Category: piperazines

Huang, Liang-Fu published the artcileSynthesis of 1,2,4-triazole and thiazole analogs of ketoconazole, Product Details of C12H16N2O2, the publication is Journal of Heterocyclic Chemistry (1997), 34(2), 469-476, database is CAplus.

The synthesis of 1,2,4-triazole and thiazole analogs of ketoconazole is described in which one of the α azole ring carbons is linked to C-2 of the ketal by means of a three methylene tether. Lithiation of 1-methyl-1,2,4-triazole and thiazole and subsequent alkylation with 2-(2,4-dichlorophenyl)-2-(3-iodopropyl)-1,3-dioxolane produced, after an aqueous acidic workup, 2,4-dichlorophenyl 3-[5-(1-methyl-1,2,4-triazolyl) and 2-thiazolyl]propyl ketones, resp. Ketalization with glycerol furnished the corresponding diastereomeric pairs of cis- and trans-1,3-dioxolanes. The reaction of 2,4-dichlorophenyl 3-[5-(1-methyl-1,2,4-triazolyl)]propyl ketone with 3-mercapto-1,2-propanediol produced the corresponding diastereomeric cis- and trans-hydroxymethyl-1,3-oxathiolanes. The diastereomeric racemates were separated by column chromatog. and their stereochem. established by NOE NMR experiments Some of these racmic cis ketal alcs. were converted by benzyl bromide to the corresponding benzyl ethers. Several of these racemic cis-ketals were reacted, first with methanesulfonyl chloride, then with 1-acetyl-4-(4-hydroxyphenyl)piperazine, to furnish the title compounds

Journal of Heterocyclic Chemistry 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, Product Details of C12H16N2O2.

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

Lee, Eun-Jeong published the artcileToxicity of cassia and cinnamon oil compounds and cinnamaldehyde-related compounds to Sitophilus oryzae (Coleoptera: Curculionidae), Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is Journal of Economic Entomology (2008), 101(6), 1960-1966, database is CAplus and MEDLINE.

The toxicity to adult Sitophilus oryzae (L.) (Coleoptera: Curculionidae) of two cassia oils (Especial and true), four cinnamon oils (tech., #500, bark, and green leaf), and (E)-cinnamaldehyde and its 41 structurally related compounds was examined by residual and vapor-phase toxicity bioassays. Results were compared with those of dichlorvos. In residual bioassays, cassia and cinnamon oils exhibited good insecticidal activity. Based on 48-h LD₅₀ values, the toxicity of allyl cinnamate (0.0003 mg/cm²) was comparable with that of dichlorvos (0.00025 mg/cm²). Potent insecticidal activity also was observed with benzaldehyde, β-caryophyllene, cinnamonitrile, hydrocinnamyl acetate, (E)-4-hydroxycinnamic acid, and α-terpineol (LD₅₀ = 0.003-0.009 mg/cm²). Structure-activity relationships indicate that types of functional groups rather than hydrophobicity or vapor pressure parameters seem to play a role in determining the toxicities to adult S. oryzae. In vapor-phase toxicity tests with weevils, these compounds were more effective in closed containers than in open ones. These results indicate that the effect of the compounds was largely a result of action in the vapor phase. Cassia and cinnamon oils and test compounds described merit further study as potential fumigants for the control of S. oryzae because of their greater activity as a fumigant.

Journal of Economic Entomology 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, Recommanded Product: (E)-1-Cinnamylpiperazine.

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

Na, Young Eun published the artcileFumigant toxicity of cassia and cinnamon oils and cinnamaldehyde and structurally related compounds to Dermanyssus gallinae (Acari: Dermanyssidae), Quality Control of 87179-40-6, the publication is Veterinary Parasitology (2011), 178(3-4), 324-329, database is CAplus and MEDLINE.

The toxicity of two cassia oils, four cinnamon oils and (E)-cinnamaldehyde and (E)-cinnamic acid and 34 structurally related compounds to adult Dermanyssus gallinae (De Geer) collected from a poultry house was examined using a vapor-phase mortality bioassay. Results were compared with those of dichlorvos, a conventional acaricide. The cassia and cinnamon oils (cinnamon tech., cinnamon #500, cassia especial, cassia true, cinnamon bark and cinnamon green leaf) exhibited good fumigant toxicity (LD₅₀, 11.79-26.40 μg cm^-3). α-Methyl-(E)-cinnamaldehyde (LD₅₀, 0.45 μg cm^-3) and (E)-cinnamaldehyde (0.54 μg cm^-3) were the most toxic compounds and the toxicity of these compounds was comparable to that of dichlorvos (0.30 μg cm^-3). Potent fumigant toxicity was also observed in allyl cinnamate, ethyl-α-cyanocinnamate, (E)-2-methoxylcinnamic acid and (Z)-2-methoxylcinnamic acid (LD₅₀, 0.81-0.92 μg cm^-3). Structure-activity relationships indicate that structural characteristics, such as types of functional groups and carbon skeleton rather than vapor pressure parameter, appear to play a role in determining toxicity. The essential oils and compounds described merit further study as potential acaricides for the control of D. gallinae populations as fumigants with contact action due to global efforts to reduce the level of highly toxic synthetic acaricides in the agricultural environment.

Veterinary Parasitology 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, Quality Control of 87179-40-6.

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

Kumar, Nilesh published the artcileSmall-Molecule Diversity Using a Skeletal Transformation Strategy, HPLC of Formula: 87179-40-6, the publication is Organic Letters (2005), 7(13), 2535-2538, database is CAplus and MEDLINE.

A short synthetic sequence resulting in >4000 skeletally diverse small mols. that have three distinct skeletal frameworks among other unique structural features is described. The sequence entails skeletal transformations pioneered by Winterfeldt and co-workers. The following reaction sequence is used: epoxide ring opening and subsequent functionalization that provide, e.g., spirocyclic oxazolidines, Lewis acid catalyzed Diels-Alder cycloaddition of steroid-derived dienes with ynones, and subsequent retro-Diels-Alder fragmentation that yields 14-membered paracyclophanes.

Organic Letters 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

Yoneyama, Hiroshi published the artcileStudies on antimicrobial activity of ketoconazole (KW-1414). VI. In vitro antifungal and antibacterial activity of ketoconazole (KW-1414) and its analogs, Synthetic Route of 67914-60-7, the publication is Shinkin to Shinkinsho (1984), 25(4), 372-8, database is CAplus.

Antifungal activities of structural analogs and metabolites of the synthetic antifungal agent ketoconazole (KCZ; KW-1414) (I) were investigated. R-39519 (desacetyl derivative) and R-44319 (trans isomer) had less antifungal activity against Candida species and dermatophytes than did I. HLI-151 (oxidized derivative) had no antifungal activity against any of the yeasts or fungi. Two known physiol. metabolites of I, R-43568 and T-1141, also showed no antifungal activity. I, R-39519, R-43568, and T-1141 showed no antibacterial activity against 12 strains of Lactobacillus species which are normal flora of the vagina. In blood of human volunteers administered orally 200 mg of I, no antifungal activity was detected except for I by bioautog. seeded with Kluyveromyces fragilis. In human urine of the same volunteers, no antifungal activity was detected by the bioautog.

Shinkin to Shinkinsho 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 C14H10O4S2, Synthetic Route of 67914-60-7.

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

Irie, Osamu published the artcileDiscovery of Orally Bioavailable Cathepsin S Inhibitors for the Reversal of Neuropathic Pain, Synthetic Route of 67914-60-7, the publication is Journal of Medicinal Chemistry (2008), 51(18), 5502-5505, database is CAplus and MEDLINE.

Cathepsin S inhibitors are well-known to be an attractive target as immunol. therapeutic agents. Recently, our gene expression anal. identified that cathepsin S inhibitors could also be effective for neuropathic pain. Herein, we describe the efficacy of selective cathepsin S inhibitors as antihyperalgesics in a model of neuropathic pain in rats after oral administration.

Journal of Medicinal Chemistry 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, Synthetic Route of 67914-60-7.

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

Hou, Jinqiang published the artcileDevelopment of Candidates for Positron Emission Tomography (PET) Imaging of Ghrelin Receptor in Disease: Design, Synthesis, and Evaluation of Fluorine-Bearing Quinazolinone Derivatives, Computed Properties of 67914-60-7, the publication is Journal of Medicinal Chemistry (2018), 61(3), 1261-1275, database is CAplus and MEDLINE.

Mol. imaging with positron emission tomog. (PET) is an attractive platform for noninvasive detection and assessment of disease. The development of a PET imaging agent targeting the ghrelin receptor (growth hormone secretagogue receptor type 1a or GHS-R1a) has the potential to lead to the detection and assessment of the higher than normal expression of GHS-R1a in diseases such as prostate, breast, and ovarian cancer. To enable the development of ¹⁸F radiopharmaceuticals, we have designed and synthesized three series of quinazolinone derivatives, resulting in the identification of two compound with subnanomolar binding affinity and one fluorine-bearing compound I with picomolar binding affinity (20 pM), representing the highest binding affinity for GHS-R1a reported to date. Two lead compounds (II, IC₅₀ = 20.6 nM; III, IC₅₀ = 9.3 nM) were successfully ¹⁸F-radiolabeled with radiochem. purity of greater than 99%. Mol. modeling studies were performed to shed light on ligand-receptor interactions.

Journal of Medicinal Chemistry 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, Computed Properties of 67914-60-7.

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

Severinsen, Kasper published the artcileBinding of the Amphetamine-like 1-Phenyl-piperazine to Monoamine Transporters, Recommanded Product: 1-Biphenyl-4-yl-piperazine, the publication is ACS Chemical Neuroscience (2012), 3(9), 693-705, database is CAplus and MEDLINE.

The human serotonin transporter (hSERT), the human dopamine transporter (hDAT), and the human norepinephrine transporter (hNET) facilitate the active uptake of the neurotransmitters serotonin, dopamine, and norepinephrine from the synaptic cleft. Drugs of abuse such as MDMA (street-name ecstasy) and certain 1-phenyl-piperazine (PP) analogs such as 1-(3-chlorophenyl)-piperazine (mCPP) elicit their stimulatory effect by elevating the synaptic concentration of serotonin by blocking or reversing the normal transport activity of hSERT. Recent data suggest that certain analogs of PP may be able to counteract the addictive effect of cocaine. Little is still known about the precise mechanism by which MDMA and PP analogs function at hSERT, hDAT, and hNET and even less is known about the specific protein-ligand interactions. In this study, we provide a comprehensive biochem. examination of a repertoire of PP analogs in hSERT, hDAT, and hNET. Combined with induced fit docking models and mol. dynamics simulations of PP and 1-(3-hydroxyphenyl)-piperazine (3-OH-PP) bound to hSERT and hDAT, we present detailed mol. insight into the promiscuous binding of PP analogs in the monoamine transporters. We find that PP analogs inhibit uptake as well as induce release in all three monoamine transporters. We also find that the selectivity of the PP analogs can be adjusted by carefully selecting substituents on the PP skeleton.

ACS Chemical Neuroscience 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 C5H10N2OS, Recommanded Product: 1-Biphenyl-4-yl-piperazine.

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

Kuriyama, Masami published the artcileNickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates, Quality Control of 67914-60-7, the publication is Advanced Synthesis & Catalysis (2017), 359(6), 1043-1048, database is CAplus.

The nickel-catalyzed deoxygenative deuteration of aryl/heteroaryl sulfamates was developed, and the effective incorporation of deuterium into a variety of aromatic compounds was achieved with sufficient catalytic efficiency and high deuteration degree. This process tolerated reducible functional moieties and heterocyclic structures. Addnl., a double introduction of deuterium also successfully gave a desired product with a high yield and deuterium content.

Advanced Synthesis & Catalysis 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, Quality Control of 67914-60-7.

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

Khan, Mohammad Faheem published the artcileSynthesis of novel imbricatolic acid analogues via insertion of N-substituted piperazine at C-15/C-19 positions, displaying glucose uptake stimulation in L6 skeletal muscle cells, Name: (E)-1-Cinnamylpiperazine, the publication is Bioorganic & Medicinal Chemistry Letters (2012), 22(14), 4636-4639, database is CAplus and MEDLINE.

A new class of N-substituted piperazine analogs of imbricatolic acid have been designed and synthesized by using the appropriate synthetic routes in excellent yield. All synthesized compounds were screened for their in vitro glucose uptake stimulatory activity. Among them compounds I–IV triggered L6 skeletal muscle cells for glucose uptake at 54.73%, 40.79%, 40.90%, and 39.55% stimulation, resp. I has emerged as important lead compound showing potential antidiabetic activity. Illustration about their synthesis and in vitro glucose uptake activity is described.

Bioorganic & Medicinal Chemistry Letters 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, Name: (E)-1-Cinnamylpiperazine.

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