Month: January 2023

2-Oxo-1,8-naphthyridine-3-carboxylic acid derivatives with potent gastric antisecretory properties was written by Santilli, Arthur A.;Scotese, Anthony C.;Bauer, Raymond F.;Bell, Stanley C.. And the article was included in Journal of Medicinal Chemistry in 1987.Name: 2-(Methylamino)nicotinonitrile This article mentions the following:

The syntheses of 2-oxo-1,8-naphthyridine-3-carboxylic acid derivatives, e.g., I (R = H, Me, Et, Pr, allyl, etc.; R¹ = NH₂, 4-methylpiperazinyl, etc.; R² = H, Me), having potent gastric antisecretory properties in the Shay rat model are described. Two of the more potent compounds tested that were selected for more detailed dose-response evaluation were I (R = Et, R¹ = NH₂, R² = H; II) and I (R = Et, R¹ = 4-methylpiperazinyl, R² = Me; III). II and III lowered total acid output in a dose-related fashion, were more potent than cimetidine, and showed inhibitory activity in food-stimulated acid secretion in the Pavlov dog. The mechanism of action for this series is not known. Details of structure-activity relationships are described. In the experiment, the researchers used many compounds, for example, 2-(Methylamino)nicotinonitrile (cas: 52583-87-6Name: 2-(Methylamino)nicotinonitrile).

2-(Methylamino)nicotinonitrile (cas: 52583-87-6) 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. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Name: 2-(Methylamino)nicotinonitrile

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Studies on anticoccidial agents. 12. Synthesis and anticoccidial activity of methyl-2(6)-nitro- and -3(5)-nitropyridinecarboxamides was written by Morisawa, Yasuhiro;Kataoka, Mitsuru;Sakamoto, Toshiaki;Nagahori, Hitoshi;Kitano, Noritoshi;Kusano, Kenichi. And the article was included in Journal of Medicinal Chemistry in 1978.COA of Formula: C7H10N2 This article mentions the following:

Twelve methyl-2-nitro- and 9 methyl-3-nitropyridinecarboxamides were prepared and tested in vivo for anticoccidial activity against Eimeria tenella. Almost all the compounds were active, with optimal activity shown by 5-methyl- (I) [65169-65-5] and 6-methyl-2-nitroisonicotinamide (II) [60780-18-9], which were as potent as 2-nitroisonicotinamide. At least 1 H atom adjacent to the NO₂ group is important for anticoccidial activity and a Me group adjacent to the CONH₂ function sometimes enhances activity. In the experiment, the researchers used many compounds, for example, 3,6-Dimethyl-2-pyridinamine (cas: 823-61-0COA of Formula: C7H10N2).

3,6-Dimethyl-2-pyridinamine (cas: 823-61-0) 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. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. COA of Formula: C7H10N2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

New Triazacycloalkane Derivatives as Cytotoxic Agents for CLL Treatment: From Proof of Concept to the Targeting Biomolecule was written by Marlin, Axia;Le Pape, Fiona;Le Goff, Jocelyn;Hamon, Nadege;Troadec, Thibault;Tripier, Raphael;Berthou, Christian;Patinec, Veronique. And the article was included in Bioconjugate Chemistry in 2022.Safety of (4-Bromopyridin-2-yl)methanol This article mentions the following:

The 1,4,7-tris-(2-pyridinylmethyl)-1,4,7-triazacyclononane ligand (no3py) and its bifunctional analog no3pyCOOK were synthesized to investigate their action toward zinc(II) depletion related to the apoptosis phenomenon in chronic lymphocytic leukemia (CLL) cells. no3py was used as the “free” ligand, while its “graftable” derivative was conjugated on a newly synthesized bifunctional sialoglycan, 6′-SL-NH₂, selected to specifically bind CD22 biomarker expressed on the B-CLL cell surface. Both compounds were produced with good yields thanks to a Sonogashira coupling reaction and an orthoester function, resp., for the chelator and the targeting moiety. The newly reported bioconjugate 6′-SL-no3py was then obtained through a peptidic coupling reaction. Biol. in vitro studies of no3py and 6′-SL-no3py consisting of real-time detection of cell health (cytotoxicity and proliferation) and caspases 3/7 activation (crucial enzymes whose activation triggers cell death signaling pathways) have been investigated. First, Ramos, Daudi, and Raji B-cell lines, which present different sensitivity to zinc(II) content variation, were incubated with no3py and 6′-SL-no3py. Then, a videomicroscope allowed the real-time monitoring of the morphol. changes leading to cell death from the detection of the cytotoxicity, the antiproliferative effect, and the caspasic activity. In terms of mechanism, the Zn²⁺ chelator cytotoxic effect of no3py has been evidenced by a culture medium ion supplementation study and by the decrease of intracellular fluorescence of Zn-specific fluorophore zinquin in the presence of no3py and 6′-SL-no3py chelators. Finally, flow cytometry anal. with classical Annexin V staining was conducted to detect no3py- and 6′-SL-no3py-induced apoptotic cell death in B-CLL cells. Time-course anal., using the Incucyte Live-Cell Anal. System, demonstrated that no3py induced cell death in a time- and dose-dependent manner with variability across cell lines. 6′-SL-no3py exhibited the same dose-dependent trend as no3py, showing the efficiency of the targeting moiety. In both cases, the chelators depicted proliferation curves that were inversely correlated with kinetic death. Morphol. changes specific to apoptosis and caspase 3/7 activation were observed for the three cell lines treated with no3py and 6′-SL-no3py, highlighting their role as apoptotic agents. A higher concentration of 6′-SL-no3py is needed to reach 50% of the B-CLL mortality, confirming a targeting of the chelator to the cell membrane. Overall, our results proved that the biol. properties of the triazamacrocyclic chelator still remain even after addition of the targeting moiety. The free chelator as well as the bioconjugate constitute promising cytotoxic agents for CLL therapy through apoptosis induction. In the experiment, the researchers used many compounds, for example, (4-Bromopyridin-2-yl)methanol (cas: 131747-45-0Safety of (4-Bromopyridin-2-yl)methanol).

(4-Bromopyridin-2-yl)methanol (cas: 131747-45-0) 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. 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. Safety of (4-Bromopyridin-2-yl)methanol

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Novel bipyridinyl oxadiazole-based metal coordination complexes: High efficient and green synthesis of 3,4-dihydropyrimidin-2(1H)-ones through the Biginelli reactions was written by Wang, Jin-Hua;Zhang, E.;Tang, Gui-Mei;Wang, Yong-Tao;Cui, Yue-Zhi;Ng, Seik Weng. And the article was included in Journal of Solid State Chemistry in 2016.Category: pyridine-derivatives This article mentions the following:

Three new metal coordination complexes, namely, [Co(BPO)₂(H₂O)₄](BS)₂(H₂O)₂ (1), [Co(BPO)₂(H₂O)₄](ABS)₂(H₂O)₂ (2), [Co(BPO)₂(H₂O)₄](MBS)₂(H₂O)₂ (3) [BPO = 2,5-di(pyridin-4-yl)-1,3,4-oxadiazole, BS = benzenesulfonate, ABS = 4-aminobenzenesulfonate, MBS = 4-methylbenzenesulfonate] were obtained under hydrothermal conditions. Complexes 1–3 were structurally characterized by single-crystal x-ray diffraction, powder X-ray diffraction, IR and thermogravimetric analyses (TGA). All of them display a zero-dimensional motif, in which strong intermol. H bonding interactions (O-H···O/N) and packing interactions (C-H···π and π···π) make them achieve a three-dimensional supramol. architecture. The primary catalytic results of these three complexes show that high efficiency for the green synthesis of a variety of 3,4-dihydropyrimidin-2(1H)-ones was observed under solvent free conditions through Biginelli reactions. The present catalytic protocols exhibit advantages such as excellent yield, easy isolation, eco-friendly conditions, and short reaction time. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Category: pyridine-derivatives).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic studies towards the mannolides: Construction of the bowl-shaped B/C/D ring system was written by Wang, Kunkai;Xu, Zhezhe;Tan, Xiangchuang;Xie, Zhixiang. And the article was included in Tetrahedron in 2020.Safety of (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole This article mentions the following:

The bowl-shaped tricyclo[6.3.1.0^4,12]dodecane moiety is the core feature of cephalotane-type diterpenoids. As part of our efforts directed towards a total synthesis of mannolide B, the bowl-shaped tricyclo[6.3.1.0^4,12]dodecane skeleton, a common intermediate of cephalotane-type diterpenoids bearing up to five contiguous stereocenters including two quaternary carbon centers had been constructed. The synthetic strategy was enabled by an efficient application of oxidative dearomatization/intramol. Diels-Alder reaction to access highly functionalized building block with the tricyclo[5.2.2.0^2,6]undecane unit from com. available materials. The key feature was firstly used the cyclic olefins with secondary alc. as dienophile for the intramol. inverse electron demand Diels-Alder reaction. Further synthetic studies led to construct ring D by a regioselective Aldol reaction. In the experiment, the researchers used many compounds, for example, (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2Safety of (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole).

(S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole (cas: 1257527-14-2) 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.Safety of (S)-4-(tert-Butyl)-2-(4-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Thermal degradation of esters/ethers derived from tartaric acid was written by Howell, Bob A.;Sun, Wenxiao. And the article was included in Journal of Thermal Analysis and Calorimetry in 2015.COA of Formula: C5H6ClN This article mentions the following:

Because of the increasing concern about the potential risks to human health presented by phthalate esters and, in particular, di(2-ethylhexyl)phthalate the development of non-toxic, environmentally-friendly plasticizers is rather urgent. Biobased materials derived from an annually renewable source are particularly attractive in this regard. A series of esters/ethers generated from tartaric acid, an edible, renewable byproduct of wine-making, has been synthesized and fully characterized using chromatog., spectroscopic and thermal methods. The thermal degradation characteristics of these compounds have been established using thermogravimetry and IR spectroscopy. These materials are stable to temperatures approaching 200 °C and degrade via elimination processes. They should function as effective plasticizers for a variety of polymeric materials including poly(vinyl chloride). In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7COA of Formula: C5H6ClN).

Pyridinehydrochloride (cas: 628-13-7) 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. 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.COA of Formula: C5H6ClN

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Production of 2-hydroxyacetylfuran from lignocellulosics treated with ionic liquid-water mixtures was written by Yoshioka, Koichi;Yamada, Tatsuhiko;Ohno, Hiroyuki;Miyafuji, Hisashi. And the article was included in RSC Advances in 2015.Related Products of 628-13-7 This article mentions the following:

Japanese cedar (Cryptomeria japonica) was treated with 12 ionic liquid (IL)-water mixtures at 120 °C for 1 h. Production of 5-hydroxymethylfurfural, furfural and 2-hydroxyacetylfuran (2-HAF) was observed by HPLC and GC-MS. This is the first report to identify 2-HAF from lignocellulosics using ILs. The optimal IL-water mixture was found to be a 90% pyridinium chloride and 10% water weight/weight solution, although any IL-water mixture that contained pyridinium or imidazolium salts produced all three compounds in varying yields. In the experiment, the researchers used many compounds, for example, Pyridinehydrochloride (cas: 628-13-7Related Products of 628-13-7).

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. 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.Related Products of 628-13-7

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Carboline synthesis by the method of Graebe Ullmann I was written by Namirski, Pawel Nantka. And the article was included in Acta Poloniae Pharmaceutica in 1961.COA of Formula: C5H2Cl2N2O2 This article mentions the following:

3-Nitro-4-pyridone (14 g.) in 200 ml. 50% AcOH treated at 25-30° with Cl gave 46% 3-nitro-4-hydroxy-5-chloropyridine (I), m. 263°. I (17.5 g.), 25 g. P₂O₅, and 10 ml. POCl₃ heated to give a brown solution, volatile portion evaporated in vacuo, the residue neutralized with Na₂CO₃, extracted with Et₂O, and the extract distilled gave 19.1 g. 3-nitro-4,5-dichloropyridine (II), m. 43-7°, strong lachrymator. II (1.9 g.) in 15 ml. Me₂CO heated 2 hrs. on a water bath with 20 ml. 25% NH₄OH yielded 1 g. light yellow 3-nitro-4-amino-5-chloropyridine, m. 181° (EtOH); similarly, 1.9 g. II in 15 ml. EtOH heated 30 min. with 5 ml. 80% (NH₂)₂.H₂O gave 1.3 g. 3-nitro-4-hydrazino-5-chloropyridine, golden needles, m. 199° (EtOH). I (17.5 g.) and 25 g. PCl₅ in 50% AcOH treated at 25-30° with Cl, the volatile products distilled, the residue treated portionwise with 100 g. SnCl₂ in 250 ml. concentrated HCl, heated 30 min. on a water bath, cooled, treated with 30 ml. concentrated HCl, the precipitated adduct decomposed with 20% NaOH, the mixture extracted with Et₂O, and the extract treated with concentrated HNO₃ gave 16.5 g. 3-amino-4,5-dichloropyridine (III) nitrate, m. 169° (EtOH); III, needles m. 108°. Analogously, 22.5 g. 3 nitro-4-hydroxy-5-bromopyridine yielded 21 g. 3-amino-4-chloro-5-bromopyridine nitrate, m. 176°, and free base, m. 108.5°. II (19.3 g.) and 25 ml. PhNH₂ heated 2 hrs. on a water bath, alkalized with NH₄OH the excess PhNH₂ steam distilled, the residue dissolved in HCl, treated with C, and then with NH₄OH yielded 50% yellow 3-nitro-4-anilino-5-chloropyridine (IV), m. 148-8.5° (EtOH). IV was also prepared in 93% yield when 17.5 g. I was chlorinated as above, the volatile products distilled, the residue heated 2 hrs. on a water bath with 150 ml. AcOH, 10 g. PhNH₂, and 15 g. anhydrous AcONa, the mixture diluted with 500 ml. H₂O, neutralized with NH₄OH, the gummy precipitate extracted with HCl, and reprecipitated with NH₄OH; the 5-bromo analog of IV, m. 153.5-54°, was prepared by this method in 94% yield. IV (25 g.) added portionwise to 75 g. Na₂S in 300 ml. H₂O, the mixture heated 3 hrs. at 90-100°, the precipitate extracted with Et₂O, and the extract treated with concentrated HNO₃ gave 3-amino-4-anilino-5-chloropyridine (V) nitrate, which alkalized with Na₂CO₃ in aqueous solution yielded 71% V, m. 149.5° (H₂O); the 5-bromo analog (79%) m. 144.5° (EtOH). V (11 g.) diazotized in 300 ml. 50% H₂SO₄ with 3.5 g. NaNO₂ in 50 ml. H₂O and the solution treated with NH₄OH yielded 92% 1-phenyl-7-chloro-v-triazolo[4,5-c]pyridine (VI), m. 141-1.5°; the 7-bromo analog (96%) m. 149° (50% EtOH). Evolution of N began at 240° and ceased at 290° when 9.6 g. VI was heated in 30 ml. H₃PO₄; the residue was dissolved in 200 ml. H₂O, treated with NH₄OH, the mixture extracted repeatedly with Et₂O, and the extract evaporated to give 2.9 g. crude, yellow 1-chloro-β-carboline (VII), m. 233-4° after repeated crystallizations from H₂O and EtOH; purification via the HCl salt (m. 311-12°) raised the m.p. of VII to 270° and gave a colorless product. Analogously were prepared: 1-bromo-γ-carboline, m. 240-1.5° (crude 233-4°) (HCl salt (VIII) m. 301-3°); 1-iodo-γ-carboline, yellowish crystals, m. 242-3° (crude 229-32°). In biol. tests, the inhibition of monoamine oxidase by VIII was 80% of that of phenethylhydrazine. In the experiment, the researchers used many compounds, for example, 3,4-Dichloro-5-nitropyridine (cas: 56809-84-8COA of Formula: C5H2Cl2N2O2).

3,4-Dichloro-5-nitropyridine (cas: 56809-84-8) 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. 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.COA of Formula: C5H2Cl2N2O2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Thione-thiol rearrangement of xanthates catalyzed by pyridine N-oxides. Remarkable enhanced reactivity of 4-dialkylaminopyridine N-oxides was written by Harano, Kazunobu;Nakagawa, Hidetoshi;Kamei, Kumiko;Kiyonaga, Hideo;Hisano, Takuzo. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.Category: pyridine-derivatives This article mentions the following:

Pyridine N-oxides (III; R = electron-donating substituents) are efficient catalysts for rearrangement of O-alkyl S-Me dithiocarbonates (xanthates) (I) to the corresponding S-alkyl S-Me dithiocarbonates (dithiolcarbonates) (II). Of the catalysts tested, III [R = piperidino (IV)] is the best from the viewpoints of catalytic activity and solubility in I. Heating of I in the presence of catalytic amounts (0.02-0.05 M eq) of IV gave II together with the sym. S,S-dialkyl and S,S-di-Me dithiocarbonates in good yields. The catalytic behavior of III is discussed on the basis of kinetic and MO data. The complete calculation of the perturbation equation on the initial stage of the reaction was consistent with the exptl. observed activity of the catalysts. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Category: pyridine-derivatives).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Copper-catalyzed cross-coupling of aryl-, primary alkyl-, and secondary alkylboranes with heteroaryl bromides was written by Bergmann, Allison M.;Oldham, Adam M.;You, Wei;Brown, M. Kevin. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2018.Category: pyridine-derivatives This article mentions the following:

A method for the Cu-catalyzed cross-coupling of both aryl and alkylboranes with aryl bromides was described. The method employed an inexpensive Cu-catalyst and functions for a variety of heterocyclic as well as electron deficient aryl bromides. In addition, aryl iodides of varying substitution patterns and electronic properties worked well. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Category: pyridine-derivatives).

2-Isopropylpyridine (cas: 644-98-4) 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. 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.Category: pyridine-derivatives

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem