38897-99-3

Upstream product

• 1530-39-8 (4-chlorobenzyl)triphenylphosphonium chloride 
• 622-95-7 4-chlorobenzyl bromide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 6048-06-2 ethyl-p-chlorocinnamate 
• 108141-65-7 6-(4-chlorophenyl)-5-phenyl-1,2-dithiafulvene 
• 127536-25-8 (E)-3-(4-Chloro-phenyl)-2-ethoxy-acrylic acid ethyl ester 
• 127536-17-8 (Z)-3-(4-Chloro-phenyl)-2-ethoxy-acrylic acid ethyl ester 
• 59625-66-0 4-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2,3-diphenyl-cyclobut-2-enone 
• 222547-18-4 1-Chloro-4-((Z)-3,3,3-trifluoro-2-hexylsulfanyl-propenyl)-benzene 
• 222547-27-5 1-Chloro-4-((Z)-3,3,4,4,4-pentafluoro-2-hexylsulfanyl-but-1-enyl)-benzene 
• 652968-68-8 (Z)-4'-chloro-6-methyl-3-styrylchromone 
• 685902-73-2 {5-[2-(4-chloro-phenyl)-vinyl]-naphthalen-2-yl}-carbamic acid tert-butyl ester 
• 1257982-99-2 C₁₈H₁₄ClNO 
• 1257983-04-2 (E)-3-[2-(4-chlorophenyl)vinyl]-1-methylquinolin-4(1H)-one 
• 1257983-10-0 C₁₇H₁₁Cl₂N 
• 1257983-14-4 C₁₇H₁₁Cl₂N 
• 1417619-85-2 (Z)-1-chloro-4-(2-(1-(phenylethynyl)cyclopropyl)vinyl)benzene 

Relevant academic research and scientific papers

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

One-pot synthesis of gem-difluorostyrenes from benzyl bromide via olefination of phosphonium ylide with difluorocarbene

A new approach for the synthesis of gem-difluorostyrenes from benzyl bromide is described. Quaternization of triphenylphosphine with benzyl bromide to give phosphonium salts, deprotonation of the corresponding phosphonium salts to produce phosphonium ylide, and the subsequent olefination of phosphonium ylide with difluorocarbene generated from difluoromethylene phosphobetaine (Ph3P+CF2CO2-) by decarboxylation can occur smoothly in one-pot, furnishing the final gem-difluorostyrenes in good yields.

New synthesis of (Z)-and (E)-3-styryl-4-quinolones

A novel and efficient route for the synthesis of (Z)-and (E)-3-styryl-4-quinolones is described. Wittig reaction of 4-(chloroquinoline- and quinolone)-3-carbaldehydes with benzylic ylides is the key transformation for this synthetic route. The (Z)-1-methyl-3-styryl-4-quinolone is obtained with high diastereoselectivity from the reaction of 1-methyl-4-quinolone-3- carbaldehyde; while (E)-3-styryl-4-quinolone is prepared through the Wittig reaction of 4-chloroquinoline-3-carbaldehyde followed by acid hydrolysis. Both synthetic routes are efficient regardless of the substituents on the benzylic ylides. Georg Thieme Verlag Stuttgart - New York.

PHENANTHRENE DERIVATIVES AS MPGES-1 INHIBITORS

The invention encompasses novel compounds of Formula or pharmaceutically acceptable salts thereof. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (mPGES-1) enzyme and are therefore useful to treat pain and/or inflammation from a variety of diseases or conditions, such as osteoarthritis, rheumatoid arthritis and acute or chronic pain. Methods of treating diseases or conditions mediated by the mPGES-1 enzyme and pharmacuetical compositions are also encompassed

Wittig reactions of chromone-3-carboxaldehydes with benzylidenetriphenyl phosphoranes: A new synthesis of 3-styrylchromones

An efficient route to 3-styrylchromones has been developed and applied to syntheses of several new derivatives. Wittig reactions of chromone-3- carboxaldehydes with some benzylic ylides gave a diastereomeric mixture of (E) and (Z)-3-styrylchromones that a

3-(Substituted) vinyl cephalosporins

New 3-(substituted) vinyl cephalosporin compounds, e.g., 3-(2'-ethoxycarbonylvinyl)-7-phenoxyacetamido-3-cephem-4-carboxylic acid, which are useful as antibiotics, and 3-(substituted) vinyl cephalosporin compounds which are useful as intermediates in preparing antibiotic substances.