Category: pyridine-derivatives

Sturrock, Keith R. published the artcileThe preparation of ketene dithioacetals and thiophenes from chloropyridines containing an active methylene group, COA of Formula: C9H10ClNO2, the publication is Heterocycles (2011), 82(2), 1657-1662, database is CAplus.

The base-catalyzed reaction of CS₂ with the active methylene groups of 6-chloropyridine-3-acetonitrile and -3-acetate, followed by alkylation with reagents also containing active methylene groups, led to ketene dithioacetals. Further reaction with base afforded highly substituted thiophenes.

Heterocycles published new progress about 164464-60-2. 164464-60-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Chloride,Ester, name is Ethyl 2-(2-chloropyridin-3-yl)acetate, and the molecular formula is C9H17NO, COA of Formula: C9H10ClNO2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Hawlitschek, Christina published the artcileAntihypertensive and cardioprotective effects of different monotherapies and combination therapies in young spontaneously hypertensive rats – A pilot study, Product Details of C17H18N2O6, the publication is Saudi Journal of Biological Sciences (2022), 29(1), 339-345, database is CAplus and MEDLINE.

Spontaneously hypertensive rats (SHR) are an established animal model for antihypertensive treatment. The aim of this pilot study was a systematic search for two lines of antihypertensive treatment – a monotherapy and a combination of two drugs – to be applied in a future study on old SHR. Originally, representatives of three drug classes recommended for antihypertensive therapy in humans should be applied, namely captopril (CAP) as an antagonist of the renin-angiotensin-aldosterone system, nifedipine (NIF) as calcium channel blocker and propranolol (PROP) as β-adrenergic blocker. As we observed that PROP had been poorly ingested, all groups with PROP therapy were excluded from the study. CAP (60 mg kg^-1 d^-1), NIF (10 mg kg^-1 d^-1) or both were administered orally to seven-week-old SHR over 3 wk. A further group of SHR received no treatment (SHR/CTRL). Age-matched normotensive Wistar-Kyoto rats served as normotensive controls. We examined the effect of the antihypertensive therapies on systolic blood pressure, heart weight and on histol. and biochem. markers of cardiac hypertrophy and fibrosis. CAP proved to be the most effective treatment reducing blood pressure and relative heart weight significantly compared to SHR/CTRL without reaching normotensive values. Beginning cardiac fibrosis observed in SHR/CTRL was completely abrogated with CAP treatment. Similar effects were achieved with a combination of CAP and NIF. CAP as monotherapy and CAP + NIF as combination therapy were chosen for the forthcoming study on old SHR.

Saudi Journal of Biological Sciences published new progress about 21829-25-4. 21829-25-4 belongs to pyridine-derivatives, auxiliary class Membrane Transporter/Ion Channel,Calcium Channel, name is Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and the molecular formula is C17H18N2O6, Product Details of C17H18N2O6.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Boot, Arnoud published the artcileAnticancer activity of novel pyrido[2,3-b]indolizine derivatives: the relevance of phenolic substituents, Formula: C7H7ClN2, the publication is Anticancer Research (2014), 34(4), 1673-1678, database is CAplus and MEDLINE.

Background/Aim: The potential of indolizine derivatives as anticancer agents has been shown through recent studies. Herein, we present our exptl. results, showing that pyrido[2,3-b]indolizine derivatives are effective against colorectal cancer (CRC) cell lines. Materials and Methods: Several pyrido[2,3-b]indolizine derivatives were synthesized and their anticancer potential was evaluated against three CRC cell lines and two normal fibroblast cultures. Results: Our experiments identified 4-(3,4)-dihydroxyphenyl)-2-phenylpyrido[2,3-b]indolizine-10-carbonitrile (4f) as being active against all CRC cell lines at concentrations non-cytotoxic against fibroblast cultures. Addnl., cell-cycle anal. indicated that pyrido[2,3-b]indolizines can affect cell-cycle progression, with treated cells accumulating in the S- and G₂/M-phase. Conclusion: The hydroxyl groups in both the 3- and 4- positions of the aromatic substituent on C4 of the indolizine nucleus are crucial for activity against CRC cell lines. Further manipulation of the number and position of hydroxyl substituents on the aromatic rings may lead to improved anticancer activity of this class of compounds

Anticancer Research published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Formula: C7H7ClN2.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Yao, Xin published the artcileSurfactants Accelerate Crystallization of Amorphous Nifedipine by Similar Enhancement of Nucleation and Growth Independent of Hydrophilic-Lipophilic Balance, Computed Properties of 21829-25-4, the publication is Molecular Pharmaceutics (2022), 19(7), 2343-2350, database is CAplus and MEDLINE.

Amorphous formulations, increasingly employed to deliver poorly soluble drugs, generally contain surfactants to improve wetting and dissolution These surfactants are often liquids and can potentially increase the mobility of the drug and reduce its stability, but little is known about this effect. Here we investigate the effect of four common nonionic surfactants (Tween 80, Span 80, Triton X-100, and Poloxamer 407) on the crystallization of amorphous nifedipine (NIF). We find that the surfactants significantly enhance the rates of crystal nucleation and growth even at low concentrations, by up to 2 orders of magnitude at 10 wt %. The surfactants tested show similar enhancement effects independent of their structural details and hydrophilic-lipophilic balance (HLB), suggesting that surfactant adsorption at solid/liquid interfaces does not play a major role in crystal nucleation and growth. Importantly, the surfactants accelerate crystal nucleation and growth by a similar factor. This result mirrors the previous finding that a polymer dopant in a mol. glass-former causes similar slowdown of nucleation and growth. These results indicate that nucleation and growth in a deeply supercooled liquid are both mobility-limited, and a dopant mainly functions as a mobility modifier (enhancer or suppressor depending on the dopant). The common surfactants tested are all mobility enhancers and destabilize the amorphous drug, and this neg. effect must be managed using stabilizers such as polymers. The effect of surfactants on nucleation can be predicted from the effect on crystal growth and the crystallization kinetics of the pure system, using the same principle previously established for drug-polymer systems. We show how the independently measured nucleation and growth rates enable predictions of the overall crystallization rates.

Molecular Pharmaceutics published new progress about 21829-25-4. 21829-25-4 belongs to pyridine-derivatives, auxiliary class Membrane Transporter/Ion Channel,Calcium Channel, name is Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and the molecular formula is C9H7NO2, Computed Properties of 21829-25-4.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Martinez, Kristina published the artcilePhotophysics of Ru(II) complexes with hydroxylated diimine ligands: Photoinduced electron/proton transfer to anthraquinone, Name: 2-Pyridinylboronic acid, the publication is Polyhedron (2021), 115376, database is CAplus.

This manuscript reports the reaction of the ³MLCT excited states of two luminescent chromophores, [(bpy)₂Ru(OHbpy)]²⁺ and [(bpy)₂Ru(OMebpy)]²⁺ (bpy = 2,2â€?bipyridine, OHbpy = 4-hydroxy-2,2â€?bipyridine, OMebpy = 4-methoxy-2,2â€?bipyridine), with anthraquinone (AQ). A series of luminescence, electrochem., spectrophotometric and transient absorption studies were done in order to determine free energies for the potential reaction paths between the photoexcited complexes and AQ. For the OMebpy complex, only excited state electron transfer (ET*) from the ³MLCT state of the complex to AQ was possible. However, for the OHbpy complex, the excited state could react with AQ via a variety of pathways including excited state electron transfer, ET*, excited state proton transfer (PT*) and excited state proton coupled electron transfer (PCET*). The thermodn. anal. revealed that, for the OHbpy complex PT* was very endergonic and not a viable reaction pathway, however both ET* and PCET* could occur. Luminescence quenching studies revealed that both the OHbpy and the OMebpy excited complexes reacted with AQ (k_q âˆ?10⁹ M^-1s^-1 for both). Transient absorption anal. showed that, for the OMebpy complex, no photoproducts escaped the encounter complex associated with the quenching reaction. The result is consistent with strong electrostatic association of the 3+/1- encounter complex. For the OHbpy complex transient absorption results clearly show the formation of PCET* products from the encounter complex. The result represents one of a small number of examples of excited states of chromophores reacting via proton coupled electron transfer within an encounter complex.

Polyhedron published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, Name: 2-Pyridinylboronic acid.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Pelchowicz, Zvi published the artcileSubstituted tryptamines and their derivatives, HPLC of Formula: 102236-19-1, the publication is Journal of the Chemical Society (1960), 4699-701, database is CAplus.

o-MeC₆H₄NH₂ (21.3 g.), 54 ml. concentrated HCl, and 236 ml. H₂O diazotized with 15 g. NaNO₂, 10% aqueous Na₂CO₃ added at 0° to bring the pH to 5-6, the whole filtered, added to 34 g. Et 2-oxopiperidine-3-carboxylate (I), 400 ml. H₂O, and 12 g. KOH (kept 24 hrs. at room temperature before use), the pH adjusted to 34 with AcOH, and the whole kept 48 hrs. at 0° gave 35 g. 3-(o-tolyl)hydrazone of 2,3-dioxopiperidine (II), m. 140.0-40.5° (aqueous alc.). 3-(p-Tolyl)hydrazone of 2,3-dioxopiperidine (III) was similarly obtained, 81%, m. 209-9.5°. Crude II (45 g.), 200 ml. AcOH, and 100 ml. concentrated HCl refluxed 1 hr., cooled, and diluted with H₂O gave 28.8 g. 1,2,3,4-tetrahydro-8-methyl-1-oxo-β-carboline (IV), m. 228.5-29° (aqueous alc.); III similarly gave 83% 6-Me analog of IV, m. 187.5-8.5° (aqueous alc.). III (28 g.), 260 ml. alc., and 260 ml. 4N aqueous KOH refluxed 1 hr., concentrated to half volume, diluted with 250 ml. H₂O, and neutralized with AcOH gave 24 g. 7-methyltryptamine-2-carboxylic acid (V), m. 278-81°; the 5-Me analog (VI) of V was obtained similarly, 83%, m. 267-7.5° (decomposition). V (10.5 g.) and 400 ml. 5% HCl refluxed until CO₂ evolution ceased, the whole cooled, and neutralized with NaOH gave 7.2 g. 7-methyltryptamine (VII), purified by sublimation, m. 130-1°; 5-methyltryptamine, obtained in 76% yield from VI, m. 99-9.5° (Et₂O-petr. ether). Diazotized 5,2-FMeC₆H₃NH₂ and I as above gave 72% 5-F derivative (VIII) of II, m. 204.5-5.0°, and VIII was used as above to obtain 73% 5-F derivative of IV, m. 204.5-5.0° (aqueous alc.), 80% 4-F derivative of V, m. 273° (decomposition) (H₂O), and 4-F derivative of VII, m. 141-2° (after sublimation). VIII (5 g.), 100 ml. 10% aqueous AcH, 16 ml. 2N H₂SO₄, and 100 ml. H₂O heated 0.33 hr. at 110°, cooled, and treated with excess alkali gave 4.9 g. 6-fluoro-1,2,3,4-tetrahydroharmaline, m. 201-2° (by sublimation) (L.D.₅₀ 600 mg./kg. in mice). VIII (5.74 g.), 1 g. NaHCO₃, and 25 ml. Ac₂O refluxed 0.25 hr., poured into H₂O, the whole treated with excess Na₂CO₃, and extracted with Et₂O gave 5.5 g. N^α-Ac derivative (IX), m. 127.5-8.0° (Et₂O-petr. ether). To 5 g. IX in 200 ml. hot xylene was added in small portions 50 g. P₂O₅; the whole refluxed 2 hrs., the solid filtered off and added in small portions to 500 ml. 5% HCl, the whole heated at 80°, filtered, the filtrate cooled, treated with excess alkali and extracted with Et₂O gave 6-fluoro-3,4-dihydroharmaline, m. 206-7° (aqueous alc.).

Journal of the Chemical Society published new progress about 102236-19-1. 102236-19-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Chloride, name is 5-(tert-Butyl)-2-chloropyridine, and the molecular formula is C9H12ClN, HPLC of Formula: 102236-19-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Lazcano-Perez, Fernando published the artcileA Sea Anemone Lebrunia neglecta Venom Fraction Decreases Boar Sperm Cells Capacitation: Possible Involvement of HVA Calcium Channels, Computed Properties of 21829-25-4, the publication is Toxins (2022), 14(4), 261, database is CAplus and MEDLINE.

Sea anemones produce venoms characterized by a complex mixture of low mol. weight compounds, proteins and peptides acting on voltage-gated ion channels. Mammal sperm cells, like neurons, are characterized by their ion channels. Calcium channels seem to be implicated in pivotal roles such as motility and capacitation. In this study, we evaluated the effect of a low mol. weight fraction from the venom of the sea anemone Lebrunia neglecta on boar sperm cells and in HVA calcium channels from rat chromaffin cells. Spermatozoa viability seemed unaffected by the fraction whereas motility and sperm capacitation were notoriously impaired. The sea anemone fraction inhibited the HVA calcium current with partial recovery and no changes in chromaffin cells’ current kinetics and current-voltage relationship. These findings might be relevant to the pharmacol. characterization of cnidarian venoms and toxins on voltage-gated calcium channels.

Toxins published new progress about 21829-25-4. 21829-25-4 belongs to pyridine-derivatives, auxiliary class Membrane Transporter/Ion Channel,Calcium Channel, name is Dimethyl 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate, and the molecular formula is C17H18N2O6, Computed Properties of 21829-25-4.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Gentile, Gabriella published the artcileIdentification of 2-(4-pyridyl)thienopyridinones as GSK-3β inhibitors, HPLC of Formula: 612845-44-0, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(16), 4823-4827, database is CAplus and MEDLINE.

The discovery of a novel series of 2-(4-pyridyl)thienopyridinone GSK-3β inhibitors is reported. X-ray crystallog. reveals its binding mode and enables rationalization of the SAR. The initial optimization of the template for improved cellular activity and predicted CNS penetration is also presented.

Bioorganic & Medicinal Chemistry Letters published new progress about 612845-44-0. 612845-44-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Ether,Boronic Acids,Boronic acid and ester, name is (6-Ethoxypyridin-3-yl)boronic acid, and the molecular formula is C7H10BNO3, HPLC of Formula: 612845-44-0.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Banks, R. Eric published the artcileN-Fluoropyridinium trifluoromethanesulfonate and 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate: the first experimental determination of the F-N⁺ bond length involving sp² nitrogen, Safety of 1-Fluoropyridiniumtriflate, the publication is Acta Crystallographica, Section C: Crystal Structure Communications (2003), C59(4), m141-m143, database is CAplus and MEDLINE.

The crystal structures of N-fluoropyridinium trifluoromethanesulfonate (I) and 1-fluoro-2,4,6-trimethoxy-1,3,5-triazinium hexafluoroantimonate (II) were determined I is monoclinic, space group P2₁/c, with a 6.027(2), b 12.901(4), c 12.490(3) Å, β 103.96(3)°; Z = 4, d_c = 1.742; R = 0.045, R_w(F²) = 0.149 for 1658 reflections. II is monoclinic, space group P2₁/n, with a 7.616(2), b 11.843(3), c 14.924(3) Å, β 97.43(2)°; Z = 4, d_c = 2.119; R = 0.034, R_w(F²) = 0.071 for 2335 reflections. The N-F bond lengths in I, a known electrophilic fluorinating agent, and its novel analog II are 1.357(4) and 1.354(4) Å, resp.

Acta Crystallographica, Section C: Crystal Structure Communications published new progress about 107263-95-6. 107263-95-6 belongs to pyridine-derivatives, auxiliary class Fluorination reagent, name is 1-Fluoropyridiniumtriflate, and the molecular formula is C6H5F4NO3S, Safety of 1-Fluoropyridiniumtriflate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Kolekar, Yuvraj A. published the artcilePd-Catalyzed Oxidative Aminocarbonylation of Arylboronic Acids with Unreactive Tertiary Amines via C-N Bond Activation, HPLC of Formula: 197958-29-5, the publication is Journal of Organic Chemistry (2021), 86(20), 14028-14035, database is CAplus and MEDLINE.

An efficient synthesis of tertiary amides from aryl boronic acids and inert tertiary amines through the oxidative carbonylation via C(sp³)-N bond activation is presented. This protocol significantly restricts the homocoupling biarylketone product. It involves the use of a homogeneous PdCl₂/CuI catalyst and a heterogeneous Pd/C based catalyst, which promotes C(sp³)-N bond activation of tertiary amines with aryl boronic acids. This process represents a ligand-free, base-free, and recyclable catalyst along with an ideal oxidant like mol. oxygen.

Journal of Organic Chemistry published new progress about 197958-29-5. 197958-29-5 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester, name is 2-Pyridinylboronic acid, and the molecular formula is C5H6BNO2, HPLC of Formula: 197958-29-5.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem