2201-24-3

Usage

Uses

Used in Organic Chemistry:
1-Amino-1-phenylcyclohexane is used as a starting material for the synthesis of various organic compounds. Its unique structure and functional groups make it a valuable building block in the creation of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
APOCH is used as a building block for the production of pharmaceuticals. Its versatile structure allows for the development of new drugs with potential therapeutic effects. Researchers leverage its properties to design and synthesize novel drug candidates for the treatment of various diseases and conditions.
Used in Agrochemical Industry:
1-Amino-1-phenylcyclohexane is used as a precursor in the synthesis of agrochemicals. Its unique structure and functional groups contribute to the development of new agrochemicals with improved efficacy and selectivity, enhancing crop protection and yield.
Used in Materials Science Research:
APOCH is used as a building block in the development of new materials with specific properties. Its versatile structure allows for the creation of materials with tailored characteristics, such as improved mechanical strength, thermal stability, or electrical conductivity, for use in various applications.
Used in Drug Development:
1-Amino-1-phenylcyclohexane is used in drug development as a key component in the design and synthesis of new pharmaceutical agents. Its unique structure and functional groups enable the development of drugs with novel mechanisms of action and potential therapeutic benefits.
Used in Neuroscience Research:
APOCH is used in neuroscience research to study the interactions between molecules and biological systems. Its unique structure and properties make it a valuable tool for investigating the mechanisms underlying various neurological disorders and for developing new treatments for these conditions.

Upstream product

• 78176-22-4 1-nitro-1-phenylcyclohexane 
• 2890-42-8 1-phenylcyclohexylcarbonyl chloride 
• 1135-67-7 1-phenyl-cyclohexanecarboxylic acid 
• 1589-60-2 1-phenylcyclohexanol 
• 66021-71-4 1-(1-azidocyclohexyl)benzene 
• 7732-18-5 water 
• 1443469-89-3 2,2,2-trifluoro-N-(1-phenylcyclohexyl)acetamide 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 886615-49-2 (1-phenyl-cyclohexyl)-carbamic acid benzyl ester 
• 140-29-4 phenylacetonitrile 
• 2890-60-0 1-phenylcyclohexane-1-carboxamide 
• 771-98-2 1-Phenylcyclohexene 
• 2201-23-2 1-phenyl-1-cyclohexanecarbonitrile 

Downstream Products

• 110-83-8 cyclohexene 
• 2201-17-4 N,N-dimethyl-1-phenylcyclohexyl-1-amine 
• 20640-21-5 2-(1-Phenyl-cyclohexylamino)-ethanthiol 
• 2626-61-1 1-butylcyclohexylamine 
• 108-94-1 cyclohexanone 
• 2201-49-2 Allyl-<1-phenyl-cyclohexyl>-amin 
• 91281-26-4 N,N-diallyl-1-phenylcyclohexylamine 
• 22904-94-5 N,N-Dimethyl-1-phenylcyclohexylamin-methoiodid 
• 5769-23-3 N-<4-Nitro-benzolsulfonyl>-N'-<1-phenyl-cyclohexyl>-harnstoff 
• 5769-17-5 N-<4-Methyl-benzolsulfonyl>-N'-<1-phenyl-cyclohexyl>-harnstoff 
• 886615-50-5 4-chloro-N-(1-phenyl-cyclohexyl)-butyramide 
• 929212-03-3 Mo(1-phenylcyclohexylimido)2Cl₂(dme) 
• 1934-71-0 IEM 1921 
• 1821-36-9 N-phenyl-2-cyclohexylamine 

Relevant academic research and scientific papers

Spiro [benzo [c] aza-1, 1 '-cyclohexyl]-3-ketone compound

The invention belongs to the technical field of medicines, relates to a compound with anti-tumor activity and a specific chemical structure, and particularly relates to a 4, 5-dihydrospiro [benzo [c] aza-1, 1 '-cyclohexyl]-3 (2H)-ketone compound as well as a preparation method and application of the 4, 5-dihydrospiro [benzo [c] aza-1, 1'-cyclohexyl]-3 (2H)-ketone compound. The structural general formula of the compound is shown in the specification, wherein an R group on an a benzene ring is substituted by a 2-position, 3-position or 4-position monosubstituted fluorine atom, methyl, chlorine atom, methoxyl, bromine atom or hydrogen atom. Pharmacological studies show that the compound provided by the invention has certain inhibitory activity on human colon cancer HCT-116 cells, can be used for preparing antitumor drugs, and opens up a new way for deep research and development of tumor drugs in the future. The preparation method provided by the invention is simple and feasible, relatively high in yield and easy for large-scale production.

Novel 4,5-dihydrospiro[benzo[c]azepine-1,1′-cyclohexan]-3(2H)-one derivatives as PARP-1 inhibitors: Design, synthesis and biological evaluation

To further explore the research of novel PARP-1 inhibitors, we designed and synthesized a series of novel amide PARP-1 inhibitors based on our previous research. Most compounds displayed certain antitumor activities against four tumor cell lines (A549, HepG2, HCT-116, and MCF-7). Specifically, the candidate compound R8e possessed strong anti-proliferative potency toward A549 cells with the IC50 value of 2.01 μM. Compound R8e had low toxicity to lung cancer cell line. And the in vitro enzyme inhibitory activity of compound R8e was better than rucaparib. Molecular docking studies provided a rational binding model of compound R8e in complex with rucaparib. The following cell cycle and apoptosis assays revealed that compound R8e could arrest cell cycle in the S phase and induce cell apoptosis. Western blot analysis further showed that compound R8e could effectively inhibit the PAR's biosynthesis and was more effective than rucaparib. Overall, based on the biological activity evaluation, compound R8e could be a potential lead compound for further developing novel amide PARP-1 inhibitors.

1-azaspiro[5.5]undecyl-3-one and 1-azaspiro[5.5]undecyl-3-alcohol compounds

The invention belongs to the technical field of medicines, and particularly relates to 1-azaspiro[5.5]undecyl-3-one and 1-azaspiro[5.5]undecyl-3-alcohol compounds and a preparation method and application thereof. The general formulas of the 1-azaspiro[5.5]undecyl-3-one compound and the 1-azaspiro[5.5]undecyl-3-alcohol compounds are shown in a formula I and a formula II in the specification. A six-membered spiro structure is synthesized for the first time, a brand-new compound with a better anti-tumor effect is obtained, and pharmacological research shows that the compound has certain inhibitory activity on human colon cancer HCT-116 cells. The preparation method of the 1-azaspiro[5.5]undecyl-3-one compound and the 1-azaspiro[5.5]undecyl-3-alcohol compound is simple and feasible, the yieldis relatively good, and the method is suitable for industrial production.

Design, synthesis and biological evaluation of erythrina derivatives bearing a 1,2,3-triazole moiety as PARP-1 inhibitors

Inhibitors of poly (ADP-ribose) polymerase-1 (PARP-1) have shown to be promising in clinical trials against cancer, and many researchers are interested in the development of new PARP-1 inhibitors. Herein, we designed and synthesized 44 novel erythrina derivatives bearing a 1,2,3-triazole moiety as PARP-1 inhibitors. MTT assay results indicated that compound 10b had the most potent anti-proliferative activity against A549 cells among five cancer cells. The enzyme inhibitory activity in vitro of compound 10b was also significantly better than rucaparib. Furthermore, the selectivity index of compound 10b was higher than rucaparib for lung cancer cells. Flow cytometry analysis showed that compound 10b induced apoptosis of A549 cells by the mitochondrial pathway. Western blot analysis indicated that compound 10b was able to inhibit the biosynthesis of PAR effectively, and it was more potent than rucaparib. Also, compound 10b was able to up-regulate the ratio of bax/bcl-2, activate caspase-3, and ultimately induced apoptosis of A549 cells. The combined results revealed that the discovery of novel non-amide based PARP-1 inhibitors have great research significance and provide a better choice for the future development of drugs.

Design, synthesis and biological evaluation of homoerythrina alkaloid derivatives bearing a triazole moiety as PARP-1 inhibitors and as potential antitumor drugs

A series of homoerythrina alkaloid derivatives containing a 1,2,3-triazole moiety as PARP-1 inhibitors were designed and synthesized. And their anti-proliferative activity was further evaluated. Compound 10n had excellent activity to inhibit proliferation of A549 cells (IC50 = 1.89 μM), which was higher than harringtonine (IC50 = 10.55 μM), pemetrexed (IC50 = 3.39 μM), and rucaparib (IC50 = 4.91 μM). Furthermore, the selectivity index of compound 10n was higher than rucaparib and pemetrexed for lung cancer cells. Flow cytometry analysis showed that compound 10n significantly arrested the cell cycle in the S phase, then induced apoptosis of A549 cells (apoptosis rate is 46%), which effectively inhibited cell proliferation. Simultaneously, western blot analysis revealed that compound 10n could prevent the biosynthesis of PAR. Further analysis results revealed that compound 10n could inhibit the expression of cyclin A, down-regulate the expression of bcl-2/bax, activate caspase-3, and ultimately induce apoptosis of A549 cells. All the results indicated that compound 10n had potential research value as a novel PARP-1 inhibitor in antitumor, and it provided a new reference for further development of PARP-1 inhibitors.

Synthesis and Pharmacological Properties of 1-(6-Aminohexylamino)-1-Phenylcyclohexyl Dihydrochloride (IEM-2062) as Compared with Memantine

1-(6-Aminohexylamino)-1-phenylcyclohexyl dihydrochloride (IEM-2062) had significantly greater antihypoxic, anticonvulsant, antidepressant, and analgesic activity than memantine and similar antiparkinsonism activity as memantine; it had low toxicity and was safer for use. IEM-2062 produced significant pharmacological effects in the dose range 0.3 – 3 mg/kg.

7-azaspiro[5.6]dodecane-10-ketone compound as well as preparation method and application thereof

The invention belongs to the field of medicine, and specifically relates to 7-azaspiro[5.6]dodecane-10-ketone compound as well as a preparation method and application thereof. According to the invention, a seven-membered ring structure is synthesized for the first time to obtain a novel compound with a better anti-tumor effect; reports of related structures have not been found; pharmacological studies show that the compound provided by the invention has certain inhibitory activity for human lung cancer A549 cells and human ovarian cancer OVCAR-3 cells, and provides a basis for subsequent preparation of anti-tumor drugs.

Chemo- and Site-Selective Alkyl and Aryl Azide Reductions with Heterogeneous Nanoparticle Catalysts

Site-selective modification of bioactive natural products is an effective approach to generating new leads for drug discovery. Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. The nanoparticle catalysts are highly chemoselective for reduction of alkyl and aryl azides under mild conditions and in the presence of a variety of easily reduced functional groups. High regioselectivity for monoazide reduction is shown to favor reduction of the least sterically hindered azide. We hypothesize that the observed selectivity is derived from the greater ability of less-hindered azide groups to interact with the surface of the nanoparticle catalyst. These results are complementary to previous Staudinger reduction methods that report a preference for selective reduction of electronically activated azides.

Convergent Synthesis of Diverse Nitrogen Heterocycles via Rh(III)-Catalyzed C-H Conjugate Addition/Cyclization Reactions

The development of Rh(III)-catalyzed C-H conjugate addition/cyclization reactions that provide access to synthetically useful fused bi- and tricyclic nitrogen heterocycles is reported. A broad scope of C-H functionalization substrates and electrophilic olefin coupling partners is effective, and depending on the nature of the directing group, cyclic imide, amide, or heteroaromatic products are obtained. An efficient synthesis of a pyrrolophenanthridine alkaloid natural product, oxoassoanine, highlights the utility of this method.

Syntheses and N-methyl-D-aspartate receptor antagonist pharmacology of fluorinated arylcycloheptylamines

Selective uncompetitive antagonists of the phencyclidine (PCP) binding site of the N-methyl-D-aspartate receptor (NMDAR) are known to have therapeutic potential as anticonvulsants and neuroprotective agents. Several fluorinated molecules with each containing a cycloheptane ring were designed to probe the PCP pharmacophore and test the influence of fluorine substitution on NMDAR binding and in vivo efficacy. Syntheses and analyses of six novel compounds, 1-(4-fluorophenyl)cycloheptanamine (3), 1-(1-(4-fluorophenyl)cycloheptyl)piperidine (4), 1-(1-(4-fluorophenyl)cycloheptyl) pyrrolidine (5), 1-(3-fluorophenyl)cycloheptanamine (6), 1-(1-(3-fluorophenyl)cycloheptyl)piperidine (7), 1-(1-(3-fluorophenyl)cycloheptyl)pyrrolidine (8) and several related reference arylcyloalkylamines are described. Receptor binding was performed at the PCP site of NMDAR for each compound using [3H]-(+)-MK-801 displacement. Unexpectedly, the 3-fluoro-primary amine 6 had the greatest affinity of the series and these binding results support a different structure activity relationship (SAR) profile for arylcycloheptylamines when compared to arylcyclohexylamines like PCP. Five of the novel compounds have affinity (Ki) in the hundred nM (10-7) range. In addition, compounds 3, 5, 6, 7 and 8 were evaluated and found to exhibit neuroprotective effects from NMDA induced toxicity in vitro and compounds 6, 7 and 8 exhibited anticonvulsant activities in rats. An ED50 of 13.84 mg/kg was found for compound 6 in rat maximal electroshock (MES) test with a protective index (PI) of 3.66 against ataxia. These results support further investigation of the arylcycloheptylamine class.