227626-60-0

Basic information

• Product Name: [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID
• Synonyms: 2-N-BOC-AMINOMETHYL-2-CYCLOHEXYLACETIC ACID;[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID;[1-(N-BOC-AMINOMETHYL)-CYCLOHEXYL]-ACETIC ACID;BOC-GABAPENTIN;BOC-GPN;BOC-1-AMINOMETHYL-CYCLOHEXANE ACETIC ACID;Boc-2-(1-(aMinoMethyl)cyclohexyl)acetic acid;N-rt-Butyloxycarbonyl Gabapentin
• CAS NO: 227626-60-0
• Molecular Formula: C₁₄H₂₅NO₄
• Molecular Weight: 271.35
• Product Categories: pharmacetical
• Mol File: 227626-60-0.mol

Chemical Properties

• Melting Point: 127-128 °C
• Boiling Point: 422.9°Cat760mmHg
• Flash Point: 209.6°C
• Appearance: /
• Density: 1.072g/cm³
• Vapor Pressure: 2.45E-08mmHg at 25°C
• Refractive Index: 1.478
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane
• PKA: 4.72±0.10(Predicted)
• CAS DataBase Reference: [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID(227626-60-0)
• EPA Substance Registry System: [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID(227626-60-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 227626-60-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
[1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID is used as a protected form of Gabapentin (G117250) for its ability to cross the blood-brain barrier. It serves as an anticonvulsant, which is essential in treating various neurological conditions such as epilepsy and neuropathic pain. The compound's structural similarity to γ-Aminobutyric Acid (GABA) allows it to interact with the GABAergic system, potentially enhancing its therapeutic effects.
Used in Chemical Synthesis:
Due to its unique molecular structure, [1-(TERT-BUTOXYCARBONYLAMINO-METHYL)-CYCLOHEXYL]-ACETIC ACID can be utilized as an intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity and functional groups can be exploited to create a wide range of derivatives with diverse applications.
Used in Research and Development:
The compound's structural features and potential applications make it a valuable tool for researchers in the fields of medicinal chemistry, drug discovery, and materials science. It can be used to study the interactions between molecules and biological targets, as well as to develop new methodologies for the synthesis of complex organic molecules.

InChI:InChI=1/C14H25NO4/c1-13(2,3)19-12(18)15-10-14(9-11(16)17)7-5-4-6-8-14/h4-10H2,1-3H3,(H,15,18)(H,16,17)

Upstream product

• 898552-75-5 3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester 
• 64744-50-9 gabapentin-lactam 
• 24424-99-5 di-tert-butyl dicarbonate 
• 60142-96-3 H-Gpn-OH 

Downstream Products

• 1050227-23-0 Boc-Gpn-Aib-NHMe 
• 675624-82-5 Boc-Gpn-NHMe 
• 898552-78-8 (1-diethylcarbamoylmethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester 
• 1345016-64-9 (1R₂R,1S₂S)-3-(2-((dimethylamino)methyl)-1-hydroxycyclohexyl)phenyl 2-(1-((tert-butoxycarbonylamino)methyl)cyclohexyl)acetate 
• 1554303-70-6 tert-butyl ((1-(2-(benzylamino)-2-oxoethyl)cyclohexyl)methyl)carbamate 
• 898552-80-2 N,N-diethyl-2-(1-isothiocyanatomethyl-cyclohexyl)-acetamide 
• 898552-55-1 2-{1-[2-(4-chloro-phenyl)-6-oxo-4-thioxo-6H-1-oxa-3b,5-diaza-cyclopenta[a]pentalen-5-ylmethyl]-cyclohexyl}-N,N-diethyl-acetamide 
• 925236-95-9 [1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid 3-hydroxy-2,2-dimethyl-propyl ester 
• 925236-84-6 [1-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-acetic acid 2-hydroxy-ethyl ester 

Relevant articles and documents

Structural and morphological diversity of self-assembled synthetic γ-amino acid containing peptides

Regulating the nanostructural morphology of synthetic hybrid peptides through external stimuli is still a great challenge. Here, we report the synthesis of constrained amino acid building block gabapentin (Gpn) based hybrid peptides and their structural a

Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect

An intermolecular, two-component vicinal carboimination of alkenes has been accomplished by energy transfer catalysis. Oxime esters of alkyl carboxylic acids were used as bifunctional reagents to generate both alkyl and iminyl radicals. Subsequently, addition of the alkyl radical to an alkene generates a transient radical for selective radical–radical cross-coupling with the persistent iminyl radical. Furthermore, this process provides direct access to aliphatic primary amines and α-amino acids by simple hydrolysis.

Novel cilengitide-based cyclic RGD peptides as αvβ3 integrin inhibitors

In this letter, we report a series of five new RGD-containing cyclic peptides as potent inhibitors to αvβ3 integrin protein. We have incorporated various unnatural lipophilic amino acids into the cyclic RGD framework of cilengitide, which is selective for αvβ3 integrin. All the newly synthesized cyclic peptides were evaluated in vitro solid phase binding assay and investigated for their binding behaviour towards integrin subtypes. All the cyclic peptides were synthesized in excellent yield following solution-phase coupling strategy. The cyclic RGD peptides 1a-e exhibited IC50 of 9.9, 5.5, 72, 11 and 3.3 nM, respectively, towards αvβ3 integrin protein. This finding offers further opportunities for the introduction unusual amino acids into the cyclic peptide framework of cilengitide.

Design, synthesis and anti-bacterial studies of piperazine derivatives against drug resistant bacteria

In current research, five series of mono- and di-substituted piperazine derivatives have been synthesized. For di-substituted derivatives, ciprofloxacin was selected and hybrids were synthesized via substitution at piperazinyl-N4. In vitro anti

SUBSTITUTED TRIAZOLES AND METHODS RELATING THERETO

Substituted 1,2,3-triazole compounds are disclosed which have utility in the treatment of a variety of neurological disorders. The compounds provided herein have the general structure wherein R1, R2, R3 and n are as defined herein, including stereoisomers, esters, solvates and pharmaceutically acceptable salts thereof. Also disclosed are compositions containing a compound provided herein in combination with a pharmaceutically acceptable carrier, as well as methods relating to the use thereof for treating neurological disorders in a subject in need thereof.

FUNCTIONALIZED 9-BROMO-CAMPTOTHECIN DERIVATIVES

The present invention relates to new functionalized 9-bromo-camptothecin derivatives which have cytotoxic activity and are useful in treating diseases such as cancer, cellular proliferation disorders and viral infections. The present invention also provides methods for preparing these compounds, pharmaceutical compositions comprising them and methods of treating diseases utilizing such compounds or the pharmaceutical composition containing them. The invention also relates to the use of these functionalized 9-bromo-camptothecin derivatives in the preparation of conjugates.

Gabapentin hybrid peptides and bioconjugates

Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (L-Ala-Gbp, L-Val-Gbp, L-Ala-L-Phe-Gbp, Gly-L-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.

Oxadiazolone bioisosteres of pregabalin and gabapentin

A series of oxadiazolone bioisosteres of pregabalin 1 and gabapentin 2 were prepared, and several were found to exhibit similar potency for the α2-δ subunit of voltage-gated calcium channels. Oxadiazolone 9 derived from 2 achieved low brain upt

Rigidified Compounds for Modulating Heparanase Activity

Disclosed are novel rigidified compounds having a rhodanine-like residue and at least one aryl or heteroaryl residue linked to the rhodanine-like residue, whereby a core structure of these compounds, as defined in the specification, is characterized as having one or zero free-to-rotate bonds. Also disclosed are pharmaceutical compositions containing these rigidified compounds and uses thereof for modulating the activity of heparanase and hence in the treatment of heparanase-associated diseases and disorders, and uses thereof for modulating the activity of heparin-binding proteins and hence in the treatment of heparin-binding proteins-associated diseases and disorders as well as in the treatment of medical conditions that are at least partially treatable by rhodanine or a rhodanine analog.

Prodrugs containing novel bio-cleavable linkers

The invention provides the compounds of formula (I) or pharmaceutically acceptable salts thereof. The invention also provides pharmaceutical compositions comprising one or more compounds of formula I or intermediates thereof and one more of pharmaceutically acceptable carriers, vehicles or diluents. The invention further provides methods of preparation and methods of use of prodrugs including NO-releasing prodrugs, double prodrugs and mutual prodrugs comprising the compounds of formula I.