90149-97-6

Upstream product

• 54976-38-4 (E)-3-phenylbut-2-en-1-ol 
• 54976-39-5 (E)-1-bromo-3-phenyl-2-butene 
• 50-00-0 formaldehyd 
• 98-83-9 isopropenylbenzene 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 90149-91-0 2-Hydroxy-3-((E)-3-phenyl-but-2-enyl)-[1,4]naphthoquinone 

Downstream Products

• 1219801-82-7 3,4-dihydro-2-methyl-2-phenyl-2H-naphtho[2,3-b]pyran-5,10-dione 

Relevant academic research and scientific papers

Site-selectivity control in hetero-Diels-Alder reactions of methylidene derivatives of lawsone through modification of the reactive carbonyl group: An experimental and theoretical study

A new perspective on the reactivity of hydroxyquinones was revealed as an acetal derivative of lawsone was synthesized, isolated, and used in tandem Knoevenagel/hetero-Diels-Alder reactions catalyzed by S-proline. The intermediate alkylidene-1,3-diones that were formed in situ reacted with electron rich alkenes to predominantly afford pyrano-1,2-naphthoquinone (β-lapachone) derivatives along with the isomeric pyrano-1,4-naphthoquinone (α-lapachone) derivatives in high to excellent total yields. Interestingly, the highly reactive arylidene-1,3-dione derivatives were found to be stable and isolable. DFT calculations suggest that these hetero-Diels-Alder reactions have a high polar character, taking place through a two-stage one-step mechanism. An analysis of the conceptual DFT indices allows explaining the remarkable site-selectivity observed.

Synthesis and anti-Trypanosoma cruzi activity of β-lapachone analogues

The available chemotherapy for Chagas disease, caused by Trypanosoma cruzi, is unsatisfactory; therefore, there is an intense effort to find new drugs for the treatment of this disease. In our laboratory, we have analyzed the effect on bloodstream trypoma

Synthesis of new o-quinone methides from β-lapachone analogues

In this work, we synthesized six new o-quinone methides from β-lapachone analogues by treating β-lapachone with acetone and a catalytic amount of iodine under thermal conditions and microwave irradiation. The yields of isolated o-quinone methides ranged f

Trapping of active methylene intermediates with alkenes, indoles or thiols: Towards highly selective multicomponent reactions

In this paper, a basic method to access new multicomponent reactions (MCRs) is reported. The mechanism of these MCRs is based on the trapping of methylene intermediates, formed in situ by reaction of formaldehyde with electron-rich carbons, with alkene, thiol or indole derivatives. According to our strategy, a wide range of valuable skeletons has been obtained in a one-pot reaction, thus allowing a minimization of waste, cost and labor. The presented methodology exhibits a broad substrate scope and electron-rich carbons in the α-position of a hydroxy or carbonyl group were found to be particularly efficient. More generally, this work offers new tools for creating molecular complexity and diversity from one of the simplest organic building blocks, formaldehyde.

PHARMACEUTICAL COMPOSITION FOR TREATMENT AND PREVENTION OF RESTENOSIS

Provided is a pharmaceutical composition for the treatment and/or prevention of restenosis including (a) a therapeutically effective amount of a particular compound represented by Formula 1 and 2, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE

Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

β-Lapachone: Synthesis of Derivatives and Activities in Tumor Models

In order to find a 3,4-dihydro-2H-naphthopyran-5,6-dione more potent than the naturally occurring 2,2-dimethyl derivative , we synthesized a series of analogous compounds with modifications at position 2 of the pyran ring or at positions 8 and 9 of the benzene ring.Of the compounds tested in vitro for inhibition of RNA-dependent DNA polymerase and in mice infected with Rauscher leukemia, all retained good enzyme activity.Inhibition of the reverse transcriptase activity of the 2,2-substituted derivatives 10b-e was as strong as 10a.However, only the 2-methyl-2-phenyl derivative 10e proved to be about as potent as 2,2-dimethyl reference compound 10a in prolonging the mean survival time of mice with Rauscher leukemia virus induced leukemia.