95558-32-0

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

PTAB mediated open air synthesis of sulfonamides, thiosulfonates and symmetrical disulfanes

A facile methodology has been described which has successfully simplified the generation of sulfonamides, thiosulfonates and symmetric disulfanes. This “trio” of reactions occur in an open air metal free atmosphere and has also been scaled up to grams making it suitable for commercialization. The reactions also have been successfully carried out with asymmetric variants, thus contributing to the chiral pool. The user friendly “trio” enables easy generation of these versatile sulfur analogues and the reaction condition employed depict an economic outline.

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.

One-step cyclization: Synthesis of N -heteroalkyl-N′-tosylpiperazines

Piperazine derivatives are important intermediates in organic synthesis and useful building blocks in pharmaceutical and fine chemical industries. Currently available synthetic routes for these heterocyclic compounds have limited scope owing to the harsh reaction conditions, low yields, and multistep process. Herein, we reported a practical method for synthesis of alkyl-, alcohol-, amine-, and ester-extended tosylpiperazines under mild conditions with moderate to high yields. This protocol exhibits potential applicability in the synthesis of pharmaceuticals and natural products because of the operational simplicity and the conveniently available reactants. On the basis of the experimental and theoretical results, a plausible mechanism of aliphatic nucleophilic substitution (SN) in the cyclization has been postulated and evidence for the formation of a six-membered ring has also been confirmed by means of density functional theory (DFT) calculations.

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.

Design, synthesis and antimalarial activity of benzene and isoquinoline sulfonamide derivatives

A new series of benzene and isoquinoline sulfonamide derivatives were synthesized by nucleophilic displacement reaction on benzene and isoquinoline sulfonyl chlorides by substituted amines (primary and secondary). The title compounds were evaluated for an

Nitrolysis of urethanes derived from secondary alcohols as a new method for the synthesis of secondary N-nitroamines

The reactions of dialkylurethanes R12NCOOR (RO is the residue of a secondary but not a primary alcohol) with nitrating reagents leads to the formation of the corresponding secondary N-nitroamines R12NNO2.