Tag: 200-300

Liegeois, Jean Francois F.; Bruhwyler, Jacques; Damas, Jacques; Nguyen, Thuy Phuong; Chleide, Eric M. G.; Mercier, Michel G. A.; Rogister, Francoise A.; Delarge, Jacques E. published an article in Journal of Medicinal Chemistry. The title of the article was 《New pyridobenzodiazepine derivatives as potential antipsychotics: synthesis and neurochemical study》.Synthetic Route of C12H8ClN3O3 The author mentioned the following in the article:

The discovery of a new, safe, atypical antipsychotic remains an important challenge. To achieve this goal, a series of N-methylpiperazinopyrido[2,3-b][1,4]- and -[1,5]- and -pyrido[4,3-b][1,4]- and -[1,5]-benzodiazepines I (A = Y = N, B = CH, R1 = H, 8-, 9-Cl, 8-F, 8-Me, R2 = H, 3-Me, R3 = H, Me, CHO, X = C-NMP, NMP = N-methylpiperazino; A = X = N, B = CH, R1 = R2 = H, R3 = H, CHO, Y = C-NMP; A = CH, B = Y = N, R1 = R2 = R3 = H, X = C-NMP; A = CH, B = X = N, R1 = R2 = H, R3 = H, CHO) were synthesized. Thus, (chloropyridinyl)aminobenzamides II (R1 = H, 8-, 9-Cl, 8-F, 8-Me, R2 = H, Me) cyclized and were condensed with N-methylpiperazine to give I. The dopaminergic (D1, D2), serotonergic (5-HT2), and cholinergic (M) affinities, frequently remarked in the action mechanisms of antipsychotic drugs, were determined using their resp. in vitro receptor binding assays. All affinities were reduced for each compound Optimal substituents were found to be in the 2- or 8-position for the retention of affinities, while substitution at the 5-position by acyl or alkyl groups dramatically diminished binding affinities. Pyridobenzodiazepine derivatives, such as clozapine, were found to be inactive or only weakly effective against apomorphine-mediated stereotypes in rats. In an original and complex behavioral model developed in dogs and successfully used to differentiate distinct classes of psychotropic drugs and to discriminate between typical and atypical neuroleptic drugs, I (A = N, B = CH, R1 = 8-Cl, 8-Me, R2 = R3 = H, X = C-NMP, Y = N; A = N, B = CH, R1 = R2 = R3 = H, X = N, Y = C-NMP) showed most of the behavioral characteristics previously described for neuroleptics. Their neurochem. profiles, particularly their 5-HT2/D2 pKi ratios, were compatible with an atypical antipsychotic effect. In the experiment, the researchers used N-(2-Chloropyridin-3-yl)-2-nitrobenzamide(cas: 1028-86-0Synthetic Route of C12H8ClN3O3)

N-(2-Chloropyridin-3-yl)-2-nitrobenzamide(cas: 1028-86-0) belongs to anime. Many important products require amines as part of their syntheses. Methylamine is utilized in the production of the analgesic meperidine (trade name Demerol) and the photographic developer Metol (trademark), and dimethylamine is used in the synthesis of the antihistamine diphenhydramine (trade name Benadryl), the solvent dimethylformamide (DMF), and the rocket propellant 1,1-dimethylhydrazine. The synthesis of the insect repellent N,N-diethyl-m-toluamide (DEET) incorporates diethylamine while that of the synthetic fibre Kevlar requires aromatic amines.Synthetic Route of C12H8ClN3O3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

HPLC of Formula: 138219-98-4On March 6, 2007, Karthikeyan, C. S.; Peter, Katja; Wietasch, Helga; Thelakkat, Mukundan published an article in Solar Energy Materials & Solar Cells. The article was 《Highly efficient solid-state dye-sensitized TiO2 solar cells via control of retardation of recombination using novel donor-antenna dyes》. The article mentions the following:

Two series of heteroleptic tris(bipyridyl)Ru(II) and bis(bipyridyl)(NCS)2Ru(II) complexes have been synthesized and characterized. This is a part of a new concept of covalent linkage of donor-antenna groups, e.g., triphenylamine or N,N’-bis(phenyl)-N,N’-bis(3-methylphenyl)-1,1′-biphenyl-4,4′-diamine (TPD) to Ru(II) dye center. For the covalent attachment of donor units, a multi-step synthesis was carried out starting from 4,4′-dimethyl-2,2′-bipyridine followed by chlorination and Wittig reaction with donor aldehydes. This was followed either by a metalation reaction using bis(4,4′-dicarboxy-2,2′-bipyridyl)Ru(II)dichloride (bpy(COOH)2Ru(II)2Cl2 2H2O) as precursor to get tris(bipyridyl) dyes or by a one pot synthesis starting from dichloro(p-cymene)Ru(II) dimer resulting in bis(bipyridyl)(NCS)2 dyes. The complexes (bpy(COOH)2)2(bpyMe2)Ru(II) 2PF6 and (bpy(COOH)2)(bpyMe2)(NCS)2Ru(II) without donor-antenna groups were also prepared to study and compare the properties. The influence of donor-antenna groups in these complexes was studied using UV-Vis spectroscopy and cyclic voltammetry. The heteroleptic complexes carrying donor groups show appreciably broad absorption ranges and extraordinarily high extinction coefficients These high extinction coefficients are explained as due to the extended delocalization of π-electrons in the donor-antenna ligands. The HOMO/LUMO energy values obtained from cyclic voltammetry support the multi-step charge transfer cascade possible in these donor-antenna dyes. Examples of solid-state dye-sensitized solar cell utilizing these novel donor-antenna dyes revealed spectacular performances of power conversion efficiencies of up to 3.4%, for the dye carrying a TPD donor group as measured under AM 1.5 spectral conditions. This is attributed to highly efficient light harvesting of these novel dyes and the improved charge transfer dynamics at TiO2-dye and dye-hole conductor interfaces. The experimental part of the paper was very detailed, including the reaction process of 4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4HPLC of Formula: 138219-98-4)

4,4′-Bis(chloromethyl)-2,2′-bipyridine(cas: 138219-98-4) belongs to pyridine derivatives. Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals. HPLC of Formula: 138219-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Reference of 2,5-DibromopyridineIn 2020 ,《Exploration of the Solid-State Sorption Properties of Shape-Persistent Macrocyclic Nanocarbons as Bulk Materials and Small Aggregates》 was published in Journal of the American Chemical Society. The article was written by Schaub, Tobias A.; Prantl, Ephraim A.; Kohn, Julia; Bursch, Markus; Marshall, Checkers R.; Leonhardt, Erik J.; Lovell, Terri C.; Zakharov, Lev N.; Brozek, Carl K.; Waldvogel, Siegfried R.; Grimme, Stefan; Jasti, Ramesh. The article contains the following contents:

Porous mol. materials combine benefits such as convenient processability and the possibility for atom-precise structural fine-tuning which makes them remarkable candidates for specialty applications in the areas of gas separation, catalysis, and sensing. In order to realize the full potential of these materials and guide future mol. design, knowledge of the transition from mol. properties into materials behavior is essential. In this work, the class of compounds termed cycloparaphenylenes (CPPs)-shape-persistent macrocycles with built-in cavities and radially oriented π-systems-was selected as a conceptually simple class of intrinsically porous nanocarbons to serve as a platform for studying the transition from analyte sorption properties of small aggregates to those of bulk materials. In our detailed investigation, two series of CPPs were probed: previously reported hoop-shaped [n]CPPs and a novel family of all-phenylene figure-8 shaped (lemniscal) bismacrocycles, termed spiro[n,n]CPPs. A series of nanocarbons with different macrocycle sizes and heteroatom content have been prepared by atom-precise organic synthetic methods, and their structural, photophys., and electronic attributes were disclosed. Detailed exptl. studies (X-ray crystallog., gas sorption, and quartz-crystal microbalance measurements) and quantum chem. calculations provided ample evidence for the importance of the solid-state arrangement on the porosity and analyte uptake ability of intrinsically porous mol. nanocarbons. We demonstrate that this mol. design principle, i.e., incorporation of sterically demanding spiro junctions into the backbone of nanohoops, enables the manipulation of solid-state morphol. without significantly changing the nature and size of the macrocyclic cavities. As a result, the novel spiro[n,n]CPPs showed a remarkable performance as high affinity material for vapor analyte sensing. The experimental process involved the reaction of 2,5-Dibromopyridine(cas: 624-28-2Reference of 2,5-Dibromopyridine)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Reference of 2,5-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Application of 29682-15-3In 2008 ,《Design, synthesis, and biological evaluation of 8-biarylquinolines: A novel class of PDE4 inhibitors》 appeared in Bioorganic & Medicinal Chemistry Letters. The author of the article were Gallant, Michel; Chauret, Nathalie; Claveau, David; Day, Stephen; Deschenes, Denis; Dube, Daniel; Huang, Zheng; Lacombe, Patrick; Laliberte, France; Levesque, Jean-Francois; Liu, Susana; Macdonald, Dwight; Mancini, Joseph; Masson, Paul; Mastracchio, Anthony; Nicholson, Donald; Nicoll-Griffith, Deborah A.; Perrier, Helene; Salem, Myriam; Styhler, Angela; Young, Robert N.; Girard, Yves. The article conveys some information:

The structure-activity relationship of a novel series of 8-biarylquinolines, e.g., I, acting as type 4 phosphodiesterase (PDE4) inhibitors is described herein. Prototypical compounds from this series are potent and non-selective inhibitors of the four distinct PDE4 (IC50 < 10 nM) isoenzymes (A-D). In a human whole blood in vitro assay, they inhibit (IC50 < 0.5 μM) the LPS-induced release of the cytokine TNF-α. Optimized inhibitors were evaluated in vivo for efficacy in an ovalbumin-induced bronchoconstriction model in conscious guinea pigs. Their propensity to produce an emetic response was evaluated by performing pharmacokinetic studies in squirrel monkeys. This work has led to the identification of several compounds with excellent in vitro and in vivo profiles, including a good therapeutic window of efficacy over emesis. In the part of experimental materials, we found many familiar compounds, such as Methyl 5-bromopicolinate(cas: 29682-15-3Application of 29682-15-3)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine and pyridine-derived structures are privileged pharmacophores in medicinal chemistry and an essential functionality for organic chemists. As the prototypical π-deficient heterocycle, pyridine illustrates distinctive chemistry as both substrate and reagent. Application of 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

COA of Formula: C7H4F3NO3On November 30, 2010 ,《A General Approach to (Trifluoromethoxy)pyridines: first X-ray Structure Determinations and Quantum Chemistry Studies》 appeared in European Journal of Organic Chemistry. The author of the article were Manteau, Baptiste; Genix, Pierre; Brelot, Lydia; Vors, Jean-Pierre; Pazenok, Sergiy; Giornal, Florence; Leuenberger, Charlotte; Leroux, Frederic R.. The article conveys some information:

The previously unknown 2-, 3-, and 4-(trifluoromethoxy)pyridines have now become readily accessible by means of an efficient and straightforward large-scale synthesis. Their regioselective functionalization by organometallic methods has been studied and has afforded new and highly important building blocks for life-sciences-oriented research. In addition, the first X-ray crystallog. structure determinations of (trifluoromethoxy)pyridines have been performed. Lowest-energy conformations of (trifluoromethoxy)pyridines and (trifluoromethoxy)pyridinium cations were determined by in silico studies.3-(Trifluoromethoxy)picolinic acid(cas: 1221171-81-8COA of Formula: C7H4F3NO3) was used in this study.

3-(Trifluoromethoxy)picolinic acid(cas: 1221171-81-8) belongs to pyridine. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. As ligands, solvents, and catalysts they facilitate reactions; thus descriptions of these new ligands and their applications abound each year.COA of Formula: C7H4F3NO3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Zinc(II) Complexes of N,N-Di(2-picolyl)hydrazones》 was written by Barsoum, David N.; Kyeremeh-Mensah, Lawrence; Meisner, Quinton J.; Clark, Ronald J.; Masson, Eric; Zhu, Lei. Quality Control of 2-(Bromomethyl)pyridine hydrobromideThis research focused onzinc dipicolylhydrazone complex preparation NMR spectra crystal structure. The article conveys some information:

The authors report on N,N-di(2-picolyl)hydrazone (DPH) ligands that are capable of binding metal ions in two isomeric forms depending on the nature of the hydrazone substituent. When the hydrazone substituent is not coordinating, the metal ion prefers the N,N-di(2-picolyl)amino (DPA) site, which is a known tridentate ligand that anchors on the sp3-hybridized amino nitrogen atom. When the hydrazone substituent is coordinating, the metal ion instead anchors on the sp2-hybridized imino nitrogen atom to afford a different structural isomer. Zinc(II) was used as a representative transition-metal ion for characterizing the coordination chem. of DPH in both solution and solid states, to form [Zn(L)Cl2], [Zn(L)2](ClO4)2 and [Zn(L)](ClO4)2. The experimental part of the paper was very detailed, including the reaction process of 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Quality Control of 2-(Bromomethyl)pyridine hydrobromide)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Quality Control of 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Progressive structural modification to a zinc-actuated photoinduced electron transfer (PeT) switch in the context of intracellular zinc imaging》 was written by Macias-Contreras, Miguel; Daykin, Kirsten L.; Simmons, J. Tyler; Allen, John R.; Hooper, Zachary S.; Davidson, Michael W.; Zhu, Lei. Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromideThis research focused onzinc actuated photoinduced electron transfer switch intracellular imaging. The article conveys some information:

Photoinduced electron transfer (PeT)-type fluorescent mol. switches are often applied in ion-selective sensors. Zinc-targeting sensors that contain an anilino-based electron donor (aka, the PeT ‘switch’) have multiple advantages over those with an aliphatic amino switch. In addition to the lower pKa value of an aniline than that of a comparably substituted aliphatic amine, which reduces the interference of pH on the spectral properties of the attached fluorophore, the oxidation potentials of anilino groups are lower than those of aliphatic amino counterparts, which make them better electron donors in PeT. The effectiveness of anilino as a PeT switch is evaluated in a series of zinc-sensitive sensors that contain different fluorophores, zinc-binding ligands, and alkyl linkers between ligand and fluorophore. The abilities of these compounds to distinguish high and low intracellular zinc concentrations in living cells are demonstrated. In addition to this study using 2-(Bromomethyl)pyridine hydrobromide, there are many other studies that have used 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide) was used in this study.

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) belongs to pyridine. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Additionally, pyridine-based natural products continue to be discovered and studied for their properties and to understand their biosynthesis.Application In Synthesis of 2-(Bromomethyl)pyridine hydrobromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Formula: C7H6BrNO2In 2019 ,《Design, biological evaluation and X-ray crystallography of nanomolar multifunctional ligands targeting simultaneously acetylcholinesterase and glycogen synthase kinase-3》 was published in European Journal of Medicinal Chemistry. The article was written by Oukoloff, Killian; Coquelle, Nicolas; Bartolini, Manuela; Naldi, Marina; Le Guevel, Remy; Bach, Stephane; Josselin, Beatrice; Ruchaud, Sandrine; Catto, Marco; Pisani, Leonardo; Denora, Nunzio; Iacobazzi, Rosa Maria; Silman, Israel; Sussman, Joel L.; Buron, Frederic; Colletier, Jacques-Philippe; Jean, Ludovic; Routier, Sylvain; Renard, Pierre-Yves. The article contains the following contents:

Two scaffolds, targeting AChE (tacrine) and GSK-3α/β (valmerin) simultaneously, were assembled, using copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), to generate a new series of multifunctional ligands. A series of eight multi-target directed ligands (MTDLs) was synthesized and evaluated in-vitro and in cell cultures. Mol. docking studies, together with the crystal structures of three MTDL/TcAChE complexes, with three tacrine-valmerin hybrids allowed designing an appropriate linker containing a 1,2,3-triazole moiety whose incorporation preserved and even increased, the original inhibitory potencies of the two selected pharmacophores toward the two targets. Most of the new derivatives exhibited nanomolar affinity for both targets and the most potent compound of the series displayed inhibitory potencies of 9.5 nM for human acetylcholinesterase (hAChE) and 7 nM for GSK-3α/β. These novel dual MTDLs was served as suitable leads for further development, since, in the micromolar range, they exhibited low cytotoxicity on a panel of representative human cell lines including the human neuroblastoma cell line SH-SY5Y. Moreover, these tacrine-valmerin hybrids displayed a good ability to penetrate the blood-brain barrier (BBB) without interacting with efflux pumps such as P-gp. In the experimental materials used by the author, we found Methyl 5-bromopicolinate(cas: 29682-15-3Formula: C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridines, quinolines, and isoquinolines have found a function in almost all aspects of organic chemistry. Pyridine has found use as a solvent, base, ligand, functional group, and molecular scaffold. As structural elements, these moieties are potent electron-deficient groups, metal-directing functionalities, fluorophores, and medicinally important pharmacophores. Formula: C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C7H6BrNO2In 2014 ,《Synthesis and Late-Stage Functionalization of Complex Molecules through C-H Fluorination and Nucleophilic Aromatic Substitution》 appeared in Journal of the American Chemical Society. The author of the article were Fier, Patrick S.; Hartwig, John F.. The article conveys some information:

The authors report the late-stage functionalization of multisubstituted pyridines and diazines at the position α to nitrogen. By this process, functional groups and substituents bound to the ring through nitrogen, oxygen, sulfur, or carbon are installed. This functionalization is accomplished by a combination of fluorination and nucleophilic aromatic substitution of the installed fluoride. A diverse array of functionalities can be installed because of the mild reaction conditions revealed for nucleophilic aromatic substitutions (SNAr) of the 2-fluoroheteroarenes. An evaluation of the rates for substitution vs. the rates for competitive processes provides a framework for planning this functionalization sequence. This process is illustrated by the modification of medicinally important compounds, as well as the increase in efficiency of synthesis of several existing pharmaceuticals. After reading the article, we found that the author used Methyl 5-bromopicolinate(cas: 29682-15-3Synthetic Route of C7H6BrNO2)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. The basicity and metallophilic high donor number of these π-deficient systems has long favored them as ligands in metal catalysis. The last decade saw pyridine assume a stronger role as functional group for directed C–H oxidation/activation.Synthetic Route of C7H6BrNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

HPLC of Formula: 29682-15-3In 2010 ,《Towards the synthesis of substituted porphyrins with a pyridyl group bearing a reactive functionality》 appeared in Journal of Porphyrins and Phthalocyanines. The author of the article were El Ojaimi, Maya; Habermeyer, Benoit; Gros, Claude P.; Barbe, Jean-Michel. The article conveys some information:

Pyridyl-substituted porphyrins bearing a reactive functionality were prepared via Suzuki cross-coupling reactions and resulted in very good yields. These compounds are precursors of new porphyrin architectures able to coordinate two metals: one in the porphyrin core and the second around the pyridyl moiety. During the coupling reactions, a higher reactivity of a chloro picolyl group was evidenced compared to a bromo function on the same reacting mol. In the experiment, the researchers used Methyl 5-bromopicolinate(cas: 29682-15-3HPLC of Formula: 29682-15-3)

Methyl 5-bromopicolinate(cas: 29682-15-3) belongs to pyridine. Pyridine derivatives lend themselves to many roles in the spirited field of supramolecular chemistry – whether as the ligand backbone of metal-organic polymers or presiding over the key electronic stations of nanodevices. In biochemistry, pyridine-containing cofactors are necessary nutrients on which our lives depend. HPLC of Formula: 29682-15-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem