16814-08-7

Basic information

• Product Name: Phosphonic acid, (aminophenylmethyl)-, diethyl ester
• CAS NO: 16814-08-7
• Molecular Formula: C11H18NO3P
• Molecular Weight: 243.243
• Mol File: 16814-08-7.mol

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, (aminophenylmethyl)-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, (aminophenylmethyl)-, diethyl ester(16814-08-7)
• EPA Substance Registry System: Phosphonic acid, (aminophenylmethyl)-, diethyl ester(16814-08-7)

Safety Data

• Hazardous Substances Data: 16814-08-7(Hazardous Substances Data)

Upstream product

• 121-44-8 triethylamine 
• 762-04-9 phosphonic acid diethyl ester 
• 92-29-5 hydrobenzamide 
• 18108-19-5 Fluorsulfonylaminophenylmethanphosphonsaeurediethylester 
• 74732-28-8 (1-Isocyanato-1-phenyl)methylphosphonate de diethyle 
• 100-47-0 benzonitrile 
• 64244-30-0 diethyl N-benzylidene-1-amino-1-phenylmethylphosphonate 
• 100-52-7 benzaldehyde 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 77526-41-1 [Phenyl-(phenyl-hydrazono)-methyl]-phosphonic acid diethyl ester 
• 77526-40-0 diethyl ((2,2-dimethylhydrazono)(phenyl)methyl)phosphonate 
• 67764-57-2 diethyl 1-diphenylphosphinamino-1-phenylmethanephosphonate 
• 38428-05-6 diethyl ether of α-(N-benzyloxycarbonyl)aminobenzylphosphonic acid 
• 63207-62-5 [Phenyl-(1-phenyl-cyclopentylamino)-methyl]-phosphonic acid diethyl ester; hydrochloride 

Downstream Products

• 146304-11-2 [(2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-phenyl-methyl]-phosphonic acid diethyl ester 
• 111512-31-3 3-(diethoxyphosphinoyl)-3-phenyl-1-(2-thienyl)-2-azapropene 
• 699000-73-2 diethyl {[(E)-2-ethyl-1-butylidene]amino}(phenyl)methylphosphonate 
• 869937-99-5 diethyl (phenyl){[(E)-1H-indole-3-ylmethylidene]amino}methylphosphonate 
• 3277-27-8 diethyl benzoylphosphonate 
• 1265828-82-7 N-(1-phenyl-1-phosphonomethyl)-1-amino-1-(2-pyridyl)-methylphosphonic acid 
• 1265828-85-0 N-(1-phenylphosphonomethyl)-1-amino-1-(3-pyridyl)-methylphosphonic acid 
• 1265828-88-3 N-(1-phenylphosphonomethyl)-1-amino-1-(4-pyridyl)-methylphosphonic acid 
• 1246495-54-4 diethyl {[(2-hydroxy-3-(isopropoxy)propyl)amino](phenyl)methyl}phosphonate 
• 1246495-57-7 diethyl {[(2-hydroxy-2-(phenyl)ethyl)amino]-(phenyl)methyl}phosphonate 
• 1246495-58-8 C₁₉H₂₆NO₄P 

Relevant articles and documents

1-Aminoalkanephosphonates. Part II. A facile conversion of 1-aminoalkanephosphonic acids into O,O-diethyl 1-aminoalkanephosphonates

1-(N-Trifluoroacetylamino)alkanephosphonate O,O-diethyl esters 2C, obtained from parent 1-aminoalkanephosphonic acids 1, have been selectively deprotected on the amino function affording O,O-diethyl 1-aminoalkanephosphonates 3. Protonation constants of all amino esters 3 synthesized have been determined by potentiometric titration.

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.

Carbon Dioxide-Mediated C(sp2)-H Arylation of Primary and Secondary Benzylamines

C-C bond formation by transition metal-catalyzed C-H activation has become an important strategy to fabricate new bonds in a rapid fashion. Despite the pharmacological importance of ortho-arylbenzylamines, however, effective ortho-C-C bond formation of free primary and secondary benzylamines using PdII remains an outstanding challenge. Presented herein is a new strategy for constructing ortho-arylated primary and secondary benzylamines mediated by carbon dioxide (CO2). The use of CO2 with Pd is critical to allowing this transformation to proceed under relatively mild conditions, and mechanistic studies indicate that it (CO2) is directly involved in the rate-determining step. Furthermore, the milder temperatures furnish free amine products that can be directly used or elaborated without the need for deprotection. In cases where diarylation is possible, an interesting chelate effect is shown to facilitate selective monoarylation.

Design and synthesis of C-19 isosteviol derivatives as potent and highly selective antiproliferative agents

Six series of novel isosteviol derivatives; modified in the C-19 position; were synthesized; and their antiproliferative activity was evaluated against three human cancer cell lines (HCT-116; BEL-7402; HepG2) and the human L02 normal cell line in vitro. M

Synthesis and Biological Evaluation of (+)-Usnic Acid Derivatives as Potential Anti- Toxoplasma gondii Agents

Six series of (+)-usnic acid derivatives were synthesized. The IC50 values of these compounds were determined in T. gondii infected HeLa cells (μM) and in HeLa cells (μM), and their selectivity indexes (SI) were calculated. In vitro, most of th

Nickel-Catalyzed Hydrophosphonylation and Hydrogenation of Aromatic Nitriles Assisted by Lewis Acid

In this paper, we describe the catalytic hydrophosphonylation of several aromatic nitriles used to synthesize α-aminophosphonates (α-APs) using commercially available trialkyl phosphites (P(OR)3, R=Et, iPr, Bu,) and simple and inexpensive nickel chloride (NiCl2.6H2O) as the catalytic precursor. The use of triethylborane (Et3B) as a Lewis acid (LA) was mandatory in order to successfully perform H-phosphite moiety incorporation at the CN bond of non-activated benzonitriles (BN) derivatives. Interestingly, when a highly activated BN such as 2,3,4,5,6-pentafluorobenzonitrile (BN-g) was employed, it was possible to perform the reaction in the absence of an LA using milder reaction conditions. Also, we found that using HP(O)(OiPr)2 as a starting material afforded the aminobisphosphonate derivative with better selectivity than using the method involving P(OiPr)3 as the initial reagent. Remarkably, when using HP(O)(OiPr)2 with an excess of Et3B, the reaction's selectivity completely changed to yield N-benzyl- benzylimine (BBI) and 2,4,5-triphenylimidazole.

Improved facile synthesis of α-amino phosphonates by the reaction of α-amido sulfones with dialkyl trimethyl silyl phosphites catalyzed by Fe(III) chloride

An improved efficient synthesis of α-amino phosphonates has been discovered by the reaction of N-benzyloxycarbonylamino sulfones with dialkyl trimethyl silyl phosphites in the presence of FeCl3as a catalyst. The products were formed in high yie

Novel α,β-unsaturated amide derivatives bearing α-amino phosphonate moiety as potential antiviral agents

Based on flexible construction and broad bioactivity of ferulic acid, a series of novel α,β-unsaturated amide derivatives bearing α-aminophosphonate moiety were designed, synthesized and systematically evaluated for their antiviral activity. Bioassay results indicated that some compounds exhibited good antiviral activities against cucumber mosaic virus (CMV) and tobacco mosaic virus (TMV) in vivo. Especially, compound g18 showed excellent curative and protective activities against CMV, with half-maximal effective concentration (EC50) values of 284.67 μg/mL and 216.30 μg/mL, which were obviously superior to that of Ningnanmycin (352.08 μg/mL and 262.53 μg/mL). Preliminary structure-activity relationships (SARs) analysis revealed that the introduction of electron-withdrawing group at the 2-position or 4-position of the aromatic ring is favorable for antiviral activity. Present work provides a promising template for development of potential inhibitor of plant virus.

Synthesis of derivatives of artesunate α-aminophosphonate and their antimicrobial activities

Thirteen α-aminophosphonate derivatives with artesunate were synthesized by introducing bioactive α-aminophosphonate combination with artesunate in this work. The reaction were easily carried out at normal pressure, low temperature and without any catalys

Novel coumarin-containing aminophosphonatesas antitumor agent: synthesis, cytotoxicity, DNA-Binding and apoptosis evaluation

A series of novel coumarin-containing α-aminophosphonates were synthesized and evaluated for their antitumor activities against Human colorectal (HCT-116), human nasopharyngeal carcinoma (human KB) and human lung adenocarcinoma (MGC-803) cell lines in vit