Category: piperazines

Glutathione. X. Human erythrocyte membrane diffusion coefficients for diazene derivatives of the DIP [diazenedicarboxylic acid bis(N’-methylpiperazide)] series via intracellular thiol oxidation was written by Kosower, Nechama S.;Kosower, Edward M.;Saltoun, Gilda;Lev, Lilly. And the article was included in Biochemical and Biophysical Research Communications in 1975.Application of 21867-64-1 This article mentions the following:

The thiol-oxidizing agent, DIP and its homologs with different N’-alkyl groups can be used to obtain membrane diffusion coefficients for human erythrocytes at 1°. From the initial rates of intracellular glutathione oxidation and the 2-octanol partition coefficients for the specific DIP homolog, diffusion coefficients of ∼1 × 10-8 cm2/sec were observed The method (irreversible loss of permeant through well-defined intracellular reaction) may be used to evaluate membrane properties and possibly for the study of substituent effects on drug entry into cells. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Application of 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Intermediate for a wide range of pharmaceuticals, polymers, dyes, corrosion inhibitors, rubber accelerators and surfactants.Application of 21867-64-1

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

Design and synthesis of novel antifungal triazole derivatives with good activity and water solubility was written by Cao, Xu-Feng;Chu, Wen-Jing;Cao, Yong-Bing;Yang, Yu-She. And the article was included in Chinese Chemical Letters in 2013.Product Details of 119285-07-3 This article mentions the following:

To find novel antifungal agents with good activity and aqueous solubility, a series of SYN-2869 analogs containing a pyridine ring were synthesized and were evaluated for their in vitro antifungal activity and water-solubility Some of the compounds showed potent activity against pathogenic fungi. In particular, an analog having an iso-Bu substitution on the triazolone exhibited significant broad spectrum antifungal activity. In addition, the water solubility of this compound was sufficiently improved over SYN-2869. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate (cas: 119285-07-3Product Details of 119285-07-3).

tert-Butyl 4-(5-aminopyridin-2-yl)piperazine-1-carboxylate (cas: 119285-07-3) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. Piperazine is formed as a co-product in the ammoniation of 1,2-dichloroethane or ethanolamine. These are the only routes to the chemical used commercially.Product Details of 119285-07-3

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

Discovery of a First-in-Class Gut-Restricted RET Kinase Inhibitor as a Clinical Candidate for the Treatment of IBS was written by Schenck Eidam, Hilary;Russell, John;Raha, Kaushik;De Martino, Michael;Qin, Donghui;Guan, Huiping Amy;Zhang, Zhiliu;Zhen, Gong;Yu, Haiyu;Wu, Chengde;Pan, Yan;Joberty, Gerard;Zinn, Nico;Laquerre, Sylvie;Robinson, Sharon;White, Angela;Giddings, Amanda;Mohammadi, Ehsan;Greenwood-Van Meerveld, Beverly;Oliff, Allen;Kumar, Sanjay;Cheung, Mui. And the article was included in ACS Medicinal Chemistry Letters in 2018.SDS of cas: 630125-91-6 This article mentions the following:

Abdominal pain and abnormal bowel habits represent major symptoms for irritable bowel syndrome (IBS) patients that are not adequately managed. Although the etiol. of IBS is not completely understood, many of the functions of the gastrointestinal (GI) tract are regulated by the enteric nervous system (ENS). Inflammation or stress-induced expression of growth factors or cytokines may lead to hyperinnervation of visceral afferent neurons in GI tract and contribute to the pathophysiol. of IBS. Rearranged during transfection (RET) is a neuronal growth factor receptor tyrosine kinase critical for the development of the ENS as exemplified by Hirschsprung patients who carry RET loss-of-function mutations and lack normal colonic innervation leading to colonic obstruction. Similarly, RET signaling in the adult ENS maintains neuronal function by contributing to synaptic formation, signal transmission, and neuronal plasticity. Inhibition of RET in the ENS represents a novel therapeutic strategy for the normalization of neuronal function and the symptoms of IBS patients. Herein, we describe our screening effort and subsequent structure-activity relationships (SARs) in optimizing potency, selectivity, and mutagenicity of the series, which led to the discovery of a first-in-class, gut-restricted RET kinase inhibitor, 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(5-(1,1,1-trifluoro-2-methylpropan-2-yl)isoxazol-3-yl)acetamide (15, GSK3179106), as a clin. candidate for the treatment of IBS. GSK3179106 is a potent, selective, and gut-restricted pyridone hinge binder small mol. RET kinase inhibitor with a RET IC₅₀ of 0.3 nM and is efficacious in vivo. In the experiment, the researchers used many compounds, for example, 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (cas: 630125-91-6SDS of cas: 630125-91-6).

4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (cas: 630125-91-6) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Although many piperazine derivatives occur naturally, piperazine itself can be synthesized by reacting alcoholic ammonia with 1,2-dichloroethane, by the action of sodium and ethylene glycol on ethylene diamine hydrochloride, or by reduction of pyrazine with sodium in ethanol.SDS of cas: 630125-91-6

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

Synthesis and biological properties of heterylalkylamides of 4-substituted piperazin-1-ylacetic acids was written by Vartanyan, S. O.;Avakyan, A. S.;Sargsyan, A. B.;Arutyunyan, S. A.;Gukasyan, T. G.;Tsatinyan, A. S.;Noravyan, O. S.;Markaryan, I. A.. And the article was included in Hayastani Kimiakan Handes in 2010.Related Products of 21867-64-1 This article mentions the following:

Reaction of chloroacetyl chloride with 1,4-benzodioxan-2-yl or isochroman-1-yl-containing aliphatic amines gave the corresponding N-substituted chloroacetamides. Subsequent treatment of the latter with monosubstituted piperazines afforded the corresponding substituted piperazineacetamides. The biol. properties of these compounds have been investigated. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Related Products of 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Piperazine was first introduced as an anthelmintic in 1953. Piperazine compounds mediate their anthelmintic action by generally paralyzing parasites, allowing the host body to easily remove or expel the invading organism. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Related Products of 21867-64-1

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

Photoswitchable Inhibitor of the Calcium Channel TRPV6 was written by Cunha, Micael R.;Bhardwaj, Rajesh;Lindinger, Sonja;Butorac, Carmen;Romanin, Christoph;Hediger, Matthias A.;Reymond, Jean-Louis. And the article was included in ACS Medicinal Chemistry Letters in 2019.Reference of 182618-86-6 This article mentions the following:

Herein the authors report the first photoswitchable inhibitor of Transient Receptor Potential Vanilloid 6 (TRPV6), a selective calcium channel involved in a number of diseases and in cancer progression. By surveying analogs of a previously reported TRPV6 inhibitor appended with a phenyl-diazo group, the authors identified a compound switching between a weak TRPV6 inhibitor in its dark, E-diazo stereoisomer (Z/E = 3:97, IC₅₀ >> 10 μM) and a potent inhibitor as the Z-diazo stereoisomer accessible reversibly by UV irradiation at λ = 365 nm (Z/E = 3:1, IC₅₀ = 1.7±0.4 μM), thereby allowing precise spatiotemporal control of inhibition. This new tool compound should be useful to deepen the understanding of TRPV6. In the experiment, the researchers used many compounds, for example, 1-Boc-4-(4-Nitrophenyl)piperazine (cas: 182618-86-6Reference of 182618-86-6).

1-Boc-4-(4-Nitrophenyl)piperazine (cas: 182618-86-6) belongs to piperazine derivatives. Piperazine causes primary dermal irritation and skin burns at high concentrations. Piperazine also causes eye irritation in humans. Outside the body, piperazine has a remarkable power to dissolve uric acid and producing a soluble urate, but in clinical experience it has not proved equally successful. Reference of 182618-86-6

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

Discovery of a Nanomolar Multikinase Inhibitor (KST016366): A New Benzothiazole Derivative with Remarkable Broad-Spectrum Antiproliferative Activity was written by El-Damasy, Ashraf Kareem;Cho, Nam-Chul;Nam, Ghilsoo;Pae, Ae Nim;Keum, Gyochang. And the article was included in ChemMedChem in 2016.Application of 630125-91-6 This article mentions the following:

Herein we report the discovery of compound 6 [KST016366; 4-((2-(3-(4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)ureido)benzo[d]thiazol-6-yl)oxy)picolinamide] as a new potent multikinase inhibitor through minor structural modification of our previously reported RAF kinase inhibitor A. In vitro anticancer evaluation of 6 showed substantial broad-spectrum antiproliferative activity against 60 human cancer cell lines. In particular, it showed GI₅₀ values of 51.4 and 19 nM against leukemia K-562 and colon carcinoma KM12 cell lines, resp. Kinase screening of compound 6 revealed its nanomolar-level inhibitory activity of certain oncogenic kinases implicated in both tumorigenesis and angiogenesis. Interestingly, 6 displays IC₅₀ values of 0.82, 3.81, and 53 nM toward Tie2, TrkA, and ABL-1 (wild-type and T315I mutant) kinases, resp. Moreover, 6 is orally bioavailable with a favorable in vivo pharmacokinetic profile. Compound 6 may serve as a promising candidate for further development of potent anticancer chemotherapeutics. In the experiment, the researchers used many compounds, for example, 4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (cas: 630125-91-6Application of 630125-91-6).

4-((4-Ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)aniline (cas: 630125-91-6) belongs to piperazine derivatives. The piperazine scaffold is often found in biologically active compounds in different therapeutic areas. These therapeutic areas include antifungals, antidepressants, antivirals, and serotonin receptor (5-HT) antagonists/agonists. Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.Application of 630125-91-6

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

Design, Synthesis and Evaluation of Antidepressant Activity of Novel 2-Methoxy 1, 8 Naphthyridine 3-Carboxamides as 5-HT₃ Receptor Antagonists was written by Mahesh, Radhakrishnan;Dhar, Arghya Kusum;Jindal, Ankur;Bhatt, Shvetank. And the article was included in Chemical Biology & Drug Design in 2014.Application In Synthesis of 1-Propylpiperazine This article mentions the following:

A series of novel 1,8-naphthyridine-3-carboxamides as 5-HT₃ receptor antagonists were synthesized with an intention to explore the antidepressant activity of these compounds The title carboxamides were designed using ligand-based approach keeping in consideration the structural requirement of the pharmacophore of 5-HT₃ receptor antagonists. The compounds were synthesized using appropriate synthetic route from the starting material nicotinamide. 5-HT₃ receptor antagonism of all the compounds, which was denoted in the form of pA₂ value, was determined in longitudinal muscle myenteric plexus preparation from guinea-pig ileum against 5-HT₃ agonist, 2-methyl-5-HT. 2-Methoxy-1, 8-naphthyridin-3-yl (2-methoxy Ph piperazine-1-yl) methanone was identified as the most active compound, which expressed a pA₂ value of 7.67. The antidepressant activity of all the compounds was examined in mice model of forced swim test (FST); importantly, none of the compounds was found to cause any significant changes in the locomotor activity of mice at the tested dose levels. In FST, the compounds with considerably higher pA₂ value exhibited promising antidepressant-like activity, whereas compounds with lower pA₂ value did not show antidepressant-like activity as compared to the control group. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Application In Synthesis of 1-Propylpiperazine).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.Application In Synthesis of 1-Propylpiperazine

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

M₃ muscarinic acetylcholine receptor antagonists: SAR and optimization of bi-aryl amines was written by Budzik, Brian;Wang, Yonghui;Shi, Dongchuan;Wang, Feng;Xie, Haibo;Wan, Zehong;Zhu, Chongye;Foley, James J.;Nuthulaganti, Parvathi;Kallal, Lorena A.;Sarau, Henry M.;Morrow, Dwight M.;Moore, Michael L.;Rivero, Ralph A.;Palovich, Michael;Salmon, Michael;Belmonte, Kristen E.;Laine, Dramane I.;Jin, Jian. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.Category: piperazines This article mentions the following:

Exploration of multiple regions of a bi-aryl amine template led to the identification of highly potent M₃ muscarinic acetylcholine receptor antagonists such as (I) (pA₂ = 11.0) possessing good sub-type selectivity for M₃ over M₂. The structure-activity relationships (SAR) and optimization of the bi-aryl amine series are described. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Category: piperazines).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. Industrial applications of piperazine include the manufacture of plastics, resins, pesticides and brake fluids. Intermediate for a wide range of pharmaceuticals, polymers, dyes, corrosion inhibitors, rubber accelerators and surfactants.Category: piperazines

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

Syntheses of piperazines. III. Catalytic syntheses of N-substituted piperazines was written by Ishiguro, Takeo;Kitamura, Eiichi;Matsumura, Masaki;Ogawa, Hiroshi. And the article was included in Yakugaku Zasshi in 1955.Related Products of 21867-64-1 This article mentions the following:

Vapor phase reaction of 53 g. RN(CH₂CH₂OH)₂ (I, R = H) and 23 l. NH₃ 3-5 hrs. at 300-400° over dehydration catalysts (activated earth, ZnO-acid clay, CrO₃-acid clay, Cu-Ni-Al₂O₃ or SiO₂-Al₂O₃) gives no piperazine; 60 g. I (R = Me) (II) and 25 l. NH₃ heated 6 hrs. at 300°, yielded 14% 1-substituted piperazine (R = substituent) (III, R = Me) (IV), b. 134-6°; di(2,4-dinitrophenolate, m. 209-9.5°). The same reaction with 24 l. NH₃ 5 hrs. at 325°, yielded 20% IV; 23 l. NH₃, 5 hrs. at 350° yielded 18% IV; 24 l. NH₃, 5.5 hrs. at 375° yielded 8% IV; 27 l. NH₃, 5.5 hrs. at 425° yielded 4% IV. Similarly, 53 g. I (R = Et) (V) and 21 l. NH₃ 5 hrs. at 325° yielded 8% III (R = Et) (VI). V (53 g.) and 22 l. NH₃ 5.5 hrs. at 350° yielded 2% VI, b. 155-8° (p-toluenesulfonate, m. 73-4°). I (R = Pr) (VII) (59 g.) and 23 l. NH₃ 5.5 hrs. at 325° yielded 8% III (R = Pr) (VIII), b. 165-70°, dipicrate, m. 235-6° (decomposition). I (R = Bu) (IX) (56 g.) and 18 l. NH₃ 5.5 hrs. at 350° yielded 4% III (R = Bu), b. 186-92°; dipicrate, m. 249° (decomposition). Similarly, 60 g. II and 26 g. MeNH₂ heated 6 hrs. at 325° yielded 32% RN.CH₂.CH₂.NR¹CH₂.CH₂ (X, R = Me = R¹), b. 131-3°; di(2,4-dinitrophenolate, m. 216.5-7.5°. Neither IX and BuNH₂ nor I (R = H) and PhNH₂ give X. IV and PhNH₂ yielded 7% X (R = Me, R¹ = Ph) (XI), b₂₀ 145-50°; dipicrate, m. 215° (decomposition); monomethiodide, m. 234-5°. The maximum yield of XI was 14% when heated 5.5 hrs. at 450°. V (33 g.) and 23 g. PhNH₂ heated 6.2 hrs. at 450° yielded 9% X (R = Et, R¹ = Ph), b₁₈ 165-70°; monomethiodide, m. 233-5°. I (R = Ph) and PhNH₂ give no X. SiO₂-Al₂O₃ coprecipitate was the best catalyst; the best reaction temperature was 325° for NH₃ and aliphatic amines, and 450° for aromatic amines. In the experiment, the researchers used many compounds, for example, 1-Propylpiperazine (cas: 21867-64-1Related Products of 21867-64-1).

1-Propylpiperazine (cas: 21867-64-1) belongs to piperazine derivatives. The piperazine scaffold is often found in biologically active compounds in different therapeutic areas. These therapeutic areas include antifungals, antidepressants, antivirals, and serotonin receptor (5-HT) antagonists/agonists. Piperazines are very broad chemical group, covering a wide range of drugs from antidepressants to antihistamines. The connecting property of all these chemicals is the presence of a piperazine functional group.Related Products of 21867-64-1

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

Discovery of novel N-aryl piperazine CXCR4 antagonists was written by Zhao, Huanyu;Prosser, Anthony R.;Liotta, Dennis C.;Wilson, Lawrence J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Safety of 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid This article mentions the following:

A novel series of CXCR4 antagonists with substituted piperazines as benzimidazole replacements is described. These compounds showed micromolar to nanomolar potency in CXCR4-mediated functional and HIV assays, namely inhibition of X4 HIV-1_IIIB virus in MAGI-CCR5/CXCR4 cells and inhibition of SDF-1 induced calcium release in Chem-1 cells. Preliminary SAR investigations led to the identification of a series of N-aryl piperazines as the most potent compounds Results show SAR that indicates type and position of the aromatic ring, as well as type of linker and stereochem. are significant for activity. Profiling of several lead compounds showed that one (49b) reduced susceptibility towards CYP450 and hERG, and the best overall profile when considering both SDF-1 and HIV potencies (6-20 nM). In the experiment, the researchers used many compounds, for example, 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (cas: 149057-19-2Safety of 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid).

4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid (cas: 149057-19-2) belongs to piperazine derivatives. Piperazine is a fairly basic compound and is an amine solvent. Piperazine is an anthelminthic especially useful in the treatment of partial intestinal obstruction caused by Ascaris worms, which is a condition primarily seen in children. Piperazine hydrate and piperazine citrate are the main anthelminthic piperazines.Safety of 4-((Benzyloxy)carbonyl)-1-(tert-butoxycarbonyl)piperazine-2-carboxylic acid

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