184576-10-1

Basic information

• Product Name: (S)-4-benzyloxycarbonylaminoacetyl-3-(3-tert-butoxycarbonylaminopropyl)-2-oxopiperazine-1-acetic acid tert-butyl ester
• Synonyms: (S)-4-benzyloxycarbonylaminoacetyl-3-(3-tert-butoxycarbonylaminopropyl)-2-oxopiperazine-1-acetic acid tert-butyl ester
• CAS NO: 184576-10-1
• Molecular Weight: 562.663
• Mol File: 184576-10-1.mol

Chemical Properties

• CAS DataBase Reference: (S)-4-benzyloxycarbonylaminoacetyl-3-(3-tert-butoxycarbonylaminopropyl)-2-oxopiperazine-1-acetic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-benzyloxycarbonylaminoacetyl-3-(3-tert-butoxycarbonylaminopropyl)-2-oxopiperazine-1-acetic acid tert-butyl ester(184576-10-1)
• EPA Substance Registry System: (S)-4-benzyloxycarbonylaminoacetyl-3-(3-tert-butoxycarbonylaminopropyl)-2-oxopiperazine-1-acetic acid tert-butyl ester(184576-10-1)

Safety Data

• Hazardous Substances Data: 184576-10-1(Hazardous Substances Data)

Upstream product

• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 184576-06-5 tert-butyl 2-[(3S)-3-[3-[(tert-butoxycarbonyl)amino]propyl]-2-oxopiperazinyl]acetate 
• 247068-71-9 benzyl (2S)-2-[3-[(tert-butoxycarbonyl)amino]propyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxo-3,4-dihydro-1(2H)-pyrazinecarboxylate 

Downstream Products

• 184576-16-7 2-[(3S)-4-[2-[(benzyloxycarbonyl)amino]acetyl]-3-[3-[[6-[(tert-butoxycarbonyl)amino]hexanoyl]amino]propyl]-2-oxopiperazinyl]acetic acid 
• 184575-70-0 (S)-4-(4-Amidinobenzoylamino)acetyl-3-[3-(4-guanidinobenzoylamino)]propyl-2-oxopiperazine-1-acetic acid trifluoroacetate 
• 184576-42-9 (S)-4-(N-benzyloxycarbonylamino)acetyl-3-(3-benzyloxycarbonylamino)propyl-2-oxopiperazine-1-acetic acid 
• 356535-22-3 2-[(3S)-4-[2-[(benzyloxycarbonyl)amino]acetyl]-3-[3-[[4-[2-[(tert-butoxycarbonyl)amino]ethyl]benzoyl]amino]propyl]-2-oxopiperazinyl]acetic acid 
• 184576-17-8 (S)-4-benzyloxycarbonylaminoacetyl-3-{3-(5-tert-butoxycarbonylaminopentanoylamino)propyl}-2-oxopiperazine-1-acetic acid 
• 356535-18-7 2-[(3S)-4-[2-[(benzyloxycarbonyl)amino]acetyl]-3-[3-[(4-guanidinobenzoyl)amino]propyl]-2-oxopiperazinyl]acetic acid 
• 184576-18-9 (S)-4-benzyloxycarbonylaminoacetyl-3-{3-(4-tert-butoxycarbonylaminobutanoylamino)-propyl)-2-oxopiperazine-1-acetic acid 
• 184576-31-6 2-[(3S)-3-[3-[(4-amidinobenzoyl)amino]propyl]-4-[2-[(benzyloxycarbonyl)amino]acetyl]-2-oxopiperazinyl]acetic acid 
• 221687-50-9 (S)-[4-(benzyloxycarbonylamino)-acetyl-3-{3-(4-guanidinobutyrylamino)-propyl}-2-oxopiperazin-1-yl]-acetic acid 

Relevant articles and documents

Potent dibasic GPIIb/IIIa antagonists with reduced prolongation of bleeding time: Synthesis and pharmacological evaluation of 2-oxopiperazine derivatives

A series of 2-oxopiperazine derivatives, possessing basic moieties at the 3- and the 4-positions, were synthesized and evaluated for their abilities to inhibit platelet aggregation and for their effects on bleeding time. Among the compounds, 2-[(3S)-4-[2-[(4-guanidinobenzoyl)amino] acetyl]3-[3-[(4-guanidinobenzoyl)amino]propyl]-2-oxopiperazinyl]acetic acid (12c) showed a potent inhibitory effect on platelet aggregation and good dissociation between the efficacy and the bleeding side effect. Intravenous infusion of compound 12c at 1.6 μg/mL/min. completely prevented arterial thrombus formation induced by endothelial injury in guinea pigs. The dose of 12c that prolonged the bleeding time to three times the control value was 5.8/μg/mL/min. These results suggest that compound 12c might be useful in the clinical treatment of thrombotic diseases, and we selected 12c (TAK-024) as a candidate for the clinical trials.

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