193073-45-9

Basic information

• Product Name: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-, methyl ester
• CAS NO: 193073-45-9
• Molecular Formula: C15H19FN2O6
• Molecular Weight: 342.324
• Mol File: 193073-45-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-, methyl ester(193073-45-9)
• EPA Substance Registry System: L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-3-nitro-, methyl ester(193073-45-9)

Safety Data

• Hazardous Substances Data: 193073-45-9(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 20367-99-1 ethyl 2-(acetylamino)-2-(ethoxycarbonyl)-3-(4'-fluoro-3'-nitrophenyl)propanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 178744-39-3 L-4-fluoro-3-nitrophenylalanine methyl ester 
• 15017-52-4 4-(bromomethyl)-1-fluoro-2-nitrobenzene 
• 459-57-4 4-fluorobenzaldehyde 
• 42564-51-2 4-fluoro-3-nitrobenzaldehyde 
• 20274-69-5 (4-fluoro-3-nitrophenyl)methanol 

Downstream Products

• 193074-08-7 [2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 193074-12-3 [2-({(S)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 249757-19-5 (R)-[(S)-2-{[(S)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester 
• 193074-05-4 [2-{(R)-[amino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 249757-14-0 [2-({(R)-(3,5-dichloro-4-methoxyphenyl)-[2-(3-hydroxyphenyl)acetylamino]acetyl}methylamino)-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(S)-(4-methoxyphenyl)acetic acid methyl ester 
• 249757-20-8 (S)-[(S)-2-{[(R)-2-Amino-2-(3,5-dichloro-4-methoxy-phenyl)-acetyl]-methyl-amino}-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-(4-methoxy-phenyl)-acetic acid methyl ester 
• 193074-02-1 [2-{(R)-[tert-butoxycarbonylamino-(3,5-dichloro-4-methoxyphenyl)acetyl]methylamino}-(3S)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 193073-96-0 [(2S)-2-(tert-butoxycarbonylmethylamino)-3-(4-fluoro-3-nitrophenyl)propionylamino]-(R)-(4-methoxyphenyl)methyl ester 
• 193073-99-3 [3-(4-fluoro-3-nitrophenyl)-(2S)-2-methylaminopropionylamino]-(R)-(4-methoxyphenyl)acetic acid methyl ester 
• 193073-38-0 (S)-N-(tert-butoxycarbonyl)-N-methyl-(S)-(4-fluoro-3-nitro)phenylalanine 
• 193073-48-2 (S)-N-(tert-butoxycarbonyl)-N-methyl-(S)-(4-fluoro-3-nitro)phenylalanine methyl ester 

Relevant articles and documents

Quantitative insight into the design of compounds recognized by the L-type amino acid transporter 1 (LAT1)

L-Type amino acid transporter 1 (LAT1) is a transmembrane protein expressed abundantly at the blood-brain barrier (BBB), where it ensures the transport of hydrophobic acids from the blood to the brain. Due to its unique substrate specificity and high expression at the BBB, LAT1 is an intriguing target for carrier- mediated transport of drugs into the brain. In this study, a comparative molecular field analysis (CoMFA) model with considerable statistical quality (Q2=0.53, R2=0.75, Q2 SE=0.77, R2 SE=0.57) and good external predictivity (CCC=0.91) was generated. The model was used to guide the synthesis of eight new prodrugs whose affinity for LAT1 was tested by using an in situ rat brain perfusion technique. This resulted in the creation of a novel LAT1 prodrug with l-tryptophan as the promoiety; it also provided a better understanding of the molecular features of LAT1-targeted high-affinity prodrugs, as well as their promoiety and parent drug. The results obtained will be beneficial in the rational design of novel LAT1-binding prodrugs and other compounds that bind to LAT1.

Synthesis of a model of chloropeptins I, II western subunit by the intramolecular S(N)Ar based methodology

Formation of a biaryl ether bond between the termini of a tetrapeptide containing a highly racemization prone amino acid by the intramolecular SNAr reaction afforded two diastereomeric 16-membered macrocycles along with their respective atropoisomers. The (R,S,R) and its atropoisomer constituted model of chloropeptins I, II, western part.