35779-32-9

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 102852-88-0 (2R,3R)-2-(4-Methyl-benzyl)-3-phenyl-oxaziridine 
• 108-88-3 toluene 

Downstream Products

• 51625-68-4 1,3,5-tris(3-nitrophenyl)-2,4-diazapenta-1,4-diene 
• 109253-44-3 3-amino-2-phenyl-3-p-tolyl-propionic acid ethyl ester 
• 33515-43-4 2,4,5-tri-p-methylphenylimidazole 
• 102747-54-6 2,4,5-tri-p-tolyl-4,5-dihydro-1H-imidazole 
• 107772-64-5 4-methyl-5-(4-methyl-benzyl)-2-phenyl-thiazole 
• 108367-86-8 4-methyl-5-(4-methyl-benzyl)-2-p-tolyl-thiazole 
• 1588-49-4 4,4'-dimethylstilbene 
• 98180-43-9 bis(4-methylbenzyl)amine 
• 1224850-72-9 N-(4-methylbenzylideneamino)(4-methylphenyl)methyl-2-(4-methyl-phenyl)-4,5-diphenyl-1,2-dihydro-3H-pyrrol-3-one 
• 1347740-01-5 C₂₄H₃₄NO₃P 
• 1347740-02-6 C₁₈H₂₂NO₃P 
• 871315-36-5 (p-Tolyl-{[1-p-tolyl-meth-(E)-ylidene]-amino}-methyl)-phosphonic acid diethyl ester 

Relevant academic research and scientific papers

Design, synthesis of novel celastrol derivatives and study on their antitumor growth through HIF-1α pathway

Four series of hypoxia-inducible factor-1 alpha (HIF-1α) functioning derivatives stemming from modifications to the C-29 carboxyl group of celastrol were designed and synthesized, and their anticancer activities were evaluated. To address the structure and activity relationship of each derivative, extensive structural changes were made. HRE luciferase reporter assay demonstrated that 12 modified compounds showed superior HIF-1α inhibitory activity. Among them, compound C6 exhibited the best features: firstly, the strongest HIF-1α inhibitory activity (IC50 = 0.05 μM, 5-fold higher than that of celastrol); secondly, lower cytotoxicity (22-fold lower, C6-16.85 μM vs celastrol-0.76 μM). Thus, the safety factor of C6 was about 112 times higher than that of celastrol. Western blot assay indicated that C6 may inhibit the expression of HIF-1α protein in cells. Additionally, C6 hindered tumor cell cloning, migration and induced cell apoptosis. It is worth mentioning that in the mouse tumor xenograft model, C6 (10 mg/kg) displayed good antitumor activity in vivo, showing a better inhibition rate (74.03%) than the reference compound 5-fluorouracil (inhibition rate, 59.58%). However, the celastrol treatment group experienced collective death after four doses of the drug. Moreover, C6 minimally affected the mouse weight, indicating that its application in vivo has little toxic effect. H&E staining experiments show that it could also exacerbate the degree of tumor cell damage. The results of water solubility experiment show that the solubility of C6 is increased by 1.36 times than that of celastrol. In conclusion, C6 is a promising antitumor agent through HIF-1α pathway.

Synthesis of β-Phosphinolactams from Phosphenes and Imines

Various cis-β-phosphinolactams are synthesized stereoselectively for the first time from imines and diazo(aryl)methyl(diaryl)phosphine oxides under microwave irradiation. Diazo(aryl)methyl(diaryl)phosphine oxides first undergo the Wolf rearrangement to generate phosphenes. Imines nucleophilically attack the phosphenes followed by an intramolecular nucleophilic addition via less steric transition states to give final cis-β-phosphinolactams. C-Styrylimines generally give rise to β-phosphinolactams in higher yields than C-arylimines. The stereoselectivity and proposed mechanism are rationalized by DFT theoretical calculation.

Design, Synthesis, and in Vitro and in Vivo Biological Evaluation of Limonin Derivatives for Anti-Inflammation Therapy

In this study, limonin derivatives were used to design new anti-inflammatory compounds with high pharmacological activity and low toxicity. A total of 23 new limonin derivatives were discovered, synthesized, and screened for their anti-inflammatory activity against lipopolysaccharide (LPS)-treated RAW 264.7 cells. Of them, compound f4 was found to be the most active, with a higher efficiency compared with limonin and celecoxib. Subsequently, we studied the mechanism underlying the activity of f4 and found that it inhibited proinflammatory cytokines by blocking the NF-κB/MAPK signaling pathway in LPS-treated RAW 264.7 cells as well as mice. In conclusion, f4 may be a promising anti-inflammatory lead compound.

Stereoselective Synthesis of α,α′-Dihydroxy-β,β′-diaryl-β-amino Acids by Mannich-Like Condensation of Hydroarylamides

Dual α,α′-Dihydroxy-β-amino acids are highly interesting tools for several industrial applications. Nevertheless, only few derivatives are reported in the literature and knowledge concerning the substitution pattern as well as their enantioselective syntheses are lacking. Herein, we report on the preparation of enantiopure α,α′-dihydroxy-β,β′-diaryl-β-amino acid (dual) derivatives by an efficient Mannich-like condensation of hydroarylamides with 5,6-diethoxy-5,6-dimethyl-1,4-dioxan-2-one (triethylsilyl)ketene acetal. The synthetic protocol has been optimized affording the dual compounds in very good yields and with different aryl substitution patterns. Taking advantage of the “double stereodifferentiation” concept, a highly stereoselective reaction was performed: of the 16 possible isomers, only two diastereoisomers (d.r. up to 93:7) formed. Insights into the high stereocontrol of this condensation were given.

Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds

Triallylborane-amines adducts are effective stoichiometric allylating agents in the aminoallylation reaction of carbonyl compounds in methanol. Moreover, copper-catalyzed diastereoselective allylation of Ellman's imine was achieved with triallylborane-methylamine adduct.

Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates

A series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido] (substituted phenyl)methyl}phosphonates was synthesized and their cytotoxic activities were tested against various human tumor cell lines. Some compounds (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. Especially, compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells with IC50 7.1 and 11.4 μM, respectively. Their inhibitory activities against KB and CNE2 cells were even higher than that of fluorouracil.

Novel method for the synthesis of α-amino-α- hydroxyalkylphosphinic acids and bis(α-aminoalkyl)phosphinic acids: Nuclephilic addition of α-hydroxy-H-phosphinic acids to diimines

We report here a novel and simple method for the synthesis of α-amino-α-hydroxyalkylphosphinic acids in good yields in two simple steps without any protection-deprotection steps. We have developed an efficient method for the synthesis of α-amino-α-hydroxyalkylphosphinic acids via the reaction of easily available α-hydroxyalkylphosphinic acids with diimines. Treatment of α-hydroxyalkylphosphinic acids with diimines in the presence of trimethylsilyl chloride (TMSCl) gives α-amino-α- hydroxyalkylphosphinic acids in good yields. The reaction gave a mixture of two diastereomeric forms of α-amino-α-hydroxyalkylphosphinic acids. The difference in solubility in organic solvents allowed us to readily separate the diastereoisomers. Georg Thieme Verlag Stuttgart · New York.

Synthesis and biological evaluation of novel phosphonates derivatives of as potential antitumor agents

A series of dialkyl [2-(4,6-dimethoxypyrimidin-2-yloxy)benzamido](aryl) methylphosphonates derivatives were designed and synthesized. All the new compounds were identified by elemental analysis, IR, 1H NMR, 31P NMR, and MS. Their antitumor activity against KB and CNE1 cells was examined. Some of the compounds showed potential antitumor activity, which provided some hints for further study of structure modification. In particular, the compounds 6i and 6j displayed more potent cytotoxic activities against KB in comparison with 5-FU. Copyright Taylor & Francis Group, LLC.

Synthesis and complexation properties of N, N-bis(phosphinomethyl)amine as a new class of 1-aminophosphinic acids with transition metals and lanthanide ions in aqueous solution

The treatment of aromatic aldehydes with ammonia and hypophosphorus acid gave novel C2-symmetric N,N-bis(phosphinomethyl)amines as a new class of 1-aminophosphinic acid compounds. Complexation properties of N,N-bis(phosphinomethyl)amines with transition metals such as Co2+, Ni2+, Zn2+, Cu2+, and Cd2+ and lanthanide ions La3+ and Gd3+ were studied in aqueous solution by the pH-potentiometric method. Dissociation constants (pK) of the compound were determined by the pH-potentiometric technique. The complexation studies with compound dl-2a showed the best fit of the titration curves were obtained when the ligand-metal stoichiometric ratio was 1:1 and 2:1.

Reaction of 1-amino bisphosphinic acids with acid chlorides: Synthesis of novel cyclic 1-Hydroxy-1-amino-1,1-bisphosphinic acids

Treatment of 1-amino bisphosphinic acids with HMDS followed by reaction with acid chlorides gives 1′-hydroxy-1′-amino-1,1-bisphosphinic acid in good yields. The reaction gave a mixture of the racemate and meso form of 1′-hydroxy-1′-amino-1,1-bisphosphinic acid. The stereochemistry of the readily separable diastereomer was confirmed after converting to the corresponding novel cyclic 1-hydroxy-1-amino-1,1-bisphosphinic acid. Georg Thieme Verlag Stuttgart.