Month: October 2022

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

In 2013,Majo, Vattoly J.; Arango, Victoria; Simpson, Norman R.; Prabhakaran, Jaya; Kassir, Suham A.; Underwood, Mark D.; Bakalian, Mihran; Canoll, Peter; John Mann, J.; Dileep Kumar, J. S. published 《Synthesis and in vitro evaluation of [18F]BMS-754807: A potential PET ligand for IGF-1R》.Bioorganic & Medicinal Chemistry Letters published the findings.Computed Properties of C5H5BrN2 The information in the text is summarized as follows:

Radiosynthesis and in vitro evaluation of [18F](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide ([18F]BMS-754807 or [18F] I) a specific IGF-1R inhibitor was performed. [18F]I demonstrated specific binding in vitro to human cancer tissues. Synthesis of reference standard II(X= F) and corresponding bromo derivative II(X = X = Br), the precursor for radiolabeling were achieved from 2,4-dichloropyrrolo[2,1-f][1,2,4]triazine in three steps with 50% overall yield. The radioproduct was obtained in 8% yield by reacting 1a with [18F]TBAF in DMSO at 170 °C at high radiochem. purity and specific activity (1-2 Ci/μmol, N = 10). The proof of concept of IGF-IR imaging with [18F]I was demonstrated by in vitro autoradiog. studies using pathol. identified surgically removed grade IV glioblastoma, breast cancer and pancreatic tumor tissues. These studies indicate that [18F]I can be a potential PET tracer for monitoring IGF-1R. In addition to this study using 6-Bromopyridin-3-amine, there are many other studies that have used 6-Bromopyridin-3-amine(cas: 13534-97-9Computed Properties of C5H5BrN2) was used in this study.

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Amines characteristically form salts with acids; a hydrogen ion, H+, adds to the nitrogen. With the strong mineral acids (e.g., H2SO4, HNO3, and HCl), the reaction is vigorous. Salt formation is instantly reversed by strong bases such as NaOH. Neutral electrophiles (compounds attracted to regions of negative charge) also react with amines; alkyl halides (R′X) and analogous alkylating agents are important examples of electrophilic reagents.Computed Properties of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Pollice, Robert; Bot, Marek; Kobylianskii, Ilia J.; Shenderovich, Ilya; Chen, Peter published 《Attenuation of London Dispersion in Dichloromethane Solutions》.Journal of the American Chemical Society published the findings.Safety of 2-Bromonicotinaldehyde The information in the text is summarized as follows:

London dispersion constitutes one of the fundamental interaction forces between atoms and between mols. While modern computational methods have been developed to describe the strength of dispersive interactions in the gas phase properly, the importance of inter- and intramol. dispersion in solution remains yet to be fully understood because exptl. data are still sparse in that regard. We herein report a detailed exptl. and computational study of the contribution of London dispersion to the bond dissociation of proton-bound dimers, both in the gas phase and in dichloromethane solution, showing that attenuation of inter- and intramol. dispersive interaction by solvent is large (about 70% in dichloromethane), but not complete, and that current state-of-the-art implicit solvent models employed in quantum-mech. computational studies treat London dispersion poorly, at least for this model system. The results came from multiple reactions, including the reaction of 2-Bromonicotinaldehyde(cas: 128071-75-0Safety of 2-Bromonicotinaldehyde)

2-Bromonicotinaldehyde(cas: 128071-75-0) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Safety of 2-Bromonicotinaldehyde

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Puttreddy, Rakesh; von Essen, Carolina; Rissanen, Kari published 《Halogen Bonds in Square Planar 2,5-Dihalopyridine-Copper(II) Bromide Complexes》.European Journal of Inorganic Chemistry published the findings.Recommanded Product: 53939-30-3 The information in the text is summarized as follows:

Halogen bonding in self-complementary 1:2 metal-ligand complexes obtained from copper(II) bromide (CuBr2) and seven 2,5-dihalopyridines were analyzed using single-crystal x-ray diffraction. All presented discrete complexes form 1D polymeric chains connected with C-X···Br-Cu halogen bonds (XB). In (2-chloro-5-X-pyridine)2·CuBr2 (X = Cl, Br, and I) only the C5-halogen and in (2-bromo-5-X-pyridine)2·CuBr2 (X = Cl, Br, and I) both C2- and C5-halogens form C-X···Br-Cu halogen bonds with the X acting as the XB donor and copper-coordinated bromide as the XB acceptor. The electron-withdrawing C2-chloride in (2-chloro-5-X-pyridine)2·CuBr2 complexes has only a minor effect on the C5-X5···Br-Cu XBs, and the X5···Br distances follow the expected order I5 < Br5 < Cl5 with RXB values of 0.91, 0.94, and 0.99, resp. In (2-bromo-5-X-pyridine)2·CuBr2 complexes, due to the polarization of both halogens, the C2-X2···Br-Cu and C5-X5···Br-Cu RXB values are very similar [0.92-0.99] as a result of the competition between C2- and C5-halogens for XB formation. In addition to the classical halogen bonds, the square-planar CuII complexes exhibit C2-X2···Cu(X = Cl and Br) contacts perpendicular to the Br-Cu-Br plane with shorter C2-Br2···Cu than C2-Cl2···Cu contacts. These interactions induce a pseudo-octahedral geometry for CuII ions. Notably, C2-X2···Br-Cu halogen bonds and the addnl. C2-X2···Cu contacts are slightly enhanced by the C5-halogen electronegativity. In the experiment, the researchers used many compounds, for example, 5-Bromo-2-chloropyridine(cas: 53939-30-3Recommanded Product: 53939-30-3)

5-Bromo-2-chloropyridine(cas: 53939-30-3) belongs to pyridine. Pyridines are often used as catalysts or reagents; particular notice has been paid recently to how pyridine coordinates to metal centers enabling a wide range of valuable reactions. Recommanded Product: 53939-30-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Dual inhibition of Kif15 by oxindole and quinazolinedione chemical probes》 were Dumas, Megan E.; Chen, Geng-Yuan; Kendrick, Nicole D.; Xu, George; Larsen, Scott A.; Jana, Somnath; Waterson, Alex G.; Bauer, Joshua A.; Hancock, William; Sulikowski, Gary A.; Ohi, Ryoma. And the article was published in Bioorganic & Medicinal Chemistry Letters in 2019. COA of Formula: C5H6BNO2 The author mentioned the following in the article:

The mitotic spindle is a microtubule-based machine that segregates a replicated set of chromosomes during cell division. Many cancer drugs alter or disrupt the microtubules that form the mitotic spindle. Microtubule-dependent mol. motors that function during mitosis are logical alternative mitotic targets for drug development. Eg5 (Kinesin-5) and Kif15 (Kinesin-12), in particular, are an attractive pair of motor proteins, as they work in concert to drive centrosome separation and promote spindle bipolarity. Furthermore, we hypothesize that the clin. failure of Eg5 inhibitors may be (in part) due to compensation by Kif15. In order to test this idea, we screened a small library of kinase inhibitors and identified GW108X, an oxindole that inhibits Kif15 in vitro. We show that GW108X has a distinct mechanism of action compared with a com. available Kif15 inhibitor, Kif15-IN-1 and may serve as a lead with which to further develop Kif15 inhibitors as clin. relevant agents. In addition to this study using 2-Pyridinylboronic acid, there are many other studies that have used 2-Pyridinylboronic acid(cas: 197958-29-5COA of Formula: C5H6BNO2) was used in this study.

2-Pyridinylboronic acid(cas: 197958-29-5) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.COA of Formula: C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Enantioconvergent Cu-Catalyzed Intramolecular C-C Coupling at Boron-Bound C(sp3) Atoms of α-Aminoalkylboronates Using a C1-Symmetrical 2,2′-Bipyridyl Ligand Attached to a Helically Chiral Macromolecular Scaffold》 was published in Journal of the American Chemical Society in 2020. These research results belong to Yoshinaga, Yukako; Yamamoto, Takeshi; Suginome, Michinori. Formula: C6H6BrN The article mentions the following:

Enantioconvergent intramol. coupling of α-(2-bromobenzoylamino)benzylboronic esters was achieved using a copper catalyst having helically chiral macromol. bipyridyl ligand, PQXbpy. Racemic α-(2-bromobenzoylamino)benzylboronic esters were converted into (R)-configured 3-arylisoindolinones with high enantiopurity using right-handed helical PQXbpy as a chiral ligand in a toluene/CHCl3 mixed solvent. When enantiopure (R)- and (S)-configured boronates were sep. reacted under the same reaction conditions, both afforded (R)-configured products through formal stereoinvertive and stereoretentive processes, resp. From these results, a mechanism involving deracemization of organocopper intermediates in the presence of PQXbpy is assumed. PQXbpy switched its helical sense to left-handed when a toluene/1,1,2-trichloroethane mixed solvent was used, resulting in the formation of the corresponding (S)-products from the racemic starting material. In the part of experimental materials, we found many familiar compounds, such as 2-Bromo-5-methylpyridine(cas: 3510-66-5Formula: C6H6BrN)

2-Bromo-5-methylpyridine(cas: 3510-66-5) belongs to pyridine. In industry and in the lab, pyridine is used as a reaction solvent, particularly when its basicity is useful, and as a starting material for synthesizing some herbicides, fungicides, and antiseptics.Formula: C6H6BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Bispicolyamine-based supramolecular polymeric gels induced by distinct different driving forces with and without Zn2+》 was published in International Journal of Molecular Sciences in 2020. These research results belong to Park, Jaehyeon; Kim, Ka Young; Kang, Seok Gyu; Lee, Shim Sung; Lee, Ji Ha; Jung, Jong Hwa. Application In Synthesis of Bis(pyridin-2-ylmethyl)amine The article mentions the following:

Metal-coordination polymeric gels are interesting areas as organic/inorganic hybrid supramol. materials. The bispicolylamine (BPA) based gelator (1) showed excellent gelation with typical fibrillar morphol. in acetonitrile. Upon complexing 1 with Zn2+, complexes ([1 + Zn + ACN]2+ and [1 + zinc trifluoromethanesulfonate (ZnOTf)]+) with four coordination numbers were formed, which determine the gel structure significantly. A gel-sol transition was induced, driven by the ratio of the two metal complexes produced. Through NMR anal., the driving forces in the gel formation (i.e., hydrogen-bonding and π-π stacking) were observed in detail. In the absence and the presence of Zn2+, the intermol. hydrogen-bonds and π-π stacking were the primary driving forces in the gel formation, resp. In addition, the supramol. gels exhibited a monolayer lamellar structure irresp. of Zn2+. Conclusively, the gels’ elasticity and viscosity reduced in the presence of Zn2+. The experimental part of the paper was very detailed, including the reaction process of Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Application In Synthesis of Bis(pyridin-2-ylmethyl)amine)

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. As a tridentate ligand this compound provides three nitrogen donors that affords good selectivity for Zn2+ over biologically relevant metals such as Na+, K+, Mg2+ and Ca2+, and leaves coordination sites free for anion binding. Application In Synthesis of Bis(pyridin-2-ylmethyl)amine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Comparative biological evaluation and G-quadruplex interaction studies of two new families of organometallic gold(I) complexes featuring N-heterocyclic carbene and alkynyl ligands》 was written by Meier-Menches, Samuel M.; Aikman, Brech; Dollerer, Daniel; Klooster, Wim T.; Coles, Simon J.; Santi, Nicolo; Luk, Louis; Casini, Angela; Bonsignore, Riccardo. Recommanded Product: 2510-22-7 And the article was included in Journal of Inorganic Biochemistry in 2020. The article conveys some information:

Exptl. organometallic gold(I) compounds hold promise for anticancer therapy. This study reports the synthesis of two novel families of gold(I) complexes, including N1-substituted bis-N-heterocyclic carbene (NHC) complexes of general formula [Au(N1-TBM)2]BF4 (N1-TBM = N1-substituted 9-methyltheobromin-8-ylidene) and mixed gold(I) NHC-alkynyl complexes, [Au(N1-TBM)alkynyl]. The compounds were fully characterized for their structure and stability in aqueous environment and in the presence of N-acetyl cysteine by NMR spectroscopy. The structures of bis(1-ethyl-3,7,9-trimethylxanthin-8-ylidene)gold(I), (4-ethynylpyridine)(1,9-dimethyltheobromine-8-ylidene)gold(I) and of (2,8-Diethyl-10-(4-ethynylphenyl)-5,5-difluoro-1,3,7,9-tetramethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2′,1′-f][1,3,2]diazaborinine)(1,3,7,9-tetramethylxanthin-8-ylidene)gold(I) were also confirmed by X-ray diffraction anal. The compounds were studied for their properties as DNA G-quadruplex (G4 s) stabilizers by fluorescence resonance energy transfer (FRET) DNA melting. Only the cationic [Au(N1-TBM)2]BF4 family showed moderate G4 stabilization properties with respect to the previously reported benchmark compound [Au(9-methylcaffein-8-ylidene)2]+ (AuTMX2). However, the compounds also showed marked selectivity for binding to G4 structures with respect to duplex DNA in competition experiments For selected complexes, the interactions with G4 s were also confirmed by CD (CD) studies. Furthermore, the gold(I) complexes were assessed for their antiproliferative effects in human cancer cells in vitro, displaying moderate activity. Of note, among the mixed gold(I) NHC-alkynyl compounds, one features a fluorescent boron-dipyrromethene (BODIPY) moiety which allowed determining its uptake into the cytoplasm of cancer cells by fluorescence microscopy. In the experimental materials used by the author, we found 4-Ethynylpyridine(cas: 2510-22-7Recommanded Product: 2510-22-7)

4-Ethynylpyridine(cas: 2510-22-7) belongs to pyridine. Pyridine is very deactivated towards electrophilic substitution with respect to benzene. For this reason classical formylation, using methods such as the Gattermann or Vilsmeier reactions, are not generally successful. Recommanded Product: 2510-22-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Enantioselective C-H Lactonization of Unactivated Methylenes Directed by Carboxylic Acids》 was written by Cianfanelli, Marco; Olivo, Giorgio; Milan, Michela; Klein Gebbink, Robertus J. M.; Ribas, Xavi; Bietti, Massimo; Costas, Miquel. HPLC of Formula: 624-28-2 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

The formidable challenges of controlling site-selectivity, enantioselectivity, and product chemoselectivity make asym. C-H oxidation a generally unsolved problem for nonenzymic systems. Discrimination between the two enantiotopic C-H bonds of an unactivated methylenic group is particularly demanding and so far unprecedented, given the similarity between their environments and the facile overoxidn. of the initially formed hydroxylation product. Here we show that a Mn-catalyzed C-H oxidation directed by carboxylic acids can overcome these challenges to yield γ-lactones in high enantiomeric excess (up to 99%) using hydrogen peroxide as oxidant and a Bronsted acid additive under mild conditions and short reaction times. Coordination of the carboxylic acid group to the bulky Mn complex ensures the rigidity needed for high enantioselectivity and dictates the outstanding γ site-selectivity. When the substrate contains nonequivalent γ-methylenes, the site-selectivity for lactonization can be rationally predicted on the basis of simple C-H activation/deactivation effects exerted by proximal substituents. In addition, discrimination of diastereotopic C-H bonds can be modulated by catalyst design, with no erosion of enantiomeric excess. The potential of this reaction is illustrated in the concise synthesis of a tetrahydroxylated bicyclo[3.3.1]nonane enabled by two key, sequential γ-C-H lactonizations, with the latter that fixes the chirality of five stereogenic centers in one step with 96% ee. In the part of experimental materials, we found many familiar compounds, such as 2,5-Dibromopyridine(cas: 624-28-2HPLC of Formula: 624-28-2)

2,5-Dibromopyridine(cas: 624-28-2) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.HPLC of Formula: 624-28-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Development and validation of a mass spectrometry binding assay for mGlu5 receptor》 was written by Ricart-Ortega, Maria; Berizzi, Alice E.; Catena, Juanlo; Malhaire, Fanny; Munoz, Lourdes; Serra, Carmen; Lebon, Guillaume; Goudet, Cyril; Llebaria, Amadeu. Name: 2,6-Dibromopyridine And the article was included in Analytical and Bioanalytical Chemistry in 2020. The article conveys some information:

Abstract: Mass spectrometry (MS) binding assays are a label-free alternative to radioligand or fluorescence binding assays, so the readout is based on direct mass spectrometric detection of the test ligand. The study presented here describes the development and validation of a highly sensitive, rapid, and robust MS binding assay for the quantification of the binding of the metabotropic glutamate 5 (mGlu5) neg. allosteric modulator (NAM), MPEP (2-methyl-6-phenylethynylpyridine) at the mGlu5 allosteric binding site. The LC-ESI-MS/MS (liquid chromatog.-electrospray ionization-tandem mass spectrometric) anal. method was established and validated with a deuterated analog of MPEP as an internal standard The developed MS binding assay described here allowed for the determination of MS binding affinity estimates that were in agreement with affinity estimates obtained from a tritiated MPEP radioligand saturation binding assay, indicating the suitability of this methodol. for determining affinity estimates for compounds that target mGlu5 allosteric binding sites. In the experimental materials used by the author, we found 2,6-Dibromopyridine(cas: 626-05-1Name: 2,6-Dibromopyridine)

2,6-Dibromopyridine(cas: 626-05-1) belongs to pyridine. Pyridine is a relatively complex molecule and exhibits a number of different bands in IR spectra. Among others, the bands characterizing the ν8a and ν19b modes have been found to be sensitive to the coordination or protonation of the molecule. Note that the band that is diagnostic for the PyH+ ion at about 1545 cm− 1 (ν19b mode) does not overlap with any of the other bands.Name: 2,6-Dibromopyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem