Day: January 6, 2023

Synthesis and biological activities of 3-methoxy-6-substituted-5,6-dihydropyrrolo[3,4-b]pyridin-7-ones was written by Sun, Guanglong;Zhang, Weiwei;Zhan, Xiaoping;Liu, Zenglu;Mao, Zhenmin. And the article was included in Youji Huaxue in 2014.Safety of Methyl 3-methylpicolinate This article mentions the following:

A series of thalidomide derivatives named 3-methoxy-6-substituted 5,6-dihydropyrrolo[3,4-b]pyridin-7-ones 1a-1l, which have never been reported in literature, were synthesized from 3-methoxypyridine-2-carboxylic acid Me ester (I) and different amines by cyclization reaction. The intermediate I was produced via hydrolysis, esterification, nitration reaction, methoxy substitution, bromination reaction using 3-methyl-pyridine-2-carbonitrile as the starting material. The structures of all compounds have been confirmed by ¹H NMR, ¹³C NMR and HRMS techniques. The target compounds were evaluated for their inhibitory activity against HCT-116, MG-63, MCF-7, HUVEC and HMVEC cells by MTT (thiazolyl blue tetrazolium bromide) method, and the results indicated that almost all of them had no obvious inhibitory effect on normal human cells, some compounds only displayed obvious inhibitory effect on MG-63 cells while other compounds presented excellent inhibitory activities against all the three kinds of tumor cells, among which compounds two compounds exhibited most potent activities. In the experiment, the researchers used many compounds, for example, Methyl 3-methylpicolinate (cas: 59718-84-2Safety of Methyl 3-methylpicolinate).

Methyl 3-methylpicolinate (cas: 59718-84-2) 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). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Safety of Methyl 3-methylpicolinate

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and characterization of new coordination polymers generated from oxadiazole-containing ligand and inorganic M(II) [M = Cu(II), Co(II)] salts was written by Dong, Yu-Bin;Ma, Jian-Ping;Huang, Ru-Qi;Liang, Fang-Zhen;Smith, Mark D.. And the article was included in Dalton Transactions in 2003.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

The coordination chem. of the oxadiazole-containing ligand 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (L5) with inorganic Cu(II) and Co(II) salts was studied. Three new coordination polymers (1–3) and one H-bonded polymer (4), [Cu(L5)₂(H₂O)₃(ClO₄)](ClO₄).H₂O, were prepared by solution reactions. [Cu(L5)(H₂O)(SO₄)]·2(H₂O) (1) adopts a novel chiral three-dimensional motif with rhombus channels (∼6.04 × 14.09 Å). [Co(L5)(MeOH)₂(SO₄)](MeOH)(H₂O)_3.5 (2) features a novel two-dimensional network. [Cu(L5)₂(H₂O)₂](L5)₂(ClO₄)₂(MeOH)(H₂O) (3) features a two-dimensional rhombus-grid-type layer with inner grid cavity dimensions of 13.22 × 13.22 Ų. Compound 4, however, is a mol. complex that is bound together by strong N···H-O and O···H-O H bonds into a three-dimensional H-bonded network. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Tuberculostatic substances from derivatives of pyridinecarboxylic acids was written by Palat, Karel;Celadnik, Milan;Novacek, Libor;Polster, Miroslav;Urbancik, Richard;Matuskova, Elsa. And the article was included in Acta Fac. Pharm. Brun. Bratislav. in 1962.Reference of 89978-52-9 This article mentions the following:

Among various hydrazides, amides, thioamides, hydroxamic acids, and Na salts of pyridinecarboxylic acids substituted in the ring by alkoxy, hydroxy, mercapto, or halogen, the greatest activity in vitro was shown by the hydrazide of 2,6-diethoxyisonicotinic acid, partly effective in a concentration 0.1 γ/ml. completely inhibitive of growth in a concentration of 1 γ/ml. Also effective were 2-propoxynicotinic acid hydrazide, active at 1 γ/ml., and 3- bromoisonicotinic acid hydrazide, active at 10 γ/ml. In vivo, the most effective was Na 3-iodoisonicotinate, which was inactive in vitro. In the experiment, the researchers used many compounds, for example, Ethyl 2-bromoisonicotinate (cas: 89978-52-9Reference of 89978-52-9).

Ethyl 2-bromoisonicotinate (cas: 89978-52-9) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 89978-52-9

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The Association of Picrate Ions with Amphiphilic Cations in Water and Aqueous Solutions of Nonionic Surfactant and β-Cyclodextrin was written by Ziyatdinova, A. B.;Mirsaizyanova, S. A.;Saprykova, Z. A.;Amirov, R. R.. And the article was included in Colloid Journal in 2005.Application In Synthesis of 1-Dodecylpyridin-1-ium bromide This article mentions the following:

The interaction of cetyltrimethylammonium and cetylpyridinium bromides with picrate ions in H₂O and aqueous solutions of the nonionic surfactant Brij 35 was studied by spectrophotometry. Spectral characteristics of the associates of picrate ions with long-chain N-containing cations depend on the concentration of a cationic surfactant. When β-cyclodextrin is added, these associates decompose owing to the formation of the strong inclusion complexes of the guest-host type with amphiphilic ions of a cationic surfactant or Brij 35 mols. The conclusion is made that the driving force for the formation of pre-micellar aggregates involving picrate ions is the interactions between alkyl chains of surfactant cations. In the presence of various surfactants, as β-cyclodextrin concentration increases, 1st the mols. of nonionic surfactant and then amphiphilic cations bind with the receptor cavity. There is no interaction between polyethylene glycol and β-cyclodextrin in aqueous solution In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4Application In Synthesis of 1-Dodecylpyridin-1-ium bromide).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) 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). Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Application In Synthesis of 1-Dodecylpyridin-1-ium bromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Substituent Effects of 2-Pyridones on Selective O-Arylation with Diaryliodonium Salts: Synthesis of 2-Aryloxypyridines under Transition-Metal-Free Conditions was written by Li, Xiao-Hua;Ye, Ai-Hui;Liang, Cui;Mo, Dong-Liang. And the article was included in Synthesis in 2018.Quality Control of 2-Phenoxypyridine This article mentions the following:

An efficient transition-metal-free strategy to synthesize 2-aryloxypyridine derivatives was developed by a selective O-arylation of 2-pyridones with diaryliodonium salts. The reaction was compatible with a series of functional groups for 2-pyridones and diaryliodonium salts such as halides, nitro, cyano and ester groups. The substituents at the C6-position of 2-pyridones favored O-arylation products because of steric hindrance. The reaction was easily performed on a gram-scale and 6-chloro-2-pyridone was a good precursor to access various unsubstituted 2-aryloxypyridines by dehalogenation. A P2Y₁ lead compound analog I could be prepared in good yield over two steps. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0Quality Control of 2-Phenoxypyridine).

2-Phenoxypyridine (cas: 4783-68-0) 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 groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Quality Control of 2-Phenoxypyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis of sulfur derivatives of pyridine and its N-oxide was written by Puszko, Aniela;Talik, Zofia. And the article was included in Polish Journal of Chemistry in 1991.Application In Synthesis of 2,4-Dibromo-5-methylpyridine This article mentions the following:

2,4-Pyridinedithiol N-oxide and three isomeric 2,4-picoline (3-Me, 5-Me, 6-Me) dithiol N-oxides were obtained by reaction of 2,4-dichloropyridine N-oxide and 2,4-dihalogenopicoline N-oxides with thioacetamide. 2,4-Pyridinedithiol N-oxide and 3-methylpyridine-2,4-dithiol N-oxide were deoxidized by treatment with PBr₃. In the experiment, the researchers used many compounds, for example, 2,4-Dibromo-5-methylpyridine (cas: 79055-50-8Application In Synthesis of 2,4-Dibromo-5-methylpyridine).

2,4-Dibromo-5-methylpyridine (cas: 79055-50-8) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. 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.Application In Synthesis of 2,4-Dibromo-5-methylpyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Copper-Mediated Selective Mono- and Sequential Organochalcogenation of C-H Bonds: Synthesis of Hybrid Unsymmetrical Aryl Ferrocene Chalcogenides was written by Sattar, Moh.;Patidar, Krishna;Thorat, Raviraj Ananda;Kumar, Sangit. And the article was included in Journal of Organic Chemistry in 2019.Quality Control of Pyridin-4-ol This article mentions the following:

A 8-aminoquinoline directed Cu/1,10-phenanthroline-mediated selective mono-organothiolation of C-H bond in ferroceneamide was developed using aryl/alkyl-disulfide substrates. The sequential ferrocene C-H organochalcogenation (chalcogen = S, Se, and Te) also was established for the synthesis of novel hybrid unsym. aryl chalcogenides with the aid of a catalytic amount of Cu(OAc)2 under ambient reaction conditions. The developed protocol exhibits a broad functional group tolerance to allow alkyl, aryl, hetero-aryl, bromo, chloro, and nitro containing diorgano dichalcogenides as a coupling partner. Further, the 8-aminoquinoline directing group is easily removed to afford the aldehyde functionality after C-H organochalcogenation. A mechanistic understanding of the Cu-mediated selective mono-organothiolation reaction suggests that rigid bi-coordinated 1,10-phenanthroline ligand and freshly generated Cu(II) from Cu(I) in the less polar solvent MeCN seem crucial for the selective mono-C-H functionalization of ferroceneamide. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Quality Control of Pyridin-4-ol).

Pyridin-4-ol (cas: 626-64-2) 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. 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.Quality Control of Pyridin-4-ol

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A [4 + 1] Cyclative Capture Access to Indolizines via Cobalt(III)-Catalyzed Csp²-H Bond Functionalization was written by Chen, Xun;Hu, Xinwei;Deng, Yuanfu;Jiang, Huanfeng;Zeng, Wei. And the article was included in Organic Letters in 2016.Quality Control of 2-(m-Tolyl)pyridine This article mentions the following:

A Co(III)-catalyzed [4+1] cycloaddition of 2-arylpyridines or 2-alkenylpyridines with aldehydes through Csp²-H bond activation has been developed. This protocol provides a facile approach to structurally diverse indolizines including benzoindolizines with a broad range of functional group tolerance. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Quality Control of 2-(m-Tolyl)pyridine).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Quality Control of 2-(m-Tolyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Selective C-C bond formation from rhodium-catalyzed C-H activation reaction of 2-arylpyridines with 3-aryl-2H-azirines was written by Baek, Yonghyeon;Kim, Jinwoo;Hyunseok Kim;Jung, Seung Jin;Ryu, Ho;Kim, Suyeon;Son, Jeong-Yu;Um, Kyusik;Han, Sang Hoon;Seo, Hyung Jin;Heo, Juyoung;Lee, Kooyeon;Baik, Mu-Hyun;Lee, Phil Ho. And the article was included in Chemical Science in 2019.Formula: C12H11N This article mentions the following:

A novel method for the synthesis of acylmethyl-substituted 2-arylpyridine derivatives I [R¹ = Ph, 4-MeC₆H₄, 2-ClC₆H₄, etc.; R² = 4-Me, 5-C(O)Me, 5-CF₃, etc.; R³ = H, Me, F, C(O)Me, CO₂Et] was synthesized via rhodium-catalyzed C-H activation reaction of 3-aryl-2H-azirines with 2-arylpyridines and explored a prototype reaction using DFT-calculations Computational studies quickly revealed and prototype exptl. work confirmed that neither the formation of the expected metal nitrene complexes nor the C-N coupling were viable. Instead, azirine ring-opening followed by C-C coupling was found to be much more favorable to give imines that readily underwent hydrolysis in aqueous conditions to form compounds I. This new method was highly versatile and selective toward a wide range of substrates with high functional group tolerance. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Formula: C12H11N).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Formula: C12H11N

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

2-Pyridylquinolone antimalarials with improved antimalarial activity and physicochemical properties was written by Charoensutthivarakul, Sitthivut;David Hong, W.;Leung, Suet C.;Gibbons, Peter D.;Bedingfield, Paul T. P.;Nixon, Gemma L.;Lawrenson, Alexandre S.;Berry, Neil G.;Ward, Stephen A.;Biagini, Giancarlo A.;O’Neill, Paul M.. And the article was included in MedChemComm in 2015.Application of 131747-45-0 This article mentions the following:

A series of 2-pyridylquinolones has been prepared in 5-7 steps and through lead optimization, antimalarial activity as low as 12 nM against Plasmodium falciparum (Pf) has been achieved. Compared with previous analogs in this series, selected mols. have improved solubility, a reduced potential for off-target toxicity and improved metabolic stability profiles. Docking studies performed with a homol. model of the Pfbc₁ complex target demonstrate a key role for the Tyr16 residues in the recognition of highly active quinolone based inhibitors. In the experiment, the researchers used many compounds, for example, (4-Bromopyridin-2-yl)methanol (cas: 131747-45-0Application of 131747-45-0).

(4-Bromopyridin-2-yl)methanol (cas: 131747-45-0) 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). Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 131747-45-0

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem