95558-32-0

Basic information

• Product Name: 1-benzyl-4-tosylpiperazine
• Synonyms: 1-benzyl-4-tosylpiperazine
• CAS NO: 95558-32-0
• Molecular Formula: C₁₈H₂₂N₂O₂S
• Molecular Weight: 330.44448
• Mol File: 95558-32-0.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-benzyl-4-tosylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-4-tosylpiperazine(95558-32-0)
• EPA Substance Registry System: 1-benzyl-4-tosylpiperazine(95558-32-0)

Safety Data

• Hazardous Substances Data: 95558-32-0(Hazardous Substances Data)

Upstream product

• 2759-28-6 1-phenylmethylpiperazine 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 16695-22-0 N,N-bis(tosyloxyethyl)-p-toluenesulfonamide 
• 100-46-9 benzylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 42137-88-2 N,N-bis(2-chloroethyl)-p-toluenesulfonamide 

Downstream Products

• 2759-28-6 1-phenylmethylpiperazine 
• 212609-19-3 N-cyclopentyloxycarbonyl-N'-tozylpiperazine 
• 212609-18-2 N-isopropyloxycarbonyl-N'-tozylpiperazine 

Relevant articles and documents

Impact of N-substituents on crystal packing of N-alkyl-N′-tosylpiperazines and development of new polymorph of tosylbis(2-(tosyloxy)ethyl)amine: Synthesis, DFT, photophysical, cytotoxic property

Diethanol amine (DEA) was selected as a lead compound to prepare N-tosyldiethanol amine 1, N-tosylbis(2-(tosyloxy)ethyl)amine 2 and disubstituted piperazines ca N-alkyl-N′-tosylpiperazines 3–5 in high yield. The new compounds were characterized by using relevant techniques viz. MS, IR, 1H, 13C, DEPT 135 NMR, UV–vis. absorption and fluorescence spectral studies. Single crystal X-ray diffraction technique was used to detect a new polymorphic form of 2 and to measure the influence of various N-substituents on the association of molecules of 3–5 in the solid state. Evidently, the introduction of N-cyclohexyl substituent in 3 successfully switches off all the synthons ca CH…O and CH…N seen in compound 4 and 5. Compounds 4 and 5 holding N-furfuryl and N-benzyl substituents, respectively, adopt other packing strategies based on CH…O, CH…N (4) and CH…O (5) interactions. The antitumor activity of 1–5 was evaluated in vitro against Hep 3B and IMR 32 by the MTT assay and the results were compared with cisplatin. Remarkably, some compounds were found extremely active against both the cell lines and proved to be more potent as cytotoxic agents than cisplatin. Density functional theory and molecular docking studies have been performed to rationalize the experimental results.

New adamantane phenylalkylamines with σ-receptor binding affinity and anticancer activity, associated with putative antagonism of neuropathic pain

The synthesis of the adamantane phenylalkylamines 2a-d, 3a-c, and 4a-e is described. These compounds exhibited significant antiproliferative activity, in vitro, against eight cancer cell lines tested. The σ1, σ2, and sodium channel binding affinities of compounds 2a, 3a, 4a, and 4c-e were investigated. The most interesting analogue, 4a, exhibited significant in vivo anticancer profile on pancreas, prostate, leukemia, and ovarian cancer cell line xenografts together with apoptosis and caspase-3 activation. Inhibition of the cancer cells cycle at the sub-G1 level was also obtained with 4a. Finally, encouraging results were observed with 4a in vivo on mice, suggesting putative antimetastatic and analgesic activities of this compound.

Base-free monosulfonylation of amines using tosyl or mesyl chloride in water

A mild and efficient procedure has been developed for the monosulfonylation of various amines using mesyl or tosyl chlorides in water at room temperature to afford the corresponding sulfonamides in high yields.