76308-28-6

Usage

Uses

Used in Pharmaceutical Industry:
Cyclohexaneacetic acid, 4-amino-, ethyl ester, transis utilized as an intermediate in the synthesis of pharmaceutical compounds for its unique structure and functional groups. The presence of the cyclohexane ring, amino group, and ethyl ester allows for the development of new drugs with specific therapeutic properties.
Used in Organic Synthesis:
In the field of organic synthesis, Cyclohexaneacetic acid, 4-amino-, ethyl ester, transserves as a key building block for the creation of complex organic molecules. Its versatile functional groups and transconfiguration enable chemists to design and synthesize a wide range of organic compounds with diverse applications.
Used in Drug Development:
The unique structure and functional groups of Cyclohexaneacetic acid, 4-amino-, ethyl ester, transmake it a promising candidate for drug development. Its potential use in the synthesis of new pharmaceutical compounds can lead to the discovery of novel drugs with improved efficacy and selectivity in treating various diseases and medical conditions.
Used in Chemical Reactions:
Due to its transconfiguration and functional groups, Cyclohexaneacetic acid, 4-amino-, ethyl ester, transexhibits specific properties and reactivity in chemical reactions. This makes it a valuable compound for studying reaction mechanisms and developing new synthetic methodologies in organic chemistry.

InChI:InChI=1/C10H19NO2/c1-2-13-10(12)7-8-3-5-9(11)6-4-8/h8-9H,2-7,11H2,1H3/t8-,9-

Upstream product

• 104-03-0 4-nitrobenzeneacetic acid 

Downstream Products

• 76308-38-8 N-tetramethyldiamidophosphoryl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 76308-39-9 N-tetramethyldiamidothiophosphoryl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 2952-00-3 trans-2-(4-aminocyclohexyl)acetic acid 
• 76308-32-2 N-dichlorophosphoryl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 76308-33-3 N-dichlorothiophosphoryl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 76308-34-4 N-diethylenimidophosphoryl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 76308-35-5 N-diethylenimidothiophosphoryl-trans-4-aminocyclohexylacetic acid ethyl ester 
• 76308-36-6 C₁₂H₂₁N₃O₃P^(1-)*Na⁽¹⁺⁾ 
• 76308-37-7 C₁₂H₂₁N₃O₂PS^(1-)*Na⁽¹⁺⁾ 
• 215790-29-7 trans-2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)acetaldehyde 
• 839712-12-8 Cariprazine 
• 215790-43-5 trans-2-(2-(1-4-(N-tert-butyloxycarbonyl)amino)cyclohexyl)ethyl-7-cyano-1,2,3,4-tetrahydroisoquinoline 
• 506427-91-4 trans N-tert-butoxycarbonyl-4-{2-[4-(2,3-dichlorophenyl)-piperazin-1-yl]ethyl}-cyclohexylamine 
• 791778-53-5 trans-4-(2-(4-(2,3-dichlorophenyl)piperazin-1-yl)ethyl)cyclohexane-1-amine 

Relevant academic research and scientific papers

Preparation method for converting configuration of key intermediate of cariprazine

The invention provides a preparation method for converting configuration of a key intermediate of cariprazine, which is characterized in that commercially available 2-(4-((tert-butoxycarbonyl) amino) cyclohexyl) ethyl acetate is used as a raw material to synthesize trans-2-(4-((tert-butoxycarbonyl) amino) cyclohexyl) ethyl acetate with a single configuration in two steps under certain conditions. The preparation method disclosed by the invention is high in yield, low in production cost, green, environment-friendly and suitable for industrial production.

Process Development of an Efficient Kilogram-Scale Preparation of a Preferential Dopamine D3 versus D2 Receptor Antagonist SIPI 6398 as a New Antipsychotic Candidate

Herein we describe the development of a kilogram-scale preparation of a preferential dopamine D3 versus D2 receptor antagonist SIPI 6398 (1) as a new alternative treatment for schizophrenia. Modification and optimization of the route includes one-pot synthesis of a trans/cis mixture of cyclohexyl ethyl acetate 19, direct crystallization of cyclohexyl acetic acid 21 in trans configuration, avoidance of hazardous reagents to obtain mesylate 24, and a salinization and recrystallization protocol to efficiently remove the olefinic impurity 31 from 12 (free base of 1). Ultimately these improvements led to the successful and facile preparation of 2.7 kg of SIPI 6398 in nine steps with an HPLC purity of >99.9%.

Structure-Activity Study of N -((trans)-4-(2-(7-Cyano-3,4-dihydroisoquinolin-2(1 H)-yl)ethyl)cyclohexyl)-1 H -indole-2-carboxamide (SB269652), a Bitopic Ligand That Acts as a Negative Allosteric Modulator of the Dopamine D2 Receptor

We recently demonstrated that SB269652 (1) engages one protomer of a dopamine D2 receptor (D2R) dimer in a bitopic mode to allosterically inhibit the binding of dopamine at the other protomer. Herein, we investigate structural determinants for allostery, focusing on modifications to three moieties within 1. We find that orthosteric "head" groups with small 7-substituents were important to maintain the limited negative cooperativity of analogues of 1, and replacement of the tetrahydroisoquinoline head group with other D2R "privileged structures" generated orthosteric antagonists. Additionally, replacement of the cyclohexylene linker with polymethylene chains conferred linker length dependency in allosteric pharmacology. We validated the importance of the indolic NH as a hydrogen bond donor moiety for maintaining allostery. Replacement of the indole ring with azaindole conferred a 30-fold increase in affinity while maintaining negative cooperativity. Combined, these results provide novel SAR insight for bitopic ligands that act as negative allosteric modulators of the D2R.

A structure-activity analysis of biased agonism at the dopamine D2 receptor

Biased agonism offers an opportunity for the medicinal chemist to discover pathway-selective ligands for GPCRs. A number of studies have suggested that biased agonism at the dopamine D2 receptor (D2R) may be advantageous for the treatment of neuropsychiatric disorders, including schizophrenia. As such, it is of great importance to gain insight into the SAR of biased agonism at this receptor. We have generated SAR based on a novel D2R partial agonist, tert-butyl (trans-4-(2-(3,4-dihydroisoquinolin- 2(1H)-yl)ethyl)cyclohexyl)carbamate (4). This ligand shares structural similarity to cariprazine (2), a drug awaiting FDA approval for the treatment of schizophrenia, yet displays a distinct bias toward two different signaling end points. We synthesized a number of derivatives of 4 with subtle structural modifications, including incorporation of cariprazine fragments. By combining pharmacological profiling with analytical methodology to identify and to quantify bias, we have demonstrated that efficacy and biased agonism can be finely tuned by minor structural modifications to the head group containing the tertiary amine, a tail group that extends away from this moiety, and the orientation and length of a spacer region between these two moieties.