4737-19-3

Basic information

• Product Name: 2-isocyanatopyridine
• Synonyms: 2-isocyanatopyridine;2-Pyridyl Isocyanate;Isocyanic Acid 2-Pyridyl Ester;Picolinic Isocyanate;Pyridin-2-yl Isocyanate;2-isocyanato-Pyridin
• CAS NO: 4737-19-3
• Molecular Formula: C₆H₄N₂O
• Molecular Weight: 120
• Mol File: 4737-19-3.mol

Chemical Properties

• Boiling Point: 181.9±13.0 °C(Predicted)
• Appearance: /
• Density: 1.12±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 2.29±0.12(Predicted)
• CAS DataBase Reference: 2-isocyanatopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-isocyanatopyridine(4737-19-3)
• EPA Substance Registry System: 2-isocyanatopyridine(4737-19-3)

Safety Data

• Hazardous Substances Data: 4737-19-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Isocyanatopyridine is used as a key intermediate in the preparation of ergolines, which serve as antagonists of the chemokine receptor CXCR3. These ergoline derivatives have potential applications in the treatment of various inflammatory and immune disorders.
Additionally, 2-isocyanatopyridine is utilized in the synthesis of benzothiazoles, which are analogs of BMS-243117. These benzothiazole derivatives act as potent and selective inhibitors of the protein tyrosine kinase p56lck, a target enzyme involved in various cellular processes, including T-cell activation and oncogenic transformation. This makes them promising candidates for the development of drugs targeting autoimmune diseases and cancer.

Upstream product

• 17175-39-2 N,N-dimethyl-N'-pyridin-2-yl-formamidine 
• 504-29-0 2-aminopyridine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 94258-23-8 N-(2-pyridyl)diphenylacetamide 
• 98-98-6 2-Picolinic acid 
• 541-41-3 chloroformic acid ethyl ester 
• 5029-67-4 2-iodopyridine 
• 201230-82-2 carbon monoxide 
• 18510-73-1 3-(2-pyridyl)-2H-pyrido<1,2-a>-1,3,5-triazine-2,4(3H)-dione 
• 4013-71-2 pyridine-2-carbonyl azide 

Downstream Products

• 2327-17-5 N-phenyl-N'-(pyrid-2-yl)urea 
• 21780-59-6 N-benzyl-N'-(2-pyrid-2-yl)urea 

Relevant articles and documents

Complexation of phosphates by 1,3-bis(3-(2-pyridylureido)propyl)-1,1,3,3-tetramethyldisiloxane

Rationale Compounds containing a urea or thiourea moiety form complexes with anions thanks to the ability to form quite strong hydrogen bonds. We have synthesized 1,3-bis(3-(2-pyridylureido)propyl)-1,1,3,3-tetramethyldisiloxane (1). Compound 1 contains two urea moieties connected by a long flexible linker; thus, it should be able to adopt a structure suitable for formation of quite stable complexes with anions. Methods The ability to form complexes of compound 1 with phosphates was tested by electrospray ionization mass spectrometry (ESI-MS). Full scan ESI mass spectra and collision-induced dissociation tandem mass (CID-MS/MS) spectra of the ions of interest were obtained on a quadrupole time-of-flight (QTOF) mass spectrometer. Results It has been found that compound 1 is not only much more prone to form complexes with the phosphate anion than with other inorganic anions, but it is also able to form complexes with organic phosphates, namely nucleotides and phospholipids. However, compound 1 is not able to form complexes with organic compounds not containing a phosphate group (e.g. nucleosides, sugars, glycerolipids). Conclusions Compound 1 can be regarded as selective towards phosphate-containing organic compounds. Formation of such complexes may have some interesting applications for identification of organic phosphates in crude extracts from biological materials.

A diastereoselective approach to axially chiral biaryls via electrochemically enabled cyclization cascade

A diastereoselective approach to axially chiral imidazopyridine-containing biaryls has been developed. The reactions proceed through a radical cyclization cascade to construct the biaryls with good to excellent central-to-axial chirality transfer.

UREA INHIBITORS OF MICRO-RNA

The present disclosure relates to compounds and methods which may be useful as inhibitors of the expression of miRNA, for use in the treatment or prevention of cancer.

Selective host-guest interactions in metal-organic frameworks: Via multiple hydrogen bond donor-acceptor recognition sites

Targeted recognition of medium sized molecules with mixed hydrogen bond units is essential for using porous materials for molecular separation, sensing and drug delivery. One promising way to achieve selectivity, is to make use of the key-and-lock principle guiding the design of hydrogen bond receptors matching the chemical signature of the target molecules. Among the class of porous materials metal-organic frameworks are particularly well suited for this purpose, as they allow for functionalizing the inner surfaces with various pending groups. Here we report the successful incorporation of 2-pyridyl urea (URPy) side groups with hydrogen bond donor-donor-acceptor (DDA) patterns into the framework MIL-101 with pores in the mesoporous range. Their influence on the sorption properties was investigated by competitive adsorption of 2-aminopyridine (2-AP) and 3-aminopyridine (3-AP) on MIL-101-URPy (Al, Cr) derivatives and comparison to the behaviour of a single donor function within MIL-101-NH2 (Al, Cr) derivatives. Grafting the coordinatively unsaturated sites at the inorganic building units (IBUs) with diethylamine, additionally allowed the adsorption at these sites to be suppressed and thus to focus on the hydrogen bond receptors. Compared to the single D sites the selectivity of 2-AP over 3-AP is enhanced by a factor of five for the DDA pending groups. Based on 15N NMR spectroscopy and DFT calculations this observation is explained by forming double hydrogen bonds between the pyridyl urea groups and the 2-AP molecules, while 3-AP exhibits a single hydrogen bond only. At the D site of MIL-101-NH2 both 2-AP and 3-AP form single hydrogen bonds only.

Electrochemical Synthesis of Imidazo-Fused N-Heteroaromatic Compounds through a C?N Bond-Forming Radical Cascade

We have developed a unified strategy for preparing a variety of imidazo-fused N-heteroaromatic compounds through regiospecific electrochemical (3+2) annulation reaction of heteroarylamines with tethered internal alkynes. The electrosynthesis employs a novel tetraarylhydrazine as the catalyst, has a broad substrate scope, and obviates the need for transition-metal catalysts and oxidizing reagents.

Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin

Nematodes are serious constraints of crop production worldwide. However, the traditional nematicides suffer from the side-effects, including environmental and human toxicity. Herein, more than 70 novel piperazinedione derivatives based on the natural product Barettin were synthesized and evaluated against the root-knot nematode Meloidogyne incognita (M. incognita). While most of synthesized compounds exhibited certain nematicidal activity at high concentration, the best one showed a nematicidal activity of 75% at 2.4 μmol/L.

Azine-imidazole aza-BODIPY analogues with large Stokes shift

A series of azine-imidazole aza-BODIPY analogues has been prepared by a simple synthesis from 2-azinecarboxylic acids and imidazole N-oxides. The new fluorescent complexes exhibit large Stokes shifts (up to 10?000?cm?1), fluorescence in crystal

TRIAZOLONE COMPOUNDS AND USES THEREOF

The invention disclosed herein is directed to compounds of Formula (la) and (lb) and pharmaceutically acceptable salts thereof, which are useful in the treatment of prostate, breast, colon, pancreatic, human chronic lymphocyticδ leukemia, melanoma and other cancers. The invention also comprises pharmaceutical compositions comprising a therapeutically effective amount of compound of Formula (la) or (lb), or a pharmaceutically acceptable salt thereof. The invention disclosed herein is also directed to methods of treating prostate, breast, ovarian, liver, kidney, colon, pancreatic, human chronic lymphocytic leukemia, melanoma and other cancers. The invention disclosed herein is further directed to methods of treating prostate, breast, colon, pancreatic, chronic lymphocytic leukemia, melanoma and other cancers comprising administration of a therapeutically effective amount of a compound which is a dual antagonist of PPARα and PPARδ. The compounds and pharmaceutical compositions of the invention are also useful in the treatment of viral infections, such as HCV infections and HIV infections. The invention disclosed herein is also directed to a methods of preventing the onset of and/or recurrence of acute and chronic myeloid leukemia, as well as other cancers, comprising administration of a herapeutically effective amount of a dual antagonist of PPARα and PPARδ.

Advances in tetrahydropyrido[1,2-a]isoindolone (valmerins) series: Potent glycogen synthase kinase 3 and cyclin dependent kinase 5 inhibitors

Abstract An efficient synthetic strategy was developed to modulate the structure of the tetrahydropyridine isoindolone (Valmerin) skeleton. A library of more than 30 novel final structures was generated. Biological activities on CDK5 and GSK3 as well as cellular effects on cancer cell lines were measured for each novel compound. Additionally docking studies were performed to support medicinal chemistry efforts. A strong GSK3/CDK5 dual inhibitor (38, IC50 GSK3/CDK5 32/84 nM) was obtained. A set of highly selective GSK3 inhibitors was synthesized by fine-tuning structural modifications (29 IC50 GSK3/CDK5 32/320 nM). Antiproliferative effects on cells were correlated with the in vitro kinase activities and the best effects were obtained with lung and colon cell lines.

Ketenes from N-(2-Pyridyl)amides

Methoxycarbonylketene 4a, methoxycarbonyl(methyl)ketene 4b, chloroketene 4c, cyanoketene 4d, diphenylketene 4e, and 2-pyridylketene 4f have been generated by flash vacuum thermolysis of the corresponding 2-pyridylacetamide derivatives 3a-f and isolated in Ar matrices for FT-IR spectroscopic characterisation. The N-(2-pyridyl)-2-pyridylacetamide 3f yielded 2-pyridyl isocyanate in addition to 2-pyridylketene.