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1-Benzylpiperazine is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 2759-28-6 Structure
  • Basic information

    1. Product Name: 1-Benzylpiperazine
    2. Synonyms: 4-BENZYLPIPERAZINE;N-BENZYLPIPERAZINE;N-(PHENYLMETHYL)PIPERAZINE;TIMTEC-BB SBB007534;1-BENZYLPIPERAZINE 98%;N-Benylpiperazine;1-Benzylpiperazine, 98+%;N-(Phenylmethyl)Piperaine
    3. CAS NO:2759-28-6
    4. Molecular Formula: C11H16N2
    5. Molecular Weight: 176.26
    6. EINECS: 220-423-6
    7. Product Categories: PIPERIDINE;PHARMACEUTICAL INTERMEDIATES;pharmacetical;Piperaizine;Piperazines;Building Blocks;BA - BHBuilding Blocks;Alphabetic;B;Heterocyclic Building Blocks;pharmaceutical intermediate
    8. Mol File: 2759-28-6.mol
    9. Article Data: 88
  • Chemical Properties

    1. Melting Point: 17-20 °C
    2. Boiling Point: 143-146/12mm
    3. Flash Point: >230 °F
    4. Appearance: clear colorless to yellow liquid
    5. Density: 1.014 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.00996mmHg at 25°C
    7. Refractive Index: n20/D 1.547(lit.)
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 9.25±0.10(Predicted)
    11. CAS DataBase Reference: 1-Benzylpiperazine(CAS DataBase Reference)
    12. NIST Chemistry Reference: 1-Benzylpiperazine(2759-28-6)
    13. EPA Substance Registry System: 1-Benzylpiperazine(2759-28-6)
  • Safety Data

    1. Hazard Codes: C,Xi
    2. Statements: 34
    3. Safety Statements: 26-36/37/39-45
    4. RIDADR: UN 3267 8/PG 2
    5. WGK Germany: 3
    6. RTECS:
    7. F: 9
    8. HazardClass: 8
    9. PackingGroup: III
    10. Hazardous Substances Data: 2759-28-6(Hazardous Substances Data)

2759-28-6 Usage

Chemical Properties

clear colorless to yellow liquid

Definition

ChEBI: A tertiary amino compound that is piperazine substituted by a benzyl group at position 1. It is a serotonergic agonist used as a recreational drug.

Check Digit Verification of cas no

The CAS Registry Mumber 2759-28-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 2,7,5 and 9 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 2759-28:
(6*2)+(5*7)+(4*5)+(3*9)+(2*2)+(1*8)=106
106 % 10 = 6
So 2759-28-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H22N2/c1-2-4-11(5-3-1)10-13-8-6-12-7-9-13/h11-12H,1-10H2/p+2

2759-28-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-benzylpiperazine

1.2 Other means of identification

Product number -
Other names 1-benzyl-piperazine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:2759-28-6 SDS

2759-28-6Relevant articles and documents

The effect of the structure of derivatives of nitrogen-containing heterocycles on their anti-influenza activity

Gridina, Tatyana L.,Fedchuk, Alla S.,Basok, Stephan S.,Artemenko, Anatoliy G.,Ognichenko, Liudmila N.,Shitikova, Larisa I.,Lutsyuk, Anatolii F.,Gruzevskii, Aleksandr A.,Kuz’min, Victor E.

, p. 455 - 462 (2019)

[Figure not available: see fulltext.] An adequate QSAR model based on the simplex representation of the molecular structure was built in order to optimize the search for new anti-influenza agents. Structural interpretation of the model allowed us to identify molecular fragments that determine the activity of compounds against human influenza viruses. Further virtual screening and targeted synthesis allowed us to select a group of potentially effective compounds, three of which, derivatives of piperidine and isoindoline, turned out to be the most promising.

Synthesis and biological evaluation of piperazine derivatives as novel isoform selective voltage-gated sodium (Nav) 1.3 channel modulators

Juki?, Marko,Frlan, Rok,Chan, Fiona,Kirby, Robert W.,Madge, David J.,Tytgat, Jan,Peigneur, Steve,Anderluh, Marko,Kikelj, Danijel

, p. 2366 - 2380 (2015)

Sponges of the genus Agelas produce compounds that modulate the activity of voltage-gated sodium ion channels and contribute novel scaffolds for the development of compounds with activity against a plethora of biological targets. In particular, clathrodin and dibromosceptrin were reported to decrease the average maximum amplitude of inward sodium currents in isolated chick embryo sympathetic ganglia cells; we envisaged these compounds as a starting point to design novel Nav channel modulators. This endeavor was part of our long-term goal of designing a comprehensive library of Agelas alkaloid analogs that would cover a broader chemical space and allow us to examine the activity of such compounds on Nav channels. Our series of compounds was designed by maintaining the terminal structural features found in clathrodin while rigidizing the central part of the molecule and replacing the 3-aminopropene linker with a 4-methylenepiperazine moiety. Synthesised compounds were screened for inhibitory action against the human voltage-gated sodium channel isoforms Nav 1.3, Nav 1.4, cardiac Nav 1.5, and Nav 1.7 using an automated patch clamp electrophysiology technique. The results demonstrate that we have obtained a series of compounds with a modest but selective inhibitory activity against the Nav 1.3 channel isoform. The most potent compound showed selective activity against the Nav 1.3 channel isoform with an IC50 of 19 μM and is a suitable starting point for further development of selective Nav 1.3 channel modulators. Such compounds could prove to be beneficial as a pharmacological tool towards the development of novel therapeutically useful compounds in the treatment of pain.

Microwave-assisted methods for the synthesis of pentacyclo[5.4.0.02,6.03,10.05,9]undecylamines

Joubert, Jacques,Sharma, Rajan,Onani, Martin,Malan, Sarel F.

, p. 6923 - 6927 (2013)

Efficient methodologies for the preparation of pentacyclo[5.4.0.02,6 .03,10.05,9]undecane (PCU) amine derivatives are described via microwave-assisted synthesis. The obtained results revealed that microwave-assisted synthetic procedures under controlled conditions (power, temperature and time) are very convenient, high yielding, efficient and low-cost methods for the preparation of PCU amine derivatives. The new methods show several advantages including operational simplicity, good performance, significant reduction in reaction time, less by-product formation and easier purification.

Spectroscopic and Computational Investigations of Ligand Binding to IspH: Discovery of Non-diphosphate Inhibitors

O'Dowd, Bing,Williams, Sarah,Wang, Hongxin,No, Joo Hwan,Rao, Guodong,Wang, Weixue,McCammon, J. Andrew,Cramer, Stephen P.,Oldfield, Eric

, p. 914 - 920 (2017)

Isoprenoid biosynthesis is an important area for anti-infective drug development. One isoprenoid target is (E)-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate (HMBPP) reductase (IspH), which forms isopentenyl diphosphate and dimethylallyl diphosphate from HMBPP in a 2H+/2e? reduction. IspH contains a 4 Fe?4 S cluster, and in this work, we first investigated how small molecules bound to the cluster by using HYSCORE and NRVS spectroscopies. The results of these, as well as other structural and spectroscopic investigations, led to the conclusion that, in most cases, ligands bound to IspH 4 Fe?4 S clusters by η1 coordination, forming tetrahedral geometries at the unique fourth Fe, ligand side chains preventing further ligand (e.g., H2O, O2) binding. Based on these ideas, we used in silico methods to find drug-like inhibitors that might occupy the HMBPP substrate binding pocket and bind to Fe, leading to the discovery of a barbituric acid analogue with a Ki value of ≈500 nm against Pseudomonas aeruginosa IspH.

Synthesis, biological evaluation and molecular docking studies of novel 1,2,3-triazole-quinazolines as antiproliferative agents displaying ERK inhibitory activity

Nunes, Paulo Sérgio Gon?alves,da Silva, Gabriel,Nascimento, Sofia,Mantoani, Susimaire Pedersoli,de Andrade, Peterson,Bernardes, Emerson Soares,Kawano, Daniel Fábio,Leopoldino, Andreia Machado,Carvalho, Ivone

supporting information, (2021/05/26)

ERK1/2 inhibitors have attracted special attention concerning the ability of circumventing cases of innate or log-term acquired resistance to RAF and MEK kinase inhibitors. Based on the 4-aminoquinazoline pharmacophore of kinases, herein we describe the synthesis of 4-aminoquinazoline derivatives bearing a 1,2,3-triazole stable core to bridge different aromatic and heterocyclic rings using copper-catalysed azide-alkyne cycloaddition reaction (CuAAC) as a Click Chemistry strategy. The initial screening of twelve derivatives in tumoral cells (CAL-27, HN13, HGC-27, and BT-20) revealed that the most active in BT-20 cells (25a, IC50 24.6 μM and a SI of 3.25) contains a more polar side chain (sulfone). Furthermore, compound 25a promoted a significant release of lactate dehydrogenase (LDH), suggesting the induction of cell death by necrosis. In addition, this compound induced G0/G1 stalling in BT-20 cells, which was accompanied by a decrease in the S phase. Western blot analysis of the levels of p-STAT3, p-ERK, PARP, p53 and cleaved caspase-3 revealed p-ERK1/2 and p-STA3 were drastically decreased in BT-20 cells under 25a incubation, suggesting the involvement of these two kinases in the mechanisms underlying 25a-induced cell cycle arrest, besides loss of proliferation and viability of the breast cancer cell. Molecular docking simulations using the ERK-ulixertinib crystallographic complex showed compound 25a could potentially compete with ATP for binding to ERK in a slightly higher affinity than the reference ERK1/2 inhibitor. Further in silico analyses showed comparable toxicity and pharmacokinetic profiles for compound 25a in relation to ulixertinib.

Sequential Selective C?H and C(sp3)?+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds

Babu, K. Naresh,Masarwa, Ahmad,Massarwe, Fedaa,Shioukhi, Israa

supporting information, p. 26199 - 26209 (2021/11/09)

Organophosphonium salts containing C(sp3)?+P bonds are among the most utilized reagents in organic synthesis for constructing C?C double bonds. However, their use as C-selective electrophilic groups is rare. Here, we explore an efficient and general transition-metal-free method for sequential chemo- and regioselective C?H and C(sp3)?+P bond functionalizations. In the present study, C?H alkylation resulting in the synthesis of benzhydryl triarylphosphonium salts was achieved by one-pot, four-component cross-coupling reactions of simple and commercially available starting materials. The utility of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post-functionalization of benzylic C(sp3)?+PPh3 groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of two anticancer agents from simple materials in only two to three steps. Additionally, a protocol for late-stage functionalization of bioactive drugs has been developed using benzhydrylphosphonium salts. This new approach should provide novel transformations for application in both academic and pharmaceutical research.

Direct: N -alkylation of sulfur-containing amines

Li, Chen,Ge, Min-Tong,Bai, Liang,Xia, Ai-Bao,Xu, Dan-Qian,Xu, Zhen-Yuan

supporting information, p. 4478 - 4482 (2021/05/31)

An efficient ruthenium-catalyzed method has been developed for the direct N-alkylation of sulfur-containing amines with alcohols, for the first time, by a step-economical and environmentally friendly hydrogen borrowing strategy. The present methodology features base-free conditions and broad substrate scope, with water being the only by-product. Moreover, this protocol has been applied to the synthesis of the pharmaceutical drug Quetiapine.

TARGETED BIFUNCTIONAL DEGRADERS

-

Page/Page column 171; 172, (2021/04/17)

The present invention provides, in one aspect, bifunctional compounds that can be used to promote or enhance degradation of certain circulating proteins. In another aspect, the present invention provides bifunctional compounds that can be used to promote or enhance degradation of certain autoantibodies. In certain embodiments, treatment or management of a disease and/or disorder requires degradation, removal, or reduction in concentration of the circulating protein or the autoantibody in the subject. Thus, in certain embodiments, administration of a compound of the invention to the subject removes or reduces the circulation concentration of the circulating protein or the autoantibody, thus treating, ameliorating, or preventing the disease and/or disorder. In certain embodiments, the circulating protein is TNF.

Structure-Activity Relationship Studies on Oxazolo[3,4- a]pyrazine Derivatives Leading to the Discovery of a Novel Neuropeptide S Receptor Antagonist with Potent in Vivo Activity

Albanese, Valentina,Ruzza, Chiara,Marzola, Erika,Bernardi, Tatiana,Fabbri, Martina,Fantinati, Anna,Trapella, Claudio,Reinscheid, Rainer K.,Ferrari, Federica,Sturaro, Chiara,Calò, Girolamo,Amendola, Giorgio,Cosconati, Sandro,Pacifico, Salvatore,Guerrini, Remo,Preti, Delia

, p. 4089 - 4108 (2021/04/12)

Neuropeptide S modulates important neurobiological functions including locomotion, anxiety, and drug abuse through interaction with its G protein-coupled receptor known as neuropeptide S receptor (NPSR). NPSR antagonists are potentially useful for the treatment of substance abuse disorders against which there is an urgent need for new effective therapeutic approaches. Potent NPSR antagonists in vitro have been discovered which, however, require further optimization of their in vivo pharmacological profile. This work describes a new series of NPSR antagonists of the oxazolo[3,4-a]pyrazine class. The guanidine derivative 16 exhibited nanomolar activity in vitro and 5-fold improved potency in vivo compared to SHA-68, a reference pharmacological tool in this field. Compound 16 can be considered a new tool for research studies on the translational potential of the NPSergic system. An in-depth molecular modeling investigation was also performed to gain new insights into the observed structure-activity relationships and provide an updated model of ligand/NPSR interactions.

Drug discovery of acetophenone derivatives as BRD4 inhibitors

Huang, Wenhai,Li, Chuansheng,Shen, Zhengrong,Zhang, Zhimin,Zheng, Xiaoliang

, p. 323 - 329 (2020/04/17)

Background: The bromodomain and extra-terminal proteins (BET), in particular BRD4, has recently emerged as a potential therapeutic target for the treatment of many human disorders such as cancer, inflammation, obesity and cardiovascular disease, which draw more and more attention to discover potent BRD4 inhibitors in the past years. In this article, we described the discovery process of an entirely new chemotype of BRD4 inhibitors. Methods: A fragment-based drug discovery strategy was employed in attempting to find a novel chemotype of BRD4 inhibitors. Thus, the potential hits were firstly identified by docking study with KAc binding pocket and AlphaScreen assay. Then the elected hit was further structurally optimized based on the interaction revealed by the docking study and the Structure-Activity Relationship (SAR). Results: A 1-(2-hydroxyphenyl)ethan-1-one fragment was first identified as an efficient hit to BRD4 with a weak inhibition activity and high ligand efficiency (IC50 = 8.9 μM,LE > 0.5) based on virtual screening and biochemical assay. Then, two-rounds optimization of the hit by a fragment-based drug discovery approach enabled the discovery of a potent BRD4 inhibitor 9, which exhibit nanomolar potency in biochemical assays (IC50 = 0.18 μM). Conclusion: The title compounds displayed potent inhibitory activity to BRD4, implying acetophenone core is an effective KAc residue mimic, suggesting acetophenone derivatives as a new chemotype may be promising for developing novel BRD4 inhibitors. 9.