Category: piperazines

Mastuo, Kasumi published the artcileNickel-Catalyzed Hydrodeoxygenation of Aryl Sulfamates with Alcohols as Mild Reducing Agents, Product Details of C12H16N2O2, the publication is Synthesis (2021), 53(23), 4449-4460, database is CAplus.

The nickel-catalyzed hydrodeoxygenation of aryl sulfamates ROS(O)₂R¹ [R = 2-propanoylbenzen-1-yl, 1-ethyl-1H-indol-4-yl, 4-(4-acetylpiperazin-1-yl)benzen-1-yl, etc.; R¹ = dimethylaminyl, piperidin-1-yl, bis(propan-2-yl)aminyl, etc.] has been developed with alcs. as mild reductants. A variety of functional groups and heterocycles were tolerated in this reaction system to give the desired products RH in high yields. In addition, the gram-scale process and stepwise cine-substitution were also achieved with high efficiency.

Synthesis 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

Fukunishi, Yoshifumi published the artcilePrediction of Synthetic Accessibility Based on Commercially Available Compound Databases, Name: N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate, the publication is Journal of Chemical Information and Modeling (2014), 54(12), 3259-3267, database is CAplus and MEDLINE.

A compound’s synthetic accessibility (SA) is an important aspect of drug design, since in some cases computer-designed compounds cannot be synthesized. There have been several reports on SA prediction, most of which have focused on the difficulties of synthetic reactions based on retro-synthesis analyses, reaction databases and the availability of starting materials. The authors developed a new method of predicting SA using com. available compound databases and mol. descriptors. SA was estimated from the probability of existence of substructures consisting of the compound in question, the number of symmetry atoms, the graph complexity, and the number of chiral centers of the compound The probabilities of the existence of given substructures were estimated based on a compound library. The predicted SA results reproduced the expert manual assessments with a Pearson correlation coefficient of 0.56. Since the authors method required a compound database and not a reaction database, it should be easy to customize the prediction for compound vendors. The correlation between the sales price of approved drugs and the SA values was also examined and weak. The price most likely depends on the total cost of development and other factors.

Journal of Chemical Information and Modeling published new progress about 863127-77-9. 863127-77-9 belongs to piperazines, auxiliary class TGF-beta/Smad,Bcr-Abl,Natural product, name is N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate, and the molecular formula is C22H28ClN7O3S, Name: N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate.

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

Morera, Ludovica published the artcileDevelopment and characterization of endocannabinoid hydrolases FAAH and MAGL inhibitors bearing a benzotriazol-1-yl carboxamide scaffold, Category: piperazines, the publication is Bioorganic & Medicinal Chemistry (2012), 20(21), 6260-6275, database is CAplus and MEDLINE.

A series of (1H-benzo[d][1,2,3]triazol-1-yl)(4-benzylpiperazin-1-yl)methanones and of (1H-benzo[d][1,2,3]triazol-1-yl)(4-phenylpiperazin-1-yl)methanones has been prepared and tested on human fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL). In the benzylpiperazinyl series, compound 29 (ML30) exhibited an IC₅₀ value of 0.54 nM on MAGL, combined with a 1000-fold selectivity vs. FAAH, while compounds 11 and 16 acted as potent dual FAAH-MAGL inhibitors (IC₅₀ <10 nM). In the phenylpiperazinyl series, compounds 37, 38, 42, and 43 displayed IC₅₀ values against MAGL in the nanomolar range, while being between one and two orders of magnitude less potent on the FAAH, while compounds 31 and 32 were potent FAAH inhibitors (IC₅₀ <20 nM) and over 12-fold selective vs. MAGL. The key structural determinants driving the structure-activity relationships were explored by the minimization of the inhibitors inside the active site of both enzymes.

Bioorganic & 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, Category: piperazines.

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

Sun, Jun-Rong published the artcile3D-QSAR and docking studies on pyrrolopyrimidine derivatives as LIM-kinase 2 inhibitors, Computed Properties of 1116571-01-7, the publication is Letters in Drug Design & Discovery (2011), 8(3), 229-240, database is CAplus.

The pyrrolopyrimidine derivatives have been regarded as a novel class of LIM-kinase 2 inhibitor. To explore the relationship between the structures of substituted pyrrolopyrimidine derivatives and their inhibitory activities against LIMK2, CoMFA and CoMSIA analyses, and mol. docking studies were performed on a dataset of forty-one compounds The two 3D-QSAR models resulted from thirty-one mols. in the training set gave r²_cv values of 0.635 and 0.660, r² values of 0.973 and 0.965, resp. The predictive ability of CoMFA and CoMSIA, determined using a test set of ten compounds, gave predictive correlation coefficients of 0.971 and 0.964, resp. 3D contour maps generated from CoMFA and CoMSIA along with the docking binding structures provided enough information about the structural requirements for better activity. The results can serve as a useful guideline to design novel LIMK2 inhibitors with better potencies.

Letters in Drug Design & Discovery published new progress about 1116571-01-7. 1116571-01-7 belongs to piperazines, auxiliary class Other Aromatic Heterocyclic,Piperazine,Chiral,Nitrile,Bromide,Carbamidine,Amine,Benzene, name is (S)-N-(3-Bromophenyl)-N’-cyano-2-methyl-4-(5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboximidamide, and the molecular formula is C12H14BNO2, Computed Properties of 1116571-01-7.

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

Boeckler, Frank published the artcileModeling the Similarity and Divergence of Dopamine D₂-like Receptors and Identification of Validated Ligand-Receptor Complexes, Quality Control of 337972-47-1, the publication is Journal of Medicinal Chemistry (2005), 48(3), 694-709, database is CAplus and MEDLINE.

Focusing on the similarity and divergence of GPCR subtypes and their ligand interactions, we generated dopamine D₂, D₃, and D₄ receptor models based on the rhodopsin crystal structure and refined these with an extensive MM/MD protocol. After validation by diagnostic exptl. data, subtype-specific relative positions of TM1, 2, 6, and 7 and bending angles of TM7 were found. To sample the conformational space of the complex, we performed simulated-annealing runs of the receptor protein with the sub-nanomolar antagonist spiperone. Docking a representative set of ligands, we were able to identify one superior model for each subtype when excellent correlations between predicted energies of binding and exptl. affinities (r² = 0.72 for D₂, 0.91 for D₃ and 0.77 for D₄) could be observed Further anal. revealed general ligand interactions with ASP3.32 and aromatic residues in TM6/7 and individual key interactions with TM1 and TM2 residues of the D₃ and D₄ receptor models, resp.

Journal of Medicinal Chemistry published new progress about 337972-47-1. 337972-47-1 belongs to piperazines, auxiliary class Inhibitor, name is 2-((4-(4-Chlorophenyl)piperazin-1-yl)methyl)pyrazolo[1,5-a]pyridine, and the molecular formula is C18H19ClN4, Quality Control of 337972-47-1.

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

Ryu, Jae Chun published the artcileSynthesis of ketoconazole derivatives, Recommanded Product: 1-(4-(4-Hydroxyphenyl)piperazin-1-yl)ethanone, the publication is Bulletin of the Korean Chemical Society (2003), 24(4), 460-466, database is CAplus.

For the drug master file (DMF) of ketoconazole, four impurities contained in ketoconazole were synthesized. During the synthesis of I, a new synthetic method of 1,4-dihydropyrazine was established. To oxidize the aminoalc. of I to the aminal I, the standard Swern oxidation condition was modified to mask the nucleophilicity of the amino group temporarily using one equivalent of acetic acid. Derivative II was synthesized via regioselective bromination at the I position of the 4-aminophenol derivative of II using Br₂ in the presence of p-TsOH. The etherification of aryl bromide with a phenol derivative compound was accomplished by a modification of the general Cu-mediated reaction condition using excess of the phenol derivative itself as a solvent at elevated temperature (190 °C).

Bulletin of the Korean Chemical Society 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

Kong, Jeong-Ok published the artcileNematicidal activity of cassia and cinnamon oil compounds and related compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae), Recommanded Product: (E)-1-Cinnamylpiperazine, the publication is Journal of Nematology (2007), 39(1), 31-36, database is CAplus and MEDLINE.

The nematicidal activity of two cassia, Cinnamomum cassia, oils (Especial and true), four cinnamon, Cinnamomum zeylanicum, oils (tech., #500, bark and green leaf), and their compounds (e.g., trans-cinnamaldehyde and trans-cinnamic acid) toward adult Bursaphelenchus xylophilus was examined by a direct contact bioassay. Results were compared with those of 34 related compounds As judged by 24-h LC₅₀ values, two cassia oils (0.084-0.085 mg/mL) and four cinnamon oils (0.064-0.113 mg/mL) were toxic toward adult B. xylophilus. Of 45 test compounds, trans-cinnamaldehyde (0.061 mg/mL) was the most active nematicide, followed by Et cinnamate, α-methyl-trans-cinnamaldehyde, Me cinnamate and allyl cinnamate (0.114-0.195 mg/mL). Potent nematicidal activity was also observed with 4-methoxycinnamonitrile, trans-4-methoxycinnamaldehyde, trans-2-methoxycinnamaldehyde, Et α-cyanocinnamate, cinnamonitrile and cinnamyl bromide (0.224-0.502 mg/mL). Structure-activity relationships indicate that structural characteristics, such as types of functional groups, saturation and carbon skeleton, appear to play a role in determining the toxicities to adult B. xylophilus. Cassia and cinnamon oils and test compounds described merit further study as potential nematicides or leads for the control of pine wilt disease caused by B. xylophilus.

Journal of Nematology 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

Jiang, Xiong-Jie published the artcilePreparation and in vitro photodynamic activities of novel axially substituted silicon (IV) phthalocyanines and their bovine serum albumin conjugates, Formula: C12H16N2O2, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(9), 2450-2453, database is CAplus and MEDLINE.

Two novel axially substituted phthalocyanines, namely bis(4-(4-acetylpiperazine)phenoxy)phthalocyaninatosilicon (IV) (1) and its N-methylated derivative 2, have been synthesized. The dicationic phthalocyanine 2 is non-aggregated in water and exhibits good photophys. properties. The non-covalent BSA conjugates of these compounds have also been prepared Compound 2 and the conjugate 2-BSA show extremely high photodynamic activities toward B16 melanoma cancer cell lines. The corresponding 50% growth-inhibitory (IC₅₀) ratios are 33 and 38 nM, resp.

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

Yu, Lei published the artcileA structure-guided optimization of pyrido[2,3-d]pyrimidin-7-ones as selective inhibitors of EGFR^L858R/T790M mutant with improved pharmacokinetic properties, Recommanded Product: 6-(4-Methylpiperazin-1-yl)pyridin-3-amine, the publication is European Journal of Medicinal Chemistry (2017), 1107-1117, database is CAplus and MEDLINE.

Structural optimization of pyrido[2,3-d]pyrimidin-7-ones was conducted to yield a series of new selective EGFR^T790M inhibitors with improved pharmacokinetic properties. One of the most promising compound 9s (N-(3-(2-((2-methoxy-4-(4-methylpiperazin-1-yl)phenyl)amino)-5-methyl-7-oxopyrido[2,3-d]pyrimidin-8(7H)-yl)-5-(trifluoromethyl)phenyl)acrylamide) potently suppressed EGFR^L858R/T790M kinase and inhibited the proliferation of H1975 cells with IC₅₀ values of 2.0 nM and 40 nM, resp. The compound dose-dependently induced reduction of the phosphorylation of EGFR and downstream activation of ERK in NCI-H1975 cells. It also exhibited moderate plasma exposure after oral administration and an oral bioavailability value of 16%. Compound 9s may serve as a promising lead compound for further drug discovery overcoming the acquired resistance of non-small cell lung cancer (NSCLC) patients.

European Journal of Medicinal Chemistry published new progress about 55403-35-5. 55403-35-5 belongs to piperazines, auxiliary class Pyridine,Piperazine,Amine, name is 6-(4-Methylpiperazin-1-yl)pyridin-3-amine, and the molecular formula is C15H14O, Recommanded Product: 6-(4-Methylpiperazin-1-yl)pyridin-3-amine.

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

Loeber, Stefan published the artcileRationally Based Efficacy Tuning of Selective Dopamine D4 Receptor Ligands Leading to the Complete Antagonist 2-[4-(4-Chlorophenyl)piperazin-1-ylmethyl]pyrazolo[1,5-a]pyridine (FAUC 213), Related Products of piperazines, the publication is Journal of Medicinal Chemistry (2001), 44(17), 2691-2694, database is CAplus and MEDLINE.

Structure dependent efficacy studies in the field of selective D4 ligands led to the 2-aminomethyl substituted azaindole 2 (FAUC 213) that displayed strong D4 binding, high subtype selectivity, and complete antagonist properties in ligand-induced mitogenesis experiments According to our schematic mol. model, the intrinsic activity of the regioisomers investigated is controlled by the ability of the heterocyclic unit to interact with both elements of the D4 binding-site crevice, the aromatic microdomain in TM6, and a serine residue in TM5.

Journal of Medicinal Chemistry published new progress about 337972-47-1. 337972-47-1 belongs to piperazines, auxiliary class Inhibitor, name is 2-((4-(4-Chlorophenyl)piperazin-1-yl)methyl)pyrazolo[1,5-a]pyridine, and the molecular formula is C18H19ClN4, Related Products of piperazines.

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