57184-23-3

Usage

Uses

Used in Pharmaceutical Industry:
1-(Cyclohexylmethyl)piperazine is used as an intermediate in the synthesis of various pharmaceuticals, including antihistamines, antipsychotics, and antiviral agents, for its ability to modulate neurotransmitter levels and contribute to the development of effective medications.
Used in Organic Synthesis:
1-(Cyclohexylmethyl)piperazine is used as a reagent in organic synthesis for its versatility in creating diverse molecular structures, which is essential for the development of new compounds with potential applications in various fields.
Used in Medicinal Chemistry:
1-(Cyclohexylmethyl)piperazine is used as a building block in medicinal chemistry for its potential to form complex molecular structures that can be tailored for specific therapeutic applications, enhancing the discovery of novel drugs.
Used in Neurological and Mood Disorder Treatment:
1-(Cyclohexylmethyl)piperazine is studied for its potential as a therapeutic agent in the treatment of neurological disorders and mood-related conditions, leveraging its neurotransmitter-modulating properties to improve patient outcomes.

Upstream product

• 7755-92-2 piperazine-1-carbaldehyde 
• 2550-36-9 Cyclohexylmethyl bromide 
• 5625-67-2 2-Ketopiperazine 
• 98-89-5 Cyclohexanecarboxylic acid 
• 2043-61-0 cyclohexanecarbaldehyde 
• 1206676-28-9 tert-butyl 4-(cyclohexylmethyl)piperazine-1-carboxylate 
• 412293-89-1 4-Cyclohexylmethyl-piperazine-1-carbaldehyde 

Downstream Products

• 102535-29-5 3-(4-Cyclohexylmethyl-piperazine-1-carbonyl)-4-methoxy-benzenesulfonamide 
• 1220889-19-9 C₂₃H₂₇ClN₂O₂ 
• 1220889-21-3 C₂₄H₂₇N₃O₂ 
• 1254211-04-5 (E)-ethyl 3-(3-(4-(cyclohexylmethyl)piperazine-1-carbonyl)-phenyl)acrylate 
• 1277167-61-9 C₂₁H₂₇ClN₄O 
• 1428245-55-9 C₁₈H₂₇ClN₂O₃ 
• 1377239-83-2 2-[4-(cyclohexylmethyl)piperazin-1-yl]-8-nitro-6-(trifluoromethyl)-4H-1,3-benzothiazin-4-one 

Relevant academic research and scientific papers

Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Efficient Synthesis of Benzothiazinone Analogues with Activity against Intracellular Mycobacterium tuberculosis

8-Nitrobenzothiazinones (BTZs) are a promising class of antimycobacterial agents currently under investigation in clinical trials. Starting from thiourea derivatives, a new synthetic pathway to BTZs was established. It allows the formation of the thiazinone ring system in one synthetic step and is applicable for preparation of a wide variety of BTZ analogues. The synthetic procedure furthermore facilitates the replacement of the sulphur atom in the thiazinone ring system by oxygen or nitrogen to afford the analogous benzoxazinone and quinazolinone systems. 36 BTZ analogues were prepared and tested in luminescence-based assays for in vitro activity against Mycobacterium tuberculosis (Mtb) using the microdilution broth method and a high-throughput macrophage infection assay.

A practical catalytic reductive amination of carboxylic acids

We report reductive alkylation reactions of amines using carboxylic acids as nominal electrophiles. The two-step reaction exploits the dual reactivity of phenylsilane and involves a silane-mediated amidation followed by a Zn(OAc)2-catalyzed amide reduction. The reaction is applicable to a wide range of amines and carboxylic acids and has been demonstrated on a large scale (305 mmol of amine). The rate differential between the reduction of tertiary and secondary amide intermediates is exemplified in a convergent synthesis of the antiretroviral medicine maraviroc. Mechanistic studies demonstrate that a residual 0.5 equivalents of carboxylic acid from the amidation step is responsible for the generation of silane reductants with augmented reactivity, which allow secondary amides, previously unreactive in zinc/phenylsilane systems, to be reduced.

Discovery of 3-aryl-5-acylpiperazinyl-pyrazoles as antagonists to the NK3 receptor

A series of 3-aryl-5-acylpiperazinyl-pyrazoles (e.g., 3a-b) initially identified through a high-throughput screening campaign using the aequorin Ca2+ bioluminescence assay as novel, potent small molecule antagonists of the G protein-coupled hum

Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines featuring an intramolecular radical-oxidative cyclization of polysubstituted pyrroles, and evaluation of their cytotoxic activity

A three-step protocol for the synthesis of 1,2,3,8,9-pentasubstituted-5,6- dihydropyrrolo[2,1-a]isoquinolines is described, using van LeuseN′s polysubstituted pyrrole construction followed by intramolecular radical-oxidative cyclization of the isoquinoline system. The cytotoxic activities of the dihydropyrroloisoquinolines were tested on six tumor cell lines. Preliminary structure-activity studies revealed the importance of the identity of the aromatic substituent at the C-2 position, particularly a phenyl, m-(amino) phenyl or m-(cyclohexylmethylpiperazinamide) phenyl substituent, for cytotoxic activity.

Inhibitors of Blood Platelet cAMP Phosphodiesterase. 3. 1,3-Dihydro-2H-imidazoquinolin-2-one Derivatives with Enhanced Aqueous Solubility

Two series of 1,3-dihydro-2H-imidazoquinolin-2-one derivatives incorporating an additional site for acid salt formation were synthesized and evaluated as inhibitors of human blood platelet cAMP phosphodiesterase (PDE) and ADP-induced platelet aggregation.The objective of this study was to identify compounds that blended potent biological activity with a satisfactory level of aqueous solubility.From a series of 7-aminoimidazoquinolin-2-ones, biological and physical properties were optimally combined in the 1-piperidinyl derivative 11c.However, this compound offered no significant advantage over earlier studied compounds as an antithrombotic agent in an animal model of small vessel thrombosis.A series of 7-alkoxy alkanoic piperazinamide derivatives, in which the additional basic nitrogen atom was remote from the heterocyclic nucleus and accomodated in a secondary binding region of the cAMP PDE enzyme, demonstrated greater intrinsic cAMP PDE inhibitory activity.Structural modifications of this series focused on variation of the piperazine substituent and side-chain length.The lipophilicity of the N-substituent influenced biological potency and aqueous solubility, with substituents of seven carbon atoms or less generally providing acceptable solubility properties.The N-(cyclohexylmethyl)piperazinamide 21h was identified from this series of compounds as a potent inhibitor of platelet cAMP PDE, IC50 = 0.4 nM and ADP-induced platelet aggregation, IC50 = 0.51 μM after a 3-min exposure and 0.1 μM after a 15-min exposure of platelet-rich plasma to the drug.Evaluation of 21h and representative analogues in vivo using a rabbit model of small vessel thrombosis revealed significantly greater antithrombotic efficacy compared to that of previously studied compounds with similar intrinsic biological activity measured in vitro but inferior aqueous solubility.