104-16-5

Usage

Uses

Used in Pharmaceutical Industry:
1-(3-Chloropropyl)-4-methylpiperazine is used as a key intermediate for the synthesis of various pharmaceutically active compounds, such as antiulcer agents, antitumor agents, antibiotics, and anxiolytics. Its structural diversity and reactivity make it a valuable component in the development of new drugs with improved therapeutic properties.
Used in Antitumor Applications:
1-(3-Chloropropyl)-4-methylpiperazine is used as a reactant in the synthesis of pyrimidines, which serve as novel sigma-1 receptor antagonists. These antagonists are being investigated for their potential in treating neuropathic pain, offering a new approach to managing this debilitating condition.

InChI:InChI=1/C8H17ClN2/c1-10-5-7-11(8-6-10)4-2-3-9/h2-8H2,1H3

Upstream product

• 109-01-3 1-methyl-piperazine 
• 109-70-6 1.3-chlorobromopropane 

Downstream Products

• 128992-12-1 1-{3-[1,5-Bis-(4-chloro-phenyl)-1H-[1,2,4]triazol-3-yloxy]-propyl}-4-methyl-piperazine; hydrochloride 
• 62040-85-1 3-(N-methylpiperazino)propylhydrazine 
• 93699-33-3 1-(2-methoxyphenyl)-1-{4-[3-(4-methylpiperazin-1-yl)-propoxy]-phenyl}-propan-1-ol 
• 1130354-08-3 C₂₅H₂₉ClFN₅O₃ 
• 1130354-17-4 C₂₅H₂₉ClFN₅O₃ 
• 98455-00-6 3-(4-methylpiperazino)propylthiol 
• 320366-02-7 4-(2-bromo-4-fluorophenoxy)-6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]quinazoline 

Relevant academic research and scientific papers

Discovery of phenylselenoether-hydantoin hybrids as ABCB1 efflux pump modulating agents with cytotoxic and antiproliferative actions in resistant T-lymphoma

Multidrug resistance (MDR) in cancer cells is a crucial aspect to consider for a successful cancer therapy. P-gp/ABCB1, a member of ABC transporters, is involved in the main tumour MDR mechanism, responsible for the efflux of drugs and cytotoxic substances. Herein, we describe a discovery of potent selenium-containing ABCB1 MDR efflux pump modulators with promising anticancer activity. On three groups of selenoethers comprehensive studies in terms of design, synthesis, and biological assays, including an insight into cellular mechanisms of anticancer action as well as an ADMET-screening in vitro were performed, followed by in-depth SAR analysis. Among the investigated new phenylselenoether hybrids, four compounds showed significant cytotoxic and anti-proliferative effects, in particular, in resistant cancer cells. Hydantoin derivatives (5–7) were significantly more effective than the reference inhibitor verapamil (up to 2.6-fold at a 10-fold lower concentration) modulating ABCB1-efflux pump, also possessing a good drug-drug interaction profile. The best compound (6) was further evaluated in human JURKAT T-lymphocytic cancer cells for its impact on cell proliferation rate. Mechanistically, the expression of cyclin D1, an enhancer of the cell cycle, decreases, while p53, an inhibitor of cell proliferation, was up-regulated upon the treatment with compound 6 alone or in combination with the chemotherapeutic agent doxorubicin. In summary, a new chemical space of highly active selenium-containing anticancer agents has been discovered, with a new lead compound 6 that warrants more in-depth biological evaluation and further pharmacomodulation.

Synthesis and trazodone-like pharmacological profile of 1- and 2--propyl>benzotriazoles

A series of 1- and 2--propyl>benzotriazoles were prepared and evaluated for their trazodone-like pharmacological profile; as preliminary pharmacological screening, the compounds were tested for their antiserotonergic, antiadrenergic and antihistaminic in vitro activity as well as for their analgesic in vivo action.Structure-activity relationships showed that among the synthesized compounds, the analogues bearing on the 4-piperazine nitrogen either an unsubstituted phenyl ring or a 2- or 3-chloro phenyl moiety show a pharmacological profilesimilar to that of the antidepressant trazodone. benzotriazoles / antiserotonergic / antiadrenergic / antihistaminic/ analgesic

Discovery of novel TNNI3K inhibitor suppresses pyroptosis and apoptosis in murine myocardial infarction injury

Myocardial infarction (MI) injury is a highly lethal syndrome that has, until recently, suffered from a lack of clinically efficient targeted therapeutics. The cardiac troponin I interacting kinase (TNNI3K) exacerbates ischemia-reperfusion (IR) injury via oxidative stress, thereby promoting cardiomyocyte death. In this current study, we designed and synthesized 35 novel TNNI3K inhibitors with a pyrido[4,5]thieno[2,3-d] pyrimidine scaffold. In vitro results indicated that some of the inhibitors exhibited sub-micromolar TNNI3K inhibitory capacity and good kinase selectivity, as well as cytoprotective activity, in an oxygen-glucose deprivation (OGD) injury cardiomyocyte model. Furthermore, investigation of the mechanism of the representative derivative compound 6o suggested it suppresses pyroptosis and apoptosis in cardiomyocytes by interfering with p38MAPK activation, which was further confirmed in a murine myocardial infarction injury model. In vivo results indicate that compound 6o can markedly reduce myocardial infarction size and alleviate cardiac tissue damage in rats. In brief, our results provide the basis for further development of novel TNNI3K inhibitors for targeted MI therapy.

Zinc mediated alkylation of cyclic secondary amines

Zinc metal mediated simple and efficient alkylation of cyclic secondary amines e.g., piperazines and morpholine with allyl bromide, chlorobromo propane and p-methoxy benzyl bromide is described in good yields.

ARYLNAPHTHALENE COMPOUNDS AS VACUOLAR-ATPASE INHIBITORS AND THE USE THEREOF

Ebola virus and Marburg virus are filoviruses and are responsible for outbreaks that cause up to 90% fatality, including the recent outbreak in West Africa that has resulted in over 11,000 deaths. The present disclosure generally relates to novel arylnaphthalene compounds as a vacuolar-ATPase inhibitor that are useful for the treatment of various viral infections, including those infections caused by filoviruses. Pharmaceutical composition matters and methods of use are within the scope of this invention.

NITROGEN-CONTAINING HETEROCYCLIC COMPOUND OR SALT THEREOF

A compound represented by Formula [1] (in the formula, Z1 represents N, CH, or the like; X1 represents NH or the like; R1 represents a heteroaryl group or the like; each of R2, R3, and R4 represents a hydrogen atom, a halogen atom, an alkoxy group, or the like; and R5 represents a heteroaryl group or the like) or salt thereof.

Design, synthesis and biological evaluation of novel podophyllotoxin derivatives bearing 4β-disulfide/trisulfide bond as cytotoxic agents

A novel series of C-4β-disulfide/trisulfide-containing podophyllotoxin derivatives were designed, synthesized, and biologically evaluated for their cytotoxic activities against human cancer cell lines, including KB (Mouth Epidermal Carcinoma Cells) and KB/VCR (Vincristine-resistant Mouth Epidermal Carcinoma Cells). Most of these compounds exhibited promising moderate to good cytotoxic activities. In particular, some of them displayed even superior activities to that of etoposide, especially for KB/VCR cell lines, indicating that introduction of the disulfide/trisulfide moiety would be beneficial for overcoming the multi-drug resistant limitation of etoposide. Moreover, the metabolic evaluation of the most promising compound was further performed to reveal that disulfide bond can be stable in human plasma over 8 hours, indicating good potential of these compounds for in vivo anti-cancer activities.

Microwave-assisted solvent-free synthesis of 3-[(4-substituted piperazin-1-yl)alkyl] imidazo[2,1-b][1,3]benzothiazol-2(3H)-ones as serotonin3 (5-HT3) receptor antagonists

A series of novel 3-[(4-substituted piperazin-1-yl)alkyl]imidazo[2,1-b][1, 3]benzothiazol-2(3H)-ones were prepared by microwave irradiation using alumina as solid support and also by a conventional method. The compounds were characterized by spectral data and the purity was ascertained by microanalysis. The synthesized compounds were evaluated for 5-hydroxytryptamine3 antagonisms in a longitudinal muscle-myenteric plexus preparation from guinea pig ileum against the 5-hydroxytryptamine3 agonist, 2-methyl-5-hydroxytryptamine. Among the test compounds, 3-[2-(4-methylpiperazin- 1-yl)ethyl]imidazo[2,1-6][1,3]benzothiazol-2(3H)-one (3b) showed most favorable 5-hydroxytryptamine3 antagonism (pA2 6.7) in the isolated guinea pig ileum.

Quinazoline derivatives

The invention concerns quinazoline derivatives of Formula (I) wherein Q1includes a quinazoline ring optionally substituted with a group such as halogeno, trifluoromethyl and cyano, or a group of the formula: Q3—X1— wherein X1includes a direct bond and O and Q3includes aryl, aryl-(1-6C)alkyl, heterocyclyl and heterocyclyl-(1-6C)alkyl; each of R2and R3is hydrogen or (1-6C)alkyl; Z includes O, S and NH; and Q2includes aryl and aryl-(1-3C)alkyl or a pharmaceutically-acceptable salt thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the manufacture of a medicament for use in the prevention or treatment of T cell mediated diseases or medical conditions in a warm-blooded animal.

Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8

The invention relates to isoxazole and oxadiazole compounds of Formulae I and II, pharmaceutical compositions containing the compounds, and methods for their production and use. These compounds are effective in inhibiting the action of IL-8 and are thus useful as anti-inflammatory agents for a variety of diseases.