124994-66-7

Basic information

• Product Name: Butanoicacid, 2-[[(1,1-diMethylethoxy)carbonyl]aMino]-4-oxo-, phenylMethyl ester, (2S)-
• Synonyms: Butanoicacid, 2-[[(1,1-diMethylethoxy)carbonyl]aMino]-4-oxo-, phenylMethyl ester, (2S)-;(S)-2-tert-Butoxycarbonylamino-4-oxo-butyric acid benzyl ester
• CAS NO: 124994-66-7
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.34164
• Mol File: 124994-66-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Butanoicacid, 2-[[(1,1-diMethylethoxy)carbonyl]aMino]-4-oxo-, phenylMethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoicacid, 2-[[(1,1-diMethylethoxy)carbonyl]aMino]-4-oxo-, phenylMethyl ester, (2S)-(124994-66-7)
• EPA Substance Registry System: Butanoicacid, 2-[[(1,1-diMethylethoxy)carbonyl]aMino]-4-oxo-, phenylMethyl ester, (2S)-(124994-66-7)

Safety Data

• Hazardous Substances Data: 124994-66-7(Hazardous Substances Data)

Upstream product

• 105183-60-6 (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-hydroxybutanoate 
• 30925-18-9 2-tert-butoxycarbonylamino-succinic acid 1-benzyl ester 
• 100-39-0 benzyl bromide 
• 40856-59-5 tert-butyl (3S)-2-oxotetrahydrofuran-3-ylcarbamate 
• 41088-86-2 L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 34036-07-2 3,4 difluorobenzaldehyde 
• 1079307-01-9 (S)-benzyl 2-(tert-butoxycarbonylamino)-4-(methoxy(methyl)amino)-4-oxobutanoate 

Downstream Products

• 156350-27-5 tert-butyl (2S,2'S,3'S,3S)-(3-benzyloxycarbonyl-3-tert-butoxycarbonylaminopropylamino)-3'-tert-butoxycarbonyl-2'-methoxymethoxypropyl-2-azetidinecarboxylate 
• 158534-32-8 (S)-benzyl-4-<(O-benzylhydroxy)amino>-2-<<(1,1-dimethylethoxy)carbonyl>amino>butanoate 
• 474766-44-4 (E)-(S)-2-tert-Butoxycarbonylamino-6-oxo-dec-4-enoic acid benzyl ester 
• 250291-82-8 (2S)-2-tert-butoxycarbonylamino-4-oxo-hexane-dioic acid 1-benzyl ester 6-ethyl ester 
• 682742-72-9 (2'S)-4-(2'-benzyloxycarbonyl-2'-tert-butoxycarbonylamino-ethyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 250291-84-0 (2S)-2-tert-butoxycarbonylamino-4-oxo-hexane-dioic acid 1-benzyl ester 6-tert-butyl ester 
• 682742-71-8 (2'S)-4-(2'-benzyloxycarbonyl-2'-tert-butoxycarbonylamino-ethyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 848785-45-5 (S)-1-((S)-3-Benzyloxycarbonyl-3-tert-butoxycarbonylamino-propyl)-azetidine-2-carboxylic acid 
• 848785-46-6 (S)-1-((S)-3-Amino-3-benzyloxycarbonyl-propyl)-azetidine-2-carboxylic acid 
• 848785-47-7 (S)-1-[(S)-3-Benzyloxycarbonyl-3-((S)-3-benzyloxycarbonyl-3-hydroxy-propylamino)-propyl]-azetidine-2-carboxylic acid 
• 860795-17-1 (S)-1-{(S)-3-Benzyloxycarbonyl-3-[(S)-3-benzyloxycarbonyl-3-(tetrahydro-pyran-2-yloxy)-propylamino]-propyl}-azetidine-2-carboxylic acid 
• 682742-81-0 (2'S)-4-(2'-amino-2'-benzyloxycarbonyl-ethyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 682742-82-1 (2'S)-4-(2'-amino-2'-benzyloxycarbonyl-ethyl)-2,6-dimethyl-pyridine-3,5-dicarboxylic acid di-tert-butyl ester 
• 596828-16-9 (2'S)-4-(2'-tert-butoxycarbonylamino-2'-carboxyethyl)-2,6-dimethylpyridine-3,5-dicarboxylic acid di-tert-butyl ester 

Relevant articles and documents

NOVEL HISTONE METHYLTRANSFERASE INHIBITORS

The present invention relates to novel compounds of formula (I) as defined herein. The compounds are inhibitors of histone methyltransferases of the seven-beta-strand family, in particular of KMT9.

Esterase-sensitive prodrugs of a potent bisubstrate inhibitor of nicotinamide n-methyltransferase (Nnmt) display cellular activity

A recently discovered bisubstrate inhibitor of Nicotinamide N-methyltransferase (NNMT) was found to be highly potent in biochemical assays with a single digit nanomolar IC50 value but lacking in cellular activity. We, here, report a prodrug strategy designed to translate the observed potent biochemical inhibitory activity of this inhibitor into strong cellular activity. This prodrug strategy relies on the temporary protection of the amine and carboxylic acid moieties of the highly polar amino acid side chain present in the bisubstrate inhibitor. The modification of the carboxylic acid into a range of esters in the absence or presence of a trimethyl-lock (TML) amine protecting group yielded a range of candidate prodrugs. Based on the stability in an aqueous buffer, and the confirmed esterase-dependent conversion to the parent compound, the isopropyl ester was selected as the preferred acid prodrug. The isopropyl ester and isopropyl ester-TML prodrugs exhibit improved cell permeability, which also translates to significantly enhanced cellular activity as established using assays designed to measure the enzymatic activity of NNMT in live cells.

A practical route to long-chain non-natural α,ω-diamino acids

An efficient method for the synthesis of long-chain α,ω-diamino acids, starting from natural α-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an ω-hydroxy-alkyl phosphonium salt. After conversion of the ω-hydroxy group into an amine, catalytic hydrogenation produced the N,N'-protected α,ω-diamino acid. The present route to α,ω-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.