103322-56-1

Basic information

• Product Name: BOC-BETA-CYCLOHEXYL-L-ALANINOL
• Synonyms: BOC-L-CYCLOHEXYLALANINOL;BOC-CHA-OL;BOC-BETA-CYCLOHEXYL-L-ALANINOL;BOC-3-CYCLOHEXYL-L-ALANINOL;BOC-BETA-CYCLOHEXYLALANINOL;(S)-(-)-2-(TERT-BUTOXYCARBONYLAMINO)-3-CYCLOHEXYL-1-PROPANOL;N-T-BUTOXYCARBONYL-L-CYCLOHEXYLALANINOL;(s)-(-)-2-N-Bco-3-cyclohexyl-1-propanol
• CAS NO: 103322-56-1
• Molecular Formula: C₁₄H₂₇NO₃
• Molecular Weight: 257.37
• Product Categories: Amino Alcohols;Chiral Building Blocks;Organic Building Blocks
• Mol File: 103322-56-1.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 214 °C(lit.)
• Flash Point: 137 °F
• Appearance: UN 3272
• Density: 1.126 g/mL at 25 °C(lit.)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Storage Temp.: -15°C
• CAS DataBase Reference: BOC-BETA-CYCLOHEXYL-L-ALANINOL(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-BETA-CYCLOHEXYL-L-ALANINOL(103322-56-1)
• EPA Substance Registry System: BOC-BETA-CYCLOHEXYL-L-ALANINOL(103322-56-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 103322-56-1(Hazardous Substances Data)

Usage

Uses

Precursor to (S)-N-t-Boc-cyclohexylalaninal. This precursor was oxidized to the corresponding α-amino aldehyde in good yield and high optical purity.

InChI:InChI=1/C14H27NO3/c1-14(2,3)18-13(17)15-12(10-16)9-11-7-5-4-6-8-11/h11-12,16H,4-10H2,1-3H3,(H,15,17)/t12-/m0/s1

Upstream product

• 37736-82-6 (S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid 
• 121056-95-9 trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 117160-99-3 (2S)-2-amino-3-cyclohexylpropan-1-ol hydrochloride 
• 251325-59-4 (2-cyclohexyl-1-hydroxymethyl-vinyl)-carbamic acid tert-butyl ester 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 131288-67-0 (2S)-2-amino-3-cyclohexyl-1-propanol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 27527-05-5 L-cyclohexylalanine 
• 98105-41-0 methyl S-3-cyclohexyl-2-(t-butoxycarbonylamino)propionate 

Downstream Products

• 127559-35-7 Succinic acid mono-((S)-2-tert-butoxycarbonylamino-3-cyclohexyl-propyl) ester 
• 904324-62-5 [1-(5-bromo-pyridin-3-yloxymethyl)-2-cyclohexyl-ethyl]-carbamic acid tert-butyl ester 
• 943407-70-3 2-[(2S)-2-amino-3-cyclohexylpropyl]-1H-isoindole-1,3(2H)-dione 
• 1430058-94-8 2-[(2S)-2-(5-bromo-1-oxo-1,3-dihydro-2H-isoindol-2-yl)-3-cyclohexylpropyl]-1H-isoindole-1,3(2H)-dione 
• 1430058-96-0 2-{(2S)-3-cyclohexyl-2-[5-(1-methyl-1H-pyrazol-5-yl)-1-oxo-1,3-dihydro-2H-isoindol-2-yl]propyl}-1H-isoindole-1,3(2H)-dione 
• 1430057-76-3 2-[(1S)-2-amino-1-(cyclohexylmethyl)ethyl]-5-(1-methyl-1H-pyrazol-5-yl)isoindolin-1-one 
• 904324-74-9 [1-cyclohexylmethyl-2-(5-isoquinolin-6-yl-pyridin-3-yloxy)-ethyl]-carbamic acid tert-butyl ester 
• 303975-60-2 methyl (S)-4-[4-[2-(tert-butoxycarbonylamino)-3-cyclohexylpropyloxy]phenyl]benzoate 
• 253449-32-0 (S)-2-(tert-butoxycarbonylamino)-3-cyclohexylpropyl methanesulfonate 
• 139429-01-9 Thioacetic acid S-((S)-2-tert-butoxycarbonylamino-3-cyclohexyl-propyl) ester 
• 131288-67-0 (2S)-2-amino-3-cyclohexyl-1-propanol 
• 98105-42-1 (S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal 
• 129593-15-3 (-)-N-((S)-1-hydroxy-3-cyclohexylpropyl)benzamide 
• 1093865-10-1 1,1-dimethylethyl [(1S)-2-azido-1-(cyclohexylmethyl)ethyl]methylcarbamate 

Relevant articles and documents

Structure-Based Inhibitor Design for Evaluation of a CYP3A4 Pharmacophore Model

Human cytochrome P450 3A4 (CYP3A4) is a key xenobiotic-metabolizing enzyme that oxidizes and clears the majority of drugs. CYP3A4 inhibition may lead to drug-drug interactions, toxicity, and other adverse effects but, in some cases, could be beneficial and enhance therapeutic efficiency of coadministered pharmaceuticals that are metabolized by CYP3A4. On the basis of our investigations of analogs of ritonavir, a potent CYP3A4 inactivator and pharmacoenhancer, we have built a pharmacophore model for a CYP3A4-specific inhibitor. This study is the first attempt to test this model using a set of rationally designed compounds. The functional and structural data presented here agree well with the proposed pharmacophore. In particular, we confirmed the importance of a flexible backbone, the H-bond donor/acceptor moiety, and aromaticity of the side group analogous to Phe-2 of ritonavir and demonstrated the leading role of hydrophobic interactions at the sites adjacent to the heme and phenylalanine cluster in the ligand binding process. The X-ray structures of CYP3A4 bound to the rationally designed inhibitors provide deeper insights into the mechanism of the CYP3A4-ligand interaction. Most importantly, two of our compounds (15a and 15b) that are less complex than ritonavir have comparable submicromolar affinity and inhibitory potency for CYP3A4 and, thus, could serve as templates for synthesis of second generation inhibitors for further evaluation and optimization of the pharmacophore model.

ISOINDOLINONE AND PYRROLOPYRIDINONE DERIVATIVES AS AKT INHIBITORS

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