52063-83-9

Usage

Uses

Used in Pharmaceutical Research:
1-(THIEN-2-YLCARBONYL)PIPERAZINE is used as a potential drug candidate for its structural similarity to biologically active compounds, which positions it as a promising entity in the development of new medications.
Used in Psychiatry and Neurology:
In the field of psychiatry and neurology, 1-(THIEN-2-YLCARBONYL)PIPERAZINE is used as a therapeutic agent for its high affinity to central nervous system receptors, making it a candidate for treating conditions such as depression, schizophrenia, and anxiety disorders.
Used in Anticancer Research:
1-(THIEN-2-YLCARBONYL)PIPERAZINE is also used as a potential anticancer agent, with studies indicating its capacity to induce apoptosis in cancer cells and inhibit their proliferation, thereby offering a new avenue for cancer treatment development.

InChI:InChI=1/C9H12N2OS/c12-9(8-2-1-7-13-8)11-5-3-10-4-6-11/h1-2,7,10H,3-6H2/p+1

Upstream product

• 110-85-0 piperazine 
• 2810-04-0 Ethyl thiophene-2-carboxylate 
• 527-72-0 2-thiophenylcarboxylic acid 
• 473733-88-9 tert-butyl 4-(thiophen-2-ylcarbonyl)piperazine-1-carboxylate 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 91059-63-1 4-nitrophenyl 2-thiophenecarboxylic acid ester 

Downstream Products

• 910909-46-5 7-benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 910909-50-1 7-benzyl-6-oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile 
• 910909-54-5 7-(3-fluoro-benzyl)-2-methyl-6-oxo-4-[4-(thiophene-2-carbonyl)piperazin-1-yl]-6,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 
• 1391636-34-2 C₂₀H₂₃ClN₂O₃S 
• 1260098-47-2 1-{4-[3-((R)-2-methyl-pyrrolidin-1-yl)-propoxy]-phenyl}-2-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-ethanone 

Relevant academic research and scientific papers

Reactions of 2,4-Dinitrophenyl 5-substituted-2-thiophenecarboxylates with R2NH/R2NH2 + in 20 Mol % DMSO(aq). Effects of 5-Thienyl Substituent and Leaving Group on the Reaction Mechanism

Reactions of 2,4-dinitrophenyl 2-thiophenecarboxylate (2a–d) with R2NH/R2NH2 + in 20 mol % DMSO(aq) have been studied. The reactions are overall second order, first order to the substrates, and first order to th

Design, synthesis and biochemical evaluation of novel carbonic anhydrase inhibitors triggered by structural knowledge on hCA VII

To tackle the challenge of isoform selectivity, we explored the entrance of the cavity for selected druggable human Carbonic Anhydrases (hCAs). Based on X-ray crystallographic studies on the 4-(4-(2-chlorobenzoyl)piperazine-1-carbonyl)benzenesulfonamide in complex with the brain expressed hCA VII (PDB code: 7NC4), a series of 4-(4(hetero)aroylpiperazine-1-carbonyl)benzene-1-sulfonamides has been developed. To evaluate their capability to fit the hCA VII catalytic cavity, the newer benzenesulfonamides were preliminary investigated by means of docking simulations. Then, this series of thirteen benzenesulfonamides was synthesized and tested against selected druggable hCAs. Among them, the 4-(4-(furan-2-carbonyl)piperazine-1-carbonyl)benzenesulfonamide showed remarkable affinity towards hCA VII (Ki: 4.3 nM) and good selectivity over the physiologically widespread hCA I when compared to Topiramate (TPM).

Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Design, synthesis, and biological evaluation of matrine derivatives possessing piperazine moiety as antitumor agents

Using matrine (1) as the lead compound, a series of new piperazinyl matrine derivatives were designed, synthesized and evaluated for their antitumor activities in vitro and in vivo. Structure activity relationship (SAR) analysis indicated that introductio

Synthesis, characterization, and anti-inflammatory activities of methyl salicylate derivatives bearing piperazine moiety

In this study, a new series of 16 methyl salicylate derivatives bearing a piperazine moiety were synthesized and characterized. The in vivo anti-inflammatory activities of target compounds were investigated against xylol-induced ear edema and carrageenan-induced paw edema in mice. The results showed that all synthesized compounds exhibited potent anti-inflammatory activities. Especially, the anti-inflammatory activities of compounds M15 and M16 were higher than that of aspirin and even equal to that of indomethacin at the same dose. In addition, the in vitro cytotoxicity activities and anti-inflammatory activities of four target compounds were performed in RAW264.7 macrophages, and compound M16 was found to significantly inhibit the release of lipopolysaccharide (LPS)-induced interleukin (IL)-6 and tumor necrosis factor (TNF)-α in a dose-dependent manner. In addition, compound M16 was found to attenuate LPS induced cyclooxygenase (COX)-2 up-regulation. The current preliminary study may provide information for the development of new and safe anti-inflammatory agents.

Synthesis and biological evaluation of substituted 4-(thiophen-2-ylmethyl)- 2H-phthalazin-1-ones as potent PARP-1 inhibitors

We have developed a series of substituted 4-(thiophen-2-ylmethyl)-2H- phthalazin-1-ones as potent PARP-1 inhibitors. Preliminary biological evaluation indicated that most compounds possessed inhibitory potencies comparable to, or higher than AZD-2281. Among these compounds, 18q appeared to be the most notable one, which displayed an 8-fold improvement in enzymatic activity compared to AZD-2281. These efforts lay the foundation for our further investigation.

Reactions of 4-nitrophenyl 2-thiophenecarboxylates with R 2NH/R2NH2+ in 20 mol % DMSO (aq). Effects of 5-thienyl substituent and base strength

Reactions of 4-nitrophenyl 2-thiophenecarboxylate (1a-e) with R 2NH/R2NH2+ in 20 mol % DMSO (aq) have been studied kinetically. The 2nd order kinetics, βnuc = 0.88-0.98, and linear Hammett and Yukawa-

Substituted phenoxypropyl-(R)-2-methylpyrrolidine aminomethyl ketones as histamine-3 receptor inverse agonists

Optimization of a series of aminomethyl ketone diamine H3R antagonists to reduce the brain exposure by lowering the pKa, led to molecules with improved pharmacokinetic properties. Compounds 9, 19, and 25 had high affinity for human H3R and demonstrated in vivo H3R functional activity in the rat dipsogenia model. Compound 9 displayed modest wake-promoting activity in the rat EEG/EMG model.

Efficient and continuous monoacylation with superior selectivity of symmetrical diamines in microreactors

Efficient and continuous monoacylation of symmetrical diamines performed in microreactors yielded superior selectivity to that predicted by statistical considerations. It is highly valuable that the kinetically controlled product in high yields was achieved without any special catalyst at ambient temperature.

NOVEL 9-SUBSTITUTED-5-CARBOXY-OXADIAZINO-QUINOLONE DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATION AS ANTI-BACTERIALS

A subject of the invention is the compounds of formula (I): wherein R1, R2, R3, R′3, R4, R′4, R5, R6 and R7 are as described in the application, in the form of enantiomers or mixtures, as well as their salts with acids and bases, their preparation and their application as anti-bacterials, in both human and veterinary medicine.