1932-03-2

Basic information

• Product Name: 1-(2-Chloroethyl)-piperidine
• Synonyms: 1-(2-chloroethyl)-piperidin;2-(1-piperidyl)ethylchloride;2-piperidinoethylchloride;beta-piperidinoethylchloride;n-(2-chloroethyl)piperidine;n-(beta-chloroethyl)piperidine;1-(2-CHLOROETHYL)PIPERIDINE;2-CHLOROETHYL PIPERIDINE
• CAS NO: 1932-03-2
• Molecular Formula: C₇H₁₄ClN
• Molecular Weight: 147.65
• Mol File: 1932-03-2.mol

Chemical Properties

• Melting Point: 229-230 °C(Solv: chloroform (67-66-3); acetone (67-64-1))
• Boiling Point: 190.309 °C at 760 mmHg
• Flash Point: 68.897 °C
• Appearance: /
• Density: 1.008 g/cm³
• Vapor Pressure: 0.545mmHg at 25°C
• Refractive Index: 1.469
• PKA: 8.33±0.10(Predicted)
• CAS DataBase Reference: 1-(2-Chloroethyl)-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Chloroethyl)-piperidine(1932-03-2)
• EPA Substance Registry System: 1-(2-Chloroethyl)-piperidine(1932-03-2)

Safety Data

• Hazardous Substances Data: 1932-03-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Chloroethyl)-piperidine is used as a key intermediate for the synthesis of various drugs, contributing to the development of new drug candidates and the enhancement of existing therapeutic agents. Its chloroethyl group facilitates the creation of diverse chemical entities with improved efficacy and selectivity.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2-Chloroethyl)-piperidine is utilized as a building block for the production of agrochemicals, such as pesticides and herbicides. Its reactivity allows for the design of novel compounds with targeted pest control properties, enhancing crop protection and yield.
Used in Fine Chemicals Industry:
1-(2-Chloroethyl)-piperidine is employed as a versatile intermediate in the synthesis of fine chemicals, including specialty chemicals and advanced materials. Its unique structure and reactivity enable the creation of high-value products with specific applications in various industries, such as fragrances, dyes, and coatings.
Used in Drug Modification:
1-(2-Chloroethyl)-piperidine is used for the modification of existing drugs to improve their therapeutic efficacy, pharmacokinetics, and safety profiles. Its incorporation into drug molecules can lead to enhanced drug-target interactions, improved solubility, and reduced side effects, ultimately benefiting patients and healthcare providers.

InChI:InChI=1/C7H14ClN/c8-4-7-9-5-2-1-3-6-9/h1-7H2

Upstream product

• 3040-44-6 1-piperidinoethanol 
• 110-89-4 piperidine 
• 107-04-0 1-Bromo-2-chloroethane 
• 107-20-0 2-chloroethanal 
• 540-51-2 2-bromoethanol 
• 33265-79-1 1-(2-chloroethyl)piperidine hydrochloride 
• 107-06-2 1,2-dichloro-ethane 
• 2008-75-5 N-chloroethylpiperidine hydrochloride 
• 70015-86-0 1-(2-chloroethyl)-1-nitroso-3-(3-pyridylmethyl)urea N-oxide 
• 408538-22-7 N-hydroxyethylpiperidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 107-07-3 2-chloro-ethanol 

Downstream Products

• 102004-55-7 phenyl-acetic acid-(2-piperidino-ethyl ester) 
• 94437-05-5 phenyl-[2-(2-piperidin-1-yl-ethoxy)-phenyl]-amine 
• 6244-56-0 2-biphenyl-4-yl-propionic acid-(2-piperidino-ethyl ester) 
• 111617-17-5 5-phenyl-2-(2-piperidino-ethyl)-2H-tetrazole 
• 441-92-9 1-[3-(4-fluoro-phenyl)-3-thiazol-2-yl-propyl]-piperidine 
• 788116-49-4 1-(2-trityloxy-ethyl)-piperidine 
• 100657-75-8 4-(piperidino)-2-phenyl-2-(2-pridyl)butanenitrile 
• 102395-78-8 6,7-dimethoxy-2-(2-piperidino-ethyl)-1,2,3,4-tetrahydro-isoquinoline; dihydrochloride 
• 102759-60-4 benzyl-(2,6-dimethyl-[4]pyridyl)-(2-piperidino-ethyl)-amine 
• 24158-54-1 1-phenyl-cyclopentanecarboxylic acid-(2-piperidino-ethyl ester) 
• 3626-71-9 N-benzyl-N-(2-piperidino-ethyl)-aniline 
• 875229-51-9 1-[2-(1,1-diphenyl-ethoxy)-ethyl]-piperidine 

Relevant articles and documents

Metabolomics-assisted discovery of a new anticancer GLS-1 inhibitor chemotype from a nortopsentin-inspired library: From phenotype screening to target identification

The enzyme glutaminase-1 (GLS-1) has shown a clear and coherent implication in the progression and exacerbation of different aggressive tumors such as glioblastoma, hepatocarcinoma, pancreas, bone, and triple-negative breast cancer. Few chemotypes are currently available as selective GLS-1 inhibitors, and still, fewer of them are at the clinical stage. In the present paper, starting from a naturally-inspired antitumor compound library, metabolomics has been used to putatively identify the molecular mechanism underlying biological activity. GLS-1 was identified as a potential target. Biochemical analysis confirmed the hypothesis leading to the identification of a new hit compound acting as a GLS-1 selective inhibitor (IC50 = 3.96 ± 1.05 μM), compared to the GLS-2 isoform (IC50 = 12.90 ± 0.87 μM), with remarkable antitumor potency over different aggressive tumor cell lines. Molecular modelling studies revealed new insight into the drug-target interaction providing robust SAR clues for the rational hit-to-lead development. The approach undertaken underlines the wide potential of metabolomics applied to drug discovery, particularly in target identification and hit discovery following phenotype screening.

PIM KINASE INHIBITOR COMPOSITIONS AND USES THEREOF

This disclosure relates to compounds and compositions useful as inhibitors of PIM kinases. Also provided are methods of synthesis and methods of use of PIM inhibitors in treating individuals suffering from cancerous malignancies.

C-3 NOVEL TRITERPENONE WITH C-17 REVERSE AMIDE DERIVATIVES AS HIV INHIBITORS

The present invention relates to C-3 novel triterpenone with C-17 reverse amide compounds of Formula (I); and pharmaceutically acceptable salts thereof, wherein ring Formula (II), R1, R2, R3, R4, R5, R6, R7, 'n' and 'm' are as defined in Formula (I). The invention also relates to C-3 novel triterpenone with C-17 reverse amide derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

Novel indanone derivatives as MAO B/H3R dual-targeting ligands for treatment of Parkinson's disease

The design of multi-targeting ligands was developed in the last decades as an innovative therapeutic concept for Parkinson's disease (PD) and other neurodegenerative disorders. As the monoamine oxidase B (MAO B) and the histamine H3 receptor (H3R) are promising targets for dopaminergic regulation, we synthetized dual-targeting ligands (DTLs) as non-dopaminergic receptor approach for the treatment of PD. Three series of compounds were developed by attaching the H3R pharmacophore to indanone-related MAO B motifs, leading to development of MAO B/H3R DTLs. Among synthesized indanone DTLs, compounds bearing the 2-benzylidene-1-indanone core structure showed MAO B preferring inhibition capabilities along with nanomolar hH3R affinity. Substitution of C5 and C6 position of the 2-benzylidene-1-indanones with lipophilic substituents revealed three promising candidates exhibiting inhibitory potencies for MAO B with IC50 values ranging from 1931 nM to 276 nM and high affinities at hH3R (Ki 50 = 276 nM, hH3R Ki = 6.5 nM) showed highest preference for MAO B over MAO A (SI > 36). Interestingly, IC50 determinations after preincubation of enzyme and DTLs revealed also nanomolar MAO B potency for 3e (MAO B IC50 = 232 nM), a structural isomer of 3f, and 3d (MAO B IC50 = 541 nM), suggesting time-dependent inhibition modes. Reversibility of inhibition for all three compounds were confirmed by dilution studies in excess of substrate. Thus, indanone-substituted derivatives are promising lead structures for the design of MAO B/hH3R DTLs as novel therapeutic approach of PD therapy.

Highly Water-Soluble Cyclopentadienyl and Indenyl Molybdenum(II) Complexes - Second Generation of Molybdenum-Based Cytotoxic Agents

A series of the cyclopentadienyl and indenyl molybdenum compounds bearing alkylammonium functions [(η5-Cp′)Mo(CO)2(N,NL)][BF4]2 were synthesized and characterized by analytical and spectroscopic methods. The structures of [{η5-C5H4CH2CH2NH(CH2)5}Mo(CO)2(4,7-Ph2-phen)][BF4]2 (4,7-Ph2-phen = 4,7-diphenyl-1,10-phenanthroline) and [(η5-C9H6CH2CH2NHMe2)Mo(CO)2(phen)][BF4]2 (phen = 1,10-phenanthroline) were determined by X-ray crystallography. All of the synthesized compounds exhibit high activity against the human leukemia cell lines MOLT-4 and HL-60. They are approximately one order of magnitude more active than cisplatin. This study has proven that the modification of the outer coordination sphere of molybdenum complexes has a strong impact on their activity and may be successfully used for the design of new highly cytotoxic active species. A series of highly cytotoxic molybdenum(II) complexes are synthesized, and their activity against MOLT-4 and HL-60 leukemia cells is established.

Isoflavone amide type derivative, preparation method and medical application thereof

The invention relates to the field of medicinal chemistry, and relates to an isoflavone amide type derivative, a preparation method and a medical application thereof, in particular to an isoflavone amide type derivative with the general formula (I), a preparation method thereof, medicine compositions including the isoflavone amide type derivative and a medical application thereof, especially an application of the isoflavone amide type derivative as a medicine for preventing or curing hyperlipemia, obesity or type II diabetes. The general formula (I) is shown in the description.

Exploring the Anticancer Activity of Functionalized Isoindigos: Synthesis, Drug-like Potential, Mode of Action and Effect on Tumor-Induced Xenografts

Meisoindigo has been used as an indirubin substitute for the treatment of chronic myeloid leukemia (CML) for several years. In view of its poor solubility and erratic absorption, several investigations have focused on developing analogues with more desirable physicochemical profiles. Here, we investigated the structure-activity relationship (SAR) of meisoindigo with respect to its antiproliferative activity on leukemic K562 cells and found that appending a phenalkyl side chain onto the lactam NH resulted in analogues that retained good activity. Furthermore, analogues in which the phenyl ring was substituted with a basic heterocycle were significantly more soluble than meisoindigo while retaining acceptable antiproliferative profiles. The most promising analogue (E)-1-(2-(4-methylpiperazin-1-yl)ethyl)-[3,3′-biindolinylidene]-2,2′-dione (5-4) is more potent than meisoindigo across a panel of malignant cells, with at least 40 times greater solubility than meisoindigo, little or no tendency to aggregate in solution and capable of significantly extending the lifespans of animals with K562 induced xenografts. Mechanistically, it induced apoptotic cell death and disrupted the progression of K562 cells from the G1 to G2 phase. Taken together, our findings highlighted the feasibility of addressing the physicochemical deficits of the isoindigo scaffold by systematic modifications which was achieved without overt loss of growth inhibitory activity.

Bulk gold-catalyzed reactions of diazoalkanes with amines and O2 to give enamines

Bulk gold powder, consisting of approximately 5-50 μm particles, catalyzes reactions of diazoalkanes E(H)C=N2, where E is CO 2Et or PhC(O), with amines R1R2NH and O 2 to give enamine products (R1R2N)(E)C=CH(E) in 58-94% yield. The reactions are proposed to occur by initial formation of surface-bound (E)(H)C: carbene groups that are attacked by nucleophilic amines. The enamine products are very different than those obtained in reactions catalyzed by homogeneous transition metal complexes. These reactions of diazoalkanes, amines, and O2 represent a new type of bulk gold-catalyzed reaction.

A study of 2-piperidino-1-ethanol and its derivatives as antimicrobial additives to oils

Some derivatives of 1-hydroxy-2-pyperidinoethane were studied as antimicrobial additives to lubricant oils.