546086-95-7

Usage

Uses

Used in Organic Synthesis:
2,8-Diazaspiro[4.5]decan-1-one is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique spiro ring system provides a structural foundation that can be further modified or functionalized to yield a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,8-Diazaspiro[4.5]decan-1-one is used as a key intermediate in the synthesis of various drug candidates. Its versatile chemical structure allows for the development of new therapeutic agents with potential applications in treating a variety of diseases and medical conditions.
Used in Agrochemicals:
2,8-Diazaspiro[4.5]decan-1-one is utilized as a starting material or intermediate in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique spiro ring system can be tailored to create compounds with specific biological activities, making it a valuable component in the development of effective and targeted agrochemical products.
Used in Medicinal Chemistry Research:
2,8-Diazaspiro[4.5]decan-1-one is employed as a research tool in medicinal chemistry to explore its potential biological activities and evaluate its suitability as a lead compound for drug discovery. Its unique structure and the possibility of modifying its functional groups make it an attractive candidate for the development of novel therapeutic agents.
Used in Chemical Biology Studies:
In the field of chemical biology, 2,8-Diazaspiro[4.5]decan-1-one is used to investigate its interactions with biological targets, such as proteins, enzymes, or receptors. Understanding these interactions can provide insights into the compound's potential applications in modulating biological processes and developing new therapeutic strategies.

InChI:InChI=1/C8H14N2O/c11-7-8(3-6-10-7)1-4-9-5-2-8/h9H,1-6H2,(H,10,11)

Upstream product

• 1126-09-6 4-carbethoxypiperidine 
• 212782-43-9 1-tert-butyl 4-ethyl 4-(2-chloroethyl)piperidine-1,4-dicarboxylate 
• 268550-48-7 1-oxo-2,8-diaza-spiro[4.5]decane-8-carboxylic acid tert-butyl ester 
• 142851-03-4 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate 
• 268550-47-6 C₁₅H₂₆N₄O₄ 
• 495414-81-8 4-(cyanomethyl)piperidine-1,4-dicarboxylic acid O₁-tert-butyl O₄-ethyl ester 
• 498-94-2 isonipecotic acid 
• 2971-79-1 isonipecotic acid methyl ester 
• 1350475-42-1 1-tert-butyl 4-methyl 4-(cyanomethyl)piperidine-1,4-dicarboxylate 
• 124443-68-1 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate 
• 1123242-53-4 8-benzyl-2,8-diazaspiro[4.5]decan-1-one 

Downstream Products

• 1409968-55-3 C₂₇H₂₉FN₂O 

Relevant academic research and scientific papers

Novel complex crystal structure of prolyl hydroxylase domain-containing protein 2 (PHD2): 2,8-Diazaspiro[4.5]decan-1-ones as potent, orally bioavailable PHD2 inhibitors

We have discovered a novel complex crystal structure of the PHD2 enzyme with its inhibitor, the 2,8-diazaspiro[4.5]decan-1-one analogue 4b. The widely reported salt bridge between Arg383 of the enzyme and its inhibitors in all complex structures published thus far was not observed in our case. In our complex structure compound 4b forms several novel interactions with the enzyme, which include a hydrogen bond with Arg322, a π-cation interaction with Arg322, a π-π stacking with Trp389, and a π-π stacking with His313. Guided by the structural information, SAR studies were performed on the 2,8-diazaspiro[4.5]decan-1-one series leading to the discovery of compound 9p with high potency and good oral pharmacokinetic profile in mice.

Identification of a Novel 2,8-Diazaspiro[4.5]decan-1-one Derivative as a Potent and Selective Dual TYK2/JAK1 Inhibitor for the Treatment of Inflammatory Bowel Disease

In this study, we described a series of 2,8-diazaspiro[4.5]decan-1-one derivatives as selective TYK2/JAK1 inhibitors. Systematic exploration of the structure-activity relationship through the introduction of spirocyclic scaffolds based on the reported selective TYK2 inhibitor 14l led to the discovery of the superior derivative compound 48. Compound 48 showed excellent potency on TYK2/JAK1 kinases with IC50 values of 6 and 37 nM, respectively, and exhibited more than 23-fold selectivity for JAK2. Compound 48 also demonstrated excellent metabolic stability and more potent anti-inflammatory efficacy than tofacitinib in acute ulcerative colitis models. Moreover, the excellent anti-inflammatory effect of compound 48 was mediated by regulating the expression of related TYK2/JAK1-regulated genes, as well as the formation of Th1, Th2, and Th17 cells. Taken together, these findings suggest that compound 48 is a selective dual TYK2/JAK inhibitor, deserving to be developed as a clinical candidate.

Design, synthesis and biological evaluation of novel diazaspiro[4.5]decan-1-one derivatives as potential chitin synthase inhibitors and antifungal agents

A series of 2,8-diazaspiro[4.5]decan-1-one derivatives were designed, synthesized and screened for their inhibition activities against chitin synthase (CHS) and antimicrobial activities in vitro. The biological assays revealed that compounds 4a, 4e, 4h, 4j, 4o, 4q and 4r exhibited moderated to excellent potency against CHS with IC50 values ranging from 0.12 to 0.29 mM. Compounds 4e, 4j with IC50 value of 0.13 mM, 0.12 mM respectively, showed excellent inhibition potency among these compounds, which were similar to that of polyoxin B whose IC50 value was 0.08 mM. Meanwhile, the screening of the antifungal activity showed that compounds 4j and 4r had the same potency of inhibiting the growth of A. fumigatus with MIC value of 0.08 mmol/L. Compound 4d displayed excellent activity against C. albicans (ATCC 90023) with MIC value of 0.04 mmol/L, which was superior to fluconazole (0.104 mmol/L) and polyoxin B (0.129 mmol/L). The result of antibacterial assay showed that these compounds had little potency against those selected bacteria strains including three Gram-positive bacteria and three Gram-negative bacteria. Furthermore, the combination use of 4c-fluconazole, 4i-fluconazole, 4j-fluconazole, and 4o-fluconazole against C. albicans,A. fumigatus and A. flavus showed additive or synergistic effects. These results indicated that the designed compounds serve as potential chitin synthase inhibitors and have selectively antifungal activities.

INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula (I) and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir11) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and chronic kidney disease and conditions associated with excessive salt and water retention.

SPIRO - FUSED PIPERIDINE DERIVATIVES FOR USE AS INHIBITORS OF THE RENAL OUTER MEDULLARY POTASSIUM CHANNEL

The present invention provides compounds of Formula I and the pharmaceutically acceptable salts thereof, which are inhibitors of the ROMK (Kir1.1) channel. The compounds may be used as diuretic and/or natriuretic agents and for the therapy and prophylaxis of medical conditions including cardiovascular diseases such as hypertension, heart failure and conditions associated with excessive salt and water retention.

Pyrrolidinyl phenylurea derivatives as novel CCR3 antagonists

Optimization starting with our lead compound 1 (IC50 = 4.9 nM) led to the identification of pyrrolidinyl phenylurea derivatives. Further modification toward improvement of the bioavailability provided (R)-1-(1-((6-fluoronaphthalen-2-yl)methyl)pyrrolidin-3-yl)-3-(2-(2- hydroxyethoxy)phenyl)urea 32 (IC50 = 1.7 nM), a potent and orally active CCR3 antagonist.

Substituted benzothiazole amide derivatives

A compound of formula I and a method of treatment of diseases, related to modulation of the adenosine A2 receptor system comprising administering a compound of formula 1to a person in need of such treatment.