15268-31-2

Usage

Uses

Used in Pharmaceutical Industry:
3-Isocyanatopyridine is used as a key intermediate in the synthesis of diarylurea derivatives. These derivatives have been found to be effective as IDH2 (isocitrate dehydrogenase 2) mutant inhibitors, which play a crucial role in the treatment of various types of cancer. By targeting the IDH2 mutation, these inhibitors can help regulate cellular metabolism and potentially halt the progression of cancer cells.

Upstream product

• 4013-72-3 nicotinoyl azide 
• 462-08-8 pyridin-3-ylamine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 98-92-0 nicotinamide 
• 75-44-5 phosgene 
• 79-37-8 oxalyl dichloride 
• 636-79-3 nicotinic acid hydrochloride 
• 553-53-7 Nicotinic acid hydrazide 
• 59-67-6 nicotinic acid 
• 20260-53-1 pyridine-3-carbonyl chloride hydrochloride 

Downstream Products

• 143797-63-1 N-(1-methyl-1H-indol-5-yl)-N'-3-pyridinyl-urea 
• 60572-69-2 1-(2,2-dimethyl-propyl)-3-pyridin-3-yl-urea 
• 108832-79-7 N-cyclohexyl-N'-(3-pyridyl)carbodiimide 
• 60572-68-1 SDZ 114-712 

Relevant academic research and scientific papers

Encapsulation of [(SO4)4(H2O)12]8- clusters in a metal organic framework of pyridyl functionalized cyanuric acid based tris-urea

Encapsulation of hydrated sulfate in a bowl-shaped metal organic coordination polymer formed by Zn2+ assisted self-assembly of a 3-pyridyl terminated cyanuric acid platform based urea receptor is reported in aqueous medium. Trapping of an unusual [(SO4)4(H2O)12]8- cluster in a [Zn(H2O)6]2+ capped self-assembled structure is characterized by single crystal X-ray crystallography. Furthermore, selective binding of SO42- is established from the 1H-NMR titration study.

Naphthalene linked pyridyl urea as a supramolecular gelator: a new insight into naked eye detection of I- in the gel state with semiconducting behaviour

The gelation and anion responsive behavior of some 3-aminopyridine-based urea molecules 1-5 have been examined. Of the different pyridyl ureas, compounds 1 and 2 form an instant gel from DMSO/H2O and DMF/H2O solvents. Between the gels 1 and 2, only the gel state of 2 has been noted, for the first time, to detect iodide ions over a series of other anions through a colour change involving no phase transformation. Furthermore, the gel state of 2 is a poor semiconductor and the presence of iodide ions considerably enhances its conductivity that varies with temperature.

Stimuli-Responsive Metallogels for Synthesizing Ag Nanoparticles and Sensing Hazardous Gases

A newly synthesized bis-pyridyl ligand having a diphenyl ether backbone (LP6) displayed the ability to form crystalline coordination polymers (CP1-CP6) which were fully characterized by single crystal X-ray diffraction. Most of the resulting polymers were lattice-occluded crystalline solids—a structural characteristic reminiscent to gels. The reactants of the coordination polymers produced metallogels in DMSO/water confirming the validity of the design principles with which the coordination polymers were synthesized. Some of the metallogels displayed material properties like in situ synthesis of Ag nanoparticles and stimuli-responsive gel–sol transition including sensing hazardous gases like ammonia and hydrogen sulfide.

Novel antitumor 2-cyanoaziridine-1-carboxamides

A set of 20 2-cyanoaziridine-1-carboxamides was synthesized from 2- cyanoaziridine and appropriate isocyanates. These compounds were active against a variety of solid and hematological tumor cells in culture, including strains resistant to doxorubicin and mitoxantrone. Their potencies in these assays correlated with the lipophilicity of substituents. The N- phenyl derivative was more potent and equally effective to imexon, a cyclized 2-cyanoaziridine-1-carboxamide of clinical interest, against cloned fresh human tumors.

Synthesis and crystal structures of ZnCl2 and CdCl2 containing helical coordination polymers derived from a flexible bis(pyridylurea) ligand

A flexible bis(pyridylurea) ligand, 1,1′-[oxybis(2,1-phenylene)] bis(3-pyridin-3-ylurea) (L), has been synthesized and characterized. The interaction of L with ZnCl2 and CdCl2 has been investigated. In the structure of {[ZnLCl2]·2DMF}n (1), the flexible ligands bridge the ZnII centers to form 1D helical chains with a pitch of 9.743 ?. The P and M helical chains are arranged equally, and the whole complex 1 is racemic. In the structure of [CdLCl2(DMF)]n (2), the flexible ligands bridge CdII centers to form one-dimensional P and M helical chain structures in a similar manner. Then the chlorine atoms act as bridges in bidentate modes linking the P helical chain with M helical chain to form a 1D looped chain coordination polymer.

Spectroscopic Characterization of Nicotinoyl and Isonicotinoyl Nitrenes and the Photointerconversion of 4-Pyridylnitrene with Diazacycloheptatetraene

Recently, nicotinoyl nitrene (2) has been generated from the photodecomposition of nicotinoyl azide (1) and used as the key intermediate in probing nucleobase solvent accessibility inside cells. Following the 266 nm laser photolysis of nicotinoyl azide (1) and isonicotinoyl azide (5) in solid N2 matrices at 15 K, nicotinoyl nitrene (2) and isonicotinoyl nitrene (6) have now been identified by matrix-isolation infrared (IR) spectroscopy. Both aroyl nitrenes 2 and 6 adopt closed-shell singlet ground states stabilized by significant Nnitrene···O interactions, which is consistent with the spectroscopic analysis and calculations at the CBS-QB3 level of theory. Upon subsequent visible light irradiations, 2 (400 ± 20 nm) and 6 (532 nm) undergo rearrangement to pyridyl isocyanates 3 and 7. Further dissociation of 3 and 7 under 193 nm laser irradiation results in CO elimination and formation of ketenimines 12 and 13 via the ring opening of elusive pyridyl nitrenes 4 and 8, respectively. In addition to the IR spectroscopic identification of 8 in the triplet ground state, its reversible photointerconversion with ring expansion to diazacycloheptatetraene 9 has been observed directly. The spectroscopic identification of the nitrene intermediates was aided by calculations at the B3LYP/6-311++G(3df,3pd) level, and the mechanism for their generation in stepwise decompositions of the azides is discussed in the light of CBS-QB3 calculations.

Anchoring Drugs to a Zinc(II) Coordination Polymer Network: Exploiting Structural Rationale toward the Design of Metallogels for Drug-Delivery Applications

A new series of coordination polymers (CPs) were synthesized and crystallographically characterized by single-crystal X-ray diffraction with the aim of developing drug-delivery systems via metallogel formation. Structural rationale was employed to design such coordination-polymer-based metallogels. As many as nine CPs were obtained by reacting two bis(pyridyl)urea ligands, namely, 1,3-dipyridin-3-ylurea (3U) and 1,3-dipyridin-4-ylurea (4U), and the sodium salt of various nonsteroidal antiinflammatory drugs, namely, ibuprofen (IBU), naproxen (NAP), fenoprofen (FEN), diclofenac (DIC), meclofenamic acid (MEC), mefenamic acid (MEF), and Zn(NO3)2. All of the CPs displayed 1D polymeric chains that were self-assembled through various hydrogen-bonding interactions involving the urea N-H and carboxylate O atoms and, in a few cases, lattice-occluded water molecules. The reacting components of the CPs produced five metallogels in dimethyl sulfoxide/water. The gels were characterized by rheology and transmission electron microscopy. Three selected metallogelators, namely, 3UMEFg, 3UNAPg, and 3UMECg, showed in vitro anticancer, cell imaging, and multidrug delivery for antibacterial applications, respectively. The shear-thinning properties of 3UMECg (rheoreversibility and injectability) make it a potential candidate for plausible topical application.

1H and 13C NMR spectra of some unsymmetric N,N′-dipyridyl ureas: Spectral assignments and molecular conformation

The 1H NMR spectra of N-(2-pyridyl), N′-(3-pyridyl)ureas and N-(2-pyridyl), N′-(4-pyridyl)ureas in CDCl3 and (CD3)2CO have been assigned with the aid of COSY and NOE experiments and chemical shift and coupling constant correlations. The 13C NMR spectra in CDCl3 were analysed utilizing the HETCOR and proton coupled spectra. The 1H NMR spectra, NOE effects and MINDO/3 calculations have been utilized to show that the molecular conformation of these compounds has the 2-pyridyl ring coplanar with the urea plane with the N-H group hydrogen bonded to the nitrogen of the 2-pyridyl group on the other urea nitrogen while the 3/4-pyridyl group rotates rapidly about the N-C3TN-C4 bond.

Synthesis and crystal structures of metallomacrocyclic and helical Hg(II) complexes with two bis(pyridylurea) ligands

Two complexes, [Hg2L12Cl4]·2DMF (1) and {[HgL2Br2]·2DMSO}n (2), have been synthesized and characterized from two flexible bis(pyridylurea) ligands (L1 and L2) with mercury(II) halides respectively. In the two complexes, both Hg(II) centers adopt four-coordination mode, but they present different architectures with slightly adjusted 3- and 4-position of nitrogen atom in the pyridyl ring. Complex 1 exists as a centrosymmetric metallamacrocycle with L1 as bidentate ligand bridging two HgCl2 units, and complex 2 exists as a 1D helical chain coordination polymer with L2 as bridging ligand and Br? as terminal ligand, which indicates that the nature of the ligand plays an important role in the coordination networks.

Consequence of presence and absence of π-clouds at strategic locations of designed binuclear Pd(II) complexes on packing: Self-assembly of self-assembly by intermolecular locking and packing

Self-assembled binuclear coordination cages of general formula [Pd 2(N-N)2(L)2](X)4, 1a/b-4a/b are prepared by the combination of N,N′-bis(m-pyridyl)urea, L, with a variety of cis-protected palladium(II) components, Pd(N-N)(X)2. The cis-protecting units "N-N" employed for the synthesis of 1-4 are ethylenediamine (en), tetramethylethylenediamine (tmeda), 2,2′-bipyridine (bpy), and 1,10-phenanthroline (phen), respectively. The term "X" stands for nitrate and perchlorate for a and b, respectively. The assemblies are characterized by NMR and electrospray ionization mass spectrometry (ESI-MS) techniques, and in some cases (i.e., 1a, 2b, 3b, 4a, and 4b) the structures are confirmed by single crystal X-ray diffraction. The conformations of bound L in the crystal structures of all the Pd(II) complexes are found to be syn-syn. The influence of the presence and absence of π cloud at the cis-protecting units on the crystal packing has been studied in detail. In the packing of [Pd 2(phen)2L2](NO3)4, 4a, one unit of [Pd2(phen)2L2]4+ is associated with two other units by π-π stacking interactions thus giving a one-dimensional growth as envisioned on the basis of a design principle. In the case of [Pd2(en)2(L)2](NO3) 4, 1a, and [Pd2(tmeda)2(L)2] (ClO4)4, 2b, such packing is not observed due to the absence of π-cloud at the strategic locations, instead notable H-bonding interactions are seen. However, [Pd2(bpy)2(L) 2](ClO4)4, 3b, displays a π-π interactions using only two units of [Pd2(bpy)2(L) 2]4+(ClO4)-.