4-benzo[1,3]dioxol-5-yl-2,6-bis-(4-bromo-phenyl)-pyridine 

Relevant academic research and scientific papers

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

Organocatalytic asymmetric vinylogous 1,4-addition of α,α-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity

The organocatalysed asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of α,α-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity.

Design, synthesis and biological evaluation of novel pyrazoline-containing derivatives as potential tubulin assembling inhibitors

Abstract A series of novel pyrazoline-containing derivatives (15-47) has been designed, synthesized and evaluated for their biological activities. Among them, compound 18 displayed the most potent antiproliferative activity against A549, MCF-7 and HepG-2 cells line (IC50 Combining double low line 0.07 μM, 0.05 μM, 0.03 μM, respectively) and the tubulin polymerization inhibitory activity (IC50 Combining double low line 1.88 μM), being comparable to CA-4. Furthermore, we also tested that compound 18 was a potent inducer of apoptosis in HepG-2 cells and it had cellular effects typical for microtubule interacting agents, causing accumulation of cells in the G2/M phase of the cell cycle. These studies, along with molecular docking, provided a new molecular scaffold for the further development of antitumor agents that target tubulin.

Antimycobacterial and anti-inflammatory activities of substituted chalcones focusing on an anti-tuberculosis dual treatment approach

Tuberculosis (TB) remains a serious public health problem aggravated by the emergence of M. tuberculosis (Mtb) strains resistant to multiple drugs (MDR). Delay in TB treatment, common in the MDR-TB cases, can lead to deleterious life-threatening inflammation in susceptible hyper-reactive individuals, encouraging the discovery of new anti-Mtb drugs and the use of adjunctive therapy based on anti-inflammatory interventions. In this study, a series of forty synthetic chalcones was evaluated in vitro for their anti-inflammatory and antimycobacterial properties and in silico for pharmacokinetic parameters. Seven compounds strongly inhibited NO and PGE2 production by LPS-stimulated macrophages through the specific inhibition of iNOS and COX-2 expression, respectively, with compounds 4 and 5 standing out in this respect. Four of the seven most active compounds were able to inhibit production of TNF-α and IL-1β. Chalcones that were not toxic to cultured macrophages were tested for antimycobacterial activity. Eight compounds were able to inhibit growth of the M. bovis BCG and Mtb H37Rv strains in bacterial cultures and in infected macrophages. Four of them, including compounds 4 and 5, were active against a hypervirulent clinical Mtb isolate as well. In silico analysis of ADMET properties showed that the evaluated chalcones displayed satisfactory pharmacokinetic parameters. In conclusion, the obtained data demonstrate that at least two of the studied chalcones, compounds 4 and 5, are promising antimycobacterial and anti-inflammatory agents, especially focusing on an anti-tuberculosis dual treatment approach.

Synthesis of Some 1,4,6-Trisubstituted-2-oxo-1,2-dihydropyridine-3-carbonitriles and Their Biological Evaluation as Cytotoxic and Antimicrobial Agents

A series of novel 1,4,6-trisubstituted-2-oxo-1,2-dihydropyridine-3-carbonitriles supported with some functionalities reported to contribute to significant chemotherapeutic potential were synthesized and evaluated for their antimicrobial and/or cytotoxic activities. Thirteen compounds exhibited cytotoxic potential against a panel of three human tumor cell lines. Compounds 15, 23, and 24 proved to be the most active agents with a broad spectrum of cytotoxic activity. Analog 24 was considered as the most active cytotoxic agent, being 2.5 times more active than doxorubicin against the colon HT29 carcinoma cell line. Seventeen compounds were able to exert a variable antimicrobial profile, among which analogs 15, 20, 21, 23, and 24 were prominently active. The highest antimicrobial potential was displayed by analog 24, being equipotent to ampicillin against Staphylococcus aureus and Escherichia coli, together with a considerable antifungal activity comparable with clotrimazole. Collectively, compounds 15, 23, and 24 could be considered as possible dual antimicrobial-anticancer candidates. Novel substituted 2-oxo-1,2-dihydropyridine-3-carbonitriles (A, B) and some derived 1,2,4-triazolo[4,3-a]-pyridinones (C) were synthesized and evaluated for their antimicrobial and cytotoxic activities. Three analogs are possible dual antimicrobial-anticancer candidates.

4,5-Dihydropyrazole derivatives containing oxygen-bearing heterocycles as potential telomerase inhibitors with anticancer activity

Telomere and telomerase were closely related to the occurrence and development of some cancers. After the key active site of telomerase was identified, to enhance the ability of dihydropyrazole derivatives to inhibit telomerase, we designed a series of novel 4,5-dihydropyrazole derivatives containing heterocyclic oxygen moiety based on previous studies. The telomerase inhibition assay showed that compound 10a displayed the most potent inhibitory activity with an IC50 value of 0.6 μM for telomerase. The antiproliferative assay showed that 10a exhibited high activity against human gastric cancer cell SGC-7901 with an IC50 value of 10.95 ± 0.60 μM. Flow cytometric analysis and western blot results showed that 10a induced both apoptosis and autophagy. A docking simulation showed that 10a could bind well to the active site of telomerase and act as a telomerase inhibitor. The 3D-QSAR model was also built to provide a more pharmacological understanding that could be used to design new agents with more potent telomerase inhibitory activity.

Synthesis, molecular docking and evaluation of thiazolyl-pyrazoline derivatives containing benzodioxole as potential anticancer agents

A series of novel thiazolyl-pyrazoline derivatives containing benzodioxole (C1-C20) have been designed and synthesized. Among of the synthesized compounds, 2-(5-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-1-yl)- 4-(4-bromophenyl)thiazole (C6) displayed the most potent inhibitory activity for HER-2 (IC50 = 0.18 μM for HER-2). Antiproliferative assay results indicated that compound C6 owned high antiproliferative activity against MCF-7 and B16-F10 in vitro, with IC50 value of 0.09 and 0.12 μM, respectively, being comparable with the positive control Erlotinib. Docking simulation was further performed to determine the probable binding model. Based on the preliminary results, compound C6 with potent inhibitory activity in tumor growth would be a potential anticancer agent.

Synthesis, biological evaluation, 3D-QSAR studies of novel aryl-2H-pyrazole derivatives as telomerase inhibitors

A series of novel aryl-2H-pyrazole derivatives bearing 1,4-benzodioxan or 1,3-benzodioxole moiety were designed as potential telomerase inhibitors to enhance the ability of aryl-2H-pyrazole derivatives to inhibit telomerase, a target of anticancer. The telomerase inhibition tests showed that compound 16A displayed the most potent inhibitory activity with IC50 value of 0.9 μM for telomerase. The antiproliferative tests showed that compound 16A exhibited high activity against human gastric cancer cell SGC-7901 and human melanoma cell B16-F10 with IC50 values of 18.07 and 5.34 μM, respectively. Docking simulation showed that compound 16A could bind well with the telomerase active site and act as telomerase inhibitor. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent telomerase inhibitory activity.

Green synthesis of novel chalcone and coumarin derivatives via Suzuki coupling reaction

Chalcones and coumarins are important naturally occurring plant constituents and display a wide range of pharmacological and biological activities. In an environmentally benign approach, synthesis of biphenyl chalcone and coumarin derivatives was successfully accomplished via Suzuki coupling by using PEG-400 as a solvent under microwave irradiation. Salient feature of this methodology includes: short reaction time, good to excellent yields, and prominent tolerance of different functional groups.

Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C6-C 3-C6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Springer Science+Business Media, LLC 2011.