Category: pyridine-derivatives

Willems, J. published the artcile< Aliphatic hydroxysulfonic acids and their internal esters: the sultones. II. The sultones>, Formula: C9H13NO3S, the main research area is .

CHR.(CH2)n.CHR’.SO2 (I) were prepared by concentration of an alc. solution of HOCHR(CH2)nCHR’SO3H (II) (from treating the Na salt in alc. with dry HCl) and distillation in vacuo (those of high mol. weight may decompose), by addition of Butyl Cellosolve (III) to the concentrated solution, distillation at 760 mm. until the b.p. (170°) of III is reached, and rectification in vacuo, and by addition of the alc. solution of II dropwise to boiling, stirred xylene (3 l. per mol), and the H2O distilled off as an azeotropic mixture of H2O-alc.-xylene until the b.p. of xylene is reached, the volume kept constant by dropwise addition of xylene, the solution cooled, washed with 2% NaHCO3 (important to keep from decomposition), and with H2O, dried, and the I obtained by distillation or precipitation with ligroine. The last method is generally applicable, simplest, and gives the best yields. The rate of reaction is not influenced by the pH, or by dehydrating agents. The reaction takes place near 150°, and not in low-boiling diluents, e.g. C6H6. 5- and 6-membered sultone rings are easily formed, and a 7-membered ring was obtained, but I could not be formed when n = 2 or 11. The following derivatives of I were prepared [R, n, R’, b.p./mm., m.p., d25, n25, M R, and m.p. of the corresponding pyridinoalkylsulfonic acid betaine (from boiling I in excess C5H5N), and its crystallizing solvent given]: H, 1, H (IV), 121°/1 (140°/8), 31°, -, -, -, 261°, alc.-H2O; H, 2, H (V), 153°/14, 15°, 1.3319, 1.4615, 28.15, 239°, isoamyl alc.; Me, 1, H (VI), 124°/2 (157.5°/14), -, 1.2929, 1.4500, 28.20, 240°, EtOH; H, 1, Me (VII), 124°/1.5, -, 1.3004, 1.4525, 28.24, 246°, MeOH; Me, 1, Me, 129°/1, -, 1.2220, 1.4511, 33.00, 270-71°, EtOH; H, 3, H (VIII), 155-6°/2, -, 1.2542, 1.4605, 32.65, 233-4°, EtOH; Me, 1, Pr (IX), 143-3.5°/4.2, -, 1.3359, 1.4520, 42.10, 230-32°, BuOH-Et2O; Bu, 1, H, 141°/2, -, -, -, -, 262-3°, EtOH-Et2O; Pr, 2, H, 126°/0.4, -, -, -, -, 263-4°, EtOH-Et2O; Me2CH(CH2)2, 1, H, 130°/1.5, -, -, -, -, 229-30°, absolute EtOH-Et2O; Me, 1, Me(CH2)5, 145°/0.6, -, -, -, -, 185°, EtOH-Et2O; Me(CH2)7, 1, H, 160-3°/0.5, -, -, -, -, 222.5-3.0°, BuOH; Me, 1, Me(CH2)13, -, half solid oil, -, -, -, 155°, EtOH/Et2O; Me(CH2)15, 1, H, -, 81° (EtOH), -, -, -, 214-15°, absolute EtOH; Me, 1, Ph, -, 106° (EtOH), -, -, -, 295-6.5°, EtOH-H2O. Also prepared were: O.CHMe.CH2.CMe2.SO2 (X), 160°/16, 50.5° (ligroine-Et2O), -, -, -, 253-4°, AmOH; O.CHMe.CHMe.CHPr.SO2, 128°/1.5, -, -, -, -, 245-6°, BuOH; O.CHMe.CHMe.CH[(CH2)5Me].SO2, 155°/1.5, -, -, -, -, -, – (C5H5N derivative very hygroscopic). Anilino sulfonic acids (PhNHCHRCH2CHR’SO3H) were prepared quant. by boiling equivalent amounts of PhNH2 and the following sultones 3-4 h. in C6H6 (m.p. of the PhNH derivative and crystallizing solvent given): IV, 248-9°, 90% EtOH; VI, 276-8°, H2O; VII, 254°, MeOH; X, 267-8°, EtOH; IX, 235.5-6°, BuOH. The reactions with PhNH2 and C5H5N show I to be alkylating agents, which provide a method for introducing the SO3 group and the attendant H2O solubility into certain compounds Also 1.g. IV mixed in a mortar with 1.09 g. p-H2NC6H4OH, the mixture heated 30 min. on the H2O bath, boiled with Me2CO to remove unreacted p-H2NC6H4OH, and crystallized from H2O, yielded 83% p-HOC6H4NH(CH2)3SO3H, m. 249°; 1.36 g. V boiled 6 h. in 25 cc. xylene with 1.29 g. octylamine gave Me(CH2)7NH(CH2)4SO3H.H2O, m. 172-3°. V (2.72 g.) with 2.88 g. β-naphthol in 0.8 g. NaOH solution precipitated immediately β-C10H7O(CH2)4CO3Na (beautiful crystals from EtOH-H2O). Similarly, VIII yielded 93% β-C10H7O(CH2)5SO3Na. The sultones keep their sulfoalkylating properties when reacting with RMgBr. V (13.6 g.) in absolute Et2O, dropped into Et2O containing EtMgBr (from 10.9 g. EtBr and 3 g. Mg) yielded 60% Me(CH2)5SO3K (phenylhydrazine salt, m. 101.5-2°, gave no depression of the m.p. of an authentic sample).

Bulletin des Societes Chimiques Belges published new progress about Lactones, sultones. 21876-43-7 belongs to class pyridine-derivatives, and the molecular formula is C9H13NO3S, Formula: C9H13NO3S.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Rechitskaya, E. D.; Kuratieva, N. V.; Lider, E. V.; Eremina, J. A.; Klyushova, L. S.; Eltsov, I. V.; Kostin, G. A. published the artcile< Tuning of cytotoxic activity by bio-mimetic ligands in ruthenium nitrosyl complexes>, Application In Synthesis of 93-60-7, the main research area is ruthenium nitrosyl isonicotinate nicotinate complex preparation cytotoxic activity; crystal structure ruthenium nitrosyl isonicotinate nicotinate complex.

Three novel ruthenium nitrosyl complexes [Ru(NO)Cl3(InicMe)2] (1b), [RuNOCl3(NicEt)2] (1c) and [RuNOCl3(NicMe)2] (1d) (InicMe = Me isonicotinate, NicEt = Et nicotinate, NicMe = = Me nicotinate)were prepared and crystal structure of the complexes were determined by single crystal XRD anal. In all complexes, the organic ligands are coordinated by a pyridine nitrogen atom and located in trans-position each to other and in cis-position to NO group. In the crystal package of all compounds stacking interactions of two types were determined: πarene-πarene and πCOO-πarene stacking. Finally, cytotoxicity of the compounds was tested on Hep2 and HepG2 cell lines. In the set of similar compounds mer-[RuNO(L)2Cl3] (L = Py, γ-Pic, β-Pic, Inic-Alk, Nic-Alk), complexes with iso-nicotinic acid esters are the most toxic, while nicotinic acid derivatives are less toxic and compared with pyridine complex.

Journal of Molecular Structure published new progress about Antitumor agents. 93-60-7 belongs to class pyridine-derivatives, and the molecular formula is C7H7NO2, Application In Synthesis of 93-60-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Pegu, David published the artcile< Analysis of molecular structure, vibrational spectra and electronic properties of 2-amino-3-nitro-6-picoline by density functional methods>, Recommanded Product: 2-Amino-3-nitro-6-picoline, the main research area is amino nitro picoline mol structure IR Raman electrostatic potential.

In the present study the geometrical parameters and vibrational spectroscopic properties of the compound 2-amino-3-nitro-6-picoline (2A3N6P) have been calculated by using Harteree-Fock and D. functional method (B3LYP) with 6-311++G(d,p) basis set. The calculated optimized structural parameters and the scaled frequencies are investigated and compared with earlier reported data. The complete vibrational assignment and anal. of the fundamental modes of the mol. were carried out. In addition, mol. electrostatic potential and total electron d. has been analyzed to investigate size, shape, charge d. distribution and site on chem. reactivity of the mol. Finally the Mullikan at. charges of the compound have been studied.

Pharma Chemica published new progress about Atomic charge. 21901-29-1 belongs to class pyridine-derivatives, and the molecular formula is C6H7N3O2, Recommanded Product: 2-Amino-3-nitro-6-picoline.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Alper, Pinar; Erkisa, Merve; Genckal, Hasene Mutlu; Sahin, Saliha; Ulukaya, Engin; Ari, Ferda published the artcile< Synthesis, characterization, anticancer and antioxidant activity of new nickel(II) and copper(II) flavonoid complexes>, Recommanded Product: 2,2′-Bipyridine, the main research area is nickel copper naringenin quercetin bipyridine terpyridine flavonoid preparation; anticancer antioxidant activity nickel copper flavonoid complex.

Flavonoids are natural products which are known to have biol. activity for human health. In this study, new mixed ligand complexes of Ni(II) and Cu(II) were synthesized by using flavonoid (quercetin or naringenin) and heterocyclic imine (2,2′:6′,2”-terpyridine or 2,2′-bipyridine) ligands. The new complexes are [Ni(narH-1)(terpy)Cl].4H2O (1, nar = naringenin, terpy = 2,2′:6′,2”-terpyridine), [Cu(narH-1)(terpy)Cl].H2O (2), and [Cu(queH-1)(bpy)(O3N)].1.5H2O (3, que = quercetin, bpy = 2,2′-bipyridine). The structural features of the synthesized mixed ligand complexes were investigated using elemental anal., thermogravimetric anal., Fourier transform IR spectroscopy, magnetic susceptibility and molar conductivity measurements. The resulting data demonstrated an octahedral geometry for Complex 1 and Complex 2 and square pyramidal geometry for Complex 3. Antioxidant capacity and total phenolic content of Complexes 1-3 were measured by the Folin-Ciocalteu and ABTS methods. Antiproliferative effect of complexes were tested by SRB and ATP assays on MCF-7 (breast cancer), A549 (nonsmall cell lung cancer), PC-3 (prostate cancer) and HeLa (human cervical cancer) cell lines. Apoptosis was identified using by the fluorescence imaging, caspase cleaved cytokeratin-18 and flow cytometry anal. Complex 2 and 3 had high total phenolic content and antioxidant activity. Complex 2 was found to show selective cytotoxicity through the induction of apoptosis on MCF-7 cells with having a very low IC50 value (<0.8 μM; the half maximum inhibitory concentration) while its ligands showed much higher cytotoxicity (IC50 > 50 μM). In conclusion, Complex 2 is a highly promising and novel compound for breast cancer and warrants further animal experiments

Journal of Molecular Structure published new progress about Antioxidants. 366-18-7 belongs to class pyridine-derivatives, and the molecular formula is C10H8N2, Recommanded Product: 2,2′-Bipyridine.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Duplantier, Allen J.; Becker, Stacey L.; Bohanon, Michael J.; Borzilleri, Kris A.; Chrunyk, Boris A.; Downs, James T.; Hu, Lain-Yen; El-Kattan, Ayman; James, Larry C.; Liu, Shenping; Lu, Jiemin; Maklad, Noha; Mansour, Mahmoud N.; Mente, Scot; Piotrowski, Mary A.; Sakya, Subas M.; Sheehan, Susan; Steyn, Stefanus J.; Strick, Christine A.; Williams, Victoria A.; Zhang, Lei published the artcile< Discovery, SAR, and Pharmacokinetics of a Novel 3-Hydroxyquinolin-2(1H)-one Series of Potent D-Amino Acid Oxidase (DAAO) Inhibitors>, COA of Formula: C6H6N2O, the main research area is amino acid oxidase inhibitor hydroxyquinolinone preparation SAR.

3-Hydroxyquinolin-2(1H)-one (2) was discovered by high throughput screening in a functional assay to be a potent inhibitor of human DAAO, and its binding affinity was confirmed in a Biacore assay. Cocrystn. of 2 with the human DAAO enzyme defined the binding site and guided the design of new analogs. The SAR, pharmacokinetics, brain exposure, and effects on cerebellum D-serine are described. Subsequent evaluation against the rat DAAO enzyme revealed a divergent SAR vs. the human enzyme and may explain the high exposures of drug necessary to achieve significant changes in rat or mouse cerebellum D-serine.

Journal of Medicinal Chemistry published new progress about Cerebellum. 55279-29-3 belongs to class pyridine-derivatives, and the molecular formula is C6H6N2O, COA of Formula: C6H6N2O.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Fizer, Maksym; Fizer, Oksana; Sidey, Vasyl; Mariychuk, Ruslan; Studenyak, Yaroslav published the artcile< Experimental and theoretical study on cetylpyridinium dipicrylamide - A promising ion-exchanger for cetylpyridinium selective electrodes>, SDS of cas: 123-03-5, the main research area is exptl theor cetylpyridinium dipicrylamide ion exchanger; cetylpyridinium phthalate ion selective electrode.

The cetylpyridinium (CP) dipicrylamide (DPA) ion pair was synthesized and characterized by the FTIR and NMR (1H and 13C) spectroscopy, theor. studied and tested as ion-exchanger for cetylpyridinium selective electrodes. The mol. dynamics and further DFT optimization indicate face-to-face π-π stacking interaction between pyridinium and 2,4,6-trinitrophenyl rings. The presence of weak interactions between hydrogens of cetyl chain and oxygens of nitro groups of DPA anion was confirmed by RDG function anal. Numeric reactivity descriptors computed at the B3LYP/6-31+G(d,p) level of theory show that CP-DPA has electrophilic character and can readily react with bases. Two fabricated electrodes with the CP-DPA ion-exchanger showed near-Nernstian responses towards CP chloride in the concentration range from 1 × 10-2 to 1 × 10-5 mol/L. In the case where di-Bu phthalate was used as plasticizer, the slope is 57.2 ± 1.3 mV/decade, whereas for the case of dioctyl phthalate the slope is 61.6 ± 1.2 mV/decade.

Journal of Molecular Structure published new progress about Density functional theory, B3LYP. 123-03-5 belongs to class pyridine-derivatives, and the molecular formula is C21H38ClN, SDS of cas: 123-03-5.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Schubert, S.; Brans, R.; Reich, A.; Hansen, A.; Buhl, T.; Skudlik, C.; Mempel, M.; Schoen, M. P.; John, S. M.; Geier, J. published the artcile< Assessment of occupational exposure and spectrum of contact sensitization in metalworkers with occupational dermatitis: results of a cohort study within the OCCUDERM project>, Recommanded Product: 2-Mercaptopyridinen-oxide sodiumsalt, the main research area is occupational exposure contact sensitization dermatitis.

Background : Metalworkers occupationally exposed to metals, tools, metalworking fluids (MWFs), tech. oils, gloves, skin care products etc. frequently suffer from occupational dermatitis (OD). Objectives : To investigate occupational exposure and to identify relevant occupational sensitizers in metalworkers with OD, and to evaluate suitability of current German patch test recommendations for this occupational group. Patients and methods : As part of the OCCUDERM project, occupational exposure of 230 metalworkers with suspected OD patch tested in the departments of dermatol. in Goettingen and Osnabrueck (both Lower Saxony, Germany) in 2012-2017 was recorded by questionnaire. These data, as well as results, of patch testing with standardized allergens and with workplace material were analyzed. Results : Metalworking fluids and skin care products were the most important exposures. Among MWF allergens, most frequently sensitizations to formaldehyde and formaldehyde releasers, colophony/abietic acid and monoethanolamine were observed Sensitization to methylisothiazolinone (MI) was frequent, probably as part of the general European epidemic of contact allergy to MI in leave-on cosmetics. Sensitization to glove ingredients only played a minor role. Conclusions : The known occupational allergen spectrum could largely be confirmed. In order not to miss relevant sensitizations, patch testing with material from the patients workplaces in parallel to baseline and MWF series is recommended. Sensitizations diagnosed could not always be linked to particular occupational exposures.

Journal of the European Academy of Dermatology and Venereology published new progress about Allergic contact dermatitis. 3811-73-2 belongs to class pyridine-derivatives, and the molecular formula is C5H4NNaOS, Recommanded Product: 2-Mercaptopyridinen-oxide sodiumsalt.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Jiang, Xiaoyue; Ye, Weidong; Song, Xiaohua; Ma, Wenxin; Lao, Xuejun; Shen, Runpu published the artcile< Novel ionic liquid with both Lewis and Bronsted acid sites for Michael addition>, Reference of 21876-43-7, the main research area is ionic liquid Lewis Bronsted acid preparation Michael addition; Lewis and Brønsted acid sites; Michael addition; novel ionic liquid.

Ionic liquid with both Lewis and Bronsted acid sites has been synthesized and its catalytic activities for Michael addition were carefully studied. The novel ionic liquid was stable to water and could be used in aqueous solution The molar ratio of the Lewis and Bronsted acid sites could be adjusted to match different reactions. The results showed that the novel ionic liquid was very efficient for a Michael addition and the synthesis of the target compounds was achieved in good to excellent yield within several min. Operational simplicity, high stability to water and air, small amount used, low cost of the catalyst used, high yields, chemoselectivity, applicability to large-scale reactions and reusability are the key features of this methodol., which indicated that this novel ionic liquid also holds great potential for environmentally friendly processes (green chem. methods).

International Journal of Molecular Sciences published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 21876-43-7 belongs to class pyridine-derivatives, and the molecular formula is C9H13NO3S, Reference of 21876-43-7.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Mizukawa, Yuki; Ikegami-Kawai, Mayumi; Horiuchi, Masako; Kaiser, Marcel; Kojima, Masayoshi; Sakanoue, Seiki; Miyagi, Seiya; Nanga Chick, Christian; Togashi, Hiroyuki; Tsubuki, Masayoshi; Ihara, Masataka; Usuki, Toyonobu; Itoh, Isamu published the artcile< Quest for a potent antimalarial drug lead: Synthesis and evaluation of 6,7-dimethoxyquinazoline-2,4-diamines>, Reference of 3731-53-1, the main research area is dimethoxyquinazolinediamine preparation antimalarial; Antimalarial drug; Derivatization; Quinazoline-2,4-diamines; SAR.

Quinazolines have long been known to exert varied pharmacol. activities that make them suitable for use in treating hypertension, viral infections, tumors, and malaria. Since 2014, author’s have synthesized approx. 150 different 6,7-dimethoxyquinazoline-2,4-diamines and evaluated their antimalarial activity via structure-activity relationship studies. Here, author’s summarize the results and report the discovery of 6,7-dimethoxy-N4-(1-phenylethyl)-2-(pyrrolidin-1-yl)quinazolin-4-amine, which exhibits high antimalarial activity as a promising antimalarial drug lead.

Bioorganic & Medicinal Chemistry published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 3731-53-1 belongs to class pyridine-derivatives, and the molecular formula is C6H8N2, Reference of 3731-53-1.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Wu, Yue; Jiang, Zhensheng; Li, Zhihong; Gu, Jing; You, Qidong; Zhang, Xiaojin published the artcile< Click Chemistry-Based Discovery of [3-Hydroxy-5-(1H-1,2,3-triazol-4-yl)picolinoyl]glycines as Orally Active Hypoxia-Inducing Factor Prolyl Hydroxylase Inhibitors with Favorable Safety Profiles for the Treatment of Anemia>, Synthetic Route of 870997-85-6, the main research area is preparation hydroxytriazolyl picolinoyl glycine derivative HIF PHD2 inhibitor anemia.

As a gene associated with anemia, the erythropoiesis gene is physiol. expressed under hypoxia regulated by †hypoxia-inducing factor-α (HIF-α). Thus, stabilizing HIF-α is a potent strategy to stimulate the expression and secretion of erythropoiesis. In this study, we applied click chem. to the discovery of HIF prolyl hydroxylase 2 (HIF-PHD2) inhibitors for the first time, and a series of triazole compounds showed preferable inhibitory activity in fluorescence polarization assays. Of particular note was the orally active HIF-PHD inhibitor 15i (IC50 = 62.23 nM), which was almost ten times more active than the phase III drug FG-4592 (IC50 = 591.4 nM). Furthermore, it can upregulate the Hb of cisplatin-induced anemia mice (120 g/L) to normal levels (160 g/L) with no apparent toxicity observed in vivo. These results confirm that triazole compound 15i is a promising candidate for the treatment of renal anemia.

Journal of Medicinal Chemistry published new progress about Anemia. 870997-85-6 belongs to class pyridine-derivatives, and the molecular formula is C6H5BrN2O2, Synthetic Route of 870997-85-6.

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem