112579-84-7

Basic information

• Product Name: Phosphonic acid, [amino(4-methylphenyl)methyl]-, diethyl ester
• CAS NO: 112579-84-7
• Molecular Formula: C12H20NO3P
• Molecular Weight: 257.269
• Mol File: 112579-84-7.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, [amino(4-methylphenyl)methyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [amino(4-methylphenyl)methyl]-, diethyl ester(112579-84-7)
• EPA Substance Registry System: Phosphonic acid, [amino(4-methylphenyl)methyl]-, diethyl ester(112579-84-7)

Safety Data

• Hazardous Substances Data: 112579-84-7(Hazardous Substances Data)

Upstream product

• 762-04-9 Diethyl phosphonate 
• 45708-98-3 p-Toluylaldehyd-imin 
• 104-87-0 4-methyl-benzaldehyde 
• 24431-15-0 N-benzyl-p-tolylmethanimine 
• 762-04-9 phosphonic acid diethyl ester 
• 871315-36-5 (p-Tolyl-{[1-p-tolyl-meth-(E)-ylidene]-amino}-methyl)-phosphonic acid diethyl ester 
• 135473-50-6 diethyl (benzylamino)(p-tolyl)methylphosphonate 
• 129960-70-9 benzyl (diethoxyphosphoryl)(p-tolyl)methylcarbamate 

Downstream Products

• 146304-08-7 [(2-tert-Butoxycarbonylamino-acetylamino)-p-tolyl-methyl]-phosphonic acid diethyl ester 
• 146304-05-4 [(2-Benzyloxycarbonylamino-acetylamino)-p-tolyl-methyl]-phosphonic acid diethyl ester 
• 1254692-40-4 C₁₆H₂₂N₃O₄PS 
• 1246495-52-2 diethyl {[(2-hydroxy-3-(4-phenoxy)propyl)amino](p-tolyl)methyl}phosphonate 
• 1347739-96-1 O,O-diethyl [2-(4,6-dimethoxypyrimidin-2-yloxy)phenoxyamino](p-tolyl)methylphosphonate 
• 1621069-71-3 O,O′-diethyl (4-tolyl)(2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yloxy)acetamido)methylphosphonate 
• 1621069-88-2 O,O′-diethyl (4-tolyl)(2-(1-hydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yloxy)propanamido)methylphosphonate 
• 1454615-00-9 C₃₃H₄₇N₂O₄PS 
• 1396320-36-7 O,O'-diethyl α-(thiazolo[5,4-b]pyridin-2-ylamino)(4-methylphenyl)methylphosphonate 
• 1260636-35-8 diethyl α-[(diethoxyphosphoryl)amino]-4-methylbenzylphosphonate 
• 1260249-35-1 C₂₆H₃₂N₃O₈P 
• 1218951-04-2 O,O-diethyl N-[2-(5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yloxy)benzoxyl]-1-amino-1-(p-tolyl)methyl phosphonate 
• 2942-54-3 diethyl (4-methylbenzoyl)phosphonate 

Relevant articles and documents

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.

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Synthesis and antitumor activities of novel rhein α-aminophosphonates conjugates

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