3754-50-5

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 3754-53-8 3'-Bromoflavone 
• 133359-66-7 2,3-dihydro-2-(3-bromophenyl)chromen-4-one 

Relevant academic research and scientific papers

Synthesis of chiral flavanones from tricarbonyl (η6- Arylbenzaldehyde)chromium(0)

A synthesis of chiral flavanones via the condensation of tricarbonyl(η6-arylbenzaldehyde)chromium(0) and o-hydroxyacetophenone in a shorter time at room temperature have been developed. The tricarbonylchromium(0) group was removed by virtue of light and the enantioenriched flavanones was formed with highly enantioselectivity (> 95 % ee).

Stereoselective reduction of flavanones by marine-derived fungi

Biotransformation is an alternative with great potential to modify the structures of natural and synthetic flavonoids. Therefore, the bioreduction of synthetic halogenated flavanones employing marine-derived fungi was described, aiming the synthesis of flavan-4-ols 3a-g with high enantiomeric excesses (ee) of both cis- and trans-diastereoisomers (up to >99% ee). Ten strains were screened for reduction of flavanone 2a in liquid medium and in phosphate buffer solution. The most selective strains Cladosporium sp. CBMAI 1237 and Acremonium sp. CBMAI1676 were employed for reduction of flavanones 2a-g. The fungus Cladosporium sp. CBMAI 1237 presented yields of 72–87% with 0–64% ee cis and 0–30% ee trans with diastereoisomeric ratio (dr) from 52:48 to 64:36 (cis:trans). Whereas Acremonium sp. CBMAI 1676 resulted in 31% yield with 77–99% ee of the cis and 95–99% ee of the trans-diastereoisomers 3a-g with a dr from 54:46 to 96:4 (cis:trans). To our knowledge, this is the first report of the brominated flavon-4-ols 3e and 3f. The use of fungi, with emphasis for these marine-derived strains, is an interesting approach for enantioselective reduction of halogenated flavanones. Therefore, this strategy can be explored to obtain enantioenriched compounds with biological activities.

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

Mycobactin Analogues with Excellent Pharmacokinetic Profile Demonstrate Potent Antitubercular Specific Activity and Exceptional Efflux Pump Inhibition

In this study, we have designed and synthesized pyrazoline analogues that partially mimic the structure of mycobactin, to address the requirement of novel therapeutics to tackle the emerging global challenge of antimicrobial resistance (AMR). Our investigation resulted in the identification of novel lead compounds 44 and 49 as potential mycobactin biosynthesis inhibitors against mycobacteria. Moreover, candidates efficiently eradicated intracellularly surviving mycobacteria. Thermofluorimetric analysis and molecular dynamics simulations suggested that compounds 44 and 49 bind to salicyl-AMP ligase (MbtA), a key enzyme in the mycobactin biosynthetic pathway. To the best of our knowledge, these are the first rationally designed mycobactin inhibitors to demonstrate an excellent in vivo pharmacokinetic profile. In addition, these compounds also exhibited more potent whole-cell efflux pump inhibition than known efflux pump inhibitors verapamil and chlorpromazine. Results from this study pave the way for the development of 3-(2-hydroxyphenyl)-5-(aryl)-pyrazolines as a new weapon against superbug-associated AMR challenges.

Chiral Hydroxytetraphenylene-Boron Complex Catalyzed Asymmetric Diels-Alder Cycloaddition of 2′-Hydroxychalcones

(S)-2,15-Cl2-DHTP-boron complex catalyst for the asymmetric Diels-Alder cycloaddition of 2′-hydroxychalcones and dienes was developed and tested. The resulting cyclohexenes with three chiral centers were obtained in high yields (up to 98%) with excellent stereoselectivities (up to >20:1 endo/exo, >99% ee). This catalytic system features high efficiency, broad substrate scopes, and mild reaction conditions. In addition, a DFT study was performed to explain the stereochemical course of the asymmetric induction.

Design, synthesis and biological evaluation of novel dihydropyrimidine-2-thione derivatives as potent antimicrobial agents: Experimental and molecular docking approach

Introduction: Dihydropyrimidine scaffold represent an important class of pharmacologically active nitrogen containing heterocyclic compounds. A wide range of molecules with dihydropyrimidine moieties have important role in medicinal chemistry on account of their potential biological activities. Methodology: A series of 3,4-dihydropyrimidine-2(1H)-thione derivatives have been designed and synthesized in a concise way through condensation of variously substituted chalcones with thiourea in alkaline alcoholic solutions. In order to investigate their biological significance, these compounds were tested for their in vitro antimicrobial potential against various bacterial and fungal strains. Moreover, the experimental results were supported by molecular docking studies. Results and Discussion: The newly synthesized compounds were characterized by the usual spectroscopic techniques In case of antibacterial activity, the compounds 5 (40.3±0.44 mm), 12 and 13 (almost 35 mm) exhibited highest zone of inhibitions against Methicillin-resistant Staphylococcus auerus (MRSA) bacterial strain as compared to the standard drug Cefixime. These compounds displayed moderate to good activities against all attempted fungal strains. In docking analysis, it has been observed that compounds 8 (-6.4017 Kcal/mol) and 10 (-6.1319 Kcal/mol) revealed significant binding affinity against penicillin binding protein (PDB ID: 1VQQ), while compounds 1 (-143.23 Kcal/mol) and 2 (-146.99 Kcal/mol) showed best activity for shikimate dehydrogenase (PDB ID: 3DON). Conclusion: In conclusion, we have designed, synthesized and characterized an interesting series of biologically active dihydropyrimidine derivatives. Remarkably, most of the synthesized compounds were found more active against all tested bacterial strains in comparison to the standard drug Cefixime as manifested by experimental as well as theoretical results.

Enantioselective biomimetic cyclization of 2′-hydroxychalcones to flavanones

A new family of organocatalysts based on aminoquinoline and pyrrolidine have been developed and shown to catalyze the direct and highly enantioselective cyclization of 2′-hydroxychalcones in imitation of the natural process of chalcone cyclization. The straightforward synthetic process occurs under mild reaction conditions, tolerates moisture and air, and gives an enantiomeric excess up to 99%. This approach provides a facile and efficient access to chiral flavanones.

Pharmacophore model of the quercetin binding site of the SIRT6 protein

SIRT6 is a histone deacetylase that has been proposed as a potential therapeutic target for metabolic disorders and the prevention of age-associated diseases. We have previously reported on the identification of quercetin and vitexin as SIRT6 inhibitors,

Cyclization of 2'-hydroxychalcones to flavones using ammonium iodide as an iodine source - An eco-friendly approach

Ammonium iodide on exposure to air decomposes to ammonia and iodine. The in situ generated iodine was used for the cyclization of 2'-hydroxychalcones to the corresponding flavones under solvent-free conditions in good to excellent yields. This method could serve as an attractive alternative to the existing methods for synthesis of flavones and the use of toxic molecular iodine is avoided. Copyright

Structure-Activity relationships of targeted RuII(η 6- P -Cymene) anticancer complexes with flavonol-Derived ligands

RuII(arene) complexes have been shown to be promising anticancer agents, capable of overcoming major drawbacks of currently used chemotherapeutics. We have synthesized RuII(η6-arene) compounds carrying bioactive flavonol ligands with the aim to obtain multitargeted anticancer agents. To validate this concept, studies on the mode of action of the complexes were conducted which indicated that they form covalent bonds to DNA, have only minor impact on the cell cycle, but inhibit CDK2 and topoisomerase IIα in vitro. The cytotoxic activity was determined in human cancer cell lines, resulting in very low IC50 values as compared to other RuII(arene) complexes and showing a structure-activity relationship dependent on the substitution pattern of the flavonol ligand. Furthermore, the inhibition of cell growth correlates well with the topoisomerase inhibitory activity. Compared to the flavonol ligands, the RuII(η6-p-cymene) complexes are more potent antiproliferative agents, which can be explained by potential multitargeted properties.