Category: 374930-88-8

Kim, Juhyeon; Kim, Yoon Jung; Londhe, Ashwini M.; Pae, Ae Nim; Choo, Hyunah; Kim, Hak Joong; Min, Sun-Joon published the artcile< Synthesis and biological evaluation of disubstituted pyrimidines as selective 5-HT2C agonists>, Application In Synthesis of 374930-88-8, the main research area is pyrimidine preparation antagonist HT receptor; 5-HT2C receptor; binding affinity; cell-based assay; disubstituted pyrimidine; selectivity.

The synthesis of disubstituted pyrimidine derivatives I [R1 = 3-F, 4-F; n = 0, 1, 2; R2 = piperazin-1-yl, (2R)-2-methylpiperazin-1-yl, 1,4-diazepan-1-yl], II [R3 = (2R)-2-(3-fluorophenyl)propyl, (2R)-2-(4-fluorophenyl)propyl, 3-fluorophenyl, 4-fluorophenyl; R4 = 1,4-diazepan-1-yl, [(3R)-pyrrolidin-3-yl]aminyl, 2,7-diazaspiro[4.4]nonan-2-yl, etc.] and their biol. evaluation as selective 5-HT2C agonists were described. To improve selectivity for 5-HT2C over other subtypes, two series of disubstituted pyrimidines with fluorophenylalkoxy groups at either the 5-position or 4-position and varying cyclic amines at the 2-position were synthesized. The in vitro cell-based assay and binding assay identified compounds II [R3 = (2R)-2-(3-fluorophenyl)propyl, R4 = 1,4-diazepan-1-yl (I); R3 = (2R)-2-(4-fluorophenyl)propyl, R4 = 1,4-diazepan-1-yl] as potent 5-HT2C agonists. Further studies on selectivity to 5-HT subtypes and drug-like properties indicated that 2,4-disubstituted pyrimidine (I) showed a highly agonistic effect on the 5-HT2C receptor, with excellent selectivity, as well as exceptional drug-like properties, including high plasma and microsomal stability, along with low CYP inhibition. Thus, pyrimidine (I) could be considered a viable lead compound as a 5-HT2C selective agonist.

Molecules published new progress about 5-HT receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

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

Yang, Yang; Mustard, Thomas J. L.; Cheong, Paul Ha-Yeon; Buchwald, Stephen L. published the artcile< Palladium-Catalyzed Completely Linear-Selective Negishi Cross-Coupling of Allylzinc Halides with Aryl and Vinyl Electrophiles>, Application In Synthesis of 374930-88-8, the main research area is Negishi coupling allyl zinc aryl vinyl halide prenyl group; cross-coupling; heterocycles; organozinc reagents; palladium; prenylation.

A linear-selective Negishi coupling reaction was developed and the synthesis of the target compounds was achieved by a reaction of (allyl)zinc reagents [i.e., (prenyl)zinc bromide, (farnesyl)zinc, etc.] with aryl halides, heteroaryl halides, vinyl halides. The reaction features mild reaction conditions and a broad reactant scope with respect to aryl halides and vinyl halides and (allyl)zinc coupling components. Under optimized reaction conditions [2′-(amino-κN)[1,1′-biphenyl]-2-yl-κC][2′-(dicyclohexylphosphino-κP)-N2,N2,N6,N6-tetramethyl[1,1′-biphenyl]-2,6-diamine](methanesulfonate-κO)palladium was used as a catalyst. This synthetic approach was applied to the preparation of 6-methyl-3-(3-methyl-2-buten-1-yl)-9H-carbazol-2-ol (siamenol).

Angewandte Chemie, International Edition published new progress about Allylic compounds Role: RCT (Reactant), RACT (Reactant or Reagent) ((alkenyl)zinc compounds). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

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

Dong, Zhe; MacMillan, David W. C. published the artcile< Metallaphotoredox-enabled deoxygenative arylation of alcohols>, Quality Control of 374930-88-8, the main research area is alc aryl halide deoxygenative arylation metallaphotoredox.

Metal-catalyzed cross-couplings are a mainstay of organic synthesis and are widely used for the formation of C-C bonds, particularly in the production of unsaturated scaffolds1. However, alkyl cross-couplings using native sp3-hybridized functional groups such as alcs. remain relatively underdeveloped2. In particular, a robust and general method for the direct deoxygenative coupling of alcs. would have major implications for the field of organic synthesis. A general method for the direct deoxygenative cross-coupling of free alcs. must overcome several challenges, most notably the in situ cleavage of strong C-O bonds3, but would allow access to the vast collection of com. available, structurally diverse alcs. as coupling partners4. Authors report herein a metallaphotoredox-based cross-coupling platform in which free alcs. are activated in situ by N-heterocyclic carbene salts for carbon-carbon bond formation with aryl halide coupling partners. This method is mild, robust, selective and most importantly, capable of accommodating a wide range of primary, secondary and tertiary alcs. as well as pharmaceutically relevant aryl and heteroaryl bromides and chlorides. The power of the transformation has been demonstrated in a number of complex settings, including the late-stage functionalization of Taxol and a modular synthesis of Januvia, an antidiabetic medication. This technol. represents a general strategy for the merger of in situ alc. activation with transition metal catalysis.

Nature (London, United Kingdom) published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Quality Control of 374930-88-8.

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

Yang, Yang; Oldenhius, Nathan J.; Buchwald, Stephen L. published the artcile< Mild and general conditions for Negishi cross-coupling enabled by the use of palladacycle precatalysts>, COA of Formula: C13H19BrN4O2, the main research area is biaryl preparation; biheteroaryl preparation; heteroarylzinc preparation aryl halide Negishi cross coupling palladacycle catalyst.

A palladacycle-catalyzed Negishi cross coupling between in situ generated heteroaryl zinc reagents and aryl or heteroaryl halides is described. A series of biaryls and biheteroaryls were obtained in good to excellent yields.

Angewandte Chemie, International Edition published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, COA of Formula: C13H19BrN4O2.

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

Xiang, Ming; Pfaffinger, Dana E.; Ortiz, Eliezer; Brito, Gilmar A.; Krische, Michael J. published the artcile< Enantioselective Ruthenium-BINAP-Catalyzed Carbonyl Reductive Coupling of Alkoxyallenes: Convergent Construction of syn-sec,tert-Diols via (Z)-σ-Allylmetal Intermediates>, Application In Synthesis of 374930-88-8, the main research area is benzhydryloxyallene aldehyde ruthenium catalyst diastereoselective enantioselective reductive coupling reaction; aryl alc benzhydryloxyallene ruthenium catalyst diastereoselective enantioselective reductive coupling; benzhydryloxy alkenol preparation.

The first catalytic enantioselective ruthenium-catalyzed carbonyl reductive couplings of allene pronucleophiles was described. Using an iodide-modified ruthenium-BINAP-catalyst and O-benzhydryl alkoxyallene, carbonyl (α-alkoxy)allylation occurs from the alc. or aldehyde oxidation level to form enantiomerically enriched syn-sec,tert-diols. Internal chelation directs intervention of (Z)-σ-alkoxyallylruthenium isomers, which engage in stereospecific carbonyl addition

Journal of the American Chemical Society published new progress about Alkenyl alcohols Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Application In Synthesis of 374930-88-8.

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

Wang, Xin; Liu, Wei-Gang; Tung, Chen-Ho; Wu, Li-Zhu; Cong, Huan published the artcile< A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions>, Safety of tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate, the main research area is monophosphine ligand anthracene photodimer preparation coupling catalyst; Miyaura borylation Suzuki couplings heterocyclic electrophile.

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from com. available anthracene derivatives The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Organic Letters published new progress about Arylation. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Safety of tert-Butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate.

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

Dong, Weizhe; Badir, Shorouk O.; Zhang, Xuange; Molander, Gary A. published the artcile< Accessing Aliphatic Amines in C-C Cross-Couplings by Visible Light/Nickel Dual Catalysis>, Product Details of C13H19BrN4O2, the main research area is trimethylsilylmethanamine aryl bromide nickel catalyst regioselective aminoalkylation; aryl methanamine preparation.

A general aminoalkylation of aryl halides were developed, overcoming intolerance of free amines in nickel-mediated C-C coupling. This transformation features broad functional group tolerance and high efficiency. Taking advantage of the fast desilylation of α-silylamines upon single-electron transfer (SET) facilitated by carbonate, α-amino radicals were generated regioselectively, which then engage in nickel-mediated C-C coupling. The reaction displays high chemoselectivity for C-C over C-N bond formation. Highly functionalized pharmacophores and peptides were also amenable.

Organic Letters published new progress about Alkylation, chemoselective. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Product Details of C13H19BrN4O2.

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

Shallal, Hassan M.; Russu, Wade A. published the artcile< Discovery, synthesis, and investigation of the antitumor activity of novel piperazinylpyrimidine derivatives>, SDS of cas: 374930-88-8, the main research area is piperazinylpyrimidine derivative preparation antitumor activity breast carcinoma kinase profiling.

Protein kinases play several pertinent roles in cell proliferation, and targeting these proteins has been shown to be a successful strategy toward controlling different malignancies. Despite the great discovery stories during the last two decades, there is still a demand for anticancer small mols. with the potential of being selective on both the protein kinase and/or the cellular level. A series of novel piperazinylpyrimidine compounds was synthesized and the members tested for their potential to selectively inhibit the growth of certain tumor cell lines included within the NCI-60 cell line panel. MDA-MB-468, a triple-neg./basal-like breast carcinoma cell line was among the most sensitive cell lines towards compounds I and II. The three most interesting compounds identified in cellular screens (I, II, and III) were subjected to kinase profiling and found to have an interesting selective tendency to target certain kinase subfamily members; PDGFR, CK1, RAF and others. Compound I showed a selective tendency to bind to and/or inhibit the function of certain KIT and PDGFRA mutants compared to their wild-type isoforms. Piperazinylpyrimidine based derivatives represent a new class of selective kinase inhibitors. Significantly, I is more potent at inhibiting oncogenic mutant forms of PDGFR family kinases, which is relevant in terms of its potential use in treating tumors that have become resistant to treatment or driven by such mutations. The clin. demand for agents useful in the control of triple-neg./basal-like breast cancer justifies interest in compound II which is a potent growth inhibitor of MDA-MB-468 cell line.

European Journal of Medicinal Chemistry published new progress about Antitumor agents. 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, SDS of cas: 374930-88-8.

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

Yang, Yang; Niedermann, Katrin; Han, Chong; Buchwald, Stephen L. published the artcile< Highly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides>, Category: piperazines, the main research area is secondary alkylzinc Negishi coupling heteroaryl halide palladium biarylphosphine catalyst.

The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described [e.g., using a palladacycle precatalyst ligated by CPhos, 3-chlorobenzisothiazole was coupled with i-PrZnBr.LiCl to afford 3-isopropylbenzisothiazole in 78% yield (normal:rearranged ratio = 98:2)]. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.

Organic Letters published new progress about Aromatic nitrogen heterocycles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (heteroaryl halides → sec-alkyl heteroaryl compounds). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, Category: piperazines.

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

El Khatib, Mirna; Serafim, Ricardo Augusto Massarico; Molander, Gary A. published the artcile< α-Arylation/Heteroarylation of Chiral α-Aminomethyltrifluoro-borates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis>, SDS of cas: 374930-88-8, the main research area is arylation heteroarylation aminomethyltrifluoroborate iridium photoredox nickel cross coupling catalyst; amino acids; cross-coupling; heterocycles; nickel; photochemistry.

Direct access to complex, enantiopure benzylamine architectures using a synergistic iridium photoredox/nickel cross-coupling dual catalysis strategy has been developed. New C(sp3)-C(sp2) bonds are forged starting from abundant and inexpensive natural amino acids.

Angewandte Chemie, International Edition published new progress about Amino acid esters Role: RCT (Reactant), RACT (Reactant or Reagent). 374930-88-8 belongs to class piperazines, and the molecular formula is C13H19BrN4O2, SDS of cas: 374930-88-8.

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