873581-17-0

Basic information

• Product Name: (2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid
• Synonyms: (2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid
• CAS NO: 873581-17-0
• Molecular Weight: 439.552
• Mol File: 873581-17-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid(873581-17-0)
• EPA Substance Registry System: (2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid(873581-17-0)

Safety Data

• Hazardous Substances Data: 873581-17-0(Hazardous Substances Data)

Usage

General Description

The chemical compound "(2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid" is a complex organic molecule consisting of various functional groups including amino, acetyl, carbonyl, and carboxylic acid groups. It is a pyrrolidine derivative with a cyclohexylacetyl side chain and a tert-butoxy protecting group. (2S)-1-[(2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetyl]pyrrolidine-2-carboxylic acid may have potential applications in pharmaceuticals or as a reagent in organic synthesis. Its precise chemical structure and composition suggest that it may have specific pharmacological, biochemical, or biophysical properties, but further research and analysis would be necessary to determine its exact functions and potential uses.

Upstream product

• 894789-27-6 (2S)-2-[(2S)-2-[[(tert-butoxy)carbonyl](methyl)amino]propanamido]-2-cyclohexylacetic acid 
• 1514923-26-2 methyl ((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-2-cyclohexylacetyl)-L-prolinate 
• 912338-14-8 methyl (2S)-2-[(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}propanamido]-2-cyclohexylacetate 
• 14328-63-3 methyl (2S)-amino(cyclohexyl)ethanoate hydrochloride 
• 16948-16-6 N-(tert-butoxycarbonyl)-N-methyl-L-alanine 
• 41324-66-7 H-Pro-OBzl 
• 109183-71-3 N-(tert-butoxycarbonyl)-L-cyclohexylglycine 

Downstream Products

• 1446183-01-2 1-[2-cyclohexyl-2-(2-methylamino-propionylamino)-acetyl]-pyrrolidine-2-carboxylic acid (2-phenyl-2H-pyrazol-3-yl)-amide 
• 1324010-58-3 C₃₀H₄₀N₄O₃ 
• 873581-49-8 tert-butyl ((S)-1-(((S)-2-((S)-2-((2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4-phenylthiazol-5-yl)carbamoyl)pyrrolidin-1-yl)-1-cyclohexyl-2-oxoethyl)amino)-1-oxopropan-2-yl)(methyl)carbamate 
• 1370605-38-1 (S)-N-(4-chlorobenzyl)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)pyrrolidine-2-carboxamide 
• 1370605-37-0 (S)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)-propanamido)acetyl)-N-(2,2-diphenylethyl)pyrrolidine-2-carboxamide 
• 873581-32-9 tert-butyl ((S)-1-(((S)-1-cyclohexyl-2-((S)-2-(fluorocarbonyl)pyrrolidin-1-yl)-2-oxoethyl)amino)-1-oxopropan-2-yl)(methyl)carbamate 

Relevant articles and documents

Design, synthesis and biological evaluation of new bivalent quinazoline analogues as IAP antagonists

We recently reported the biological evaluations of monovalent IAP antagonist 7 with good potency (MDA-MB-231, IC50 = 19 nM). In an effort to increase cellular activity and improve favorable drug-like properties, we newly designed and synthesized bivalent analogues based on quinazoline structure of 7. Optimization of cellular potency and CYP inhibition led to the identification of 27, which showed dramatic increase of over 100-fold (IC50 = 0.14 nM) and caused substantial tumor regressions in MDA-MB-231 xenograft model. These results strongly support 27 as a promising bivalent antagonist for the development of an effective anti-tumor approaches.

BIVALENT ANTAGONISTS OF INHIBITORS OF APOPTOSIS PROTEINS

The present technology is directed to compounds, compositions, and methods related to treatment of cancers and viral infections mediated by IAPs, e.g., compounds of Formula I (including Formulas IA, IB, IC, ID, IE, IF, and IG), a stereoisomer thereof, or

Discovery of a novel class of dimeric smac mimetics as potent IAP antagonists resulting in a clinical candidate for the treatment of cancer (AZD5582)

A series of dimeric compounds based on the AVPI motif of Smac were designed and prepared as antagonists of the inhibitor of apoptosis proteins (IAPs). Optimization of cellular potency, physical properties, and pharmacokinetic parameters led to the identification of compound 14 (AZD5582), which binds potently to the BIR3 domains of cIAP1, cIAP2, and XIAP (IC50 = 15, 21, and 15 nM, respectively). This compound causes cIAP1 degradation and induces apoptosis in the MDA-MB-231 breast cancer cell line at subnanomolar concentrations in vitro. When administered intravenously to MDA-MB-231 xenograft-bearing mice, 14 results in cIAP1 degradation and caspase-3 cleavage within tumor cells and causes substantial tumor regressions following two weekly doses of 3.0 mg/kg. Antiproliferative effects are observed with 14 in only a small subset of the over 200 cancer cell lines examined, consistent with other published IAP inhibitors. As a result of its in vitro and in vivo profile, 14 was nominated as a candidate for clinical development.