161709-56-4

Basic information

• Product Name: 1-NAPHTHALENYLSULFONYL-ILE-TRP-ALDEHYDE
• Synonyms: NAPSUL-ILE-TRP-CHO;N-(1-NAPHTHALENYLSULFONYL)-ILE-TRP-ALDEHYDE;1-NAPHTHALENYLSULFONYL-ILE-TRP-ALDEHYDE;1-NAPTHALENESULFONYL-ILE-TRP-ALDEHYDE
• CAS NO: 161709-56-4
• Molecular Formula: C27H29N3O4S
• Molecular Weight: 491.6
• Mol File: 161709-56-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: -15°C
• CAS DataBase Reference: 1-NAPHTHALENYLSULFONYL-ILE-TRP-ALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-NAPHTHALENYLSULFONYL-ILE-TRP-ALDEHYDE(161709-56-4)
• EPA Substance Registry System: 1-NAPHTHALENYLSULFONYL-ILE-TRP-ALDEHYDE(161709-56-4)

Safety Data

• Hazardous Substances Data: 161709-56-4(Hazardous Substances Data)

Usage

Uses

N-(1-Naphthalenylsulfonyl)-Ile-Trp-aldehyde is an inhibitor of cathepsin L.

Upstream product

• 161708-63-0 (2S,3S)-3-Methyl-2-(naphthalene-1-sulfonylamino)-pentanoic acid [(S)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-amide 
• 182216-60-0 (2S,3S)-3-Methyl-2-(naphthalene-1-sulfonylamino)-pentanoic acid [(S)-2-(1H-indol-3-yl)-1-(methoxy-methyl-carbamoyl)-ethyl]-amide 
• 85-46-1 1-Naphthalenesulfonyl chloride 
• 3160-59-6 N-Cbz-L-Isoleucine 
• 61535-47-5 benzyl (S)-(1-hydroxy-3-(1H-indol-3-yl)propan-2-yl)carbamate 
• 161005-39-6 Z-Trp-N,O-dimethylhydroxamate 
• 160235-08-5 N-(tert-butoxycarbonyl)-L-tryptophan N,O-dimethylhydroxamide 
• 161708-60-7 (2S,3S)-2-Amino-3-methyl-pentanoic acid [(S)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-amide 
• 182216-66-6 (2S,3S)-2-Amino-3-methyl-pentanoic acid [(S)-2-(1H-indol-3-yl)-1-(methoxy-methyl-carbamoyl)-ethyl]-amide 
• 161708-67-4 {(1S,2S)-1-[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethylcarbamoyl]-2-methyl-butyl}-carbamic acid benzyl ester 
• 182216-59-7 {(1S,2S)-1-[(S)-2-(1H-Indol-3-yl)-1-(methoxy-methyl-carbamoyl)-ethylcarbamoyl]-2-methyl-butyl}-carbamic acid benzyl ester 
• 154-09-6 L-tryptophanol 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 

Relevant articles and documents

Synthesis of peptide aldehyde derivatives as selective inhibitors of human cathepsin L and their inhibitory effect on bone resorption

Cathepsin L, a lysosomal cysteine protease, is secreted by osteoclasts and participates in bone collagen degradation. In a search for cathepsin L inhibitors as antiosteoporotic agents, a series of peptide aldehyde derivatives were prepared by two synthetic approaches, DMSO oxidation of the corresponding alcohol derivatives and DIBAL-H reduction of the corresponding N,O-dimethylhydroxylamide derivatives, and evaluated for inhibitory activity against human cathepsin L and for inhibitory effects on bone resorption. Some of the peptide aldehyde derivatives including α-acylamino aldehyde derivatives showed potent activities. Among these compounds, N-(1- naphthalenylsulfonyl-L-isoleucyl-L-tryptophanal (12) was selected as a candidate for further investigation. Compound 12, a potent, selective, and reversible inhibitor of human cathepsin L with an IC50 of 1.9 nM, inhibited the release of Ca2+ and hydroxyproline from bone in in vitro bone culture system and also prevented bone loss in ovariectomized mice at an oral dose of 50 mg/kg.

DERIVATIVES OF L-TRYPTOPHANAL AND THEIR USE AS MEDICINALS

The present invention provides a cathepsin L inhibitor containing a compound of the formula: STR1 wherein R 1 is a hydrogen atom or an arylalkyl, heterocyclic-alkyl or lower alkyl group which may be substituted; R 2 and R 3 independently are a hydrogen at