Home>>4-Piperidone (hydrochloride)

4-Piperidone (hydrochloride) Sale

(Synonyms: 4-氧代哌啶酮盐酸盐) 目录号 : GC42469

An Analytical Reference Standard

4-Piperidone (hydrochloride) Chemical Structure

Cas No.:41979-39-9

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Sample solution is provided at 25 µL, 10mM.

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产品描述

4-Piperidone (hydrochloride) is an analytical reference standard categorized as a piperidine. It is a starting material in the synthesis of fentanyl (hydrochloride) with phenethylbromide . The physiological and toxicological properties of this compound are not known. This product is intended for research and forensic applications.

Chemical Properties

Cas No. 41979-39-9 SDF
别名 4-氧代哌啶酮盐酸盐
Canonical SMILES O=C1CCNCC1.Cl
分子式 C5H9NO•HCl 分子量 135.6
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mM 7.3746 mL 36.8732 mL 73.7463 mL
5 mM 1.4749 mL 7.3746 mL 14.7493 mL
10 mM 0.7375 mL 3.6873 mL 7.3746 mL
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Research Update

1-[4-(2-Dimethylaminoethoxy)phenylcarbonyl]-3,5-Bis(3,4,5-Trimethoxybenzylidene)- 4-Piperidone hydrochloride and Related Compounds: Potent Cytotoxins Demonstrate Greater Toxicity to Neoplasms than Non- Malignant Cells

Med Chem 2022;18(9):1001-1012.PMID:35319387DOI:10.2174/1573406418666220322154110.

Background: The incidence of cancer has been increasing worldwide. Unfortunately, the drugs used in cancer chemotherapy are toxic to both neoplasms and normal tissues, while many available medications have low potencies. Conjugated α,β-unsaturated ketones differ structurally from contemporary anticancer medications , some of which have noteworthy antineoplastic properties. Objectives: This study aimed to design and synthesize highly potent cytotoxins with far greater toxicity to neoplasms than to non-malignant cells. Methods: A series of N-acyl-3,5-bis(benzylidene)-4-piperidone hydrochlorides 4a-n were prepared and evaluated against Ca9-22, HSC-2, HSC-3, and HSC-4 squamous cell carcinomas as well as against HGF, HPLF, and HPC non-malignant cells. QSAR and western blot analyses were performed. Results: The majority of compounds display submicromolar CC50 values towards the neoplasms; the figures for some of the compounds are below 10-7 M. In general, 4a-n have much lower CC50 values than those of melphalan, 5-fluorouracil, and methotrexate, while some compounds are equitoxic with doxorubicin. The compounds are far less toxic to the non-malignant cells, giving rise to substantial selectivity index (SI) figures. A QSAR study revealed that both potency and the SI data were controlled to a large extent by the electronic properties of the substituents in the arylidene aryl rings. Two representative compounds, 4f and 4g, caused apoptosis in HSC-2 cells. Conclusion: The compounds in series 4 are potent cytotoxins displaying tumor-selective toxicity. In particular, 4g with an average CC50 value of 0.04 μM towards four malignant cell lines and a selectivity index of 46.3 is clearly a lead molecule that should be further evaluated.

3,5-Bis(benzylidene)-1-[4-2-(morpholin-4-yl)ethoxyphenylcarbonyl]-4-piperidone hydrochloride: a lead tumor-specific cytotoxin which induces apoptosis and autophagy

Bioorg Med Chem Lett 2010 Feb 1;20(3):912-7.PMID:20064715DOI:10.1016/j.bmcl.2009.12.076.

A number of N-4-(2-aminoethoxy)phenylcarbonyl derivatives of various 3,5-bis(benzylidene)-4-piperidones 2-5 demonstrated noteworthy cytotoxic potencies towards human HL-60 leukemic cells as well as human HSC-2 and HSC-4 squamous cell carcinomas. In general, toxicity towards HGF, HPC, and HPLF normal cells was substantially lower. The highest selective toxicity was noted when the terminal base is morpholine. Lead optimization was based on finding compounds which had (i) high cytotoxic potencies, (ii) a greater toxicity to neoplasms than normal cells, and (iii) drug-likeness based on the rule of five. From the biodata generated, 5a evolved as a promising lead compound for further development. The mode of action of 5a included the induction of apoptosis in HL-60 cells in which internucleosomal DNA fragmentation and activation of caspase-3 was noted. In addition, 5a caused autophagy in HSC-2 cells.

Synthesis and biological activities of 2,6-diaryl-3-methyl-4-piperidone derivatives

Biol Pharm Bull 2003 Feb;26(2):188-93.PMID:12576678DOI:10.1248/bpb.26.188.

In the present study, a new series of 2,6-diaryl-3-methyl-4-piperidones was synthesized by Mannich reaction (condensation) of ethyl-methyl ketone, substituted aromatic aldehydes and ammonium acetate. Oximes and thiosemicarbazone derivatives of 2,6-diaryl-3-methyl-4-piperidones were synthesized by reaction with hydroxylamine hydrochloride and thiosemicarbazide respectively. The chemical structures were confirmed by means of IR, 1H-, 13C-NMR and mass spectral data. The compounds were screened for acute toxicity, analgesic, local anaesthetic and antifungal activity. 2-(4-Methylphenyl)-3-methyl-6-(4-chlorophenyl)-piperidin-4-one 2 exhibited the highest analgesic and local anaesthetic activity. The oximes and thiosemicarbazones were completely devoid of analgesic and local anaesthetic activity. 2-(4-Methylphenyl)-3-methyl-6-(4-hydroxyphenyl)-piperidin-4-oxime 21 and 2-(4-methoxyphenyl)-3-methyl-6-(4-chlorophenyl)-piperidin-4-oxime 17 exhibited potent antifungal activity against Aspergillus niger. Antifungal activity against Candida albicans was observed only with 2-(4-dimethylaminophenyl)-3-methyl-6-(4-chlorophenyl)-piperidin-4-oxime 20. 2,6-Diaryl-3-methyl-4-piperidones did not exhibit antifungal property.

Design, cytotoxic and fluorescent properties of novel N-phosphorylalkyl substituted E,E-3,5-bis(arylidene)piperid-4-ones

Eur J Med Chem 2009 May;44(5):2135-44.PMID:19046794DOI:10.1016/j.ejmech.2008.10.019.

A series of E,E-N-phosphorylalkylene-3,5-bis(arylidene)piperid-4-ones 7a-k was prepared via the condensation of aromatic aldehydes with omega-aminophosphonates 5a-c and 6a,b bearing piperidone or a protected piperidone moiety, respectively. The synthetic routes to the starting aminophosphonates 5a-c and 6a,b varied depending on the number of methylene groups in the alkylene chain and comprised the Kabachnik-Fields reaction (n=1), the aza-Michael reaction (n=2) or alkylation of 4-Piperidone hydrochloride with diethyl omega-bromoalkylphosphonates under phase transfer catalysis conditions (n=3,4). Phosphoryl substituted 3,5-bis(arylidene)piperid-4-ones 7b,c,e,f,h,i,k bearing both nitro groups and fluorine atoms in the para-position of the arene rings possess cytotoxicity toward human carcinoma cell lines CaOv3, Scov3, PC3 and A549 in the low micromolar range while their analogues having para-dimethylamino groups had IC(50) values greater than 50 microM. In contrast, only Me(2)N-substituted phosphonates 7g,j (n=3 and 4) and the salts of Me(2)N-substituted phosphonic acids 10c,f (n=2 and 3) display fluorescence.

Highly enantioselective access to primary propargylamines: 4-piperidinone as a convenient protecting group

Org Lett 2006 May 25;8(11):2437-40.PMID:16706545DOI:10.1021/ol060876w.

[reaction: see text] We report a highly enantioselective, catalytic three-component coupling of aldehydes, alkynes, and 4-Piperidone hydrochloride hydrate to afford the corresponding tertiary propargylamines in useful yields. The selective cleavage of the piperidone protecting group using either ammonia/EtOH or a polymer-supported scavenger amine furnishes primary propargylamines.