1774-66-9

Usage

Synthesis Reference(s)

Synthetic Communications, 23, p. 271, 1993 DOI: 10.1080/00397919308009778

InChI:InChI=1/C15H11BrO/c16-14-9-6-12(7-10-14)8-11-15(17)13-4-2-1-3-5-13/h1-11H/b11-8+

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 98-86-2 acetophenone 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 27895-60-9 2-(4-bromo-benzylidenamino)-ethanol 
• 10388-32-6 1-phenyl-3-(4-bromophenyl)-2,3-dibromo-1-propanone 
• 873-75-6 4-bromobenzenemethanol 
• 99-90-1 para-bromoacetophenone 
• 100-52-7 benzaldehyde 
• 98-85-1 1-Phenylethanol 
• 98-80-6 phenylboronic acid 
• 70-11-1 α-bromoacetophenone 
• 109-77-3 malononitrile 
• 536-74-3 phenylacetylene 
• 86668-30-6 1-Bromo-4-((E)-3-phenyl-propenyl)-benzene 

Downstream Products

• 20822-00-8 5-(4-bromophenyl)-3-phenyl-4,5-dihydroisoxazole 
• 10388-32-6 1-phenyl-3-(4-bromophenyl)-2,3-dibromo-1-propanone 
• 113854-26-5 4-(4-Bromo-phenyl)-3-methyl-1,6-diphenyl-4,5-dihydro-1H-pyrazolo[3,4-b]pyridine 
• 97481-49-7 6-Amino-5-[(E)-3-(4-bromo-phenyl)-1-phenyl-prop-2-en-(E)-ylideneamino]-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 86516-96-3 8-(4-Bromo-phenyl)-1,3-dimethyl-6-phenyl-7,8-dihydro-1H-pyrimido[4,5-b][1,4]oxazepine-2,4-dione 
• 111336-82-4 7-(4-Bromo-phenyl)-3-methyl-1,5-diphenyl-1,6,7,8-tetrahydro-pyrazolo[3,4-b][1,4]diazepine 
• 96570-11-5 6-Benzoyl-5-(4-bromo-phenyl)-3-methoxy-cyclohex-2-enone 
• 111607-55-7 4-{N'-[(E)-3-(4-Bromo-phenyl)-1-phenyl-prop-2-en-(E)-ylidene]-hydrazino}-benzenesulfonamide 
• 139951-53-4 [(1R,2R,3R)-2-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-cyclopropyl]-phenyl-methanone 
• 29394-23-8 [(1R,2R,3R)-2-(4-Bromo-phenyl)-3-phenyl-cyclopropyl]-phenyl-methanone 
• 117953-00-1 [(1S,2R,3R)-2-(4-Bromo-phenyl)-3-trimethylsilanylethynyl-cyclopropyl]-phenyl-methanone 
• 79422-39-2 (E)-3-[4'-((E)-3-Oxo-3-phenyl-propenyl)-biphenyl-4-yl]-1-phenyl-propenone 
• 95734-16-0 4-(4-Bromo-phenyl)-3,6-diphenyl-1H-pyridin-2-one 
• 95734-07-9 4-(4-Bromo-phenyl)-3,6-diphenyl-3,4-dihydro-1H-pyridin-2-one 

Relevant academic research and scientific papers

Water compatible multicomponent cascade suzuki/heck-aldol, suzuki-aldol-suzuki, and aldol-suzuki-aldol reactions: An ecofriendly paradigm for multiple carbon-carbon bond formation in one pot

Aryls in hot water: A versatile strategy has been devised for the synthesis of biologically active biaryl(hetero)chalcones from readily available precursors (see scheme). The method is step, pot, and carbon economic, ligand-free, devoid of toxic reagents/solvents, and has a wide substrate scope. Copyright

Selective C-C bonds formation, N-alkylation and benzo[d]imidazoles synthesis by a recyclable zinc composite

Earth abundant metals are much less expensive, promising, valuable metals and could be served as catalysts for the borrowing hydrogen reaction, dehydrogenation and heterocycles synthesis, instead of noble metals. The uniformly dispersed zinc composites were designed, synthesized and carefully characterized by means of XPS, EDS, TEM and XRD. The resulting zinc composite showed good catalytic activity for the N-alkylation of amines with amines, ketones with alcohols in water under base-free conditions, while unsaturated carbonyl compounds could also be synthesized by tuning the reaction conditions. Importantly, it was the first time to realize the synthesis of 2-aryl-1H-benzo[d]imidazole derivatives by using this zinc composite under green conditions. Meanwhile, this zinc catalyst could be easily recovered and reused for at least five times.

Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy

In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.

New nicotinic acid-based 3,5-diphenylpyrazoles: design, synthesis and antihyperlipidemic activity with potential NPC1L1 inhibitory activity

Nicotinic acid hydrazide was incorporated into new 4,5-dihydro-5-hydroxy-3,5-diphenylpyrazol-1-yl derivatives. Compounds 6a–h were synthesized, and their antihyperlipidemic activity was evaluated in high cholesterol diet-fed rat model. Compounds 6e, 6f were found to decrease the levels of serum total cholesterol by 14–19% compared to control group. Total triglycerides were also reduced by 24–28% and LDL cholesterol by 16%. As expected from parent niacin, compounds 6e and 6f caused an elevation of HDL cholesterol by 33–41%. Docking study supported the ability of designed compounds to block NPC1L1 active site in a manner similar to that observed with ezetimibe.

Naphthyl-substituted phenylpyrimidines compound and organic electroluminescent devices using the same

A naphthyl-substituted phenylpyrimidines compound having a structure represented by formula (I) (wherein Ar, R, m and n are as defined in the description) and an organic electroluminescent device using the same.

Microwave-assisted synthesis of novel pyrazole derivatives and their biological evaluation as anti-bacterial agents

Aims and Objectives: Microwave-assisted condensation of acetophenone 1 and aromatic aldehydes 2 gave chalcone analogs 3, which were cyclized to pyrazole derivatives 6a-f via the reaction with hydrazine hydrate and oxalic acid in the presence of the catalytic amount of acetic acid in ethanol. Materials and Methods: The structural features of the synthesized compounds were characterized by melting point, FT-IR,1H,13C NMR and elemental analysis. Results: The antibacterial activities of the synthesized pyrazoles were evaluated against three gram-positive bacteria, such as Enterococcus durans, Staphylococcus aureus, Bacillus subtilis and two gram-negative bacteria such as Escherichia coli and Salmonella typhimurium. Conclusion: All the synthesized pyrazoles showed relatively high antibacterial activity against S. aureus strain, and none of them demonstrated antibacterial activity against E. coli.

Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones

The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.

Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights

We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).

Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C-C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

Multi-target weapons: diaryl-pyrazoline thiazolidinediones simultaneously targeting VEGFR-2 and HDAC cancer hallmarks

In anticancer drug discovery, multi-targeting compounds have been beneficial due to their advantages over single-targeting compounds. For instance, VEGFR-2 has a crucial role in angiogenesis and cancer management, whereas HDACs are well-known regulators o