86293-49-4

Upstream product

• 99-90-1 para-bromoacetophenone 
• 90-02-8 salicylaldehyde 
• 108-95-2 phenol 
• 89-95-2 2-methyl-benzyl alcohol 
• 99-73-0 para-bromophenacyl bromide 
• 1777-57-7 p-bromobenzoylmethylenetriphenylphosphorane 

Downstream Products

• 189393-94-0 2-[5-(4-Bromo-phenyl)-3,4-dihydro-2H-pyrazol-3-yl]-phenol 
• 1323141-72-5 diethyl 3-(2-(4-bromophenyl)-2-oxoethyl)benzofuran-2,2(3H)-dicarboxylate 
• 1256639-96-9 C₁₈H₁₅BrN₂O₂S 
• 1381807-36-8 2-(4-bromophenyl)-3-tosyl-4,4a-dihydro-3H-chromeno[3,4-c]pyridin-5(10bH)-one 
• 1602919-20-9 (2R,3S,4S)-1'-tert-butyl 2-ethyl 4-(2-(4-bromophenyl)-2-oxoethyl)-2'-oxospiro[chroman-3,3'-indoline]-1',2-dicarboxylate 

Relevant academic research and scientific papers

Synthesis and spectral studies of some novel 2,5,9,10-tetrahydro[7,8-g]benzo-8-arylpyrazolo[4,5-e][1,5-b]benzoxazon ine via phase transfer catalysis

Treatment of 1H-4,5-dihydro-3-aryl-5-(2-hydroxyaryl)pyrazole with o-dibromoxylene under liquid-liquid phase transfer catalytic conditions using tetra-n-butylammonium hydrogen sulphate or [18]-crown-6 as PT catalyst, benzene/chloroform as organic phase and 50% aqueous potassium hydroxide as second phase, afforded novel 2,5,9,10-tetrahydro[7,8-g]benzo-8-arylpyrazolo[4,5-e][1,5-b]benzoxazon ines.

Development of pyrazoline-based derivatives as aminopeptidase N inhibitors to overcome cancer invasion and metastasis

Aminopeptidase N is considered as a promising anti-tumor target due to its role in tumor invasion, metastasis and angiogenesis. In this report, a new series of pyrazoline-based derivatives were designed, synthesized and evaluated for biological activities

Novel isoniazid-spirooxindole derivatives: design, synthesis, biological evaluation, in silico ADMET prediction and computational studies

In the present scenario, the Synthesis of new and desired antimycobacterial agent has an eternal demand to resist Mycobacterium tuberculosis (MTB). The design and identification of new molecules for the treatment of tuberculosis is an important task in organic as well as medicinal chemistry research. In the present study, we have reported the combination of the desired compound using two versatile and significant moieties, isoniazid and spirooxindole derivatives. A series of novel isoniazid-spirooxindole hybrid molecules (6a-6ao) were designed, synthesized, and well-characterized by various spectroscopic methods. We have evaluated for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv (MTB) strain and MDR-TB. Among them, Compound 6ab was found to be the most effective compare to other compounds. ADMET-related descriptors were to be calculated of all the compounds to predict the pharmacokinetic properties for the selection of the effective and bioavailable compounds. In addition, molecular docking and molecular dynamics studies reveal that the binding modes of all the compounds in the active site of isoniazid-resistant enoyl-ACP(COA) reductase, which helped to establish a structural basis of inhibition of Mycobacterium tuberculosis.

Hydroxyl- and Halogen-containing Chalcones for the Inhibition of LPS-stimulated ROS Production in RAW 264.7 Macrophages: Design, Synthesis and Structure–Activity Relationship Study

Oxidative stress due to overproduction of reactive oxygen species (ROS) plays a major role in inflammation, cancer, and neurodegenerative disorders. In this study, 60 chalcone derivatives with fluorine (F), trifluoromethyl (CF3), trifluoromethoxy (OCF3), chlorine (Cl), and bromine (Br) in ring A and with or without hydroxy (OH) in ring B were designed, synthesized, and screened for inhibitory activity against lipopolysaccharide (LPS)-stimulated ROS production in RAW 264.7 macrophages. Structure–activity relationship study revealed the importance of a hydroxyl moiety in ring B for enhancing inhibitory activity of ROS production. Furthermore, a hydroxyl group at the ortho-position is more essential for inhibition of ROS production followed by meta- and para-positions. Among all, compound 27 that contains para-chlorine moiety in ring A and ortho-hydroxy in ring B displayed the strongest inhibitory activity (IC50 = 3.42 μM) against LPS-stimulated ROS production in RAW264.7 macrophages.

One-Pot Allylation-Intramolecular Vinylogous Michael Addition-Isomerization Cascade of o-Hydroxycinnamates and Congeners: Synthesis of Substituted Benzofuran Derivatives

A unique intramolecular vinylogous Michael addition leading to the synthesis of heterocycles has been disclosed. Base-promoted one-pot sequential O-allylation of o-hydroxy-cinnamates or -cinnamonitrile or -chalcones with γ-bromocrotonates followed by an intramolecular conjugate addition of vinylogous Michael donors resulted in the formation of highly substituted benzofuran derivatives in good to excellent yields. The intramolecular event followed by two [1,3]-H shifts leading to aromatization appears to be the key to the success of this unprecedented transformation.

Synthesis of Functionalized Chromene and Chroman Derivatives via Cesium Carbonate Promoted Formal [4 + 2] Annulation of 2′-Hydroxychalcones with Allenoates

A new strategy has been established for the synthesis of functionalized chromene and chroman derivatives via a Cs2CO3-catalyzed domino addition of 2′-hydroxychalcone derivatives with allenoates, which can serve as a general avenue for the construction of multireplaced chromene derivatives. Chemoselectivity of this synthesis was found to depend on substituents on substrates. Good to excellent yields were achieved under simple and mild conditions at room temperature.

Novel hybrids derived from aspirin and chalcones potently suppress colorectal cancer in vitro and in vivo

Colorectal cancer (CRC) remains the fourth leading cause of cancer deaths around the world despite the availability of many approved small molecules for treatment. The issues lie in the potency, selectivity and targeting of these compounds. Therefore, new

Enantioselective synthesis of 2-amino-3-nitrile-chromenes catalyzed by cinchona alkaloids: A remarkable additive effect

2-Amino-3-nitrile-chromenes with potential antitumor activity were constructed by a novel catalytic system. In combination with α-naphthol, quinine could effectively promote the Michael-cyclization process of malononitrile with functionalized chalcones in high yields and moderate to good enantioselectivity (up to 84% ee). It is notable that the enantioselectivity could be greatly improved when α-naphthol was employed as additive.

ZrCl4-catalysed synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridine derivatives

In the presence of a catalytic amount of zirconium(IV) chloride, an efficient synthesis of new 4-(2-hydroxyphenyl)pyrazolo[3,4-b]pyridines has been developed by the reaction 2-hydroxychalcones with 3-methyl-1-phenyl-1H-pyrazol-5-amine in refluxing ethanol. All these novel compounds have been characterised by 1H NMR, 13C NMR, HRMS, IR spectra and X-ray crystallographic analysis.

Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans

Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.