24207-00-9

Usage

Chemical compound

5-hydroxy-2-methylpyridine 1-oxide

Also known as

Methyl 5-hydroxynicotinate or 2-methyl-5-pyridin-2-yl-1,2-dihydro-3H-pyridine 1-oxide

Derivative of

Pyridine

Commonly used in

Pharmaceutical and research applications

Potential properties

Antioxidant, anti-inflammatory, neuroprotective, anti-cancer

Potential therapeutic applications

Development of medications

Further research needed to

Fully understand and utilize properties in fields such as medicine and agriculture

InChI:InChI=1/C6H7NO2/c1-5-2-3-6(8)4-7(5)9/h2-4,8H,1H3

Upstream product

• 1121-78-4 5-Hydroxy-2-methylpyridine 

Downstream Products

• 31181-78-9 2-acetoxy-methyl-5-acetoxypyridine 
• 615568-73-5 5-methoxycarbonylmethoxy-2-methylpyridine N-oxide 
• 14162-88-0 3-hydroxy-6-methyl-2-pyridinecarboxylic acid 
• 727736-69-8 3-hydroxy-6-methylpicolinonitrile 
• 93080-64-9 diethyl N-(3-p-nitrophenoxycarbonyl-5-methylfuro<3,2-b>pyridine-2-amino)methylenemalonate 
• 93080-61-6 p-nitrophenyl 2-amino-5-methylfuro<3,2-b>pyridine-3-carboxylate 

Relevant academic research and scientific papers

Does the solid-liquid crystal phase transition provoke the spin-state change in spin-crossover metallomesogens?

Three types of interplay/synergy between spin-crossover (SCO) and liquid crystalline (LC) phase transitions can be predicted: (i) systems with coupled phase transitions, where the structural changes associated to the Cr?LC phase transition drives the spin-state transition, (ii) systems where both transifions coexist in the same temperature region but are not coupled, and (iii) systems with uncoupled phase transitions. Here we present a new family of Fe(II) metallomesogens based on the ligand tris[3-aza-4-((5-C n)(6-R)(2-pyridyl))but-3-enyl]amine, with Cn = hexyloxy, dodecyloxy, hexadecyloxy, octadecyloxy, eicosyloxy, R = hydrogen or methyl (Cn-trenH or Cn-trenMe), which affords examples of systems of types i, ii, and iii. Self-assembly of the ligands Cn-trenH and Cn-trenMe with Fe(A)2·xH2O salts have afforded a family of complexes with general formula [Fe(Cn-trenR)](A) 2· sH2O (s > 0), with A = ClO4 -, F-, Cl-, Br- and I-. Single-crystal X-ray diffraction measurements have been performed on two derivatives of this family, named as [Fe(C6-trenH)](ClO 4)2 (C6-1) and [Fe(C6-trenMe)] (ClO4)2 (C6-2), at 150 K for C6-1 and at 90 and 298 K for C6-2. At 150 K, C6-1 displays the triclinic space group P1, whereas at 90 and at 298 K C6-2 adopts the monoclinic P21/c space group. In both compounds the iron atoms adopt a pseudo-octahedral symmetry and are surrounded by six nitrogen atoms belonging to imino groups and pyridines of the ligands Cn-trenH and C n-trenMe. The average Fe(II)-N bonds (1.963(2) A) at 150 K denote that C6-1 is in the low-spin (LS) state. For C6-2 the average Fe(II)-N bonds (2.007(1) A) at 90 K are characteristic of the LS state, while at 298 K they are typical for the high-spin (HS) state (2.234(3) A). Compound C6-1 and [Fe-(C18-trenH)](ClO 4)2 (C18-1) adopts the LS state in the temperature region between 10 and 400 K, while compound C6-2 and [Fe(Cn-trenMe)](ClO4)2 (n = 12 (C 12-2), 18 (C18-2)) exhibit spin crossover behavior at T1/2 centered around 140 K. The thermal spin transition is accompanied by a pronounced change of color from dark red (LS) to orange (HS). The light-induced excited spin state trapping (LIESST) effect has been investigated in compounds C6-2, C12-2 and C 18-2. The T1/2LIESST is 56 K (C6-2), 48 K (C16-2), and 56 K (C18-2). On the basis of differential scanning calorimetry, optical polarizing microscopy, and X-ray diffraction findings for C18-1, C12-2, and C 18-2 at high temperature a smectic mesophase Sx has been identified with layered structures similar to C6-1 and C 6-2. The compounds [Fe(Cn-trenH)](Cl)2· sH2O (n = 16 (C16-3, s = 3.5, C16-4, s = 0.5, C16-5, s = 0), 18 (C18-3, s = 3.5, C18-4, s = 0.5, C18-5, s = 0), 20 (C20-3, s = 3.5, C20-4, s = 0.5, C20-5, s = 0)) and [Fe(C18-tren)](F) 2·sH2O (C18-6, s = 3.5, C 18-7, s= 0) show a very particular spin-state change, while [Fe(C18-tren)](Br)2·3H2O (C 18-8) together with [Fe(C18-tren)](I)2 (C 18-9) are in the LS state (10-400 K) and present mesomorphic behavior like that observed for the complexes C18-1, C12-2, and C18-2. In compounds Cn-3 50% of the Fe(II) ions undergo spin-state change at T1/2 = 375 K induced by releasing water, and in partially dehydrated compounds (s = 0.5) the Cr→SA phase transition occurs at 287 K (C16-4), 301 K (C18-4) and 330 K (C20-4). For the fully dehydrated materials Cn-5 50% of the Fe(II) ions are in the HS state and show paramagnetic behavior between 10 and 400 K. In the partially dehydrated Cn-4 the spin transition is induced by the change of the aggregate state of matter (solid?liquid crystal). For compound C18-6 the full dehydration to C18-7 provokes the spin-state change of nearly 50% of the Fe(II) ions. The compounds Cn-3 and C18-6 are dark purple in the LS state and become light purple-brown when 50% of the Fe(II) atoms are in the HS state.

(PYRIDIN-2-YL)AMINE DERIVATIVES AS TGF-BETA R1 (ALK5) INHIBITORS FOR THE TREATMENT OF CANCER

The present invention relates to pharmaceutical compounds, compositions and methods, especially as they are related to compositions and methods for the treatment and/or prevention of a proliferation disorder associated with ΤGFβR1 activity, such as a cancer or fibrosis. The invention provides compounds of Formula (I) and Formula (II) as further described herein having an acidic moiety that enhances tissue specificity for targeted tissues and organs. The invention includes pharmaceutical compositions, pharmaceutical combinations, and methods of use of these compounds for treating conditions including cancer or fibrosis.

Method for synthesizing 3-hydroxy-2-picolinic acid and derivatives thereof

The invention discloses an effective synthesis method of 3-hydroxy-2-picolinic acid and derivatives thereof. The method comprises an oxidation reaction, a cyanation reaction and a hydrolysis reaction.According to the oxidation reaction, 3-hydroxypyridine as shown in a formula I and derivatives thereof are used as substrates, and under the condition that an aqueous hydrogen peroxide solution is used as an oxidizing agent, the reaction is performed in glacial acetic acid at 60 DEG C in a nitrogen environment to obtain an oxidation product as shown in a structural general formula II. According to the cyanation reaction, the compound II and trimethylsilyl cyanide are taken as substrates and mixed with dimethylaminoformyl chloride in an ice bath, and then the reaction is conducted in dichloromethane at room temperature in the nitrogen environment to obtain a cyanation product as shown in a structural general formula III. According to the hydrolysis reaction, with the product as shown in the formula III as a substrate, the reaction is conducted in ethanol at a temperature of 80 DEG C under the condition of an aqueous sodium hydroxide solution to obtain the 3-hydroxy-2-picolinic acid asshown in the structural general formula IV and the derivatives thereof. The method is relatively economical, reaction universality is good, gram-level preparation is easy to carry out, the whole process can be industrialized, and reaction conditions are green.

Electronic absorption and emission properties of bishydrazone [2?×?2] metallosupramolecular grid-type architectures

Several ditopic ligands containing two tridentate bishydrazone coordination subunits and their Zn(II) and Cd(II) [2 × 2] grid-type complexes were prepared and their photoluminescent properties studied. A special attention was devoted to the influence of the orientation of the hydrazone group N–N[dbnd]in the core of the ligands and their complexes. Its reversal from [pyridine[dbnd]N–N–pyrimidine] (L1) to [pyridine–N–N[dbnd]pyrimidine] (L2) has a strong impact on the observed absorption and emission behaviour of particular ligands (L1 and L2) as well as of their [2 × 2] grid assemblies. The further lateral functionalization of the ligands led to different emission quantum yields of the resulting grids, while their emission and absorption spectra varied very little. The simplest derivative L1 turned out to have the best performance with, for its Zn(II) complex, relatively high quantum yield 60%.

The design of efficient and selective routes to pyridyl analogues of 3-oxo-3,4-dihydro-2H-1,4-(benzothiazine or benzoxazine)-6-carbaldehydes

This Letter describes the synthesis of challenging pyridyl analogues of 3-oxo-3,4-dihydro-2H-1,4-(benzothiazine or benzoxazine)-6-carbaldehydes. The six different routes described are high yielding, contain no major purification issues and have been used to give gram quantities of each aldehyde.

Electronically modified polymer-supported cinchona phase-transfer catalysts for asymmetric synthesis of α-alkyl-α-amino acid derivatives

Merrifield resin-supported hydrocinchonidinium salts containing particular functional groups that can participate in hydrogen bonding were prepared and evaluated as chiral phase-transfer catalysts using the asymmetric benzylation of glycine imine ester. These electronically modified Merrifield resin-supported phase-transfer catalysts generally provided better enantioselectivities compared to the unmodified ones. Copyright

FUSED FURAN COMPOUND

The present invention provides a condensed furan compound of the formula (I): wherein Ring X is benzene, pyridine, or the like; Y is an optionally substituted amino, an optionally substituted cycloalkyl, an optionally substituted aryl, an optionally substituted saturated heterocyclic group, an optionally substituted unsaturated heterocyclic group; A is a single bond, lower alkylene, lower alkenylidene, lower alkenylene or an oxygen atom; R3 is hydrogen or the like; and , R4 is hydrogen, or the like, or pharmaceutically acceptable salts thereof, which is useful as a medicament, particularly, as an activated blood coagulation factor X inhibitor.

ANTIBACTERIAL COMPOUNDS

Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives thereof useful in methods of treatment of bacterial infections in mammals, particularly man

NITROGEN-CONTAINING BICYCLIC HETEROCYCLES FOR USE AS ANTIBACTERIALS

Cyclohexane and cyclohexene derivatives and pharmaceutically acceptable derivatives hereof useful in methods of treatment of bacterial infections in mammals, particularly man.

Synthesis of the N-Terminal Amino Acid of the Nikkomycins I, J, X, and Z

A mixture of four stereoisomers of 2-amino-4-hydroxy-4-(5-hydroxy-2-pyridyl)-3-methylbutanoic acid (14), the N-terminal amino acid of the nikkomycin antibiotics could be synthesized in a twelve-step procedure.By comparison of 1H NMR spectra, mass spectra and of the gas chromatographic behaviour of various derivatives the constitution and relative configuration of the natural compound has been confirmed.