273206-92-1

Basic information

• Product Name: 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,
• Synonyms: tert-Butyl rel-(1R,5S,6S)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate;(1α,5α,6α)-6-AMino-3-azabicyclo[3.1.0]hexane-3-carboxylic Acid 1,1-DiMethylethyl Ester;exo-6-Amino-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester;3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6-amino-, 1,1-dimethylethyl ester, (1alpha,5alpha,6alpha)-;tert-butyl (1S,5R)-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate;tert-butyl (exo-6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate;trans-tert-butyl 6-amino-3-azabicyclo[3.1.0]hexane-3-carboxylate;exo-6-Amino-3-Boc-3-azabicyclo[3.1.0]hexane
• CAS NO: 273206-92-1
• Molecular Formula: C10H18N2O2
• Molecular Weight: 198.27
• Product Categories: AMINOACID
• Mol File: 273206-92-1.mol

Chemical Properties

• Boiling Point: 275℃
• Flash Point: 120℃
• Appearance: /
• Density: 1.144
• Vapor Pressure: 0.000827mmHg at 25°C
• Refractive Index: 1.512
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 8.52±0.20(Predicted)
• CAS DataBase Reference: 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,(273206-92-1)
• EPA Substance Registry System: 3-Azabicyclo[3.1.0]hexane-3-carboxylicacid,6-amino-,1,1-dimethylethylester,(273206-92-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 273206-92-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Azabicyclo[3.1.0]hexane-3-carboxylic acid, 6-amino-, 1,1-dimethylethyl ester, is used as an intermediate in the synthesis of novel Histone Deacetylase (HDAC) inhibitors. These inhibitors demonstrate class I selectivity and good oral bioavailability, making them promising candidates for the treatment of various diseases, including cancer.
Additionally, this compound is used in the synthesis of Alatrofloxacin Mesylate (A511400), a potent antibiotic with potential applications in treating bacterial infections. Its role in the development of new antibiotics highlights its importance in the pharmaceutical industry, where the need for novel and effective treatments is constantly growing.

InChI:InChI=1/C10H18N2O2/c1-10(2,3)14-9(13)12-8-6-4-11-5-7(6)8/h6-8,11H,4-5H2,1-3H3,(H,12,13)/t6-,7+,8+

Upstream product

• 497163-57-2 tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 1256448-51-7 tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 914937-14-7 tert-butyl 6-nitro-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 151860-15-0 (1α,5α,6α)-3-N-benzyl-6-nitro-2,4-dioxo-3-azabicyclo[3.1.0]hexane 
• 151860-16-1 (1α,5α,6α)-3-N-benzyl-6-nitro-3-azabicyclo[3.1.0]hexane 

Downstream Products

• 1352926-02-3 tert-butyl (2R,5S)-6-(methylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1191068-23-1 N-3-aza-bicyclo[3.1.0]hex-6-yl-4-{[(4-ethoxybenzenesulfonyl)pyridin-2-ylmethylamino]methyl}benzamide 
• 1003946-73-3 benzyl (1R,5S,6s)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate 
• 1612172-56-1 benzyl N-((1R,5S,6s)-3-(4-((1-isopropyl-1H-imidazo[4,5-c]pyridin-6-yl)amino)pyrimidin-2-yl)-3-azabicyclo[3.1.0]hexan-6-yl)carbamate 
• 1612172-51-6 (1R_.5S_.6s)-tert-butyl 6-(((benzyloxy)carbonyl)(methyl)amino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 1003946-86-8 (1R_.5S_.6s)-tert-butyl 6-(((benzyloxy)carbonyl)amino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 

Relevant articles and documents

Practical Synthesis of a 6-Triazolylazabicyclo[3.1.0]hexane

We describe a practical, scalable synthesis of an advanced heterocyclic intermediate, (1R,5S,6s)-6-(4H-1,2,4-triazol-4-yl)-3-azabicyclo[3.1.0]hexane. A robust synthetic sequence based on a Kulinkovich-de Meijere pyrroline cyclopropanation followed by tran

Discovery of 2-(6-{[(6-Fluoroquinolin-2-yl)methyl]amino}bicyclo[3.1.0]hex- 3-yl)- N -hydroxypyrimidine-5-carboxamide (CHR-3996), a class i selective orally active histone deacetylase inhibitor

A novel series of HDAC inhibitors demonstrating class I subtype selectivity and good oral bioavailability is described. The compounds are potent enzyme inhibitors (IC50 values less than 100 nM), and improved activity in cell proliferation assays was achieved by modulation of polar surface area (PSA) through the introduction of novel linking groups. Employing oral pharmacokinetic studies in mice, comparing drug levels in spleen to plasma, we selected compounds that were tested for efficacy in human tumor xenograft studies based on their potential to distribute into tumor. One compound, 21r (CHR-3996), showed good oral activity in these models, including dose-related activity in a LoVo xenograft. In addition 21r showed good activity in combination with other anticancer agents in in vitro studies. On the basis of these results, 21r was nominated for clinical development.

2-AMINO PYRIDINE COMPOUNDS

The present invention is directed to 2-aminopyrimidine compounds and pharmaceutically acceptable salts thereof, their synthesis and their use as HSP-90 inhibitors.

HISTONE DEACETYLASE INHIBITORS

Compounds of formula: (I), and salts, N-oxides, hydrates and solvates thereof are histone deacetylase inhibitors and are useful in the treatment of cell proliferative diseases, including cancers: (I) wherein Q, V and W independently represent -N= or -C=;

Mono- and disubstituted N,N-dialkylcyclopropylamines from dialkylformamides via ligand-exchanged titanium - Alkene complexes

Dibenzylformamide was treated with cyclohexylmagnesium bromide in the presence of either titanium tetraisopropoxide or methyltitanium triisopropoxide and a variety of cyclic and acyclic alkenes and alkadienes to give new mono- and disubstituted as well as bicyclic dialkylcyclopropylamines (Tables 1-3) in yields ranging from 18 to 90% (in most cases around 55%). 3-Benzyl-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane (10a) and the orthogonally bisprotected 3-tert-butoxycarbonyl-6-(N,N-dibenzyl)- 3-azabicyclo[3.1.0]hexane (10d) as well as the analogous 6-(N,N-dibenzylamino)bicyclo[3.1.0]hexane (12) were obtained as pure exo diastereomers in particularly high yields (87, 90, and 88%, respectively) from N-benzylpyrroline (15a), N-Boc-pyrroline (15d; Boc = tert-butyloxycarbonyl) and cyclopentene (19). 1,3-Butadiene (52) and substituted 1,3-butadienes were also aminocyclopropanated quite well to give 2-ethenylcyclopropylamines in good yields (51-64%). Except for alkenyl and aryl-substituted compounds, N,N-dibenzylcyclopropylamines can be debenzylated by catalytic hydrogenation to the primary cyclopropylamines as demonstrated for 10a and 10d to yield the fully deprotected 10e (93%) and mono-Boc-protected 10f (98%), respectively. The latter are interesting templates for combinatorial syntheses of libraries of small molecules with a well defined distance of 4.3 A between two nitrogen atoms.