Month: October 2022

In 2013,Guan, Ai-Ying; Liu, Chang-Ling; Huang, Guang; Li, Hui-Chao; Hao, Shu-Lin; Xu, Ying; Li, Zhi-Nian published 《Design, Synthesis, and Structure-Activity Relationship of Novel Aniline Derivatives of Chlorothalonil》.Journal of Agricultural and Food Chemistry published the findings.Computed Properties of C5H5BrN2 The information in the text is summarized as follows:

Chlorothalonil with both low cost and low toxicity is a popularly used fungicide in the agrochem. field. The presence of nucleophilic groups on this compound allows further chem. modifications to obtain novel chlorothalonil derivatives Fluazinam, another com. available agent with a broad fungicidal spectrum, has a scaffold of diaryl amine structure. To mimic this backbone structure, a variety of (un)-substituted Ph amines was used as nucleophilic agents to react with chlorothalonil to obtain compounds with a di-Ph amine structure. Via an elegant design, two leads, 2,4,5-trichloro-6-(2,4-dichlorophenylamino)-isophthalonitrile and 2,4,5-trichloro-6-(2,4,6-trichlorophenylamino)-isophthalonitrile, with potential fungicidal activity were discovered after a preliminary bioassay screen. These two leads were further modified to obtain final products by replacing the chlorine groups in the Ph ring in Ph amine with other functional groups. These functional groups with various electronic properties and spatial characteristics were considered to explore the relationship between structure and fungicidal activity. The results indicate that the electron-withdrawing group NO2 on the 4 position on the right Ph ring plays a unique role on enhancing the fungicidal activity. The compounds were identified by proton NMR and elemental anal. Bioassays demonstrated that some of the title compounds exhibited excellent fungicidal activities against cucumber downy mildew at 25 mg/L. 2,4,5-Trichloro-6-(2-chloro-4-nitrophenylamino)isophthalonitrile has been shown as the optimal structure with 85% control against cucumber downy mildew at 6.25 mg/L concentration The relationship between structure and fungicidal activity is reported. The present work demonstrates that chlorothalonil derivatives can be used as possible lead compounds for developing novel fungicides. In the experiment, the researchers used 6-Bromopyridin-3-amine(cas: 13534-97-9Computed Properties of C5H5BrN2)

6-Bromopyridin-3-amine(cas: 13534-97-9) belongs to anime. Hydrogen peroxide (H2O2) and peroxy acids generally add an oxygen atom to the nitrogen of amines. With primary amines, this step is normally followed by further oxidation, leading to nitroso compounds, RNO, or nitro compounds, RNO2. Secondary amines are converted to hydroxylamines, R2NOH, and tertiary amines to amine oxides, R3NO.Computed Properties of C5H5BrN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2017,Nicolaou, K. C.; Rhoades, Derek; Wang, Yanping; Bai, Ruoli; Hamel, Ernest; Aujay, Monette; Sandoval, Joseph; Gavrilyuk, Julia published 《12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents》.Journal of the American Chemical Society published the findings.Product Details of 31106-82-8 The information in the text is summarized as follows:

The synthesis and biol. evaluation of a series of 12,13-aziridinyl epothilone B analogs is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic Me ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif was achieved by application of the Ess-Kurti-Falck aziridination, while the heterocyclic side chains were introduced via stereoselective phosphonate-based olefinations. In order to ensure high (E) selectivities for the latter reaction for electron-rich heterocycles, it became necessary to develop and apply an unprecedented modification of the venerable Horner-Wadsworth-Emmons reaction, employing 2-fluoroethoxyphosphonates that may prove to be of general value in organic synthesis. These studies resulted in the discovery of some of the most potent epothilones reported to date. Equipped with functional groups to accommodate modern drug delivery technologies, some of these compounds exhibited picomolar potencies that qualify them as payloads for antibody drug conjugates (ADCs), while a number of them revealed impressive activities against drug resistant human cancer cells, making them desirable for potential medical applications. In the experiment, the researchers used 2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8Product Details of 31106-82-8)

2-(Bromomethyl)pyridine hydrobromide(cas: 31106-82-8) 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. Product Details of 31106-82-8

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In 2018,Smith, Kevin B.; Huang, Yuan; Brown, M. Kevin published 《Copper-Catalyzed Heteroarylboration of 1,3-Dienes with 3-Bromopyridines: A cine Substitution》.Angewandte Chemie, International Edition published the findings.Electric Literature of C5H3BrClN The information in the text is summarized as follows:

A method for the heteroarylboration of 1,3-dienes is presented. The process involves an unusual cine substitution of 3-bromopyridine derivatives to deliver highly functionalized heterocyclic products. Mechanistic studies are included that clarify the details of this unusual process. The experimental part of the paper was very detailed, including the reaction process of 5-Bromo-2-chloropyridine(cas: 53939-30-3Electric Literature of C5H3BrClN)

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. Electric Literature of C5H3BrClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The author of 《Phosphine-NHC Manganese Hydrogenation Catalyst Exhibiting a Non-Classical Metal-Ligand Cooperative H2 Activation Mode》 were Buhaibeh, Ruqaya; Filippov, Oleg A.; Bruneau-Voisine, Antoine; Willot, Jeremy; Duhayon, Carine; Valyaev, Dmitry A.; Lugan, Noel; Canac, Yves; Sortais, Jean-Baptiste. And the article was published in Angewandte Chemie, International Edition in 2019. Name: 4-Acetylpyridine The author mentioned the following in the article:

Deprotonation of the MnI NHC-phosphine complex fac-[MnBr(CO)3(κ2P,C-Ph2PCH2NHC)] (2, II) under a H2 atmosphere readily gives the hydride fac-[MnH(CO)3(κ2P,C-Ph2PCH2NHC)] (3, III) via the intermediacy of the highly reactive 18-e NHC-phosphinomethanide complex fac-[Mn(CO)3(κ3P,C,C-Ph2PCHNHC)] (6a, VI). DFT calculations revealed that the preferred reaction mechanism involves the unsaturated 16-e mangana-substituted phosphonium ylide complex fac-[Mn(CO)3(κ2P,C-Ph2P=CHNHC)] (6 b) as key intermediate able to activate H2 via a non-classical mode of metal-ligand cooperation implying a formal λ5-P-λ3-P phosphorus valence change. Complex 2 is shown to be one of the most efficient pre-catalysts for ketone hydrogenation in the MnI series reported to date (TON up to 6200). In addition to this study using 4-Acetylpyridine, there are many other studies that have used 4-Acetylpyridine(cas: 1122-54-9Name: 4-Acetylpyridine) was used in this study.

4-Acetylpyridine(cas: 1122-54-9) 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: 4-Acetylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

《Synthesis and characterization of new polyoctahedral silsesquioxanes containing zinc coordination compounds on the surface》 was written by Gomes, Marco Antonio G. B.; Pessanha, Quezia S. J.; Toledo, Rosane; Lube, Leonardo M.; Fernandes, Christiane; Horn, Adolfo Jr.. Electric Literature of C12H13N3 And the article was included in Journal of Molecular Structure in 2020. The article conveys some information:

The present work reports the synthesis and characterization of six new inorganic-organic hybrid materials containing Si8O12 (T8) or Si7O11H (T7) core built on polyoctahedral silsesquioxanes (POSS) backbone. To these units, tri-, penta- and hexadentate ligands containing N3, N4O and N5O coordinating sites were attached by reacting 3-(glycidyloxypropyl)trimethoxysilane (GPTMS) with primary/secondary amines followed self-condensation reaction, in basic medium. To prove that the ligands attached to the silicate backbone can bind metal ions, the materials were complexed with Zn(II) ions. The functionalized POSSs containing the ligands with N4O and N5O coordinating sites reacted with Zn(II) at 1:1 stoichiometric ratio. However, the reaction between the POSS containing the N3 ligand resulted in a stoichiometric ratio metal:ligand of 1:2. IR spectroscopy revealed the formation of siloxane cores. This feature was further confirmed by 29Si NMR, which is dominated by a signal around -67 ppm, typical of T3 sites. In addition to this study using Bis(pyridin-2-ylmethyl)amine, there are many other studies that have used Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Electric Literature of C12H13N3) was used in this study.

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. Electric Literature of C12H13N3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Matsuoka, Keitaro; Komami, Narumi; Kojima, Masahiro; Mita, Tsuyoshi; Suzuki, Kimichi; Maeda, Satoshi; Yoshino, Tatsuhiko; Matsunaga, Shigeki published their research in Journal of the American Chemical Society in 2021. The article was titled 《Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)》.Formula: C7H9NO The article contains the following contents:

Herein chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes was reported using iodine tris(trifluoroacetate). The reaction proceeded smoothly under mild conditions (-50°C to room temperature) and tolerated various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcs. NMR experiments and d. functional theory calculations on the reaction indicated that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enabled the use of unactivated tetraalkylsilanes as highly stable synthetic precursors. In the part of experimental materials, we found many familiar compounds, such as 2-(2-Hydroxyethyl)pyridine(cas: 103-74-2Formula: C7H9NO)

2-(2-Hydroxyethyl)pyridine(cas: 103-74-2) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Formula: C7H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Olson, Kirk L.; Holt, Melissa C.; Ciske, Fred L.; Kramer, James B.; Heiple, Paige E.; Collins, Margaret L.; Johnson, Carrie M.; Ho, Chi S.; Morano, M. Ines; Barrett, Stephen D. published their research in Bioorganic & Medicinal Chemistry Letters in 2021. The article was titled 《Novel amide and imidazole compounds as potent hematopoietic prostaglandin D2 synthase inhibitors》.Formula: C5H6BNO2 The article contains the following contents:

In seeking novel and potent small mol. hematopoietic prostaglandin D2 synthase (H-PGDS) inhibitors as potential therapies for PGD2-mediated diseases and conditions, we explored a series comprising multiple aryl/heteroaryl rings attached in a linear arrangement. Each compound incorporates an amide or imidazole “”linker”” between the pyrimidine or pyridine “”core”” ring and the “”tail”” ring system. We synthesized and screened twenty analogs by fluorescence polarization binding assay, thermal shift assay, glutathione S-transferase inhibition assay, and a cell-based assay measuring suppression of LPS-induced PGD2 stimulation. Amide analogs show ten-fold greater shift in the thermal shift assay in the presence of glutathione (GSH) vs. the same assay run in the absence of GSH. The imidazole analogs did not produce a significant change in thermal shift between the two assay conditions, suggesting a possible stabilization effect of the amide linker in the synthase-GSH-inhibitor complex. Imidazole analog 23, (KMN-010034) demonstrates superior potency across the in vitro assays and good in vitro metabolic stability in both human and guinea pig liver microsomes. The experimental process involved the reaction of 2-Pyridinylboronic acid(cas: 197958-29-5Formula: C5H6BNO2)

2-Pyridinylboronic acid(cas: 197958-29-5) belongs to pyridine. Pyridine is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is used as an important reagent and organic solvent.Formula: C5H6BNO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Schaffner, Arnaud-Pierre; Sansilvestri-Morel, Patricia; Despaux, Nicole; Ruano, Elisabeth; Persigand, Thierry; Rupin, Alain; Mennecier, Philippe; Vallez, Marie-Odile; Raimbaud, Eric; Desos, Patrice; Gloanec, Philippe published an article in 2021. The article was titled 《Phosphinanes and Azaphosphinanes as Potent and Selective Inhibitors of Activated Thrombin-Activatable Fibrinolysis Inhibitor (TAFIa)》, and you may find the article in Journal of Medicinal Chemistry.Category: pyridine-derivatives The information in the text is summarized as follows:

Selective and potent inhibitors of activated thrombin activatable fibrinolysis inhibitor (TAFIa) have the potential to increase endogenous and therapeutic fibrinolysis and to behave like profibrinolytic agents without the risk of major hemorrhage, since they do not interfere either with platelet activation or with coagulation during blood hemostasis. Therefore, TAFIa inhibitors could be used in at-risk patients for the treatment, prevention, and secondary prevention of stroke, venous thrombosis, and pulmonary embolisms. In this paper, we describe the design, the structure-activity relationship (SAR), and the synthesis of novel, potent, and selective phosphinanes and azaphosphinanes as TAFIa inhibitors. Several highly active azaphosphinanes display attractive properties suitable for further in vivo efficacy studies in thrombosis models. The experimental process involved the reaction of 2-Pyridinylboronic acid(cas: 197958-29-5Category: pyridine-derivatives)

2-Pyridinylboronic acid(cas: 197958-29-5) 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. Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pham, Thanh Chung; Kim, Hyun Sung; Lee, Songyi published an article in 2021. The article was titled 《Polydiacetylenes Functionalized with Chelidamic Acid and 2,2′-Dipicolylamine for Colorimetric Responses to Cadmium Ions》, and you may find the article in Bulletin of the Korean Chemical Society.Computed Properties of C12H13N3 The information in the text is summarized as follows:

A novel polydiacetylene-linked ligand derived from the reaction between chelidamic acid and bis(pyridin-2-ylmethyl)amine (PDA-CB) showed excellent selectivity and sensitivity for Cd2+ ions compared with other metal ions, including Zn2+. An obvious color change between PDA-CB and PDA-CB + Cd2+ is clearly visible to the naked eye. The Cd2+-responsive color change of PDA-CB is attributed to the coordination between Cd2+ and CB ligand units and has been characterized by 1H NMR titrationBis(pyridin-2-ylmethyl)amine(cas: 1539-42-0Computed Properties of C12H13N3) was used in this study.

Bis(pyridin-2-ylmethyl)amine(cas: 1539-42-0) is a secondary amine with two picolyl substituents. The compound is a tridentate ligand in coordination chemistry and commonly used to produce Zn-based chemosensors/probes, such as Zinpry.Computed Properties of C12H13N3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Huang, Huan-Ming; Bellotti, Peter; Erchinger, Johannes E.; Paulisch, Tiffany O.; Glorius, Frank published an article in 2022. The article was titled 《Radical Carbonyl Umpolung Arylation via Dual Catalysis》, and you may find the article in Journal of the American Chemical Society.Computed Properties of C6H6BrN The information in the text is summarized as follows:

A series of aryl benzoates I [R = iPr, tBu, cyclohexyl, etc.; R1 = 4-NCC6H4, 2-NCC6H4, 2-pyridyl, etc.] via dual nickel and photoredox catalyzed radical carbonyl umpolung arylation of aldehydes and aryl bromides was reported. This redox-neutral approach provided a complementary method to construct Grignard-type products from (hetero)aryl bromides and aliphatic aldehydes, without the need for prefunctionalization. Sequential activation, hydrogen atom transfer and halogen atom transfer process could directly converted aldehydes to the corresponding ketyl radicals, which further react with aryl-nickel intermediates in an overall polarity-reversal process. This radical strategy tolerated-among others-acidic functional groups, heteroaryl motifs and sterically hindered substrates and was applied in the late-stage modification of drugs and natural products. In the experiment, the researchers used 2-Bromo-5-methylpyridine(cas: 3510-66-5Computed Properties of 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.Computed Properties of C6H6BrN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem