177906-48-8

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-N-BOC-1,4-CYCLOHEXANEDIAMINE is used as a key intermediate in the synthesis of orally bioavailable and selective V1A receptor antagonists. These antagonists are crucial in the development of medications targeting various conditions, such as hypertension, heart failure, and other cardiovascular diseases. The compound's Boc-protected amino group allows for selective functionalization and improved pharmacokinetic properties, leading to more effective and safer therapeutic options.

InChI:InChI=1/C11H22N2O2/c1-11(2,3)15-10(14)13-9-6-4-8(12)5-7-9/h8-9H,4-7,12H2,1-3H3,(H,13,14)/t8-,9-

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2615-25-0 trans-1,4-cyclohexyldiamine 
• 870-46-2 t-butoxycarbonylhydrazine 

Downstream Products

• 184954-60-7 (4-Isothiocyanato-cyclohexyl)-carbamic acid tert-butyl ester 
• 289905-99-3 4-[(trans-4-t-butoxycarbonylamino-1-cyclohexyl)-carbamoyl]-2-decanoylamino-butyric acid benzyl ester 
• 876589-82-1 tert-butyl ((1r,4r)-4-((2-nitrophenyl)amino)cyclohexyl)carbamate 
• 412357-45-0 N-tert-butoxycarbonyl trans-4-(1-pyrrolidinyl)cyclohexyl-amine 
• 108-91-8 cyclohexylamine 
• 558442-96-9 tert-butyl N-[4-(morpholin-4-yl)cyclohexyl]carbamate 
• 873537-67-8 trans-[4-(2-chloroacetylamido)cyclohexyl]carbamic acid tert-butyl ester 
• 1123684-94-5 tert-butyl trans-[4-((2-[(E)-2-(4-chlorophenyl)ethenyl]-6-methylquinazolin-4-yl)amino)cyclohexyl]carbamate 
• 1315490-18-6 trans-3-(4-(2-methylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexylamino)propanenitrile 
• 1315491-58-7 trans-N-(4-(2-Methylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)methanesulfonamide 
• 1315486-69-1 trans-N-(4-(2-Methylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexyl)acetamide 
• 1315487-73-0 trans-methyl 4-(2-Methylimidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexylcarbamate 
• 1315500-19-6 trans-tert-butyl 4-(5-amino-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclohexylcarbamate 

Relevant academic research and scientific papers

A practical chromatography-free synthesis of a 5,6-dihydroimidazolo[1,5-f]pteridine derivative as a polo-like kinase-1 inhibitor

A practical chromatography-free synthesis of a potent polo-like kinase-1 inhibitor possessing a unique 5,6-dihydroimidazolo[1,5-f]pteridine structure has been developed. We showed that key cyanoimidazole ring formation could be conducted at benign temperature and obtained a chiral 5,6-dihydroimidazolo[1,5-f]pteridine derivative in good yield without epimerization. An aniline derivative containing a trans 1,4-cyclohexyl diamine structure was prepared by a synthesis that makes use of defined stereocenters of commercially available trans-cyclohexane-1,4-diamine via selective piperazine ring formation from a primary diamine. A coupling reaction of the 3-chloro-5,6-dihydroimidazolo[1,5-f]pteridine derivative and the aniline derivative in the endgame was closely investigated, and good yields were achieved both by palladium-catalyzed amination and acid-promoted coupling under benign reaction conditions. As a result of these investigations, the polo-like kinase-1 inhibitor was successfully obtained in a practical way without concern for generation/separation of stereoisomers.

Preparation method of N-Boc-trans-cyclohexanediamine

The invention discloses a preparation method of N-Boc-trans-cyclohexanediamine, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: dissolving trans-1, 4-cyclohexanediamine or (1S, 2S)-1, 2-cyclohexanediamine, tert-butyloxycarborylhydrazine and a copper catalyst in an organic solvent, and adding hydrogen peroxide to obtain the N-Boc-trans-cyclohexanediamine by a one-pot method. The method disclosed by the invention is simple to operate, and by controlling the equivalent weight of hydrogen peroxide, the temperature and the solvent concentration, the generation of a bis-t-butyloxycarboryl protecting group is effectively reduced, and the sufficient reaction of the raw material cyclohexanediamine is realized.

Preparation method of N-Boc-trans-1,4-cyclohexanediamine

The invention discloses a preparation method for synthesizing N-Boc-trans-1,4-cyclohexanediamine, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: protecting a 1-site amino group of trans-1,4-cyclohexanediamine by adopting equivalent benzophenone, and then reacting with Boc anhydride under an alkaline condition; and then reacting in an alcohol solvent under the catalysis of boron trifluoride diethyl etherate to obtain N-Boc-trans-1,4-cyclohexanediamine. According to the method, the technical defect that in literatures, a large amount of trans-1,4-cyclohexanediamine is needed to control a monosubstituted product as a main material is overcome, full utilization of the expensive main raw material trans-1,4-cyclohexanediamine is facilitated, and industrial production is facilitated.

Substituted-3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and Stimulator for Interferon Genes (STING) modulators as cancer immunotherapeutics

Substituted -3H-imidazo[4,5-c]pyridine and 1H-pyrrolo[2,3-c]pyridine series of novel Ectonucleotide Pyrophosphatase/Phosphodiesterase-1 (ENPP1) and related compounds, which are useful as inhibitors of ENPP1; synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of using the compounds and compositions to treat disorders associated with dysfunction of the ENPP1.

Smooth receptor ligand

The invention relates to the technical field of biology, particularly to a smooth receptor ligand, and provides a smooth receptor ligand or an isomer prodrug, a solvate and a pharmaceutically acceptable salt thereof, wherein the structural formula of the smooth receptor ligand is A-linker-B, A is an extracellular domain ligand structure, B is a transmembrane domain ligand structure, and Linker isa linear subunit inactive to the smooth receptor. According to the novel double-end small molecule ligand for the smooth receptor, by combining the crystal structure data of the smooth receptor, a linker is introduced into the proper sites of an extracellular domain ligand and a transmembrane domain ligand to obtain brand-new double-end ligand small molecules, so that the interaction between the ligand and the receptor and the biological activity of the ligand are enhanced.

TREATMENT OF CDK4/6 INHIBITOR RESISTANT NEOPLASTIC DISORDERS

This invention is to methods for treating disorders involving abnormal cellular proliferation that have developed resistance to a selective CDK4/6 inhibitor.

Synthesis method of pyrazolo[1,5-A]pyrimidine heterocyclic compound and derivative

The invention relates to a pynthesis method of pyrazolo[1,5-A]pyrimidine heterocyclic compounds and derivatives. The synthesis method comprises the following steps: (1) preparing N-boc-1,4-cyclohexanediamine; (2), preparing 2-formyl-3-methyl-butyronitrile; (3), preparing 4-isopropyl-1H-pyrazol-5-amine; (4) preparing 3-isopropylpyrazolo[1,5-a]pyrimidine-5,7-diol; (5), preparing 5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyrimidine; (6) utilizing 5,7-dichloro-3-isopropylpyrazolo[1,5-a]pyridine to prepare 5,7-dibromo-3-isopropylpyrazolo[1,5-a]pyrimidine; (7) preparing 4-(5-bromo-3-isopropylpyrazolo[1,5-a]pyrimidin-7-ylamino)-N,N-dimethylbenzenesulfonamide; and (8) preparing 4-(5-(4-(1,1-dimethylethoxy)carbonyl)-aminocyclohexylamino)-3-isopropylpyrazolo[1,5-a]pyrimidin-7-ylamino)-N,N-dimethylbenzenesulfonamide. According to the method, the reaction process is optimized, the reaction steps are simplified, and the reaction conversion rate and the product yield are improved.

Design, synthesis, and biological evaluation of radioiodinated benzo[d]imidazole-quinoline derivatives for platelet-derived growth factor receptor β (PDGFRβ) imaging

Several malignant tumors and fibrotic diseases are associated with PDGFRβ overexpression and excessive signaling, making this receptor attractive for molecular targeting and imaging approaches. A series of benzo[d]imidazole-quinoline derivatives were designed and synthesized to develop radioiodinated compounds as PDGFRβ-specific imaging probes. The structure activity relationship (SAR) evaluation of the designed compounds was performed. Among them, 2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-8-(piperazin-1-yl)quinoline (5a) and 4-{2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}morpholine (5d) exhibited a relatively high PDGFRβ-TK inhibitory potency, whereas iodinated 5a derivative 5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]-8-(piperazin-1-yl)quinoline (8) exhibited a superior inhibitory potency as PDGFRβ inhibitor than iodinated 5d derivative 4-{5-iodo-2-[5-(2-methoxyethoxy)-1H-benzo[d]imidazol-1-yl]quinolin-8-yl}morpholine (11). Furthermore, [125I]8 and [125I]11 were synthesized and evaluated for PDGFRβ radioligand ability, both in vitro and in vivo. Cellular uptake experiments showed that [125I]8 had a higher uptake in BxPC3-luc cells as PDGFRβ-positive cells than [125I]11. Incubation of [125I]8 after pretreatment of PDGFRβ ligands significantly reduced the uptake of [125I]8. In biodistribution experiments using tumor-bearing mice, [125I]8 accumulation in the tumor 1 h postinjection was higher than that of the benzo[d]imidazol-quinoline derivative [125I]IIQP, used in our previous research. These results indicate that [125I]8 could be a promising PDGFRβ imaging agent. Although its clinical application requires further structural modifications, the results obtained in this research may be useful for the development of PDGFRβ-specific radioligands.

Synthesis and antikinetoplastid evaluation of bis(benzyl)spermidine derivatives

This study describes the synthesis and the biological evaluation of twenty-four original bis(benzyl)spermidines. Structural modifications of the polyamine scaffold were performed in order to avoid easily metabolized bonds. Some bis(benzyl)polyamine derivatives have demonstrated promising activity in vitro against Trypanosoma brucei gambiense and Leishmania donovani. From the enzymatic experiments on trypanothione reductase, we observed that this enzyme was not targeted by our compounds. In vivo evaluation on Swiss mice model infected by T. b. gambiense or L. donovani was done with the most interesting compound of the series.

Development of a reversible fluorescent probe for reactive sulfur species, sulfane sulfur, and its biological application

We report a reversible off/on fluorescent probe for monitoring concentration changes of sulfane sulfur by utilizing the unique ability of sulfane sulfur to bind reversibly to other sulfur atoms and the intramolecular spirocyclization reaction of xanthene dyes. It reversibly visualized sulfane sulfur in living A549 cells and primary-cultured hippocampal astrocytes.