• 1. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 2. Emerging investigator series: first-principles and thermodynamics comparison of compositionally-tuned delafossites: cation release from the (001) surface of complex metal oxides?
  Joseph W. Bennett,Diamond T. Jones,Blake G. Hudson,Joshua Melendez-Rivera,Robert J. Hamers,Sara E. Mason Environ. Sci.: Nano, 2020,7, 1642-1651
• 3. Exceptionally high temperature spin crossover in amide-functionalised 2,6-bis(pyrazol-1-yl)pyridine iron(ii) complex revealed by variable temperature Raman spectroscopy and single crystal X-ray diffraction?
  Max Attwood,Hiroki Akutsu,Lee Martin,Toby J. Blundell,Pierre Le Maguere,Scott S. Turner Dalton Trans., 2021,50, 11843-11851
• 4. Excitation dependent bidirectional electron transfer in phthalocyanine-functionalised MoS2 nanosheets?
  Christopher J. Harrison,Kyle J. Berean,Enrico Della Gaspera,Jian Zhen Ou,Richard B. Kaner,Kourosh Kalantar-zadeh,Torben Daeneke Nanoscale, 2016,8, 16276-16283
• 5. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932

Research Brief on 2-(1r,4r)-4-aminocyclohexylacetic acid (CAS: 2952-00-3) in Chemical Biology and Pharmaceutical Applications

2-(1r,4r)-4-aminocyclohexylacetic acid (CAS: 2952-00-3) is a chiral cyclohexane derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a key intermediate in the synthesis of various bioactive molecules, particularly those targeting neurological and metabolic disorders. Its unique structural features, including the rigid cyclohexane ring and the strategically positioned amino and carboxylic acid functional groups, make it an attractive scaffold for drug design and development.

Recent studies have focused on the optimization of synthetic routes for 2-(1r,4r)-4-aminocyclohexylacetic acid to improve yield and enantiomeric purity. A 2023 publication in the Journal of Medicinal Chemistry reported a novel catalytic asymmetric synthesis method using a chiral palladium complex, achieving >99% enantiomeric excess (ee) and scalable production. This advancement addresses previous challenges in obtaining high-purity enantiomers, which is critical for pharmaceutical applications where stereochemistry significantly impacts biological activity.

In drug discovery, this compound has shown promise as a building block for GABA receptor modulators. Research published in ACS Chemical Neuroscience (2024) demonstrated its incorporation into novel positive allosteric modulators of α5-containing GABAA receptors, potentially offering new therapeutic avenues for cognitive disorders. The study highlighted how the compound's conformational rigidity contributes to enhanced receptor subtype selectivity compared to more flexible analogs.

Metabolic stability studies of derivatives containing the 2-(1r,4r)-4-aminocyclohexylacetic acid moiety have revealed interesting pharmacokinetic properties. A 2023 investigation in Drug Metabolism and Disposition showed that this scaffold confers improved metabolic stability in liver microsome assays compared to similar acyclic structures, while maintaining good aqueous solubility. These findings suggest its potential for developing orally bioavailable CNS-targeting drugs.

Emerging applications extend beyond neurological targets. A recent Nature Communications article (2024) described the use of 2-(1r,4r)-4-aminocyclohexylacetic acid-derived compounds as selective inhibitors of a novel cancer metabolism pathway. The researchers utilized the compound's structural features to design molecules that specifically target glutamine metabolism in KRAS-mutant cancers, showing promising preclinical results.

Ongoing research is exploring the compound's potential in peptide mimetics and PROTAC (Proteolysis Targeting Chimera) design. Its ability to introduce constrained conformations while maintaining hydrogen bonding capabilities makes it particularly valuable for these applications. Several pharmaceutical companies have included derivatives of 2-(1r,4r)-4-aminocyclohexylacetic acid in their pipelines, with one candidate currently in Phase I clinical trials for neurodegenerative disease.

Future directions for research on this compound include further exploration of its applications in targeted protein degradation, development of more efficient synthetic methodologies, and comprehensive structure-activity relationship studies to fully exploit its potential in drug discovery. The continued interest in 2-(1r,4r)-4-aminocyclohexylacetic acid underscores its importance as a versatile building block in medicinal chemistry and chemical biology research.

• 25912-50-9(3-aminocyclohexane-1-carboxylic acid)
• 3685-25-4(trans-4-Aminocyclohexanecarboxylic acid)
• 3235-46-9(4-Amino-4-methylpentanoic acid)
• 16636-51-4(cis-3-aminocyclohexanecarboxylicacid)
• 1197-54-2(2-(4-Aminocyclohexyl)acetic acid)
• 34583-99-8(trans-3-aminocyclohexane-1-carboxylic acid)
• 3685-23-2(cis-4-aminocyclohexanecarboxylic acid)
• 1776-53-0(4-Aminocyclohexanecarboxylic Acid)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)