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

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

Uses

Used in Pharmaceutical Development:
Spiro[isochroman-1,4'-piperidine] is used as a precursor in drug synthesis for its potential to exhibit antimicrobial, anti-inflammatory, and anti-tumor properties. Its unique structure allows it to interact with biological targets in ways that may lead to the development of novel pharmaceutical agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, spiro[isochroman-1,4'-piperidine] serves as a subject of study for its potential biological activities. Researchers are interested in exploring its interactions with various biological systems to understand its pharmacological properties and how it might be harnessed for therapeutic purposes.
Further research and investigation are necessary to fully elucidate the pharmacological properties and potential applications of spiro[isochroman-1,4'-piperidine], ensuring that its use in drug development and medicinal chemistry can be optimized for safety and efficacy.

Upstream product

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

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.

Piperazine compound and application thereof in preparation of chemokine receptor CCR2 antagonist

The invention relates to a piperazine compound as shown in a formula (I) and an application of the piperazine compound in preparation of a chemokine receptor CCR2 antagonist or a medicine for treatingCCR2-mediated diseases.

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.

SPIRO-5,6-DIHYDRO-4H-2,3,5,10B-TETRAAZA-BENZO[E]AZULENES

The present invention is concerned with spiro-dihydrotetraazabenzoazulenes, i.e. spiro-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzo[e]azulenes of formula I wherein R1, R2, R3, X, Y, Z, m and n are as described herein. The compounds according to the invention act as V1a receptor modulators and are useful as therapeutics acting peripherally and centrally in the conditions of dysmenorrhea, male or female sexual dysfunction, hypertension, chronic heart failure, inappropriate secretion of vasopressin, liver cirrhosis, nephrotic syndrome, anxiety, depressive disorders, obsessive compulsive disorder, autistic spectrum disorders, schizophrenia, and aggressive behavior.

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.

Spiro-substituted piperidines as neurokinin receptor antagonists. II. Syntheses and NK2 receptor-antagonistic activities of N-[2-aryl-4-(spiro- substituted piperidin-1'-yl)butyl]carboxamides

In the course of our research on spiro-compounds as neurokinin receptor antagonists, N-[2-aryl-4-spiro-substituted piperidin-1'-yl)butyl]carboxamides were designed, based on YM-35375 (3) as a lead compound, and evaluated for NK2 receptor-antagonistic activities. Some derivatives inhibited the binding of radio-labeled neurokinin A to the NK2 receptor with IC50 values at the level of 10-9. Among these compounds, (±)-1'-[4-(N-benzoyl-N-methylamino)- 3-(3,4-dichlorophenyl)butyl]spiro[benzo[c]thiophene-1(3H), 4'-piperidine] 2- oxide (58, YM-38336) showed 10 times more potent NK2 receptor binding affinity than compound 3 (IC50 values of 8.9 and 84nM, respectively). It showed more potent inhibitory activity (ID50 20μg/kg (i.v.)) against [β- Ala8]-NKA(4 - 10)-induced bronchoconstriction in guinea pigs than compound 3 (ID50 41 μg/kg (i.v.)). This compound was also effective intraduodenally in the same model, exhibiting an ID50 value of 0.41 μg/kg.