187610-67-9

Usage

Uses

Used in Pharmaceutical Synthesis:
1-(BOC-AMINO)-1-HYDROXYMETHYLCYCLOHEXANE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex molecular structures. The BOC-protected amine allows for selective reactions to occur elsewhere in the molecule without affecting the amine group, which can be deprotected when needed.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(BOC-AMINO)-1-HYDROXYMETHYLCYCLOHEXANE is used as a structural component in the design and development of new drugs. Its unique combination of functional groups allows for versatile chemical modifications, facilitating the creation of bioactive molecules with potential therapeutic applications.
Used in Material Science:
1-(BOC-AMINO)-1-HYDROXYMETHYLCYCLOHEXANE is also utilized in material science as a component in the development of new materials. Its functional groups can be exploited to create novel polymers, coatings, or other materials with specific properties tailored for various industrial applications.
Used in Industrial Processes:
1-(BOC-AMINO)-1-HYDROXYMETHYLCYCLOHEXANE finds application in various industrial processes, where its reactivity and functional groups are harnessed to produce intermediates for further chemical transformations. This can include the synthesis of specialty chemicals, agrochemicals, or other high-value products.

InChI:InChI=1/C12H23NO3/c1-11(2,3)16-10(15)13-12(9-14)7-5-4-6-8-12/h14H,4-9H2,1-3H3,(H,13,15)

Upstream product

• 1144505-90-7 methyl 1-((t-butoxycarbonyl)amino)cyclohexane-1-carboxylate 
• 115951-16-1 1-tert-butoxycarbonylaminocyclohexanecarboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 2756-85-6 1-aminocyclohexane carboxylic acid 
• 543-27-1 isobutyl chloroformate 

Downstream Products

• 864943-64-6 C₂₀H₂₆N₂O₄ 
• 1144505-64-5 (1-(tert-butoxycarbonylamino)cyclohexyl)methyl methanesulfonate 
• 594872-66-9 [1-(3,5-dimethyl-benzoyl)-cyclohexyl]-carbamic acid tert-butyl ester 
• 594872-67-0 (1-amino-cyclohexyl)-(3,5-dimethyl-phenyl)-methanone 
• 766550-27-0 1-[N-(tert-butoxycarbonyl)-4-chloro-D-phenylalanyl]-4-[1-(1,2,4-triazol-1-yl-methyl)cyclohexyl]piperazine 
• 1026858-98-9 methanesulfonic acid 1-(4-benzyl-piperazin-1-yl)-cyclohexylmethyl ester 
• 511538-97-9 1-benzyl-4-[1-(1,2,4-triazol-1-yl-methyl)cyclohexyl]piperazine 
• 766550-16-7 1-benzyl-4-(1-hydroxymethylcyclohexyl)piperazine 
• 511538-98-0 1-[1-(1,2,4-triazol-1-yl-methyl)cyclohexyl]piperazine 
• 5460-68-4 1-(1-aminocyclohexyl)methanol hydrochloride 
• 594872-65-8 tert-butyl (1-formylcyclohexyl)carbamate 

Relevant academic research and scientific papers

Structure-based virtual screening for insect ecdysone receptor ligands using MM/PBSA

The ecdysone receptor (EcR) is an insect nuclear receptor that is activated by the molting hormone, 20-hydroxyecdysone. Because synthetic EcR ligands disrupt the normal growth of insects, they are attractive candidates for new insecticides. In this study, the Molecular Mechanics/Poisson–Boltzmann Surface Area (MM/PBSA) method was used to predict the binding activity of EcR ligands. Validity analyses using 40 known EcR ligands showed that the binding activity was satisfactorily predicted when the ligand conformational free energy term was introduced. Subsequently, this MM/PBSA method was applied to structure-based hierarchical virtual screening, and 12 candidate compounds were selected from a database of 3.8 million compounds. Five of these compounds were active in a cell-based competitive binding assay. The most potent compound is a simple proline derivative with low micromolar binding activity, representing a valuable lead compound for further structural optimization.

Discovery of novel P3 sulfonamide-capped inhibitors of HCV NS3 protease. Inhibitors with improved cellular potencies

Hepatitis C Virus (HCV) infection is the major cause of chronic liver disease, leading to cirrhosis and hepatocellular carcinoma, which affects more than 200 million people worldwide. Currently the only therapeutic regimens are subcutaneous interferon-α or PEG-interferon alone or in combination with oral ribavirin. Although combination therapy is reasonably successful with the majority of genotypes, its efficacy against the predominant genotype (genotype 1) is moderate at best, with only ～50% of the patients showing sustained virological response. We recently disclosed the discovery of Boceprevir, SCH 503034 (1), which is a novel, potent, selective, orally bioavailable NS3 protease inhibitor that has been shown to be efficacious in humans and is currently undergoing clinical trials. As second generation compounds, we have further explored various novel structures with the aim of improving enzyme and cellular binding activities of 1. Herein, we disclose our efforts toward the identification of a novel P3 sulfonamide-capped inhibitor that demonstrated improved binding and cellular activity compared to 1. X-ray structure of one of these inhibitors bound to the enzyme revealed a hydrogen bond of the P3 sulfonamide group to Cys-159 which resulted in improved binding and cellular potency.

Stieglitz rearrangement of N,N-dichloro-β,β-disubstituted taurines under mild aqueous conditions

New topical anti-infectives comprised of N,N-dichloro-β,β-disubstituted taurines [Tetrahedron Lett. 2008, 49, 2193; Biorg. Med. Chem. Lett. 2009, 19, 196] have been examined for structure-stability relationships (SSR) based upon various alkyl, heteroalkyl

Novel potent inhibitors of hepatitis C virus (HCV) NS3 protease with cyclic sulfonyl P3 cappings

Extensive SAR studies of the P3 capping group led to the discovery of a series of potent inhibitors with sultam and cyclic sulfonyl urea moieties as the P3 capping. The bicyclic thiophene-sultam or phenyl-sultam cappings were selected for further SAR development. Modification at the P3 side chain determined that the tert-butyl group was the best choice at that position. Optimization of P1 residue significantly improved potency and selectivity. The combination of optimal moieties at all positions led to the discovery of compound 33. This compound had the best overall profile in potency and PK profile: excellent Ki* of 5.3 nM and activity in replicon (EC90) of 80 nM, extremely high selectivity of 6100, and a good rat PO AUC of 1.43 μM h.

AMIDOPYRAZOLE DERIVATIVE

A platelet coagulation inhibitor which inhibits neither COX-1 nor COX-2 is provided. The inhibitor is a compound represented by general formula (I): wherein Ar1 and Ar2 independently represent a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents, or a phenyl group optionally substituted with 1 to 3 substituents; R1 represents a lower acyl group, carboxyl group, a lower alkoxycarbonyl group, a lower alkoxy group, a lower alkyl group optionally substituted with 1 or 2 substituents, a carbamoyl group optionally substituted with 1 or 2 substituents, an oxamoyl group optionally substituted with 1 or 2 substituents, an amino group optionally substituted with 1 or 2 substituents, a 4- to 7-membered alicyclic heterocyclic group optionally substituted with 1 or 2 substituents, a phenyl group optionally substituted with 1 to 3 substituents, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with 1 to 3 substituents; and R2 represents hydrogen atom, a halogeno group, or the like.

New substituted piperazines as ligands for melanocortin receptors. Correlation to the X-ray structure of "THIQ"

A series of piperazine analogues of the melanocortin 4 receptor (MC4R) specific small-molecule agonist "THIQ" was synthesized and characterized structurally and pharmacologically. First, several THIQ imitations lacking the triazole moiety were prepared. Syntheses included acylation of 4-phenylpiperazine or 4-cyclohexylpiperazine. In two cases the tertiary amine function was replaced by the corresponding N-oxide. To obtain more complex structures, a 4-substituted piperazine ring was formed by alkylation of the primary amino group of cyclohexane-derived amino alcohols with N,N-bis(2-chloroethyl)benzylamine. The hydroxylic group of the intermediate was first activated with methanesulfonyl chloride, and the sulfonic ester formed in situ was introduced into the reaction with the sodium salt of 1,2,4-triazole. In one case (i.e., preparation of 23c) introduction of the 1,2,4-triazole moiety was performed at a carbon of the cyclohexane ring. In addition, this intermediate contained a piperazine moiety connected via its nitrogen atom to a cyclohexane ring carbon neighboring the reaction center. As established in NMR and X-ray investigations herein, this substitution proceeded with retention of the initial trans configuration of 1,2-disubstituted cyclohexane. To obtain pure enantiomers of 23c, its precursor 21c was subjected to chiral chromatography on a Chirobiotic V column. The derivatives (R,R)-21cand (S,S)-21c obtained were introduced into further syntheses steps, giving (R,R)-23c and (S,S)-23c, respectively. Melanocortin MC1,3-5 receptor binding studies showed that all tested piperazine derivatives were active. Several compounds showed clear selectivity for MC4R, with submicromolar affinities being obtained. Among them, one substance, (R,R)-23c, displayed a biphasic curve in displacement of [125I]NDP-MSH on MC4R [K(i)high = 1 nM and K(i)low = 260 nM]. This biphasic competition curve was similarly biphasic to the competition curve obtained herein using THIQ. An X-ray study performed on crystals of the THIQ sulfate salt revealed two closely related conformations, which resemble the shape of the letter "Y", where piperidine and 4-chlorophenyl groups are situated close to each other, but the 1,2,3,4-tetrahydroisoquinoline residue is remote, the triazole function being highly exposed to the environment. The crystals of the dinitrate salt of (R,R)-23c showed a different conformation, where parts of the molecule are spread out almost symmetrically around the central section. Molecular modeling, based on the THIQ crystal structure and the functional similarity of THIQ and (R,R)-23c, allowed us to suggest a possible "bioactive" conformation of (R,R)-23c that is similar to the crystal conformation of THIQ.