Tag: M.W=100-150

Oi, Norihito published the artcileDevelopment of Novel PET Probes for Central 2-Amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic Acid Receptors, SDS of cas: 903899-13-8, the publication is Journal of Medicinal Chemistry (2015), 58(21), 8444-8462, database is CAplus and MEDLINE.

The authors document the development of PET probes for central AMPA receptors and their application to in vivo animal imaging. An initial screening of perampanel derivatives was performed to identify probe candidates. Despite the high autoradiog. contrast yielded by several radioligands, rat PET scans did not support their in vivo suitability. Further focused derivatization and a second screening by ex vivo LC-MS measurements led to the selection of 2-[1-(3-methylaminophenyl)-2-oxo-5-(pyrimidin-2-yl)-1,2-dihydropyridin-3-yl]benzonitrile, 21a, and its analogs as candidates. [¹¹C]21a was shown by autoradiog. to specifically bind to the neocortex and hippocampus, consistent with AMPA receptor localization. PET imaging with [¹¹C]21a demonstrated moderate uptake of radioactivity in rat and monkey brains, with the retention of radiosignals being consistent with that from the autoradiogram data, and the uptake was blocked by pretreatment with unlabeled 21a in a dose-dependent manner. The current approach has facilitated the discovery of a PET probe potentially suitable for translational research and development focused on AMPA receptors.

Journal of Medicinal Chemistry published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C5H6BNO3, SDS of cas: 903899-13-8.

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

Shang, Ming published the artcileCu(II)-Mediated C-H Amidation and Amination of Arenes: Exceptional Compatibility with Heterocycles, Computed Properties of 18437-58-6, the publication is Journal of the American Chemical Society (2014), 136(9), 3354-3357, database is CAplus and MEDLINE.

A Cu(OAc)₂-mediated C-H amidation and amination of arenes and heteroarenes has been developed using a readily removable directing group. A wide range of sulfonamides, amides, and anilines function as amine donors in this reaction. Heterocycles present in both reactants are tolerated, making this a broadly applicable method for the synthesis of a family of inhibitors including 2-benzamidobenzoic acids and N-phenylaminobenzoates.

Journal of the American Chemical Society published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C2H3N3, Computed Properties of 18437-58-6.

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

Li, Hao published the artcileEfficient Synthesis of 1,9-Substituted Benzo[h][1,6]naphthyridin-2(1H)-ones and Evaluation of their Plasmodium falciparum Gametocytocidal Activities, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid, the publication is ACS Combinatorial Science (2017), 19(12), 748-754, database is CAplus and MEDLINE.

A novel three-component, two-step, 1-pot nucleophilic aromatic substitution (S_NAr)-intramol. cyclization-Suzuki coupling reaction was developed for the synthesis of benzo[h][1,6]naphthyridin-2(1H)-ones (Torins). On the basis of the new efficiently convergent synthetic route, a library of Torin 2 analogs was synthesized. The antimalarial activities of these compounds were evaluated against asexual parasites using a growth inhibition assay and gametocytes using a viability assay.

ACS Combinatorial Science published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C5H6BNO3, Recommanded Product: (6-Hydroxypyridin-3-yl)boronic acid.

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

Patel, Paresma R. published the artcileIn vitro evaluation of imidazo[4,5-c]quinolin-2-ones as gametocytocidal antimalarial agents, Synthetic Route of 903899-13-8, the publication is Bioorganic & Medicinal Chemistry Letters (2016), 26(12), 2907-2911, database is CAplus and MEDLINE.

Novel imidazo[4,5-c]quinolin-2-ones, such as I, were synthesized and evaluated in asexual blood stage and late stage gametocyte assays of Plasmodium falciparum, a major causative agent of malaria. The design of these compounds is based on a recently identified lead compound from a high throughput screen. A concise synthesis was developed that allowed for generation of analogs with substitution around both the quinoline and imidazolidinone rings. Through structure-activity relationship studies, a number of potent compounds were identified that possessed excellent antimalarial activity against both the asexual and sexual stages with minimal cytotoxicity in mammalian cells. This is the first Letter describing SAR and gametocytocidal activity of imidazo[4,5-c]quinolin-2-ones, a new lead series for malaria treatment and prevention.

Bioorganic & Medicinal Chemistry Letters published new progress about 903899-13-8. 903899-13-8 belongs to pyridine-derivatives, auxiliary class Pyridine,Boronic acid and ester,Alcohol,Boronic Acids,Boronic acid and ester, name is (6-Hydroxypyridin-3-yl)boronic acid, and the molecular formula is C5H6BNO3, Synthetic Route of 903899-13-8.

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

Chang, Sheng published the artcilePd-Catalyzed desulfitative reaction of aryltrifluoroborates with sodium arenesulfinates in water, Application of 2-Pyridinylboronic acid, the publication is Applied Organometallic Chemistry (2018), 32(1), n/a, database is CAplus.

An efficient procedure for the synthesis of biaryls was catalyzed by Pd(CH₃CN)₄(BF₄)₂ is reported. This Pd-catalyzed cross-coupling reaction of aryltrifluoroborates with sodium arenesulfinates was developed under mild and environmentally benign conditions, in water without any ligand or additive. The reaction gave a range of structurally diverse unsym. bi-aryl mols. with excellent yields, in which the byproduct was sulfur dioxide. It is worth noting that this protocol is also applicable to many heterocyclic aromatics such as thiophene, furan, pyridine, quinoline, isoquinoline and indole.

Applied Organometallic 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, Application of 2-Pyridinylboronic acid.

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

Devarajan, Nainamalai published the artcileCopper-catalyzed oxidative coupling of arylboronic acids with aryl carboxylic acids: Cu₃(BTC)₂ MOF as a sustainable catalyst to access aryl esters, Application In Synthesis of 197958-29-5, the publication is Organic Chemistry Frontiers (2018), 5(15), 2322-2331, database is CAplus.

A convenient and sustainable method was demonstrated for the oxidative coupling of arylboronic acids with aryl carboxylic acids via C-O cross-coupling reaction catalyzed by the unsaturated coordination sites of copper present in the Cu₃(BTC)₂ MOF. Cu₃(BTC)₂ was employed in a MOF-based catalysis reaction with high efficiency and high chemoselectivity without the use of any external oxidants, ligands or additives. The present methodol. avoided stoichiometric reagents and special reaction conditions and showed excellent functional group tolerance with decent to excellent yields of aryl esters R¹C(O)OR² [R¹ = Ph, 4-ClC₆H₄, 2-naphthyl, etc.; R² = Me, 3-MeOC₆H₄, 4-O₂NC₆H₄, etc.]. The catalyst was found to exhibit high stability and reusability, without loss in activity even after several cycles, which was evident from the FT-IR, PXRD and SEM characterizations of the reused catalyst.

Organic Chemistry Frontiers 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, Application In Synthesis of 197958-29-5.

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

Ochiai, Eiji published the artcilePolarization of aromatic heterocyclic compounds. CV. 4-Substituted derivatives of α-picoline, Application of 4-Amino-2-picoline, the publication is Pharmaceutical Bulletin (1954), 147-9, database is CAplus.

cf. C.A. 48, 10746c. PCl₃ (10 g.) added portionwise with ice cooling to 10 g. 4-nitro-α-picoline N-oxide in 200 ml. of CHCl₃, the mixture warmed at 50° for 10 min., cooled, poured onto ice, neutralized with Na₂CO₃, extracted with CHCl₃, dried over Na₂SO₄, and evaporated gave 7 g. 4-nitro-α-picoline (I), m. 42-5° (from petr. ether). I (1 g.) dissolved in MeOH and reduced over Pd-C gave 4-amino-α-picoline, purified through the picrate, m. 193°. 4-Bromo-α-picoline (II) (picrate, m. 184-5°) was prepared by 4 methods: (1) I (1 g.) heated at 150-70° for 8 hrs. with 5 g. 48% HBr, the mixture evaporated under reduced pressure, alkalinized with Na₂CO₃, extracted with Et₂O, dried over Na₂SO₄ and evaporated gave 0.2 g. II, an oily residue, which was converted to the picrate. (2) I (5 g.), 26 g. of (H₂N)₂CO and 30 ml. 48% HBr refluxed 7 hrs., diluted with H₂O, alkalinized with Na₂CO₃, steam distilled, the distillate saturated with NaCl, extracted with Et₂O, the Et₂O extract dried over Na₂SO₄, the Et₂O removed, and the residue distilled gave 1.2 g. II, b₅ 47-56°. (3) I (3 g.) and 5 ml. AcBr heated 6 hrs. on a water bath (a red color developed), the mixture evaporated in vacuo, diluted with H₂O, alkalinized with Na₂CO₃, and extracted with Et₂O, and the extract distilled gave 1.2 g. II. (4) 4-Hydroxy-α-picoline N-oxide (10 g.) in 60 ml. CHCl₃ cooled and treated portionwise with 25 g. PBr₃ in 20 ml. CHCl₃; after the reaction subsided the mixture was refluxed 6 hrs. on a water bath and a sirupy mass precipitated The CHCl₃ layer extracted with H₂O, the sirupy residue treated with 200 ml. ice water, the aqueous solutions mixed, alkalinized with Na₂CO₃, steam distilled, the distillate saturated with NaCl, extracted with Et₂O, and the extract distilled in vacuo gave 7.8 g. II. CuCN (dried at 110° for 36 hrs.) (2.5 g.) added to 4.5 g. II, the mixture gradually heated to 150-60° when the mixture melted with darkening, the temperature raised to 180° then cooled to 120°, 1 g. CuCN added, the mixture heated 0.25 hrs. at 170-80° and distilled gave 2.2 g. 4-cyano-α-picoline (III), b_11-15 about 75°, m. 45.5-6.5° (from petr. ether); picrate, decompose 163-4° (from EtOH). III (1.5 g.) reduced over Pd-C in acid solution gave 1.6 g. 4-amino-αpicoline, decompose 274° (from MeOH); picrate, m. 195-6° (from MeOH); benzoate, m. 81-3° (from benzene).

Pharmaceutical Bulletin published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Application of 4-Amino-2-picoline.

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

Ochiai, Eiji published the artcilePolarization of aromatic heterocyclic compounds. LXVI. Reduction of 4-nitro-2-picoline 1-oxide, Safety of 4-Amino-2-picoline, the publication is Yakugaku Zasshi (1947), 158-60, database is CAplus.

Reduction of 4-nitro-2-picoline 1-oxide (I) indicated that it also had certain peculiarities which were observed in the reduction of 4-nitropyridine 1-oxide (C.A. 45, 5151h). Catalytic reduction of I in 10% HCl with 60% Pd-charcoal gave a HCl salt of 4-amino-2-picoline 1-oxide (II), needles, m. 189-91°. Further reduction of the II.HCl in AcOH-Ac₂O with 60% Pd-charcoal gave 4-amino-2-picoline (III), slightly hygroscopic cubic crystals, m. 95°; picrate, m. 193°. Catalytic reduction of I to III did not proceed well in HCl and EtOH. Reduction of I in a mixture of H₂S-saturated NH₄OH and EtOH gave 4,4′-azo-2-picoline 1,1′-dioxide (IV), red needles, m. 224-5°. Reduction of I in 10% NaOH solution with NaNO₂ at about 45° gave IV and a small amount of recovered I. MeOH as a solvent gave 4-methoxy-2-picoline 1-oxide, rhomboprisms, m. 78-80°, and no azo compound was formed. Reduction of I in glacial AcOH, EtOH, and H₂O with Zn dust also gave IV, while reduction in glacial AcOH with Zn gave 4,4′-azoxy-2-picoline 1,1′-dioxide (V), orange-red crystals, m. 220-1°, and a small amount of recovered I. Reduction in EtOH-glacial AcOH with Zn gave chiefly V with a small amount of IV, and reduction in H₂O alone in a sealed tube gave V with recovery of I. Reduction in NaOH solution gave III. Since this reduction, when carried out on a water bath about 1 hr. gave only IV with recovery of I, the reduction was assumed to proceed via the azo compound Reduction of I in HCl with SnCl₂ gave IV, as well as III, while reduction in EtOH with Na₂S₂O₄ also gave III.

Yakugaku Zasshi published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Safety of 4-Amino-2-picoline.

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

Tsukada, Tomoharu published the artcileStructure-based drug design of tricyclic 8H-indeno[1,2-d][1,3]thiazoles as potent FBPase inhibitors, SDS of cas: 197958-29-5, the publication is Bioorganic & Medicinal Chemistry Letters (2010), 20(3), 1004-1007, database is CAplus and MEDLINE.

With the goal of improving metabolic stability and further enhancing FBPase inhibitory activity, a series of tricyclic 8H-indeno[1,2-d][1,3]thiazoles was designed and synthesized with the aid of structure-based drug design. Extensive SAR studies led to the discovery of 19a (I) with an IC₅₀ value of 1 nM against human FBPase. X-ray crystallog. studies revealed that high affinity of 19a was due to the hydrophobic interaction arising from better shape complementarity and to the hydrogen bonding network involving the side chain on the tricyclic scaffold.

Bioorganic & Medicinal Chemistry Letters 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 C2H8Cl2N4S2, SDS of cas: 197958-29-5.

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

Petrow, V. published the artcileAnalgesics. II. Aryloxyalkyl oxaalkylamines, Recommanded Product: 4-Amino-2-picoline, the publication is Journal of Pharmacy and Pharmacology (1958), 86-95, database is CAplus and MEDLINE.

cf. C.A. 51, 8723b. Compounds formally related to aryloxypropanolamine in which the aryl and amine residues are joined by combinations derived from glycerol and ethylene glycol are synthesized. Adding 108 g. ο-cresol to 40 g. NaOH in 450 ml. EtOH and 40 ml. H₂O followed by 143 g. (ClCH₂CH₂)₂O and refluxing 5 hrs. formed an oil with fractons b_0.3 36-95° (52.4 g.), 100-20° (111.9 g.), and 160° (26.9 g.). The 2nd fraction yielded 5-ο-tolyloxy-3-oxapentyl chloride (I), b_0.3 92°, and the 3rd fraction yielded 1,5-bis-ο-tolyloxy-3-oxapentane, b_0.3 156°. I was heated with piperidine to form N-(5-ο-tolyloxy-3-oxapentyl)piperidine, b_0.3 130° (picrate, yellow nodules from EtOAc-ligroine, m. 77- 8°). N-(5-ο-Tolyloxy-3-oxapentyl)pyrrolidine, oil, b_0.3 122°; Δ³-piperideine analog, b_0.3 138° (picrate, yellow needles from EtOAc-ligroine, m. 92-4°). 3-Phenoxy-1,2-epoxy- propane and N-(2-hydroxyethyl)piperidine in C₆H₆ were refluxed 20 hrs. to form N-(5-hydroxy-6-phenoxy-3-oxahexyl)-piperidine, b_0.1. 150°; the 6-ο-methoxyphenoxy-3-oxahexyl analog b_0.1 160°. 2-ο-Tolyloxyethanol and 2,3-epoxypropyl chloride with polyphosphoric acid were heated at 100° for 20 hrs. to form 2-hydroxy-6-ο-tolyloxy-4-oxahexyl chloride, b_0.5 136°. 2-ο-Tolyloxyethanol was refluxed with NaOMe in MeOH for several min., the residual product was suspended in dry C₆H₆, 1-chloro-2,3-epoxypropane added, and the mixture refluxed 8 hrs. to yield from the main distillation fraction 1,2-epoxy-6-ο-tolyloxy-4-oxahexane (II) (oil, b_0.05 100°) and from the top fraction a viscous oil, b_0.07 210°. Treatment of the foregoing chlorohydrin with an equivalent of KOH in MeOH at 0° followed by dilution and extraction with CHCl₃ yielded II. II in C₆H₆ with Δ³-piperideine formed N-(2-hydroxy-6-ο-tolyloxy-4-oxahexyl)-Δ³-piperideine, b_0.3 162° [HCl salt, hygroscopic, m. 50-60°; picrate, m. 81-3° (EtOAc-Et₂O)]. 3-ο-Tolyloxy-1,2-epoxypropane and allyl alc. treated carefully with H₂SO₄ and heated at 100° for 2 hrs. yielded from the residual fraction b_0.25 120° 6-hydroxy-7-ο-tolyloxy-4-oxa-1-heptene (III), b_1.2 130-2°; the fraction b_0.25-1 124-44° contained a high proportion of 3-ο-tolyloxypropane-1,2-diol. 2-Hydroxy-3-ο-tolyloxypropyl chloride (100 g.) and 232 g. allyl alc. with 33.6 g. powd. KOH added in portions then heated at 100° for 8 hrs., diluted, and extracted with CHCl₃ yielded 97.8 g. III, b_0.1 113°. Adding 63 g. III to a cold solution of 39.15 g. perbenzoic acid in 995 ml. C₆H₆, keeping at 0° for 2 days and then room temperature for 2 days, and refractionating the fraction (37.7 g.), b_0.3 118-50°, yielded 1,2-epoxy-6-hydroxy-7-ο-tolyloxy-4-oxaheptane, b_0.4 144°, which condensed with Et₂NH in C₆H₆ to form N-(2,6-dihydroxy-7-ο-tolyloxy-4-oxaheptyl)diethylamine, b_0.3 174° (piperidine analog, b_0.4 194°). 6-Hydroxy-7-phenoxy-4-oxa-1-heptene b_0.05 110°. 1,2-Epoxy-6-hydroxy-7-phenoxy-4-oxaheptane b_0.4 140°. N-(2,6-Dihydroxy-4-oxahexyl)-p-anisidine, m. 65-7° (EtOAc-ligroine), refluxed 5 hrs. in MeOH with MeI and Na₂CO₃ formed N-methyl-N-(2,6-dihydroxy-4-oxahexyl)-p-anisidine, b_0.1 180°; the N-Et analog, b_0.1 185°. N-(2,6-Dihydroxy-4-oxahexyl)-p-phenetidine (by alk. condensation in MeOH), light yellow prisms, m. 70-2° (EtOAc-ligroine) [picrate, m. 127-8° (EtOH)]; N-Et derivative, _0.3 180°. N (2,6-Dihydroxy-4-oxahexyl)-p-propoxyaniline (61% yield) b_0.1 192-8°, light yellow needles, m. 71-3° (EtOAc-ligroine); p-butoxyaniline analog, b_0.4 195-200°, yellow needles, m. 69-71° (EtOAc-ligroine); ο-phenetidine analog, b_0.4 182-6°, pale yellow needles, m. 57-8° (EtOAc-ligroine); morpholine analog, b_0.5 144°; Δ³-piperideine analog, b_0.3, 140°; pyrrolidine analog, b_0.1 118°. N-(2,9-Dihydroxy-4,7-dioxanonyl)-p-phenetidine b_0.5 220°; picrate, bright yellow needles, m. 120-1° (EtOAc). N-(2,6-Dihydroxy-4-oxaheptyl)-p-phenetidine on fractionation (b_0.04-0.05 200-5°) gave a white solid (A), m. 102-4° (EtOAc-ligroine), soluble in hot H₂O; picrate, yellow fluffy needles, m. 130-2° (EtOAc). The concentrated mother liquors from A yielded a main fraction B, b_0.8 210°, m. 54-6° (Et₂O-ligroine), more soluble in cold H₂O than A. Tentative structures were for A, p-EtC₆H₄NHCH₂CH(OH)CH₂OCH₂CH(OH)Me, for B, p-EtC₆H₄NHCH₂CH(OH)CH₂OCHMeCH₂OH. The p-anisidine analog fractionated by b_0.5 200-20° yielded 2 isomers; the less soluble crystallized from H₂O [picrate, m. 134-6° (EtOAc-ligroine)]; the more soluble m. 64-6° (Et₂O-ligroine) [picrate, m. 12 6° (EtOAc-ligroine)]. Tentative structures were analogous to those of A and B. N-p-Ethoxyphenylmorpholine b_0.5 120°, m. 75-6° (EtOH-H₂O); HCl salt, m. 170-1° (EtOH-Et₂O). 3-(3,4,5-Trimethoxyphenyl)aminopropane-1,2-diol b_0.2 210°; HCl salt, white needles with blue-green tinge, m. 148-50° (EtOH-Et₂O). 4-ο-Tolyloxybut-2-yn-1-yl chloride b_0.3 110°. 1-Diethylamino-4-phenoxybut-2-yne, from 4-phenoxybut-2-yn-1-yl chloride and Et₂NH as the base, b_0.2 110-15°; HCl salt, m. 138-9° (EtOH-Et₂O). 1-Diethylamino-4-ο-tolyloxybut-2-yne b_0.6 126-8°; HCl salt, m. 116-17° (EtOH-Et₂O). 1-Δ³-Piperideino-4-ο-tolyloxybut-2-yne b_0.5 130°; HCl salt, m. 126-7° (iso-PrOH-Et₂O).

Journal of Pharmacy and Pharmacology published new progress about 18437-58-6. 18437-58-6 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 4-Amino-2-picoline, and the molecular formula is C6H8N2, Recommanded Product: 4-Amino-2-picoline.

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