223763-92-6

Usage

Chemical structure

Contains a BOC-protected amino group and a hydroxyl group on a cyclohexane ring.

BOC group

tert-butyloxycarbonyl group used to protect amine functionality in organic synthesis.

Selective deprotection

Allows for mild conditions to remove the BOC group when needed.

Hydroxycyclohexane moiety

Suggests potential use as a building block in the synthesis of pharmaceuticals or other organic compounds.

Intermediate compound

May be used as an intermediate in the production of various organic compounds.

Applications

Potential applications in the pharmaceutical and fine chemical industries.

Further investigation

Specific properties and potential applications may warrant additional research and development.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2041-57-8 (1-(aminomethyl)cyclohexyl)methanol 
• 111-24-0 1,5-dibromo-pentane 
• 1130-21-8 ethyl 1-cyanocyclohexane-1-carboxylate 

Downstream Products

• 886990-05-2 [1-(benzothiazol-2-ylsulfanylmethyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester 
• 204514-28-3 1-(tert-butoxycarbonylamino-methyl)-cyclohexanecarboxylic acid 1-carboxy-3-methyl-butyl ester 
• 204514-17-0 1-(tert-butoxycarbonylamino-methyl)-cyclohexanecarboxylic acid 1-allyloxycarbonyl-3-methyl-butyl ester 
• 223763-97-1 (E)-(9S,12S,18R)-18-(3-Chloro-4-methoxy-benzyl)-9-isobutyl-12-((E)-(R)-1-methyl-3-phenyl-allyl)-8,11-dioxa-17,20-diaza-spiro[5.15]henicos-14-ene-7,10,16,19-tetraone 
• 223764-02-1 (E)-(9S,12S,18R)-12-((1R,2R,3S)-3-Chloro-2-hydroxy-1-methyl-3-phenyl-propyl)-18-(3-chloro-4-methoxy-benzyl)-9-isobutyl-8,11-dioxa-17,20-diaza-spiro[5.15]henicos-14-ene-7,10,16,19-tetraone 
• 1103205-39-5 C₁₄H₂₇NO₅S 

Relevant academic research and scientific papers

Design, Synthesis, and in vitro Evaluation of P2X7 Antagonists

The P2X7 receptor is a promising target for the treatment of various diseases due to its significant role in inflammation and immune cell signaling. This work describes the design, synthesis, and in vitro evaluation of a series of novel derivatives bearing diverse scaffolds as potent P2X7 antagonists. Our approach was based on structural modifications of reported (adamantan-1-yl)methylbenzamides able to inhibit the receptor activation. The adamantane moieties and the amide bond were replaced, and the replacements were evaluated by a ligand-based pharmacophore model. The antagonistic potency of the synthesized analogues was assessed by two-electrode voltage clamp experiments, using Xenopus laevis oocytes that express the human P2X7 receptor. SAR studies suggested that the replacement of the adamantane ring by an aryl-cyclohexyl moiety afforded the most potent antagonists against the activation of the P2X7 cation channel, with analogue 2-chloro-N-[1-(3-(nitrooxymethyl)phenyl)cyclohexyl)methyl]benzamide (56) exhibiting the best potency with an IC50 value of 0.39 μΜ.

2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 3: Synthesis and activity of isosteric analogs

Structure-activity relationships and efforts to optimize the pharmacokinetic profile of isosteric analogs of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among those examined, compound 25 showed potent affinity for cannabinoid receptor 1 (CB1) and receptor 2 (CB2). This compound displayed oral bioavailability and analgesic activity.

Carboxylate bioisosteres of gabapentin

A series of carboxylate bioisosteres of structures related to gabapentin 1 have been prepared. When the carboxylate was replaced by a tetrazole, this group was recognized by the α2-δ protein. Further characterization of α2-δ binding compounds 14a and 14b revealed a similar pattern of functional in vitro and in vivo activity to gabapentin 1.

Synthesis and biological evaluation of cryptophycin analogs with substitution at C-6 (fragment C region)

Analogs of the antitumor agents cryptophycins 1 and 8 with dialkyl substitution at C-6 (fragment C) were synthesized and evaluated for in vitro cytotoxicity against human leukemia cells (CCRF-CEM). The activity of these analogs decreased as the size of the substituents at C-6 increased. The C-6 spirocylopropyl compound (2g) was highly potent in vitro and showed excellent antitumor activity in animal models.