Tag: M.W=200-250

Grycova, Aneta published the artcileImpurities contained in antifungal drug ketoconazole are potent activators of human aryl hydrocarbon receptor, Related Products of piperazines, the publication is Toxicology Letters (2015), 239(2), 67-72, database is CAplus and MEDLINE.

Antifungal drug ketoconazole is a mixture of (+)/(-) cis-enantiomers, which also contains several impurities. Ketoconazole was identified as an activator of aryl hydrocarbon receptor AhR by three independent research teams. In the current paper impurities contained in ketoconazole preparations are strong activators of human AhR and inducers of CYP1A1. Impurity IMP-C had similar potency (EC₅₀), but 10-15 times higher efficacy (magnitude of induction) towards AhR, comparing to (+)-ketoconazole, as revealed by gene reporter assay in AZ-AHR stably transfected cells. Impurities IMP-B and IMP-C, and in lesser extent IMP-E, induced a formation of AhR-DNA complex, as demonstrated by electromobility shift assay EMSA. Impurities IMP-C and IMP-E dose-dependently induced CYP1A1 mRNA after 24 h, and their effects were comparable to those by (+)-ketoconazole. The level of CYP1A1 protein in HepG2 cells was strongly increased by IMP-C after 48 h. In conclusion, the authors’ data further elucidated mol. effects of ketoconazole towards AhR signaling pathway, with possible implications in ketoconazole role in skin chemoprevention and/or damage, involving AhR.

Toxicology Letters published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, Related Products of piperazines.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Yang, Renjing published the artcileSynthesis and Anti-Hepatoma Activities of U12 Derivatives Arresting G0/G1 Phase and Inducing Apoptosis by PI3K/AKT/mTOR Pathway, Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is Pharmaceuticals (2022), 15(1), 107, database is CAplus and MEDLINE.

In this study, the structural modification and optimization of U12 were further investigated and twelve U12 derivatives I [R = aminocyclopropyl, piperazin-1-yl, 4-methylanilino, etc.], II were synthesized by substitution, esterification and amidation reactions. The evaluation of the cytotoxicity of synthetic derivatives against hepatoma cell lines (HepG2) indicated that II, I [R = 4-benzylpiperazin-1-yl, [4-[(E)-cinnamyl]piperazin-1-yl], piperazin-1-yl, aziridin-1-yl, 4-hydroxyanilino] showed more effective cytotoxic effects on the growth of HepG2 cells than U12, and the preliminary structure-activity relationship was discussed. Among them, compound I [R = 4-benzylpiperazin-1-yl] exhibited the most potent anti-hepatocellular carcinoma activity. Mechanism studies indicated that compound I [R = (4-benzylpiperazin-1-yl)] inhibited HepG2 cell proliferation by arresting the G0/G1 phase, and suppressed the activation of the PI3K/AKT/mTOR pathway. Further studies showed that compound I [R = 4-benzylpiperazin-1-yl] induced HepG2 cells apoptosis through activating the caspase signaling pathway. Furthermore, compound I [R = (4-benzylpiperazin-1-yl)] evidently inhibited the growth of HepG2-derived tumor xenografts in vivo without observable adverse effects. Thus, compound I [R = 4-benzylpiperazin-1-yl] might be considered as a promising candidate for the treatment of hepatocellular carcinoma.

Pharmaceuticals published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C4H11NO, Recommanded Product: (E)-1-Cinnamylpiperazine.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Irie, Osamu published the artcileDiscovery of selective and nonpeptidic cathepsin S inhibitors, Formula: C12H16N2O2, the publication is Bioorganic & Medicinal Chemistry Letters (2008), 18(14), 3959-3962, database is CAplus and MEDLINE.

Nonpeptidic, selective, and potent cathepsin S inhibitors were derived from an inhouse pyrrolopyrimidine cathepsin K inhibitor by modification of the P2 and P3 moieties. The pyrrolopyrimidine-based inhibitors show nanomolar inhibition of cathepsin S with over 100-fold selectivity against other cysteine proteases, including cathepsin K and L. Some of the inhibitors showed cellular activities in mouse splenocytes as well as oral bioavailabilities in rats.

Bioorganic & Medicinal Chemistry Letters published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, Formula: C12H16N2O2.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Brossard, Dominique published the artcileSynthesis of bile acid derivatives and in vitro cytotoxic activity with pro-apoptotic process on multiple myeloma (KMS-11), glioblastoma multiforme (GBM), and colonic carcinoma (HCT-116) human cell lines, HPLC of Formula: 87179-40-6, the publication is European Journal of Medicinal Chemistry (2010), 45(7), 2912-2918, database is CAplus and MEDLINE.

The use of nitrogenous heterocycles as building blocks in the synthesis of conjugate bile acid derivatives was described. New piperazinyl bile acid derivatives I [R^7a = OH, R^7b = H, R¹² = OH, R²⁴ = 4-methyl-1-piperazinylamino, 4-(trans-cinnamyl)-1-piperazinyl; R^7a = H, R^7b = OH, R¹² = H, R²⁴ = 4-methyl-1-piperazinylamino, 4-(trans-cinnamyl)-1-piperazinyl; R^7a = OH, R^7b = H, R¹² = H, R²⁴ = 4-methyl-1-piperazinylamino, 4-(trans-cinnamyl)-1-piperazinyl] were synthesized and tested in vitro against various human cancer cells (GBM, KMS-11, HCT-116). The best pro-apoptotic activity was obtained with N-(4N-cinnamylpiperazin-1-yl)-3α,7β-dihydroxy-5β-cholan-24-amide I [R^7a = H, R^7b = OH, R¹² = H, R²⁴ = 4-(trans-cinnamyl)-1-piperazinyl] and N-(4N-cinnamyllpiperazin-1-yl)-3α,7α-dihydroxy-5β-cholan-24-amide I [R^7a = OH, R^7b = H, R¹² = H, R²⁴ = 4-(trans-cinnamyl)-1-piperazinyl] on these human cancer cell lines (IC₅₀: 8.5-31.4 μM). This activity was associated with nuclear and DNA fragmentation, demonstrating that I [R^7a = H, R^7b = OH, R¹² = H, R²⁴ = 4-(trans-cinnamyl)-1-piperazinyl] induces cell death by an apoptotic process as does I [R^7a = OH, R^7b = H, R¹² = H, R²⁴ = 4-(trans-cinnamyl)-1-piperazinyl]. This study shows the possibility of heterocycle-steroids as new anticancer agents with improved bioactivity and easy to synthesize.

European Journal of Medicinal Chemistry published new progress about 87179-40-6. 87179-40-6 belongs to piperazines, auxiliary class Benzenes, name is (E)-1-Cinnamylpiperazine, and the molecular formula is C13H18N2, HPLC of Formula: 87179-40-6.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Camps, Pelayo published the artcileStereoselective syntheses of both enantiomers of ketoconazole from (R)- and (S)-epichlorohydrin, HPLC of Formula: 67914-60-7, the publication is Tetrahedron: Asymmetry (1995), 6(6), 1283-94, database is CAplus.

Stereoselective syntheses of both enantiomers of ketoconazole (I) from com. available (R)- or (S)-epichlorohydrin has been developed. The key step of these syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S,4R)-II and (2R,4R)-II or of their enantiomers, followed by crystallization of the corresponding cis-benzoates, from which (+)- or (-)-I were obtained as described for (±)-I. The ee’s of (+)- and (-)-ketoconazole were determined by HPLC on the CSP Chiralcel OD-H.

Tetrahedron: Asymmetry published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, HPLC of Formula: 67914-60-7.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Power, Eoin C. published the artcilePartial structures of ketoconazole as modulators of the large conductance calcium-activated potassium channel (BK_Ca), Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(4), 887-890, database is CAplus and MEDLINE.

A series of partial structures of ketoconazole has been synthesized and tested for activity on the large conductance calcium-activated potassium channel (BK) in bovine smooth muscle cells. This has provided openers and blockers of the channel. The results suggest that the Ph and phenoxy moieties are important for interaction with BK, whereas the imidazole group is unimportant. The properties of the phenoxy moiety seem to determine whether the compounds act to open or block the channel.

Bioorganic & Medicinal Chemistry Letters published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C12H16N2O2, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Sunagar, Manjunath G. published the artcileSynthesis of novel N-9 substituted 6-(4-(4-propoxyphenyl)piperazin-1-yl)-9H-purine derivatives as inducers of apoptosis in MCF-7 breast cancer cells, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, the publication is RSC Advances (2016), 6(19), 15286-15297, database is CAplus.

A series of N-9 substituted 6-(4-(4-propoxyphenyl)piperazin-1-yl)-9H-purine derivatives (PP05-PP21) were prepared and evaluated for their anticancer activity against a panel of human cancer cell lines. Evaluation of results revealed that some of the synthesized compounds exhibited promising anticancer activity against the examined cancer cell lines. The structure-activity relationship (SAR) studies in the present work revealed that simple N-9 alkyl substituted 6-(4-(4-propoxyphenyl)piperazin-1-yl)-9H-purines are potent anticancer agents. Among all the compounds, PP17 (9-sec-butyl-6-(4-(4-propoxyphenyl)piperazin-1-yl)-9H-purine) showed good inhibitory activity against MCF-7 cells. Cell cycle anal. of the compound suggested that induces G2/M phase arrest. Biochem. experiments showed that PP17 significantly induced MCF-7 cell apoptosis. Therefore, compound PP17 with a potent in vitro anticancer activity can serve as a promising lead compound for further study.

RSC Advances published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C14H10O4, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Gunsaru, Bornface published the artcileSimplified reversed chloroquines to overcome malaria resistance to quinoline-based drugs, Application of 1-Biphenyl-4-yl-piperazine, the publication is Antimicrobial Agents and Chemotherapy (2017), 61(5), e01913-16/1-e01913-16/13, database is CAplus and MEDLINE.

Building on our earlier work of attaching a chemosensitizer (reversal agent) to a known drug pharmacophore, we have now expanded the structure-activity relationship study to include simplified versions of the chemosensitizer. The change from two aromatic rings in this head group to a single ring does not appear to detrimentally affect the antimalarial activity of the compounds Data from in vitro heme binding and β-hematin inhibition assays suggest that the single aromatic RCQ compounds retain activities against Plasmodium falciparum similar to those of CQ, although other mechanisms of action may be relevant to their activities.

Antimicrobial Agents and Chemotherapy published new progress about 180698-19-5. 180698-19-5 belongs to piperazines, auxiliary class Piperazine,Benzene, name is 1-Biphenyl-4-yl-piperazine, and the molecular formula is C16H18N2, Application of 1-Biphenyl-4-yl-piperazine.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Yan, Zihong published the artcileSynthesis and antiviral activity evaluation of derivatives of anti-influenza virus inhibitor nucleozin, Computed Properties of 180698-19-5, the publication is Huaxue Tongbao (2018), 81(11), 1015-1022, database is CAplus.

Nucleozin has good inhibitory activity as an inhibitor against influenza virus nucleoprotein. In this paper, we investigate the aromatic ring part which is connected directly with piperazine in the nucleozin mol. structure. A series of nucleozin derivatives were synthesized by palladium catalyzed coupling reaction, and the structure-activity relationship of this part in nucleozin mol. was clarified by detecting the inhibitory activities of the synthesized compounds on influenza virus H1N1. After replacing the chlorine atom in the mol. with a Me group, it was found that the inhibitory activity is significantly improved compared with the prototype mol. nucleozin. This study has a significant meaning in the drug-like improvement of this kind of mol.

Huaxue Tongbao published new progress about 180698-19-5. 180698-19-5 belongs to piperazines, auxiliary class Piperazine,Benzene, name is 1-Biphenyl-4-yl-piperazine, and the molecular formula is C13H11NO, Computed Properties of 180698-19-5.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics

Silverman, Lisa S. published the artcile3H-[1,2,4]-Triazolo[5,1-i]purin-5-amine derivatives as adenosine A_2A antagonists, SDS of cas: 67914-60-7, the publication is Bioorganic & Medicinal Chemistry Letters (2007), 17(6), 1659-1662, database is CAplus and MEDLINE.

A novel series of 3-substituted-8-aryl-[1,2,4]triazolo[5,1-i]purin-5-amine analogs related to Sch 58261 was synthesized in order to identify potent adenosine A_2A receptor antagonists with improved selectivity over the A₁ receptor, physiochem. properties, and pharmacokinetic profiles as compared to those of Sch 58261. As a result of structural modifications, numerous analogs with excellent in vitro binding affinities and selectivities were identified. Moreover, compound I (R = MeOCH₂CH₂O) displayed both superior in vitro and highly promising in vivo profiles.

Bioorganic & Medicinal Chemistry Letters published new progress about 67914-60-7. 67914-60-7 belongs to piperazines, auxiliary class Piperazine,Benzene,Phenol,Amide, name is 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, and the molecular formula is C10H16Br3N, SDS of cas: 67914-60-7.

Referemce:
https://en.wikipedia.org/wiki/Piperazine,
Piperazines – an overview | ScienceDirect Topics