6949-77-5

Usage

Uses

Used in Pharmaceutical Synthesis:
1-AMINO-1-CYCLOHEPTANECARBOXYLIC ACID is used as a building block for the synthesis of chlamydocin-hydroxamic acid analogs, which possess histone deacetylase inhibitory activities. These analogs have potential applications in the treatment of various diseases, including cancer, by modulating gene expression and cellular processes.
Used in Chemical Synthesis:
1-AMINO-1-CYCLOHEPTANECARBOXYLIC ACID is also used to prepare imidazobioxazolium triflates, which serve as precursors for sterically hindered and electron-donating N-heterocyclic carbene ligands. These ligands are important in various chemical reactions and catalysis processes, contributing to the development of new materials and compounds with diverse applications.

InChI:InChI=1/C8H15NO2/c9-8(7(10)11)5-3-1-2-4-6-8/h1-6,9H2,(H,10,11)

Upstream product

• 707-16-4 1,3-diaza-spiro[4.6]undecane-2,4-dione 
• 7647-01-0 hydrogenchloride 
• 502-42-1 cycloheptanone 
• 773837-37-9 sodium cyanide 
• 123193-99-7 1-aminocycloheptanecarbonitrile 

Downstream Products

• 92398-50-0 methyl 1-amino-cycloheptanecarboxylate hydrochloride 
• 197794-44-8 1-Benzyloxycarbonylamino-cycloheptanecarboxylic acid 
• 199330-56-8 1-(tert-butoxycarbonylamino) cycloheptanecarboxylic acid 
• 188751-56-6 Fmoc-1-aminocycloheptane-1-carboxylic acid 
• 183429-63-2 C₉H₁₇NO₂ 
• 94460-89-6 1-(1,3-dioxoisoindolin-2-yl)cycloheptane-1-carboxylic acid 
• 912771-18-7 1-(3-fluorobenzamido)cycloheptanecarboxylic acid 
• 7690-59-7 3-oxa-1-azaspiro[4.6]undecane-2,4-dione 
• 1269074-85-2 3-(2-chloro-4-nitrophenyl)-1,3-diazaspiro[4.6]undecane-2,4-dione 
• 92398-64-6 N-(benzyloxycarbonyl)-β-benzyl-L-aspartyl-α-aminocycloheptanecarboxylic acid methyl ester 
• 814254-62-1 (1-aminocycloheptyl)methanol 

Relevant academic research and scientific papers

Remote Amino Acid Recognition Enables Effective Hydrogen Peroxide Activation at a Manganese Oxidation Catalyst

Precise delivery of a proton plays a key role in O2 activation at iron oxygenases, enabling the crucial O?O cleavage step that generates the oxidizing high-valent metal–oxo species. Such a proton is delivered by acidic residues that may either

General Access to Modified α-Amino Acids by Bioinspired Stereoselective γ-C?H Bond Lactonization

α-Amino acids represent a valuable class of natural products employed as building blocks in biological and chemical synthesis. Because of the limited number of natural amino acids available, and of their widespread application in proteomics, diagnosis, drug delivery and catalysis, there is an increasing demand for the development of procedures for the preparation of modified analogues. Herein, we show that the use of bioinspired manganese catalysts and H2O2 under mild conditions, provides access to modified α-amino acids via γ-C?H bond lactonization. The system can efficiently target 1°, 2° and 3° γ-C?H bonds of α-substituted and achiral α,α-disubstituted α-amino acids with outstanding site-selectivity, good to excellent diastereoselectivity and (where applicable) enantioselectivity. This methodology may be considered alternative to well-established organometallic procedures.

Design and Synthesis of Fsp3-Rich, Bis-Spirocyclic-Based Compound Libraries for Biological Screening

The exploration of innovative chemical space is a critical step in the early phases of drug discovery. Bis-spirocyclic frameworks occur in natural products and other biologically relevant metabolites and show attractive features, such as molecular compactness, structural complexity, and three-dimensional character. A concise approach to the synthesis of bis-spirocyclic-based compound libraries starting from readily available commercial reagents and robust chemical transformations has been developed. A number of novel bis-spirocyclic scaffold examples, as implemented in the European Lead Factory project, is presented.

Two methods for spirothiohydantoin synthesis

Two methods for spirothiohydantoin synthesis are presented. The title compounds were prepared with reaction of the corresponding 1- aminocycloalkanecarboxylic acids and thiourea. These compounds were also prepared by a hydrolysis of the relevant spirodithiohydantoins with barium hydroxide. The structures of the compounds obtained were verified by comparison of 1H, and 13C NMR, IR and MS spectral data.

Microwave-assisted synthesis of cycloalkanespirohydantoins and piperidinespirohydantoins as precursors of restricted α-amino acids

Cycloalkanespirohydantoins 3 and piperidinespirohydantoins 4 were synthesized from cycloalkanones 9 and piperidones 10 under microwave-assisted conditions. Results are compared with those obtained under thermal conditions. Cycloalkanespirohydantoins 3 were N-protected with Boc group and hydrolyzed under basic conditions to obtain five, six and seven-membered ring restricted α-amino acids 12 in very good overall yields (76-94%). ARKAT USA, Inc.

Novel N-(phosphonomethyl) glycine derivatives: Design, characterization and biological activity

A series of Cα,α-disubstituted cyclic derivatives of N-(phosphonomethyl) glycine have been synthesized and characterized. They exhibited moderate clastogenicity, low antiproliferative activity on mice bone marrow cells and well expressed cytotoxicity against human tumor cell lines. The 8- and 12-membered cyclic analogs proved superior to the remaining compounds and were found to trigger apoptotic cell death in DOHH-2 cells. The latter compound caused 50% inhibition of the viability of hemobastose-derived cell lines at concentrations ranging from 20 to 67 μM.

Conformational restriction through Cai ? Cai cyclization: 1-aminocycloheptane-1-carboxylic acid (Ac7c)

A complete series of N- and C-blocked, monodispersed homo-oligopeptides to the pentamer level from 1-aminocycloheptane-1-carboxylic acid (Ac7c), an α-amino acid conformationally restricted through Cai ? Cai cyclization, and three tripeptides with Ac7c combined with Ala, Leu, and Val residues have been synthesized by solution methods and fully characterized. The solution conformational preferences have been determined by IR absorption and 1H NMR spectroscopy. In addition, the molecular structures of three derivatives (Ac7c hydantoin, ClCH2CO-Ac7c-OH, and Z-Ac7c-OH; Z = benzyloxycarbonyl) and four peptides [the dipeptide Z-Ac7c-L-Ala-OMe, the tripeptides Z-Ac7c-(L-Ala)2-OMe and Z-(Ac7c)3-OBut, the tetrapeptide Z-(Ac7c)4-OBut, and the pentapeptide Z-(Ac7c)5-OBut] have been assessed in the crystal state by X-ray diffraction. The results obtained confirm the tentative conclusions put forward on the basis of our previous preliminary study, namely that β-bends and 310-helices are preferentially adopted by Ac7c-based peptides. A comparison with the structural tendencies extracted from published work on peptides from α-aminoisobutyric acid, the prototype of Cα,α-dialkylated glycines, and the other extensively investigated members of the class of 1-aminocycloalkane-1-carboxylic acids (Acnc, with n = 3-6, 8, 9) is made and the implications for the use of the Ac7c residue in conformationally constrained analogues of bioactive peptides are briefly discussed.

Hydrogen-bonded tapes based on symmetrically substituted diketopiperazines: A robust structural motif for the engineering of molecular solids

A series of eight symmetrically substituted diketopiperazines (DKPs) derived from 1-amino-1-carboxycycloalkanes (n = 3-7; 3,3,5,5-tetramethylcyclohexane; 4,4-dimethylcyclohexane; 2-indan) were synthesized and their crystal structures determined. In the solid state, all eight compounds form two pairs of hydrogen bonds with two adjacent molecules to form a one-dimensional structure that we refer to as 'tapes'. These molecules represent a range of volumes and shapes that contain a common molecular fragment (DKP ring). We examined this series of compounds with three objectives in mind: (i) to establish the ability of the hydrogen-bonded 'tape' motif to persist through these differences in volume and shape; (ii) to provide a series of structurally related compounds to use to test computational methods of predicting crystal structure from molecular structure; (iii) to search for qualitative correlations between molecular structure and crystal packing. All compounds form tapes and with one exception, all tapes pack with their long axes parallel. When viewed down their long axis, two types of tapes emerge: planar and nonplanar. The type of tape that forms reflects the conformation adapted by the DKP ring-planar or boat. Planar tapes form when the angle (α) between the two planes defined by the cis-amides in the DKP ring is 180°; nonplanar tapes form when α 180°. Five of the eight compounds studied form planar tapes, the remaining three compounds form nonplanar tapes. Despite the variability in volume and shape represented by this series of molecules, the persistence of the tape motif in their crystalline solids suggests that the hydrogen-bonding interactions between parallel alignment of tapes that pack in a manner that permits the interdigitation of substituents on adjacent tapes.

Synthesis and tumorinhibiting activity of lanthanum(III) complexes with some 1-aminocycloalkancarboxylic acids

Complexes of La(III) with 1-aminocyclopentane-, -hexane, -heptane and -4-ethylcyclohexanecarboxylic acids were obtained. The compounds were characterized by elemental analyses, IR spectroscopy and conductivity measurements. The following general formula was derived: LaL3Cl3·5 H2O, where L is the corresponding 1-aminocycloalkanecarboxylic acid. The pharmacological studies showed that all complexes manifested higher cytostatic and cytotoxic effects in comparison with lanthanum chloride. Much higher cytotoxic (anti-P388/D1) and cytostatic (anti-L-1210 and antimelanoma-B16) activity was found for the lanthanum complex with 1-aminocyclopentanecarboxylic acid.

Peptide Sweeteners. 6. Structural Studies on the C-Terminal Amino Acid of L-Aspartyl Dipeptide Sweeteners

Stereochemical and structural aspects of the variations in the C-terminal residue of L-aspartyl-L-phenylalanine methyl ester have been investigated.Novel configurational analogues such as L-aspartyl-D-alanine benzyl ester and L-aspartyl-D-α-aminobutyric acid benzyl ester were found to be sweet.In addition, chiral and achiral α,α-dialkylglycine and α-aminocycloalkanecarboxylic acids were incorporated into the dipeptides.The L-aspartic acid based dipeptide derivatives of α-aminoisobutyric acid methyl ester, α-aminocyclopropanecarboxylic acid methyl ester, α-aminocyclobutanecarboxylic acid methyl ester, and α-aminocyclopentanecarboxylic acid methyl ester are sweet.Dipeptides with α-aminocyclohexanecarboxylic acid methyl ester and α-aminocycloheptanecarboxylic acid methyl ester are bitter, whereas the analogues with α-aminocyclooctanecarboxylic acid methyl ester, α,α-diethylglycine methyl ester, and α-aminoisobutyric acid benzyl ester are tasteless.Aspects on chirality and effective volume of the C-terminal residue are discussed and correlated with taste.