41446-22-4

Upstream product

• 5545-52-8 Z-D(tBu)-OH 
• 543-27-1 isobutyl chloroformate 
• 63327-57-1 (2S), 2-benzyloxycarbonylamino-succinic acid 1-methyl ester 4-tertiobutyl ester 

Downstream Products

• 145730-87-6 Z-Asp(β-OBu^t)-PEA 
• 460085-22-7 (1R,2R)-1-((S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionylamino)-2-phenyl-cyclohexanecarboxylic acid methyl ester 
• 460085-23-8 (1S,2S)-1-((S)-2-Benzyloxycarbonylamino-3-tert-butoxycarbonyl-propionylamino)-2-phenyl-cyclohexanecarboxylic acid methyl ester 
• 118248-02-5 Z-Asp(OBut)-CHN₂ 
• 153088-76-7 (S)-3-benzyloxycarbonylamino-5-bromo-4-oxo-pentanoic acid tert-butyl ester 
• 173675-05-3 3-benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester 
• 83436-44-6 Z-β-homo-Asp(OBut)-OMe 
• 83436-46-8 (R)-3-Benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester 
• 83436-45-7 (3R)-3-benzyloxycarbonylamino-4-tert-butyoxycarbonylbutyric acid 
• 668475-45-4 (2R)-2-tert-butoxycarbonylmethyl-aziridine-1-carboxylic acid benzyl ester 
• 350991-20-7 (3R)-3-benzyloxycarbonylamino-decanoic acid 
• 146398-04-1 (3S)-3-(benzyloxycarbonylamino)-4-(p-toluenesulfonyloxy)-butanoic acid t-butyl ester 

Relevant academic research and scientific papers

Synthesis and evaluation of indole aspartyl ketones as novel caspase-3 inhibitors

Synthesis, biological evaluation and structure-activity relationships for a series of novel nonpeptide small molecule inhibitors of caspase-3 are described. Among the synthesized compounds, 2,3,5,6-tetrafluorophenoxymethyl ketone derivatives of indole-N-a

Synthesis of substituted (S)-2-aminotetralins via ring-opening of aziridines prepared from l-aspartic acid β-tert-butyl ester

This paper describes the total synthesis of the hydrochloride salts of (2S)-2-amino-7-methoxytetralin (21-HCl) and (2S)-2-amino-6-fluoro-7- methoxytetralin (ST1214), from a common enantiomerically pure aziridine 4b, which was available from l-aspartic acid β-tert-butyl ester. The synthesis of 21-HCl and ST1214 proceeded in nine steps and 5 and 6% overall yields, respectively. Key steps are the regioselective ring-opening of 4b with ArMgBr/CuBr·SMe2 and the intramolecular Friedel-Crafts cyclisation providing α-tetralone. Substituted naphthalenes were formed as side products in the latter reaction.

CASPASE INHIBITORS BASED ON PYRIDAZINONE SCAFFOLD

The present invention relates to a pyridazinone derivative which can be used as a caspase inhibitor, process for the preparation thereof, and pharmaceutical composition for inhibiting caspase comprising the same.

Towards a biomimetic synthesis of barrenazine A

We report herein a concise and biomimetic synthesis of a precursor of barrenazine A, a cytotoxic alkaloid. The C2-symmetry of this molecule suggested the dimerization of an aminoketone, as the precursor of the central core pyrazine. This compou

(Substituted)acyl dipeptidyl inhibitors of the ICE/ced-3 family of cysteine proteases

This invention is directed to novel (substituted)acyl dipeptidyl ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of pa

N- and C-terminal modifications of negamycin

Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected β-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50=2.3 μM), has antibacterial activity (Escherichia coli, MIC=16 μg/mL), and is efficacious in an E. coli murine septicemia model (ED50=16.3 mg/kg).

Aspartame analogues containing 1-amino-2-phenylcyclohexanecarboxylic acids (c6Phe)

This report describes the synthesis and the conformational analysis of the optically pure dipeptides analogues of aspartame: H-(S)-Asp-(1R,2R)-c6Phe-OMe and H-(S)-Asp-(1S,2S)-c6Phe-OMe, in which the Phe residue of aspartame has been replaced by a restricted Phe with a cyclohexane skeleton: 1-amino-2-phenylcyclohexanecarboxylic acid (c6Phe). Of these, only the dipeptide that incorporates (1R,2R)-c6Phe is sweet, whereas that incorporates (1S,2S)-c6Phe is bitter. This relationship between the absolute configuration of the dipeptides and the properties is explained through the different conformational behaviour displayed by each molecule, based on molecular mechanics and molecular dynamics calculations, including solvent effects.

An efficient stereoselective synthesis of [3S(1S,9S)]-3-[[[9- (benzoylamino)octahydro-6,10-dioxo-6H-pyridazino-(1,2-a)(1,2)-diazepin-1- yl]-carbonyl]amino]-4-oxobutanoic acid, an interleukin converting enzyme (ICE) inhibitor

The title compound 1 is a potent interleukin-1β-converting enzyme (ICE) inhibitor. Recently, an efficient chiral synthesis of compound 1 has been accomplished in our labs. The overall yield of this 18-step stereoselective synthesis was 9.8%.

NAcSDKP analogues resistant to angiotensin-converting enzyme

Two series of analogues of the tetrapeptide NAcSDKP, an inhibitor of hematopoietic stem cell proliferation, were prepared, and their enzymatic stability toward rabbit lung angiotensin-converting enzyme (ACE) was evaluated as well as their capacity to inhibit NAcSDKP hydrolysis by this enzyme. In the first series, each of the peptide bonds has been successively replaced by an aminomethylene bond. In the second one, the C-terminus of the peptide has been modified by decarboxylation or amidation. The results reported here indicate that all of these molecules but one have good stability toward the enzyme but none of the compounds is able to inhibit NAcSDKP hydrolysis by ACE.

Synthesis of (3R)- and (3S)-3,4-diamino-butyric acid from L-aspartic acid

A short and convenient synthesis for both enantiomers of GABOB amino-analogue 1a,b is reported, starting from L-aspartic acid. The protected diester 3 is the common intermediate for the synthetic pathway.