359782-00-6

Basic information

• Product Name: (3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one
• Synonyms: (3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one;2H-Azepin-2-one, hexahydro-3-[(2-methylpropyl)amino]-, (3S)-
• CAS NO: 359782-00-6
• Molecular Formula: C₁₀H₂₀N₂O
• Molecular Weight: 184.28
• Mol File: 359782-00-6.mol

Chemical Properties

• Melting Point: 52-54 ºC
• Boiling Point: 341.2±35.0 °C(Predicted)
• Appearance: /
• Density: 0.97
• Refractive Index: 1.479
• PKA: 16.15±0.40(Predicted)
• CAS DataBase Reference: (3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one(359782-00-6)
• EPA Substance Registry System: (3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one(359782-00-6)

Safety Data

• Hazardous Substances Data: 359782-00-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one is used as an intermediate in the synthesis of pharmaceuticals for its potential pharmacological properties. Its unique structure and chirality allow for the development of new drugs with specific therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, (3S)-Hexahydro-3-[(2-methylpropyl)amino]-2H-azepin-2-one serves as a versatile building block for the creation of various organic compounds. Its cyclic amine and ketone functional groups enable it to participate in a wide range of chemical reactions, facilitating the synthesis of complex molecules with diverse applications.

InChI:InChI=1/C10H20N2O/c1-8(2)7-12-9-5-3-4-6-11-10(9)13/h8-9,12H,3-7H2,1-2H3,(H,11,13)/t9-/m0/s1

Upstream product

• 78-84-2 isobutyraldehyde 
• 21568-87-6 2-aminocaprolactam 

Downstream Products

• 938193-48-7 C₁₉H₂₉N₃O₂ 
• 449806-97-7 Nα-isobutyl-Nα-(4-acetamidobenzenesulfonyl)-L-α-amino-ε-caprolactam 
• 359782-01-7 N-isobutyl-4-nitro-N-(2-oxo-azepan-3-yl)-benzenesulfonamide 
• 449806-65-9 N-isobutyl-4-methyl-N-(2-oxo-azepan-3-yl)-benzenesulfonamide 
• 449807-06-1 N-isobutyl-N-(2-oxo-azepan-3-yl)-benzenesulfonamide 
• 900187-22-6 (1-S)-{4-[(5-tert-butoxycarbonylamino-1-hydroxymethyl-pentyl)-isobutyl-sulfamoyl]-phenyl}-carbamic acid tert-butyl ester 
• 874339-75-0 (3S)-3-{[4-(acetyl-tert-butoxycarbonyl-amino)-benzenesulfonyl]-isobutyl-amino}-2-oxo-azepane-1-carboxylic acid tert-butyl ester 
• 612547-11-2 (1S,5S)-(1-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexylcarbamoyl}-2,2-diphenyl-ethyl)-carbamic acid methyl ester 

Relevant articles and documents

Protease Inhibitors

The present invention provides HIV protease inhibitors of formulas I, IA, IB, Ib or II, or pharmaceutically acceptable salts thereof, wherein R2 may be, for example, 2-pyridyl-CH2—, 3-pyridyl-CH2—, 4-pyridyl-CH2—, a sulfonyl group as described in the formulas herein including benzenesulfonyl or thiophenesulfonyl groups, R2a—CO)—, R2a being selected from the group consisting of piperonyl, 2-pyranzinyl (unsubstituted or substituted with H, or an alkyl of 1 to 4 carbon atoms) or a picolylamine group as described herein, wherein R3 may be, for example, a phenyl group or diphenylmethyl group as described herein, and wherein Cx may be, for example, COOH, CONR5R6, CH2OH or CH2OR7.

LYSINE-BASED PRODRUGS OF ASPARTYL PROTEASE INHIBITORS AND PROCESSES FOR THEIR PREPARATION

The present invention provides processes for synthesizing lysine based compounds of the Formula (I); wherein R1 may be, for example, (HO)2P(O)-, (NaO)2P(O)-, wherein X may be, for example, NH2, Y may be H, F, Cl, or Br, and wherein n, X', Y', R2, R3, R4, R5 and R6 are as defined herein.

Lysine sulfonamides as novel HIV-protease inhibitors: Nε-Acyl aromatic α-amino acids

A series of lysine sulfonamide analogues bearing Nε-acyl aromatic amino acids were synthesized using an efficient synthetic route. Evaluation of these novel protease inhibitors revealed compounds with high potency against wild-type and multiple-protease inhibitor-resistant HIV viruses.

LYSINE BASED COMPOUNDS

The present invention provides lysine based compounds of the formula (I); and when the compound of formula (I) comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein Rl may be, for example, (HO)2P(O)-, (NaO)2P(O)-, alkyl-CO- or cycloalkyl-CO-, wherein X may be, for example, F, Cl, and Br, and wherein R2 and R3 are as defined herein. These lysine based compounds have a physiologically cleavable unit, namely R1 , whereby upon cleavage of the unit, an HIV aspartyl protease inhibitor is released,

Lysine based compounds

The present invention provides lysine based compounds of the formula; and when the compound of formula I comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein R1 may be, for example, (HO)2P(O)—, (NaO)2P(O)—, alkyl-CO— or cycloalkyl-CO—, wherein X may be, for example, F, Cl, and Br, and wherein R2 and R3 are as defined herein.

METHOD FOR IMPROVING PHARMACOKINETICS OF PROTEASE INHIBITORS AND PROTEASE INHIBITOR PRECURSORS

The present invention provides methods for improving the pharmacokinetics of protease inhibitors and protease inhibitor precursors and pharmaceutical composition comprising protease inhibitors or protease inhibitor precursors of formula I and a cytochrome P450 monooxigenase inhibitor; Formula (I) when the compound of formula I comprises an amino group, pharmaceutically acceptable ammonium salts thereof, wherein R1 may be, for example, (HO)2P(O)-, (NaO)2P(O)-, alkyl- CO- or cycloalkyl-CO-, wherein X may be, for example, F, CI, and Br, and wherein R2 and R3 are as defined herein.

Lysine derivatives as potent HIV protease inhibitors. Discovery, synthesis and structure-activity relationship studies

A screening assay program on HIV-protease was carried out on more than fifty commercially available N-protected amino acids and has revealed that those with a long side chain such as lysine, ornithine and arginine exhibited significant inhibition of HIV protease enzyme. The presence of an Fmoc group was found to be essential to obtain micromolar inhibitors and the addition of an alkyl group at the Nα-position resulted in the discovery of the lead compound 11 displaying a 5 nM inhibition constant. Although this new inhibitor series is not categorized among those mimicking the substrate with a non-hydrolyzable transition-state isoster, it was found very specific to inhibit HIV protease enzyme in comparison to the mammalian aspartyl proteases pepsin, renin and cathepsin. Furthermore, these inhibitors did not show any cytotoxicity at a concentration below 75 μM.

Lysine sulfonamides as novel HIV-protease inhibitors: Nε-disubstituted ureas

A series of lysine sulfonamide analogues bearing a Nε-benzylic ureas was synthesized using both solution-phase and solid-phase approaches. A novel synthetic route of Nα-(alkyl)-Nα-(sulfonamides)lysinol using α-amino-caprolactam was developed. Evaluation of these novel protease inhibitors revealed compounds with high potency against wild-type HIV virus.