10261-94-6

Basic information

• Product Name: 3-Nitropyridine-2-Carbaldehyde
• Synonyms: 3-Nitropyridine-2-Carbaldehyde;3-Nitropyridine-2-carboxaldehyde;3-nitropicolinaldehyde;3-nitropyridin-2-carbaldehyde;3-Nitro-2-Pyridincarboxaldehyd;3-Nitro-2-pyridinecarboxaldehyde;3-Nitro-2-pyridinecarboxaldehyde 97%
• CAS NO: 10261-94-6
• Molecular Formula: C₆H₄N₂O₃
• Molecular Weight: 152.11
• Mol File: 10261-94-6.mol

Chemical Properties

• Boiling Point: 283.2 °C at 760 mmHg
• Flash Point: 125.1 °C
• Appearance: /
• Density: 1.432 g/cm³
• Vapor Pressure: 0.00321mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.20±0.10(Predicted)
• CAS DataBase Reference: 3-Nitropyridine-2-Carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Nitropyridine-2-Carbaldehyde(10261-94-6)
• EPA Substance Registry System: 3-Nitropyridine-2-Carbaldehyde(10261-94-6)

Safety Data

• Hazardous Substances Data: 10261-94-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron, 54, p. 6311, 1998 DOI: 10.1016/S0040-4020(98)00328-7

InChI:InChI=1/C6H4N2O3/c9-4-5-6(8(10)11)2-1-3-7-5/h1-4H

Upstream product

• 150281-83-7 2-ethenyl-3-nitropyridine 
• 67-56-1 methanol 
• 18699-87-1 2-methyl-3-nitropyridine 
• 131747-33-6 2-acetoxymethyl-4-nitropyridine 
• 5236-76-0 2-methyl-3-nitropyridine 1-oxide 
• 931-19-1 2-methylpyridine N-oxide 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 65156-92-5 (E)-N,N-dimethyl-2-(3-nitropyridin-2-yl)ethenamine 
• 36625-64-6 2-hydroxymethyl-4-nitropyridine 

Downstream Products

• 59290-85-6 3-nitropyridine-2-carboxylic acid 
• 1312605-70-1 2-(2-fluorophenyl)-1,5-naphthyridine-3-carbaldehyde 
• 1312605-71-2 1-(2-(2-fluorophenyl)-1,5-naphthyridin-3-yl)ethanol 
• 1312605-72-3 2-(1-(2-(2-fluorophenyl)-1,5-naphthyridin-3-yl)ethyl)-1H-isoindole-1,3 (2H)-dione 
• 1312605-73-4 1-(2-(2-fluorophenyl)-1,5-naphthyridin-3-yl)ethanamine 
• 1312606-13-5 C₁₅H₁₁FN₂O 
• 1312605-69-8 2-(2-fluorophenyl)-1,5-naphthyridine-3-carbonitrile 

Relevant articles and documents

Synthesis and Properties of 3-, 4-, and 5-Nitro-2-pyridinecarbaldehyde 2-pyridylhydrazones and Characterization of Their Metal Complexes

Three hydrazones, 3-, 4-, and 5-nitro-2-pyridinecarbaldehyde 2-pyridylhydrazones, were synthesized.Their properties and reactivities with metal ions and the extraction and characteristics of the resultant complexes have been investigated and compared with one another.As a result, useful information on the molecular design of highly sensitive hydrazone reagents has been obtained.

Efficient synthesis of ribonucleotide reductase inhibitors 3- aminopyridine-2-carboxaldehyde thiosemicorbazone (3-AP) and 3-amino-4- methylpyridine-2-carboxaldehyde thiosemicarbazone (3-AMP) via palladium mediated cross-coupling reactions

An efficient synthesis of potent ribonucleotide reductases inhibitors 3- amino-pyridine-2-carboxaldehyde thiosemicarbazone (3-AP) end 3-amino-4- methyl-pyridine-2-carboxaldehyde thiosemicarbazone (3-AMP) is described. The synthesis of 3-AP and 3-AMP was achieved in 4 and 5 steps, with overall yields of 61% and 39%, respectively. The synthesis featured a convergent approach utilizing a Stille coupling strategy to prepare vinylpyridine derivatives. A more economic way to synthesize vinylpyridine using Heck reaction was also discussed.

HETEROCYCLIC COMPOUNDS AND THEIR USES

Substituted bicyclic heteroaryls and compositions containing them, for the treatment of general inflammation, arthritis, rheumatic diseases, osteoarthritis, inflammatory bowel disorders, inflammatory eye disorders, inflammatory or unstable bladder disorders, psoriasis, skin complaints with inflammatory components, chronic inflammatory conditions, including but not restricted to autoimmune diseases such as systemic lupus erythematosis (SLE), myestenia gravis, rheumatoid arthritis, acute disseminated encephalomyelitis, idiopathic thrombocytopenic purpura, multiples sclerosis, Sjoegren's syndrome and autoimmune hemolytic anemia, allergic conditions including all forms of hypersensitivity, The present invention also enables methods for treating cancers that are mediated, dependent on or associated with p110δ activity, including but not restricted to leukemias, such as Acute Myeloid leukaemia (AML) Myelo-dysplastic syndrome (MDS) myelo-proliferative diseases (MPD) Chronic Myeloid Leukemia (CML) T-cell Acute Lymphoblastic leukaemia (T-ALL) B-cell Acute Lymphoblastic leukaemia (B-ALL) Non Hodgkins Lymphoma (NHL) B-cell lymphoma and solid tumors, such as breast cancer.

THIENO[2,3-D]PYRIMIDIN-4(3H)-ONE, ISOXAZOLO[5,4-D]PYRIMIDIN-4(5H)-ONE AND ISOTHIAZOLO[5,4-D]PYRIMIDIN-4(5H)-ONE DERIVATIVES AS CALCIUM RECEPTOR ANTAGONISTS

The present invention is directed to novel thieno[2,3-d]pyrimidin-4(3H)-one, isoxazolo[5,4-d]pyrimidin-4(5H)-one and isothiazolo[5,4-d]pyrimidin-4(5H)-one derivatives and pharmaceutically acceptable salts thereof of structural formula (I), wherein the variables R1, R2, R3, X and Z are as described herein. Also provided are pharmaceutical compositions comprising the compounds of formula I as well as methods of treatment employing compounds of formula I to treat a disease or disorder characterized by abnormal bone or mineral homeostasis such as hypoparathyroidism, osteoporosis, osteopenia, periodontal disease, Paget's disease, bone fracture, osteoarthritis, rheumatoid arthritis, and humoral hypercalcemia of malignancy.

PYRROLO[2,3-c]PYRIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF

The present invention provides novel pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof, processes for the preparation thereof, and compositions comprising the same. The pyrrolo[2,3-c]pyridine derivatives or pharmaceutically acceptable salts thereof of the present invention have excellent proton pump inhibition effects and possess the ability to attain a reversible proton pump inhibitory effect.

Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)

Palladium-catalyzed cross-coupling of methylboronic acid with 2-chloro- 3-nitropyridine produced 2-methyl-3-nitropyridine 4 in one step in high yield. Oxidation of 4 with selenium dioxide gave aldehyde 5. Alternatively, condensation of 4 with DMFDMA followed by oxidation gave 5 in a two step higher yielding conversion. Subsequent direct coupling of 5 with thiosemicarbazide followed by reduction of the nitro group using stannous chloride or sodium sulfide provided 3-AP (3). Reduction with sodium hydrosulfite gave 3-HAP (8). Finally a route which avoids the reduction of a nitro function was devised. Thus direct coupling of styrene with 2-chloro-3- aminopyridine 9 under Heck reaction conditions gave 16 which was converted to 17, oxidized to the aldehyde 18 and converted to 3-AP (3) with in situ deblocking of the t-Boc functionality.

2-formylpyridine thiosemicarbazone compounds

A method of treatment of tumors is provided based upon a compound of the formula STR1 Some aspects of the invention were supported in part by U.S. Public Health Service Grant CA-02817 from the National Cancer Institute and support from the Northeast NMR Facility at Yale University insofar as the use of high resolution NMR spectra is concerned that was made possible by a grant from the Chemical Division of the National Science Foundation (Grant No. CHE-7916210).

Synthesis and Antitumor Activity of Amino Derivatives of Pyridine-2-carboxaldehyde Thiosemicarbazone

Variuos substituted pyridine-2-carboxaldehyde thiosemicarbazones (12 compounds) have been synthesized and evaluated for antineoplastic activity in mice bearing the L1210 leukemia.Oxidation of 3-nitro-2-picoline, 5-nitro-2-picoline, 3-nitro-2,4-lutidine, and 5-nitro-2,4-lutidine with selenium dioxide was employed to generate the corresponding pyridine-2-carboxaldehydes, which were then converted to cyclic ethylene acetals and subsequently reduced to amino and hydroxyamino derivatives by catalytic hydrogenation.Condensation of nitro aldehydes and acetals with thiosemicarbazide afforded the respective thiosemicarbazones.Acetylation of the amino acetals and alkylsulfonation of the 5-amino acetal, followed by condensation with thiosemicarbazide was employed to yield amide thiosemicarbazones.The most active compounds synthesiszed were 3-aminopyridine-2-carboxaldehyde thiosemicarbazone and 3-amino-4-methylpyridine-2-carboxaldehyde thiosemicarbazone which produced against the L1210 leukemia, percent T/C values of 246 and 255, and 40percent 60-day long-term survivors at two daily doses of 40 mg/kg and 10 mg/kg, respectively, for six consecutive days.