1210348-16-5

Basic information

• Product Name: (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester
• Synonyms: (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester;ethyl (1R,3S,4S)-3-{[(tert-butoxy)carbonyl]amino}-4-hydroxycyclohexane-1-carboxylate;(1R,3S,4S)-Ethyl 3-((tert-butoxycarbonyl)amino)-4-hydroxycyclohexanecarboxylate
• CAS NO: 1210348-16-5
• Molecular Formula: C₁₄H₂₅NO₅
• Molecular Weight: 287.352
• Mol File: 1210348-16-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester(1210348-16-5)
• EPA Substance Registry System: (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester(1210348-16-5)

Safety Data

• Hazardous Substances Data: 1210348-16-5(Hazardous Substances Data)

Usage

Description

(1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is a complex organic compound with a unique stereochemistry and functional groups. It features a cyclohexane ring with a hydroxyl group and an ethyl ester moiety, as well as a Boc-protected amino group. (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is characterized by its specific stereochemistry, with the R, S, and S configurations at the 1st, 3rd, and 4th carbons, respectively. Its molecular structure endows it with the potential to interact with biological targets and serve as a pharmaceutical agent.

Uses

Used in Pharmaceutical Industry:
(1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is used as a protein kinase inhibitor for its ability to modulate the activity of specific protein kinases. Protein kinases are enzymes that play a crucial role in various cellular processes, including cell growth, differentiation, and apoptosis. By inhibiting these enzymes, this compound can potentially be used to treat diseases associated with abnormal kinase activity, such as cancer and inflammatory disorders.
Used in Drug Development:
In the drug development process, (1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester serves as a lead compound for the design and synthesis of new pharmaceutical agents. Its unique structure and biological activity make it a valuable starting point for the development of novel therapeutics targeting protein kinases and other related pathways.
Used in Research Applications:
(1R,3S,4S)-3-(Boc-aMino)-4-hydroxy-cyclohexanecarboxylic acid ethyl ester is also used as a research tool in the study of protein kinases and their role in various diseases. Researchers can use this compound to investigate the mechanisms of kinase inhibition and to identify potential therapeutic targets for the treatment of various conditions.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 119719-61-8 (1R,4R,5R)-4-iodo-6-oxabicyclo[3.2.1]octane-7-one 
• 5709-98-8 (R)-cyclohex-3-enecarboxylic acid 
• 365997-32-6 C₉H₁₅N₃O₃ 
• 64-17-5 ethanol 

Downstream Products

• 1255529-31-7 ethyl (1R,3S,4S)-3-((tert-butoxycarbonyl)amino)-4-((methylsulfonyl)oxy)cyclohexane-1-carboxylate 
• 1057651-37-2 ethyl (1R,3S,4R)-4-(((benzyloxy)carbonyl)amino)-3-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylate 
• 1210348-23-4 C₁₄H₂₆N₂O₄ 
• 912273-65-5 N₁-(5-chloropyridin-2-yl)-N₂-{(1R,2S,4R)-4-(dimethylaminocarbonyl)-2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carboxamido]cyclohexyl}oxalamide p-toluenesulfonic acid 

Relevant articles and documents

A Remarkable Difference That One Fluorine Atom Confers on the Mechanisms of Inactivation of Human Ornithine Aminotransferase by Two Cyclohexene Analogues of γ-Aminobutyric Acid

Human ornithine aminotransferase (hOAT), a pyridoxal 5′-phosphate-dependent enzyme, plays a critical role in the progression of hepatocellular carcinoma (HCC). Pharmacological selective inhibition of hOAT has been shown to be a potential therapeutic approach for HCC. Inspired by the discovery of the nonselective aminotransferase inactivator (1R,3S,4S)-3-amino-4-fluoro cyclopentane-1-carboxylic acid (1), in this work, we rationally designed, synthesized, and evaluated a novel series of fluorine-substituted cyclohexene analogues, thereby identifying 8 and 9 as novel selective hOAT time-dependent inhibitors. Intact protein mass spectrometry and protein crystallography demonstrated 8 and 9 as covalent inhibitors of hOAT, which exhibit two distinct inactivation mechanisms resulting from the difference of a single fluorine atom. Interestingly, they share a similar turnover mechanism, according to the mass spectrometry-based analysis of metabolites and fluoride ion release experiments. Molecular dynamics (MD) simulations and electrostatic potential (ESP) charge calculations were conducted, which elucidated the significant influence of the one-fluorine difference on the corresponding intermediates, leading to two totally different inactivation pathways. The novel addition-aromatization inactivation mechanism for 9 contributes to its significantly enhanced potency, along with excellent selectivity over other aminotransferases.

FLUORINE SUBSTITUTED CECLOHEXENE ANALOGOUES OF GAMMA-AMINOBUTYRIC ACID (GABA)

Disclosed are amino, fluoro-sub stituted cyclohexene carboxylic acid compounds. The disclosed compounds and compositions thereof may be utilized in methods for modulating ornithine aminotransferase (OAT) activity, including methods for treating diseases or disorders associated with OAT activity or expression such as cell proliferative diseases and disorders.

HETEROARYL COMPOUNDS AND USES THEREOF

The present invention relates to compounds useful as inhibitors of protein kinases, containing a cysteine residue in the ATP binding site. The invention further provides for pharmaceutically acceptable compositions comprising therapeutically effective amounts of one or more of the protein kinase inhibitor compounds and methods of using said compositions in the treatment of cancers and carcinomas.