Day: January 6, 2023

Practical routes toward the synthesis of 2-halo- and 2-(alkylamino)-4-pyridinecarboxaldehydes was written by Frey, L. F.;Marcantonio, K.;Frantz, D. E.;Murry, J. A.;Tillyer, R. D.;Grabowski, E. J. J.;Reider, P. J.. And the article was included in Tetrahedron Letters in 2001.Electric Literature of C6H3FN2 This article mentions the following:

We recently required an efficient synthesis of 2-halo- and 2-(alkylamino)-4-pyridinecarboxaldehydes. Several routes to these compounds were investigated resulting in efficient and practical procedures from readily available and inexpensive starting materials. In the experiment, the researchers used many compounds, for example, 2-Fluoroisonicotinonitrile (cas: 3939-14-8Electric Literature of C6H3FN2).

2-Fluoroisonicotinonitrile (cas: 3939-14-8) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Electric Literature of C6H3FN2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Identifying specific conformations by using a carbohydrate scaffold: Discovery of subtype-selective LPA-receptor agonists and an antagonist was written by Tamaruya, Yoko;Suzuki, Masato;Kamura, Goshu;Kanai, Motomu;Hama, Kotaro;Shimizu, Kumiko;Aoki, Junken;Arai, Hiroyuki;Shibasaki, Masakatsu. And the article was included in Angewandte Chemie, International Edition in 2004.Computed Properties of C10H17NO2 This article mentions the following:

Stable and potent subtype-selective lysophosphatidic acid (LPA) analogs (agonists and an antagonist) were developed by using carbohydrates as a core structure. An array of mols. with the recognition motifs of LPA (a phosphate anion, an oleoyl group, and a hydrogen-bond acceptor) attached to carbohydrate isomers in different three-dimensional arrangements were tested for LPA-receptor activation or inhibition. In the experiment, the researchers used many compounds, for example, tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4Computed Properties of C10H17NO2).

tert-Butyl 5,6-dihydropyridine-1(2H)-carboxylate (cas: 85838-94-4) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Computed Properties of C10H17NO2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

2-(2-Chloro-6-fluorophenyl)acetamides as potent thrombin inhibitors was written by Lee, Lily;Kreutter, Kevin D.;Pan, Wenxi;Crysler, Carl;Spurlino, John;Player, Mark R.;Tomczuk, Bruce;Lu, Tianbao. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2007.Application of 199296-39-4 This article mentions the following:

2-(2-Chloro-6-fluorophenyl)acetamides having 2,2-difluoro-2-aryl/heteroaryl-ethylamine P3 and oxyguanidine P1 substituents are potent thrombin inhibitors (K_i = 0.9-33.9 nM). 2-(5-Chloropyridin-2-yl)-2,2-difluoroethylamine was the best P3 substituent, yielding the most potent inhibitor (K_i = 0.7 nM). Replacing the P3 heteroaryl group with a Ph ring or replacing the difluoro substitution with di-Me or cyclopropyl groups in the linker reduced the affinity for thrombin significantly. The aminopyridine P1s also provided an increase in potency. In the experiment, the researchers used many compounds, for example, 2-Methyl-2-(pyridin-2-yl)propan-1-amine (cas: 199296-39-4Application of 199296-39-4).

2-Methyl-2-(pyridin-2-yl)propan-1-amine (cas: 199296-39-4) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Application of 199296-39-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A flexible, convergent route to azaoxindoles, azaindolines, azaindoles, and tetrahydroazaquinolones was written by Bacque, Eric;El Qacemi, Myriem;Zard, Samir Z.. And the article was included in Heterocycles in 2012.Reference of 209798-48-1 This article mentions the following:

A variety of azaoxindoles, azaindolines, azaindoles, and tetrahydroazaquinolones were readily prepared by cyclization of xanthate-derived radicals onto pyridine rings. The xanthate precursors may themselves be produced by intermol. radical addition-transfer to allylamino- or butenoylamide side-chains. In the experiment, the researchers used many compounds, for example, (2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1Reference of 209798-48-1).

(2-Chloro-pyridin-3-yl)-carbamic acid tert-butyl ester (cas: 209798-48-1) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 209798-48-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Catalytic rearrangement of O,S-dialkyl dithiocarbonates to S,S-dialkyl dithiocarbonates by pyridine N-oxides. The reaction mechanism was written by Harano, Kazunobu;Shinohara, Ikuo;Sugimoto, Shinichiro;Matsuoka, Toshikazu;Hisano, Takuzo. And the article was included in Chemical & Pharmaceutical Bulletin in 1989.Electric Literature of C7H9NO This article mentions the following:

The reaction of O-alkyl S-Me dithiocarbonates (xanthates) (I) with pyridine N-oxides (II) gave the corresponding S-alkyl S-Me dithiocarbonates (III) together with the sym. S,S-dialkyl and S,S-di-Me dithiocarbonates in good yields. Pyridine N-oxides bearing electron-donating substituents are efficient catalysts for rearrangement of I to III. The reaction is pseudo-first-order and the apparent first-order rate constant is proportional to the concentration of II. The role of pyridine N-oxides and the reaction behavior of O,S-dialkyl dithiocarbonates are discussed on the basis of kinetic and MO calculation data. The rearrangement may proceed by nucleophilic attack of ^–SCOSR derived from a complex of I and II on the O-alkyl group of xanthates. The reaction provides a useful preparation method for alkanethiols by aminolysis of the products with ethanolamine. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Electric Literature of C7H9NO).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Electric Literature of C7H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Methylpyridine derivatives. II. Synthesis of 2-cyanomethylpyridines was written by Suzuki, Yasuyuki. And the article was included in Pharmaceutical Bulletin in 1957.Product Details of 1620-76-4 This article mentions the following:

In general, alkyl derivatives of 2-chloropyridine (I) were heated 10 hrs. in an autoclave with the calculated amount of Na₂SO₃ in H₂O, and the resulting alkyl derivative of Na 2-pyridinesulfonate fused (without previous isolation) with KCN over an open flame to give the corresponding alkyl derivatives of 2-cyanopyridine (II) (derivative of I used, temperature of autoclave, b.p. and m.p. of corresponding II derivative, yield given): I itself, 150-60°, b₂₄ 114-16°, -, 49.7%; 6-Me, 170-80°, b₃₈ 135-6°, m. 69-71°, 39%; 5-Me, 200-10°, b₂₈ 135-8°, m. 72-4°, 36.8%; 4-Me, 180-90°, b₃₈ 145-8°, m. 88-9°, 39.1%; 3-Me, 170-80°, b₃₈ 139-42°, m. 87-8°, 59%; 4,6-Me₂, 200-10°, b₁₆ 125-30°, m. 51-2°, 32.6%; 3,6-EtMe (III), 210-20°, b₃₂ 145-51°, -, 49.7%. Similarly, the 4-Cl derivative (IV) of III heated only 3 hrs. with Na₂SO₃ in an autocalve at 180-200° and fused with KCN yielded 60.6% 4-cyano derivative of III, b₁₇ 107-10°; picrate, m. 123-4°. 3-Ethyl-4-nitro-6-methylpyridine 1-oxide (9.1 g.) (Berson and Cohen, C.A. 50, 9405i) in 30 cc. CHCl₃ treated dropwise in the cold with 17.8 cc. AcCl, stirred an addnl. 30 min. at 50°, 8.8 cc. PCl₃ added dropwise in the cold, the mixture stirred 30 min. at room temperature, warmed 1 hr. at 60-70° on a H₂O bath, cooled, poured into 100 cc. ice H₂O, the aqueous layer (plus the washings from the organic layer) washed with 30 cc. ether, made alk. with Na₂CO₃, steam-distilled, and the distillate saturated with K₂CO₃ and extracted with ether yielded 5.27 g. IV, b₂₀ 92-5°; picrate, m. 133-4.5°. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Product Details of 1620-76-4).

4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Product Details of 1620-76-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A novel bio-based AB₂ monomer for preparing hyperbranched polyamides derived from levulinic acid and furfurylamine was written by Yang, Meng-Ling;Wu, Yue-Xiao;Liu, Yun;Qiu, Jin-Jun;Liu, Cheng-Mei. And the article was included in Polymer Chemistry in 2019.Electric Literature of C5H6ClN This article mentions the following:

A new AB₂ type bio-based monomer (FDA-E) with two amino functional groups and one ester functional group was prepared from renewable levulinic acid and furfurylamine using a three-step reaction. The AB₂ monomer underwent self-polycondensation under melt conditions to form a hyperbranched bio-polyamide. Polyamides show excellent solubility in a strong polar solvent and acidic solution In pure water, the rigid polyamides form a stable elastic gel by absorbing water instead of dissolving in it. Their glass transition temperatures are in the range 97-102°C and their char yields at 800°C are greater than 40%. The XRD results indicate that the three polyamides are amorphous polymers. In addition, the hyperbranched polyamides are fluorescent polymers and their photoluminescence properties depend on mol. weight, solvent, excitation wavelength, and excitation time. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Electric Literature of C5H6ClN).

Pyridinehydrochloride (cas: 628-13-7) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Many analogues of pyridine are known where N is replaced by other heteroatoms . Substitution of one C–H in pyridine with a second N gives rise to the diazine heterocycles (C4H4N2), with the names pyridazine, pyrimidine, and pyrazine.Electric Literature of C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel NNO pincer type Schiff base ligand and its complexes of Fe(IIl), Co(II) and Ni(II): Synthesis, spectroscopic characterization, DFT, antibacterial and anticorrosion study was written by Shukla, Satyendra Nath;Gaur, Pratiksha;Raidas, Mohan Lal;Chaurasia, Bhaskar;Bagri, Sanjay Singh. And the article was included in Journal of Molecular Structure in 2021.Application of 91-02-1 This article mentions the following:

A novel NNO pincer type ligand (E)-N’-(phenyl(pyridin-2-yl)methylene)isonicotinohydrazide, PPMINH, was synthesized by condensation of 2-benzoyl pyridine and isonicotinylhydrazide. The ligand PPMINH on reaction with metal ions Fe(III), Co(II) and Ni(II) yielded six metal derivatives Different anal. tools like; Elemental analyses, ESI-MS, FTIR, molar conductivity, UV-spectra, magnetic susceptibility, NMR and EPR measurement were used. Theor. FTIR, ¹H NMR and ¹³C NMR of ligand and complex 6 exhibits quite a good correlation coefficient EPR spectrum of complex 6 at LNT suggests octahedral geometry around Ni(II). The ligand and complexes were screened for antibacterial activity. DFT was carried out to optimize the geometry of the ligand and complexes. The properties most relevant to their potential action as corrosion inhibitors was calculated all parameters of DFT from the inhibitor mol. to the metal atom. The corrosion inhibition effect of compounds on mild steel in an acidic medium was studied for 24, 48, 72 h using weight loss measurement. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Application of 91-02-1).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. Pyridines are an important class of heterocycles and occur in polysubstituted forms in many naturally occurring biologically active compounds, drug molecules and chiral ligands. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 91-02-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

{[Cu^I(bpo)₂(CH₃CN)]ClO₄ CH₃CN·(H₂O)_1.5}_n: a novel three-dimensional open framework with large rectangular channels assembled from copper(I) perchlorate and 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (bpo) was written by Du, Miao;Lam, Chi-Keung;Bu, Xian-He;Mak, Thomas C. W.. And the article was included in Inorganic Chemistry Communications in 2004.Reference of 15420-02-7 This article mentions the following:

In the 1st Cu^I coordination polymer containing an angular bipyridine-type ligand 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (bpo), {[Cu(bpo)₂(MeCN)]ClO₄·MeCN·(H₂O)_1.5}_n (1), bpo exhibits different monodentate and bidentate bridging modes in binding to the Cu^I center forming a novel 1-dimensional infinite comb-like polymeric chain with the monodentate ligands on one side. The most striking feature of this structure is the formation of a 3-dimensional porous network with large rectangular channels through two distinct types of inter-chain π-π stacking interactions, which was further stabilized by weak H-bonding interactions. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Reference of 15420-02-7).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). 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.Reference of 15420-02-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Lead identification of benzimidazolone and azabenzimidazolone arylsulfonamides as CC-chemokine receptor 4 (CCR4) antagonists was written by Miah, Afjal H.;Abas, Hossay;Begg, Malcolm;Marsh, Benjamin J.;O’Flynn, Daniel E.;Ford, Alison J.;Percy, Jonathan M.;Procopiou, Panayiotis A.;Richards, Steve A.;Rumley, Sally-Anne. And the article was included in Bioorganic & Medicinal Chemistry in 2014.Safety of 2,6-Dibromo-3-hydroxypyridine This article mentions the following:

A knowledge-based library of 2,3-dichlorophenylsulfonyl derivatives of com. available aryl amines was synthesized and screened as human CCR4 antagonists, in order to identify a suitable hit for the start of a lead-optimization program. Hits were required to be more potent than an existing indazole series, have better physicochem. properties (c log P <3.5, chromatog. log D_7.4 <5.3 and CLND solubility >116 μg/mL), and be stable to acid and light. The benzimidazol-2-one core was identified as a hit suitable for further investigation. Substitution at N1 with small alkyl groups was tolerated; however, these analogs were inactive in the whole blood assay (pA₂ <5). Azabenzimidazolone analogs were all found to be active, with compound I exhibiting whole blood activity of 6.1, low mol. weight (389) and chromatog. log D_7.4 (2.4), high LE (0.43), and solubility (152 μg/mL). In addition, I had human serum albumin binding of around 93% and met all the criteria for progression to lead optimization. In the experiment, the researchers used many compounds, for example, 2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1Safety of 2,6-Dibromo-3-hydroxypyridine).

2,6-Dibromo-3-hydroxypyridine (cas: 6602-33-1) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Safety of 2,6-Dibromo-3-hydroxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem