118630-34-5

Usage

Chemical class

Piperazine derivatives

Structure

Piperazine ring substituted with a 4-tert-butylbenzoyl group

Application in medicinal chemistry

Used as a scaffold for the development of potential pharmaceutical agents

Biological activities

Exhibits antiviral, antifungal, and anticancer properties

Potential use

Investigated as a corrosion inhibitor in the petroleum industry

Research and development

Valuable compound for further research and development in various fields due to its unique structure and versatile properties

Upstream product

• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 142-64-3 piperazine dihydrochloride 
• 7196-32-9 N-(4-tert-butylbenzoyl)imidazole 
• 110-85-0 piperazine 
• 138467-42-2 C₁₇H₁₇NO₃S 
• 1710-98-1 p-tert-butyl benzoyl chloride 
• 329058-21-1 (4-Benzyl-piperazin-1-yl)-(4-tert-butyl-phenyl)-methanone 

Relevant academic research and scientific papers

A Arylheterocycle chirality bcr - abl inhibitor and its preparation method and application

The invention discloses aromatic heterocyclic biphenyl Bcr-Abl inhibitors as well as a preparation method and application thereof. A structural formula of the inhibitors is shown in the specification, wherein in the structural formula, Ar is aromatic heterocycle; R is a mono-substituent or a di-substituent, and the substituent is alkyl or halogen. The series of inhibitors have a certain inhibiting effect on ABL1 kinase in vitro, can inhibit tumor cell proliferation and can be used for preparing antitumor drugs, especially CML (chronic myelocytic leukemia) drugs. The preparation method of the aromatic heterocyclic biphenyl Bcr-Abl inhibitors, which is provided by the invention, has the advantages of easiness in obtainment of raw materials, mild reaction conditions, simplicity in operation of reaction processes and cheap used reagents.

Synthesis and biological evaluation of novel aromatic-heterocyclic biphenyls as potent anti-leukemia agents

As a continuation to our previous research, twenty-eight aromatic-heterocyclic biphenyls were designed and synthesized as novel Bcr-Abl inhibitors. The title compounds were investigated for their antiproliferative activities against wild K562 cells and Imatinib-resistant K562 cells (K562R). The results indicated that most of them exhibited potent Bcr-Abl inhibition and moderate antiproliferative potency against K562 cells. Furthermore, three compounds 3, 7 and 21 displayed moderate antiproliferative activities against K562R cells. Molecular docking indicated that 3 bound more tightly with Bcr-AblT315I compared to Bcr-AblWT. The higher affinity was consistent with its relatively promising K562R cell growth inhibition. These aromatic-heterocyclic biphenyls could be considered as novel lead compound for optimized as Bcr-AblT315I inhibitors. They provide a good starting point for the further development of novel anti-leukemia agents capable of dealing with clinical acquired resistance against Imatinib.

Discovery of novel Bcr-Abl inhibitors with diacylated piperazine as the flexible linker

Forty-two compounds (series 8, 9 and 10) incorporated with diacylated piperazine have been synthesized and evaluated as novel Bcr-Abl inhibitors based on 'six-atom linker'. Five of them, 8d, 8h, 8l, 10m and 10p, displayed potent Bcr-Abl inhibitory activity comparable with Imatinib. Moreover, compounds 8e, 10q, 10s, and 10u were potent Bcr-Abl inhibitors with IC50 values at the sub-micromolecular level. Most compounds exhibited moderate to high antiproliferative activity against K562 cells. In particular, compound 9e was the most promising Bcr-Abl inhibitor. Docking studies revealed that the binding modes of these compounds were similar with Imatinib. These compounds could be considered as promising lead compounds for further optimization.

Aminolysis of S-4-nitrophenyl X-substituted thiobenzoates: Effect of nonleaving-group substituents on reactivity and mechanism

A kinetic study is reported for aminolysis of S-4-nitrophenyl X-substituted thiobenzoates 3a-g in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. Thiol esters 3a-g are 7.8-47.6 fold more reactive than the corresponding oxygen esters (i.e., 4-nitrophenyl X-substituted benzoates 1a-g). Such reactivity order appears to be in accordance with the expectation that 4-nitrothiophenoxide in 3a-g is a better nucleofuge than 4-nitrophenoxide in 1a-g since the former is 2.64 pKa units less basic than the latter. Hammett plot for the reactions of 3a-g exhibit poor correlation coefficients (R2 = 0.977-0.986) with negative deviation by substrates possessing an electrondonating group (EDG), while the Yukawa-Tsuno plots result in excellent linear correlation (R2 = 0.995-0.997) with ? = 0.93-1.23 and r = 0.57-0.67, indicating that the negative deviation shown by substrates possessing an EDG is caused by ground-state stabilization through resonance interactions but not due to a change in ratedetermining step upon changing the nonleaving-group substituent X. The p value increases as the incoming amine becomes more basic and more reactive, indicating that the RSP is not operative in the current reactions.

5-(1-Piperazinyl)-1H-1,2,4-triazol-3-amines as antihypertensive agents

A series of 5-(1-piperazinyl)-1H-1,2,4-triazol-3-amines was synthesized and screened for antihypertensive and diuretic activity in spontaneously hypertensive rats (SHR). One compound, 5-[4-[(3-chlorophenyl)methyl]-1-piperazinyl]-1H-1,2,4-triazol-3-amine (8), was selected to define the mechanism of its antihypertensive activity. Studies in SHR suggest ganglionic blocking activity. Short-lived antihypertensive activity was observed in conscious renal hypertensive dogs.