Category: piperazines

《Synthesis and evaluation of 2-anilinopyrimidines bearing 3-aminopropamides as potential epidermal growth factor receptor inhibitors》 was written by Han, Chun; Wan, Ledong; Ji, Hongbin; Ding, Ke; Huang, Zhangjian; Lai, Yisheng; Peng, Sixun; Zhang, Yihua. Quality Control of 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine And the article was included in European Journal of Medicinal Chemistry on April 22 ,2014. The article conveys some information:

Novel compounds were synthesized and biol. evaluated. Several ones exhibited stronger inhibitory activity than gefitinib against EGFR L858R/T790M and antiproliferative effects on H1975 and HCC827 cells. The 3-aminopropamide in some compoundslike compound I could be converted to the active acrylamide in the presence of arginine. Importantly, compound I showed improved stability relative to compound WZ4002 whose structure is same to I excepting an acrylamide moiety. Interestingly, compound II, a NO donating compound of I, showed more potent and selective inhibition than compound I on H1975 cells. Significantly, compound II produced high levels of NO in H1975 cells but not in non-tumorous 16HBE cells, and its inhibition was diminished by NO scavenger. Furthermore, compound II dose-dependently produced inhibitory effects on EGFR downstream signaling in H1975 cells. In the experiment, the researchers used 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1Quality Control of 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine)

4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine(cas: 1213269-26-1) is a member of pyrimidine. Pyrimidine derivatives are an important class of N-heterocycles. They are well-known for their wide spectrum of promising biological activities such as antitumors, bactericidals, and fungicidal.Quality Control of 4-(3-Aminophenoxy)-5-chloro-N-(2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)pyrimidin-2-amine

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

《2,5-Disubstituted pyridines as potent GPR119 agonists》 was written by Wu, Yulin; Kuntz, Judith D.; Carpenter, Andrew J.; Fang, Jing; Sauls, Howard R.; Gomez, Daniel J.; Ammala, Carina; Xu, Yun; Hart, Shane; Tadepalli, Sarva. Electric Literature of C7H16N2O2S And the article was included in Bioorganic & Medicinal Chemistry Letters on April 15 ,2010. The article conveys some information:

A series of 2-piperazinyl-5-alkoxypyridines were synthesized and screened against human GPR119 receptor. Through SAR anal., compounds containing 2-alkylsulfonylpiperazinyl-5-alkoxypyridines were discovered and found to be potent agonists of the human GPR119 receptor. The experimental process involved the reaction of 1-(Isopropylsulfonyl)piperazine(cas: 534615-34-4Electric Literature of C7H16N2O2S)

1-(Isopropylsulfonyl)piperazine(cas: 534615-34-4) is a member of sulfamide. Sulfamide was used in the synthesis of: Schiff bases of the type ArCH=NSO2NH2; 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD); sulfamide analogs of oleoylethanolamide analogs in a study of PPARα activation.Electric Literature of C7H16N2O2S

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Category: piperazinesIn 2022 ,《Design and synthesis of novel quinazolinone derivatives as anti-HBV agents with TLR8 agonist effect》 appeared in European Journal of Medicinal Chemistry. The author of the article were Qiu, Jingying; Zhou, Qingqing; Zou, Yueting; Li, Shuqiong; Yang, Lihua; Chen, Wang; Gao, Jian; Gu, Xiaoke. The article conveys some information:

In this work, a series of novel quinazolinone derivatives I [R1 = benzyl, 2-furylmethyl, 2-thienylmethyl, etc.; R2 = H, 2-MeO, 3-F, etc.; R3 = (4-methylpiperazin-1-yl), (4-hydroxy-1-piperidyl), (2-aminopyrimidin-4-yl)oxy, etc.] were synthesized and evaluated as novel anti-HBV agents. Among them, compound I [R1 = 2-furylmethyl; R2 = 2-MeO; R3 = (2-aminopyrimidin-4-yl)oxy] exhibited potent inhibitory effect on HBV DNA replication in both wild type and drug resistant (lamivudine and entecavir) HBV strains with IC50 values of 0.15 and 0.10μM, resp. Notably, the selective index value of I [R1 = 2-furylmethyl; R2 = 2-MeO; R3 = (2-aminopyrimidin-4-yl)oxy] was high above 66.67, indicating the favorable safety profile. Mol. docking study indicated that compound I [R1 = 2-furylmethyl; R2 = 2-MeO; R3 = (2-aminopyrimidin-4-yl)oxy] well fitted into the binding pocket of TLR8 protein-protein interface. Dual-luciferase reporter gene assay further confirmed that compound I [R1 = 2-furylmethyl; R2 = 2-MeO; R3 = (2-aminopyrimidin-4-yl)oxy] could dose-dependently activate TLR8, thus effectively inducing the activity of TLR8-dependent NF-κB. Collectively, compound I [R1 = 2-furylmethyl; R2 = 2-MeO; R3 = (2-aminopyrimidin-4-yl)oxy] displayed potent anti-HBV activities and TLR8 agonist effect in vitro, and might be a potential immunomodulatory anti-HBV agent to warrant further investigation. In the part of experimental materials, we found many familiar compounds, such as 1-Methylpiperazine(cas: 109-01-3Category: piperazines)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Category: piperazines

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

HPLC of Formula: 109-01-3In 2022 ,《Structural and PK-guided identification of indole-based non-acidic autotaxin (ATX) inhibitors exhibiting high in vivo anti-fibrosis efficacy in rodent model》 was published in European Journal of Medicinal Chemistry. The article was written by Lei, Hongrui; Cao, Zhi; Wu, Huinan; Li, Tong; Wang, Xinyu; Chen, Yuxiang; Ma, Enlong; Sun, Lixin; Zhai, Xin. The article contains the following contents:

In recent decades, pharmacol. targeting of the autotaxin (ATX)/lysophosphatidic acid (LPA) axis accounted for excellent disease management benefits. Herein, to extend the scope of structure-activity relationships (SARs), fifteen indole-based carbamate derivatives I [R = 4-Me, 3,4-difluoro, 2,3-dichloro; R1 = pyrrolidin-1-yl, (4-methyl-1-piperidyl), (4-methylpiperazin-1-yl); R2 = H, CH3, etc] were prepared to evaluate the ATX inhibitory potency. Among them, compound I [R = 3,5-dichloro; R1 = morpholino; R2 = H] bearing morpholine moiety was identified as the optimal ATX inhibitor (0.41 nM), superior to the pos. control GLPG1690 (2.90 nM). To resolve the intractable issue of poor pharmacokinetic (PK) property, urea moiety was introduced as a surrogate of carbamate which furnished compounds II [R3 = morpholino, (4-hydroxy-1-piperidyl), [2-(hydroxymethyl)pyrrolidin-1-yl]; R4 = H, 4-Cl, 4-F, etc]. The dedicated modification identified the diethanolamine entity II [R3 = [bis(2-hydroxyethyl)amino]; R4 = (3-chloro-4-methoxy-phenyl)] with satisfactory water solubility and PK profiles with a min. sacrifice of ATX inhibition (2.17 nM). The most promising candidate II [R3 = [bis(2-hydroxyethyl)amino]; R4 = (3-chloro-4-methoxy-phenyl)] was evaluated for anti-fibrosis effect in a bleomycin challenged mice lung fibrosis model. Upon treatment with II [R3 = [bis(2-hydroxyethyl)amino]; R4 = (3-chloro-4-methoxy-phenyl)], the in vivo ATX activity in both lung homogenate and broncheoalveolar fluid (BALF) sample was significantly down-regulated. Furthermore, the gene expression of pro-fibrotic cytokines transforming growth factor-β (TGF-β), interleukin- 6 (IL-6) and tumor necrosis factor-α (TNF-α) in lung tissue was reduced to normal level. Collectively, the promising biol. effects may advocate potential application of II [R3 = [bis(2-hydroxyethyl)amino]; R4 = (3-chloro-4-methoxy-phenyl)] in fibrosis relevant diseases. In the part of experimental materials, we found many familiar compounds, such as 1-Methylpiperazine(cas: 109-01-3HPLC of Formula: 109-01-3)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..HPLC of Formula: 109-01-3

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

《Triphenylethylene analogues: Design, synthesis and evaluation of antitumor activity and topoisomerase inhibitors》 was published in European Journal of Medicinal Chemistry in 2020. These research results belong to Rani, Sudesh; Paul, Kamaldeep. SDS of cas: 109-01-3 The article mentions the following:

To structurally relate anticancer drug tamoxifen used in the treatment of breast cancer, a sequence of compounds I [R = piperidinyl, morpholino, 4-methylpiperazinyl, 4-ethylpiperazinyl, etc.] were designed and synthesized as potential drug candidates. McMurry coupling reaction was used as the key synthetic step in the preparation of these compounds I and the ratios of E/Z-isomers were determined on the basis of NMR and HPLC experiments The new compounds I were found to be cytotoxic in the micromolar range with 60 human tumor cell lines at one dose and five dose concentration levels. Detailed studies on the most active compounds I [R = 2-morpholinoethyl amine, cyclohexylamine and diethylamine] show these compounds were capable to inhibit the growth of cancer cells. Finally, with the aim to correlate the antiproliferative activity with an intracellular target(s), the effect on relaxation activity of DNA topoisomerase-II was assayed. The relevance of interaction of most active compounds with topoisomerase-II was demonstrated which was also supported by docking studies. The experimental process involved the reaction of 1-Methylpiperazine(cas: 109-01-3SDS of cas: 109-01-3)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..SDS of cas: 109-01-3

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

The author of 《Discovery of novel mutant-combating ALK and ROS1 dual inhibitors bearing imidazolidin-2-one moiety with reasonable PK properties》 were Lei, Hongrui; Jiang, Nan; Miao, Xiuqi; Xing, Lingyun; Guo, Ming; Liu, Yang; Xu, Haowen; Gong, Ping; Zuo, Daiying; Zhai, Xin. And the article was published in European Journal of Medicinal Chemistry in 2019. Reference of 1-Methylpiperazine The author mentioned the following in the article:

Aiming to identify novel potent ALK and ROS1 dual inhibitors, the relatively bulky piperidine fragment in ceritinib was replaced with substituted imidazolidin-2-one moiety which gave rise to a series of 2,4-diaryl-aminopyrimidine (DAAP) analogs. SAR studies were conducted based on cellular assays on five cell lines and most compounds exerted moderated to excellent activities. Among them, 15(I) showed excellent inhibitory activities against ROS1 and ALK pos. cell lines, especially Ba/F3G1202R, with IC50 values ranging from 14 to 37 nM. As a continuation, several compounds were tested in enzymic assays and I displayed encouraging activities against wild-type ALK (1.2 nM), ROS1(0.43 nM) as well as extremely resistant ALKL1196M and ALKG1202R mutants with IC50 values of 0.73 nM and 6.7 nM, resp. To our delight, both cellular and enzymic results of I were in good accordance with western blot assays on H2228 and HCC78 cell lines. Importantly, pharmacokinetic (PK) profiles of I were obtained with quite satisfying AUC and Cmax values. Besides, the binding models of I with ALKWT, ALKG1202R and ROS1 clearly present the essential interactions within the active site. The experimental part of the paper was very detailed, including the reaction process of 1-Methylpiperazine(cas: 109-01-3Reference of 1-Methylpiperazine)

1-Methylpiperazine(cas: 109-01-3) can be used as mimic template in the preparation of molecularly imprinted microspheres (MIMs). It was also used to prepare the difunctional strong anion-exchange stationary phase from a 1,4-diazacyclohexane derivative..Reference of 1-Methylpiperazine

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Zhang, Xin; Lv, Xiao-Qin; Tang, Sheng; Mei, Lin; Li, Ying-Hong; Zhang, Jing-Pu; Jiang, Jian-Dong; Peng, Zong-Gen; Song, Dan-Qing published an article in European Journal of Medicinal Chemistry. The title of the article was 《Discovery and evolution of aloperine derivatives as a new family of HCV inhibitors with novel mechanism》.HPLC of Formula: 1688-95-5 The author mentioned the following in the article:

Aloperine (I), a Chinese natural product with a unique endocyclic scaffold, was first identified to be a potent hepatitis C virus (HCV) inhibitor in our laboratory Thirty-four new aloperine derivatives were designed, synthesized and evaluated for their anti-HCV activities taking I as the lead. Among them, compound II exhibited the potential potency with EC50 values in a micromolar range against both wild-type and direct-acting antiviral agents (DAAs)-resistant variants, and synergistically inhibited HCV replication with approved DAAs. Furthermore, it also owned a good oral pharmacokinetic and safety profile, suggesting a highly druglike nature. The primary mechanism showed that II might target host components, distinctly different from the DAAs currently used in clinic. Therefore, we consider aloperine derivatives to be a novel class of anti-HCV agents, and compound II has been selected as a promising antiviral candidate for further investigation. In the experimental materials used by the author, we found 4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5HPLC of Formula: 1688-95-5)

4-Methyl-1-piperazinesulfonyl Chloride(cas: 1688-95-5) is a member of sulfamide. Sulfamide was used in the synthesis of: Schiff bases of the type ArCH=NSO2NH2; 1H,3H-2,1,3-benzothiadiazin-4-one-2,2-dioxide (BTDD); sulfamide analogs of oleoylethanolamide analogs in a study of PPARα activation.HPLC of Formula: 1688-95-5

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Grottelli, Silvia; Annunziato, Giannamaria; Pampalone, Gioena; Pieroni, Marco; Dindo, Mirco; Ferlenghi, Francesca; Costantino, Gabriele; Cellini, Barbara published an article in Journal of Medicinal Chemistry. The title of the article was 《Identification of Human Alanine-Glyoxylate Aminotransferase Ligands as Pharmacological Chaperones for Variants Associated with Primary Hyperoxaluria Type 1》.COA of Formula: C12H18N2O The author mentioned the following in the article:

Primary hyperoxaluria type I (PH1) is a rare kidney disease due to the deficit of alanine:glyoxylate aminotransferase (AGT), a pyridoxal-5′-phosphate-dependent enzyme responsible for liver glyoxylate detoxification, which in turn prevents oxalate formation and precipitation as kidney stones. Many PH1-associated missense mutations cause AGT misfolding. Therefore, the use of pharmacol. chaperones (PCs), small mols. that promote correct folding, represents a useful therapeutic option. To identify ligands acting as PCs for AGT, we first performed a small screening of com. available compounds We tested each mol. by a dual approach aimed at defining the inhibition potency on purified proteins and the chaperone activity in cells expressing a misfolded variant associated with PH1. We then performed a chem. optimization campaign and tested the resulting synthetic mols. using the same approach. Overall, the results allowed us to identify a promising hit compound for AGT and draw conclusions about the requirements for optimal PC activity. In the experimental materials used by the author, we found (3-(4-Methylpiperazin-1-yl)phenyl)methanol(cas: 123987-13-3COA of Formula: C12H18N2O)

(3-(4-Methylpiperazin-1-yl)phenyl)methanol(cas: 123987-13-3) belongs to piperazines. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines.COA of Formula: C12H18N2O

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Related Products of 70006-24-5On March 31, 2008, Bruins Slot, Liesbeth A.; Bardin, Laurent; Auclair, Agnes L.; Depoortere, Ronan; Newman-Tancredi, Adrian published an article in Behavioural Pharmacology. The article was 《Effects of antipsychotics and reference monoaminergic ligands on marble burying behavior in mice》. The article mentions the following:

Antipsychotics constitute efficacious augmenting agents in the treatment of anxiety disorders, including refractory obsessive-compulsive disorder. We examined the effects of 36 compounds, including typical, atypical and novel antipsychotics with dual dopamine D2/5-hydroxytryptamine 1A (D2/5-HT1A) actions on marble burying behavior in mice, a putative preclin. test for anxiety disorders. One hour after drug administration, male NMRI mice were placed individually in cages containing 20 marbles, and the total number of marbles buried after 30 min was counted. The selective serotonin reuptake inhibitors, citalopram (2.5-40 mg/kg), fluoxetine (2.5-10 mg/kg) and the benzodiazepine diazepam (2.5-10 mg/kg), reduced the number of buried marbles. The atypical antipsychotic, clozapine (0.16-10 mg/kg), but not its congener olanzapine, was effective in this test. Haloperidol, a typical antipsychotic, also reduced the number of buried marbles, albeit not in a dose-dependent manner. The atypical risperidone was partially active (0.16-0.63 mg/kg), as was the benzamide derivative, amisulpride, albeit at high (10-40 mg/kg) doses. Among the third-generation’ antipsychotics possessing combined D2/5-HT1A properties, bifeprunox was active at 0.0025 mg/kg, whereas SLV313 and aripiprazole were active only at the highest doses (2.5 and 10 mg/kg, resp.). SSR181507, F15063 and the antidyskinetic agent, sarizotan, were without any effect. Among a series of receptor subtype-selective ligands, only the 5-HT1A agonist, (+)-8-OH-DPAT (0.63-2.5 mg/kg) and the 5-HT2A/2B/2C antagonist, ritanserin (0.63-2.5 mg/kg) were active. Among novel antipsychotics with dual D2/5-HT1A properties, only bifeprunox was able to potently reduce the number of buried marbles. Inhibition of marble burying behavior may result from the interplay of several receptor systems, including 5-HT2 receptor blockade, dopamine D2 partial agonism and serotonin 5-HT1A agonism. In the part of experimental materials, we found many familiar compounds, such as Abt-724(cas: 70006-24-5Related Products of 70006-24-5)

Abt-724(cas: 70006-24-5) belongs to piperazines. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines.Related Products of 70006-24-5

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics

Product Details of 70006-24-5On October 27, 2006 ,《Gram Scale Synthesis of the Glucuronide Metabolite of ABT-724》 was published in Journal of Organic Chemistry. The article was written by Engstrom, Kenneth M.; Daanen, Jerome F.; Wagaw, Seble; Stewart, Andrew O.. The article contains the following contents:

A gram scale synthesis of the glucuronide metabolite of ABT-724 is reported. Glycosidic coupling between a trichloroacetimidate glucuronyl donor and a Cbz-protected hydroxypyridylpiperazine glycosyl acceptor is the key step in the synthesis, since attempts to directly glucuronidate the aglycon, aglycon derivatives, and other truncated glycosyl acceptors were unsuccessful. The route was used to produce 2.1 g of metabolite in eight steps from 2-chloro-5-hydroxypyridine in 21% overall yield. In the part of experimental materials, we found many familiar compounds, such as Abt-724(cas: 70006-24-5Product Details of 70006-24-5)

Abt-724(cas: 70006-24-5) belongs to piperazines. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines.Product Details of 70006-24-5

Referemce:
Piperazine – Wikipedia,
Piperazines – an overview | ScienceDirect Topics