154902-51-9

Basic information

• Product Name: BOC-L-3-BENZOTHIENYLALANINE
• Synonyms: RARECHEM BK PT 0204;N-ALPHA-T-BOC-BETA-(3-BENZOTHIENYL)-L-ALANINE;N-ALPHA-T-BUTOXYCARBONYL-3-(3-BENZOTHIENYL)-L-ALANINE;BOC-3-(3-BENZOTHIENYL)-L-ALANINE;BOC-L-3-BENZOTHIENYLALA;BOC-L-3-BENZOTHIENYLALANINE;BOC-L-3-(3-BENZOTHIENYL)ALANINE;BOC-BTA-OH
• CAS NO: 154902-51-9
• Molecular Formula: C₁₆H₁₉NO₄S
• Molecular Weight: 321.39
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Amino Acid Derivatives;a-amino
• Mol File: 154902-51-9.mol

Chemical Properties

• Boiling Point: 514.1 °C at 760 mmHg
• Flash Point: 264.7 °C
• Appearance: /
• Density: 1.274 g/cm³
• Vapor Pressure: 2.56E-09mmHg at 25°C
• Refractive Index: 1.53
• Storage Temp.: -15°C
• PKA: 3.85±0.10(Predicted)
• BRN: 7081201
• CAS DataBase Reference: BOC-L-3-BENZOTHIENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-3-BENZOTHIENYLALANINE(154902-51-9)
• EPA Substance Registry System: BOC-L-3-BENZOTHIENYLALANINE(154902-51-9)

Safety Data

• Hazard Codes: Xi
• WGK Germany: 3
• F: 10-23
• HazardClass: IRRITANT
• Hazardous Substances Data: 154902-51-9(Hazardous Substances Data)

Usage

Uses

Used in Medicinal Chemistry:
BOC-L-3-BENZOTHIENYLALANINE is used as a building block for the synthesis of peptide-based drugs and drug candidates, contributing to the development of new pharmaceuticals.
Used in Drug Development:
BOC-L-3-BENZOTHIENYLALANINE is used as a key component in the design and development of new pharmaceuticals, especially those targeting diseases and conditions that involve protein-protein interactions, enhancing the therapeutic potential of peptide-based treatments.

InChI:InChI=1/C16H21NO4/c1-11(12-8-6-5-7-9-12)10-13(14(18)19)17-15(20)21-16(2,3)4/h5-9,13H,1,10H2,2-4H3,(H,17,20)(H,18,19)/t13-/m0/s1

Upstream product

• 3216-47-5 3-chloromethylbenzothiophene 
• 63024-19-1 α-acetamido-β-<1>benzothiophene-3-ylpropionic acid 
• 23906-20-9 2-acetylamino-2-benzo[b]thiophen-3-yl-methyl-malonic acid diethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 72120-71-9 (S)-2-amino-3-<1>benzothiophene-3-ylpropionic acid 

Downstream Products

• 166519-79-5 (2S,4R)-2-[(S)-2-Benzo[b]thiophen-3-yl-1-(benzyl-methyl-carbamoyl)-ethylcarbamoyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 188728-87-2 (R)-N¹-((S)-2-Benzo[b]thiophen-3-yl-1-methylcarbamoyl-ethyl)-N⁴-benzyloxy-2-isobutyl-succinamide 
• 473259-84-6 4-{(2S)-2-amino-3-[1-(2S)-2-benzo[b]thiophen-3-yl-1-benzylcarbamoylethylcarbamoyl-(2S)-2-biphenyl-4-yl-ethylcarbamoyl]-3(S)-sulfanylpropyl}benzoic acid 
• 473260-02-5 2-amino-N-(2-benzo[b]thiophen-3-yl-1-benzylcarbamoyl-ethyl)-3-biphenyl-4-yl-propionamide 
• 158574-74-4 N²-Boc-N-methyl-N-(phenylmethyl)-3-(3-benzothienyl)-L-alaninamide 

Relevant articles and documents

INHIBITORS OF AKT ACTIVITY

Invented are novel pyridine compounds, the use of such compounds as inhibitors of PKB/AKT kinase activity and in the treatment of cancer and arthritis.

Studies of Neurokinin Antagonists. 4. Synthesis and Structure-Activity Relationships of Novel Dipeptide Substance P Antagonists: N2--L-prolyl>-N-methyl-N-(phenylmethyl)-3-(2-naphthyl)-L-alaninamide and Its Related Compounds

As an extension of our studies on discovering a novel substance P (SP) antagonist, we modified the previously reported dipeptide, N2-2-(1H-indol-3-ylcarbonyl)-L-lysyl>-N-methyl-N-(phenylmethyl)-L-phenylalaninamide (2b).The lysine part in 2b was first optimized to a (2S,4R)-hydroxyproline derivative (3h), which is 2-fold more potent than 2b in SP binding assay using guinea pig lung membranes.Next we modified the 1H-indol-3-ylcarbonyl part in 3h.Introduction of a methyl group at the indole nitrogen enhanced the oral activity, while retaining the binding activity.Finally, we modified the phenylalanine part to culminate in the most potent compound 7k (FK888), which is a potent SP antagonist with NK1 selectivity as well as oral activity.