65615-89-6

Usage

Uses

Used in Organic Synthesis:
N-Boc-4-nitro-L-phenylalanine Methyl Ester is used as a synthetic intermediate for the preparation of various pharmaceutical compounds and bioactive molecules. Its unique structure allows for the creation of complex organic molecules with potential applications in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-Boc-4-nitro-L-phenylalanine Methyl Ester is used as a building block for the development of new drugs. Its versatile structure enables the synthesis of a wide range of therapeutic agents, including those targeting specific diseases or conditions.
Used in Chemical Research:
N-Boc-4-nitro-L-phenylalanine Methyl Ester is also utilized in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. Its reactivity and functional groups make it an ideal candidate for investigating novel chemical transformations and understanding the underlying principles of organic chemistry.

InChI:InChI=1/C15H20N2O6/c1-15(2,3)23-14(19)16-12(13(18)22-4)9-10-5-7-11(8-6-10)17(20)21/h5-8,12H,9H2,1-4H3,(H,16,19)/t12-/m0/s1

Upstream product

• 186581-53-3 diazomethane 
• 33305-77-0 Boc-Phe(p-NO₂)-OH 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 24424-99-5 di-tert-butyl dicarbonate 
• 74-88-4 methyl iodide 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 586-78-7 para-nitrophenyl bromide 
• 636-98-6 p-nitrobenzene iodide 
• 63-91-2 L-phenylalanine 
• 67-56-1 methanol 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 17193-40-7 (+)-Methyl 2-amino-3-(4-nitrophenyl)propionate hydrochloride 
• 682774-41-0 [1-(S)-2-phenyl-1-(2-trimethylsilanylethoxymethoxymethyl)ethyl]carbamic acid tert-butyl ester 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 

Downstream Products

• 114346-29-1 tert-butyl N-[(2S)-1-hydroxy-3-(4-nitrophenyl)propan-2-yl]carbamate 
• 406165-11-5 ((S)-2-{4-[3-(3-Nitro-phenyl)-ureido]-phenyl}-1-trimethylsilanyloxymethyl-ethyl)-((S)-3-phenoxy-2-trimethylsilanyloxy-propyl)-carbamic acid tert-butyl ester 
• 823797-90-6 [2-(4-amino-phenyl)-1-hydroxymethyl-ethyl]-[3-(9H-carbazol-4-yloxy)-2-hydroxy-propyl]-carbamic acid tert-butyl ester 
• 406165-19-3 [(S)-2-(4-Amino-phenyl)-1-trimethylsilanyloxymethyl-ethyl]-((S)-3-phenoxy-2-trimethylsilanyloxy-propyl)-carbamic acid tert-butyl ester 
• 823797-89-3 (S)-2-[(S)-3-(9H-Carbazol-4-yloxy)-2-hydroxy-propylamino]-3-(4-nitro-phenyl)-propan-1-ol 

Relevant academic research and scientific papers

Tyrosine–chlorambucil conjugates facilitate cellular uptake through L-type amino acid transporter 1 (LAT1) in human breast cancer cell line MCF-7

l-type amino acid transporter 1 (LAT1) is an amino acid transporter that is overexpressed in several types of cancer and, thus, it can be a potential target for chemotherapy. The objectives of this study were to (a) synthesize LAT1-targeted chlorambucil d

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

Photoswitchable CENP-E Inhibitor Enabling the Dynamic Control of Chromosome Movement and Mitotic Progression

Interfering with mitosis is a potential cancer therapy strategy. However, the lack of controllability of antimitotic drugs in cell growth suppression causes severe side effects and limits their clinical utility. Herein, we developed an azobenzene-based ph

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

The Development and Scale-Up of an Antibody Drug Conjugate Tubulysin Payload

Significant development and scale-up work was completed on the synthesis of an antibody drug conjugate payload based on the tubulysin natural products. This work included the development of new routes to the tubuvaline and tubuphenylaniline portions of the molecules, as well as extensive optimization of the solid phase peptide synthesis used to assemble the molecule. The initial route (21 steps longest linear sequence, 0.01% overall yield) was improved to a new, more robust route (19 steps longest linear sequence, 2.4% overall yield) affording a 240-fold increase in overall yield and allowing delivery of over 86 g of the required molecule.

An Optically Active Polymer for Broad-Spectrum Enantiomeric Recognition of Chiral Acids

Recognition of enantiomers of chiral acids by anion–π or lone pair–π interactions has not yet been investigated but is a significant and attractive challenge. This study reports an optically active polymer-based supramolecular system with capabilities of discriminating enantiomers of various chiral acids. The polymer featuring alternate π-acidic naphthalenediimides (NDIs) and methyl l-phenylalaninates in the backbone exhibits an unprecedented slow self-assembly process that is susceptible to perturbation by various chiral acids. Thus, the combination of anion–π or lone pair–π interactions and sensitivity of the polymeric self-assembly process to external chiral species endows the system with recognition capabilities. This is the first time that anion–π or lone pair–π interactions have been applied in the recognition of enantiomers of various chiral acids with a single system. The results shed light on new strategies for material design by integrating π-acidic aromatic systems and chiral building blocks to afford relevant advanced functions.

Supramolecular self-assembly of chiral polyimides driven by repeat units and end groups

Pyromellitic diimides (PMDIs) are effective building blocks for the construction of supramolecular systems but are infrequently used in comparison with other electron-deficient aromatic systems. We report PMDI-based chiral polyimides that form polymeric supramolecular systems with unique self-assembly features that show time-dependent spectroscopic behaviour. Extensive investigations revealed the driving forces for the self-assembly of the polyimides. One is the complementary aromatic π-π stacking between electron-accepting PMDI and electron-donating phenyl ring in the polymer backbones, and another is the hydrogen bonding interactions of the end groups. The self-assembly is readily disrupted by guest molecules with strong associations with the PMDI and the end groups. The introduction of flexible arylether diimides into the PMDI-based copolymer backbones and the sequence of PMDIs and arylether diimides in the copolymer backbones significantly influence the self-assembly of the polyimides. The results elucidate the mechanisms of polymeric self-assembly of chiral polyimides, providing important information for the development of materials based on polymeric supramolecular systems with properties and functions regulated by composition, sequence and end groups.

Tubulysin compounds, methods of making and use

Tubulysin compounds of the formula (I) where R1, R2, R3a, R3b, R4, R5, W, and n are as defined herein, are anti-mitotic agents that can be used in the treatment of cancer, especially when conjugated to a targeting moiety.

Antiproliferative compounds, conjugates thereof, methods therefor, and uses thereof

Antiproliferative compounds having a structure represented by formula (II), where n, R1, R2, R3, R4, and R5 are as defined herein, can be used to treat tumors, optionally when conjugated to a ligand such as an antibody:

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.