180160-97-8

Basic information

• Product Name: spiro[isochroman-1,4'-piperidine]
• Synonyms: spiro[isochroman-1,4'-piperidine];3,4-dihydrospiro[2-benzopyran-1,4'-piperidine];3,4-Dihydrospiro[isochromene-1,4'-piperidine];Spiro[1H-2-benzopyran-1,4'-piperidine], 3,4-dihydro-
• CAS NO: 180160-97-8
• Molecular Formula: C₁₃H₁₇NO
• Molecular Weight: 203.28018
• EINECS: 604-604-1
• Mol File: 180160-97-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 341.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.12
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.21±0.20(Predicted)
• CAS DataBase Reference: spiro[isochroman-1,4'-piperidine](CAS DataBase Reference)
• NIST Chemistry Reference: spiro[isochroman-1,4'-piperidine](180160-97-8)
• EPA Substance Registry System: spiro[isochroman-1,4'-piperidine](180160-97-8)

Safety Data

• Hazardous Substances Data: 180160-97-8(Hazardous Substances Data)

Usage

General Description

Spiro[isochroman-1,4'-piperidine] is a chemical compound that is classified as a spiro compound, containing both isochroman and piperidine moieties. It is a heterocyclic compound, meaning it contains atoms other than carbon in its ring structure. This chemical has potential applications in drug synthesis and medicinal chemistry, as spiro compounds have been found to possess various biological activities, such as antimicrobial, anti-inflammatory, and anti-tumor properties. Spiro[isochroman-1,4'-piperidine] may have the potential to be utilized in the development of novel pharmaceutical agents due to its unique structure and potential biological activities. Further research and investigation on this compound are needed to fully understand its pharmacological properties and potential applications.

Upstream product

• 60-12-8 2-phenylethanol 
• 3612-20-2 1-phenylmethyl-4-piperidone 
• 32161-06-1 1-acetyl-4-piperidinone 
• 76360-25-3 1-(4,4-dimethoxypiperidin-1-yl)ethan-1-one 
• 345294-39-5 1'-benzylspiro 
• 909034-76-0 tert-butyl spiro[isochroman-1,4'-piperidine]-1'-carboxylate 
• 173943-92-5 4-Hydroxy-4-[2-(2-hydroxy-ethyl)-phenyl]-piperidine-1-carboxylic acid ethyl ester 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 
• 1074-16-4 2-bromophenylethyl alcohol 
• 173944-51-9 ethyl 3,4-dihydrospiro(1H-2-benzopyran-1,4'-piperidine)-1'-carboxylate 

Downstream Products

• 1175705-99-3 C₂₄H₂₄N₄O₂ 

Relevant articles and documents

Synthesis and biological evaluation of spirocyclic antagonists of CCR2 (chemokine CC receptor subtype 2)

Activation of chemokine CC receptors subtype 2 (CCR2) plays an important role in chronic inflammatory processes such as atherosclerosis, multiple sclerosis and rheumatoid arthritis. A diverse set of spirocyclic butanamides 4 (N-benzyl-4-(3,4-dihydrospiro[[2]benzopyran-1,4′-piperidin]-1′-yl)butanamides) was prepared by different combination of spirocyclic piperidines 8 (3,4-dihydrospiro[[2]benzopyran-1,4′-piperidines]) and γ-halobutanamides 11. A key step in the synthesis of spirocyclic piperidines 8 was an Oxa-Pictet-Spengler reaction of β-phenylethanols 5 with piperidone acetal 6. The substituted γ-hydroxybutanamides 11c-e were prepared by hydroxyethylation of methyl acetates 13 with ethylene sulfate giving the γ-lactones 14c and 14e. Aminolysis of the γ-lactones 14c and 14e with benzylamines provided the γ-hydroxybutanamides 15c-e, which were converted into the bromides 11c-e by an Appel reaction using polymer-bound PPh3. In radioligand binding assays the spirocyclic butanamides 4 did not displace the iodinated radioligand 125I-CCL2 from the human CCR2. However, in the Ca2+-flux assay using human CCR2 strong antagonistic activity of butanamides 4 was detected. Analysis of the IC50-values led to clear relationships between the structure and the inhibition of the Ca2+-flux. 4g (4-(3,4-dihydrospiro[[2]benzopyran-1,4′-piperidin]-1′-yl)-N-[3,5-bis(trifluoromethylbenzyl)]-2-(4-fluorophenyl)butanamide) and 4o (N-[3,5-bis(trifluoromethyl)benzyl]-2-cyclopropyl-4-(3,4-dihydrospiro[[2]benzopyran-1,4′-piperidin]-1′-yl)butanamide) represent the most potent CCR2 antagonists with IC50-values of 89 and 17 nM, respectively. Micromolar activities were found in the β-arrestin recruitment assay with murine CCR2, but the structure-activity-relationships detected in the Ca2+-flux assay were confirmed.

Easy-To-Synthesize Spirocyclic Compounds Possess Remarkable in Vivo Activity against Mycobacterium tuberculosis

Society urgently needs new, effective medicines for the treatment of tuberculosis. To kick-start the required hit-to-lead campaigns, the libraries of pharmaceutical companies have recently been evaluated for starting points. The GlaxoSmithKline (GSK) library yielded many high-quality hits, and the associated data were placed in the public domain to stimulate engagement by the wider community. One such series, the spiro compounds, are described here. The compounds were explored by a combination of traditional in-house research and open source methods. The series benefits from a particularly simple structure and a short associated synthetic chemistry route. Many members of the series displayed striking potency and low toxicity, and highly promising in vivo activity in a mouse model was confirmed with one of the analogues. Ultimately the series was discontinued due to concerns over safety, but the associated data remain public domain, empowering others to resume the series if the perceived deficiencies can be overcome.

1, 2, 4-TRIAZOLE DERIVATIVES AND THEIR USE AS OXYTOCIN ANTAGONISTS

The present invention relates to a class of substituted triazoles of formula (I), uses thereof, and compositions containing said compounds. These compounds have activity as oxytocin antagonists.