160801-72-9

Basic information

• Product Name: Carbamic acid, [(1S)-1-[(methoxymethylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester
• CAS NO: 160801-72-9
• Molecular Formula: C11H22N2O4
• Molecular Weight: 246.307
• Mol File: 160801-72-9.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [(1S)-1-[(methoxymethylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [(1S)-1-[(methoxymethylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester(160801-72-9)
• EPA Substance Registry System: Carbamic acid, [(1S)-1-[(methoxymethylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester(160801-72-9)

Safety Data

• Hazardous Substances Data: 160801-72-9(Hazardous Substances Data)

Usage

General Description

Carbamic acid, [(1S)-1-[(methoxymethylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester is a chemical compound that is commonly used as a pesticide and herbicide. It is typically applied to crops and plants to control pests and weeds. Carbamic acid, [(1S)-1-[(methoxymethylamino)carbonyl]propyl]-, 1,1-dimethylethyl ester is also known to have potential health hazards and can be harmful if ingested, inhaled, or comes into contact with the skin. It is important to handle and store this chemical with caution to avoid any adverse effects on human health and the environment.

Upstream product

• 34306-42-8 Boc-Abu 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 530-62-1 1,1'-carbonyldiimidazole 
• 24424-99-5 di-tert-butyl dicarbonate 
• 1117-97-1 N,0-dimethylhydroxylamine 

Downstream Products

• 208520-68-7 N2-[N-[N-[N-[N-[3-(tert-butoxycarbonyl)-propionyl]-O-tert-butyl-L-α-aspartyl]-O-tert-butyl-L-α-glutamyl]-2-methyl-L-phenylalanyl]-3-methyl-L-valyl]-N1-[1(S)-(dimethoxymethyl)propyl]-L-leucinamide 
• 1466566-11-9 (S)-3-(1-aminopropyl)-8-chloro-2-phenylisoquinolin-1(2H)-one 
• 304021-05-4 (S)-tert-butyl (2-oxopentan-3-yl)carbamate 
• 440125-16-6 1(S)-(2-cyano-1-ethyl-2-hydroxyethyl)carbamic acid tert-butyl ester 
• 911470-51-4 (Z)-(S)-2-Benzyloxycarbonylamino-4-tert-butoxycarbonylamino-hex-2-enoic acid methyl ester 
• 153371-25-6 (2S)-2-(tert-butoxycarbonyl)aminobutyraldehyde 

Relevant articles and documents

Defining the Determinants of Specificity of Plasmodium Proteasome Inhibitors

The Plasmodium proteasome is an emerging antimalarial target due to its essential role in all the major life cycle stages of the parasite and its contribution to the establishment of resistance to artemisinin (ART)-based therapies. However, because of a similarly essential role for the host proteasome, the key property of any antiproteasome therapeutic is selectivity. Several parasite-specific proteasome inhibitors have recently been reported, however, their selectivity must be improved to enable clinical development. Here we describe screening of diverse libraries of non-natural synthetic fluorogenic substrates to identify determinants at multiple positions on the substrate that produce enhanced selectivity. We find that selection of an optimal electrophilic "warhead" is essential to enable high selectivity that is driven by the peptide binding elements on the inhibitor. We also find that host cell toxicity is dictated by the extent of coinhibition of the human β2 and β5 subunits. Using this information, we identify compounds with over 3 orders of magnitude selectivity for the parasite enzyme. Optimization of the pharmacological properties resulted in molecules that retained high potency and selectivity, were soluble, sufficiently metabolically stable and orally bioavailable. These molecules are highly synergistic with ART and can clear parasites in a mouse model of infection, making them promising leads as antimalarial drugs.

Preparation and biological evaluation of soluble tetrapeptide epoxyketone proteasome inhibitors

A series of novel tetrapeptidyl epoxyketone inhibitors of 20S proteasome was designed and synthesized. To fully understand the SAR, various groups at R1, R2, R3, R4 and R5 positions, including aromatic and aliphatic substituents were designed, synthesized and biologically assayed. Based on the enzymatic results, seven compounds were selected to evaluate their cellular activities and soluble compound 36 showed strong potency against human multiple myeloma (MM) cell lines. Microsomal stability results indicated that compound 36 was more stable in mice, rat and human microsomes than marketed carfilzomib. The in vivo activities of this compound were evaluated with the xenograft mice models of MM cell lines ARH77 and RPMI-8226 with luciferase expression and the T/C value of the two models were 49.5% and 37.6%, respectively. To evaluate the potential cardiovascular toxicity, inhibition of hERG ion channel in HEK293 cells by compound 36 and carfilzomib was carried out. The results indicated that 36 had no binding affinity for the hERG ion channel while carfilzomib could bind it with IC50 of 92.1 μM.

The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement

An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.