33923-83-0

Upstream product

• 579-74-8 2-Methoxyacetophenone 
• 90-02-8 salicylaldehyde 

Downstream Products

• 73110-81-3 2'-methoxyflavan 
• 1443301-70-9 ethyl 2-((2S,3S,4R)-4-(2-(2-methoxyphenyl)-2-oxoethyl)-3-nitrochroman-2-yl)acetate 
• 1443301-91-4 (E)-ethyl 3-(2-((E)-3-(2-methoxyphenyl)-3-oxoprop-1-en-1-yl)phenoxy)acrylate 
• 1638505-32-4 7-hydroxy-9-(2-methoxyphenyl)-6H-benzo[c]chromen-6-one 
• 224818-18-2 2-amino-6-(2-hydroxy-phenyl)-4-(2-methoxy-phenyl)-nicotinonitrile 

Relevant academic research and scientific papers

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.

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.

Enantioselective Synthesis of Highly Substituted Chromans via the Oxa-Michael-Michael Cascade Reaction with a Bifunctional Organocatalyst

A highly enantioselective synthesis of chiral chroman derivatives via an oxa-Michael-Michael cascade reaction has been developed using a bifunctional thiourea organocatalyst. The products were obtained with excellent enantioselectivities (up to >99%), good yields (up to 95%), and diastereoselectivities (up to 5:1).

Reaction of ethyl acetoacetate and 2'-hydroxychalcones: Efficient route to 9-aryl-6H-benzo[c]chromen-6-ones

The reaction of ethyl acetoacetate and 2'-hydroxychalcones under atmospheric air to furnish a series of functionalized 6H-benzo[c]chromen-6-ones in moderate yields is reported. The reaction proceeds through trans-esterification, intra-molecular Michael addition, Robinson annulation and oxidative aromatization.

Fc-PIP catalyzed asymmetric synthesis of cis-2,3-dihydrobenzofurans

A highly enantioselective intramolecular Michael addition-Lactonization domino reaction of a range of enon acids catalyzed by nuleophilic organocatalyst (Fc-PIP) was developed, furnishing cis-2,3-dihydrobenzofuran derivatives with excellent enantioselecit

Organocatalyzed michael-michael cascade reaction: Asymmetric synthesis of polysubstituted chromans

An enantioselective cascade Michael-Michael reaction between chalcones enolates and nitromethane catalyzed by a bifunctional thiourea is developed. This reaction provides a mild but efficient approach to chiral benzopyrans bearing three consecutive stereocenters in high yields with excellent stereoselectivities, and the benzopyrans can be easily transformed to the corresponding tricyclic product.

An efficient synthesis of flavans from salicylaldehyde and acetophenone derivatives

An efficient total synthesis of flavans from the reactions of salicylaldehyde and acetophenone derivatives is reported. The synthesis involves preparation of chalcones through an aldol reaction followed by reduction of both the double bond and the ketone using NaBH4 and an acetic acid mediated cyclization. Methoxy groups on the aromatic rings did not affect significantly the yields of the procedure.

Reactions of Flav-2-enes and Flav-2-en-4-ones (Flavones)

Flav-2-enes, flavones, and 3-alkyl ethers of flavonols add alcohols and carboxylic acids in the presence of N-bromosuccinimide to give 2-alkoxy- and 2-acyloxy-3-bromoflavans which provide routes to cis-3-bromoflavans by reduction and to 3,4-diols by elimination and reaction with osmium tetraoxide.The 2-acyloxyflavans react with alcohols yielding 2-alkoxyflavans.Flavonols react with N-bromosuccinimide and alcohols to give bromine-free hemiacetals, the known 2,3-dialkoxy-3-hydroxyflavanones.