• Bulletin of the Korean Chemical Society
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• v.33 no.12
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• pp.4109-4116
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• 2012

An efficient solid-phase methodology has been developed for the synthesis of 2-amino and 2-amidobenzo[d]-oxazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo-[d]oxazole resins 4 by cyclization reaction of 2-hydroxy-phenylthiourea resin 3. The resin-bound 2-hydroxyphenylthiourea 3 is produced by the addition of 2-aminophenol to the isothiocyanate-terminated resin 2 and serve as a key intermediate for the linker resin. This core skeleton 2-aminobenzo[d]oxazole resin 4 undergoes functionalization reaction with various electrophiles, such as alkylhalides and acid chlorides to generate 2-amino and 2-amidobenzo[d]oxazole resins 5 and 6 respectively. Finally, 2-amino and 2-amidobenzo[d]oxazole derivatives 7 and 8 are then generated in good yields and purities by cleavage of the respective resins 5 and 6 under trifluoroacetic acid (TFA) in dichloromethane ($CH_2Cl_2$).

• Journal of the Korean Chemical Society
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• v.51 no.1
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• pp.7-13
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• 2007

The oxazole plays an important role in the binding of lexitropsin to the guanine-cytosine base pair from minor groove of DNA. The geometry optimization is performed with DFT calculations for the two possible conformations of the protonated oxazole. The proton affinities are calculated at B3LYP level of theory with 6-31G* basis set for the optimized geometry. It is found that the proton affinites of the conformations in which the oxazole nitrogen is the protonation center are greater than that of the conformations in which the oxazole oxygen is the protonation center. This result is in good agreement with molecular electrostatic potential (MEP) contour map. The proton affinities are also studied for various substituted oxazoles with the electron-donating and -withdrawing groups to estimate substitutent effect on the proton affinity at the hydrogen bonding site of the oxazoles. it is shown that the electron-donating substituents increase the proton affinity of oxazole, while the electron-withdrawing substituents decrease it.

• Journal of the Korean Chemical Society
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• v.40 no.11
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• pp.692-698
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• 1996

A synthesis of the oxazole skeleton of discokiolide B, represented by discokiic acid 1, is described. Aldol condensation of 2[2'-(4-phenyl-3-butenyl)]-1,3-oxazole 4-carboxaldehyde(4a) with lithium enolate of methyl propionate provided the discokiic acid methyl ester. The key intermediate 2[2'-(4-phenyl-3-butenyl)]-1,3-oxazole-4-carboxaldehyde (4a) has been synthesized from the rhodium-catalyzed cycloaddition of diazomalonaldehyde with nitrile. The relative stereochemistry of the 3-hydroxy-2-methylpropanoate unit of discokiic acid was assigned on the basis of $^1H$ and $^{13}C$ NMR data.

• Bulletin of the Korean Chemical Society
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• v.20 no.5
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• pp.581-586
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• 1999

A series of polyethers containing the thiazole or oxazole subcyclic moiety have been synthesized. Reaction of 2-aryl-4-hydroxymethylthiazole with tetra- and pentaethylene glycol di-p-tosylate in THF provided corresponding α,ω-bis[2'-aryl-4'-methylthiazole]polyethylene glycol in good yields. Similar treatment of 2-phenyl-4-hydroxymethyloxazole 7 and 2-phenyl-5-hydroxymethyloxazole 8 with tetraethylene glycol di-p-tosylate yielded the corresponding 1,13-bis [2'-phenyl-4'-methyloxazole]tetraethylene glycol 16 and 1,13-bis[2'-phenyl-5'-methyloxazole]tetraethylene glycol 17 in 69 and 43% yields in respectively. The potentiometric properties of PVC-based ion selective membranes containing 66 wt% o-nitrophenyloctyl ether (NPOE) and 4 wt% polyethers 9-17 have been examined. The membranes containing thiazole and oxazole polyether derivatives exhibited high selectivity toward silver (I) ion. It was observed that the response slopes of the electrodes to silver ion vary with the length of polyether chain linking two thiazole subcyclic moiety. Potentiometric data suggest that the number of ether units, CH2OCH2, for phenylthiazole derivatives be greater than 5 to result in near-Nernstian response. However, the response behaviors of the membrane electrodes based on phenyloxazole podands 16 and 17, which have different orientation, were correspondingly similar to those of the electrodes based on phenylthiazole podands 9 and 10. On the other hand, the ISEs based on thiazole polyether derivatives with different terminal substituents, e.g., phenyl 10, naphtyl 14, and thienyl 15, except that with pyridyl 12, exhibited little difference in their potentiometric properties.

• Bulletin of the Korean Chemical Society
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• v.32 no.11
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• pp.3959-3962
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• 2011

A simple propargylamide-fuctionalized chemodosimeter was prepared for the ratiometric fluorescence detection of mercuric ions in HEPES buffer. The chemodosimeter exhibited $Hg^{2+}$-induced propargyl amide-tooxazole transformation, with a significant accompanying ratiometric change in fluorescence. It afforded high selectivity for mercuric ion detection without any competitive inhibition by common alkali, alkaline earth, or other transition metal ions. The probe showed a $17{\times}10^{-6}M$ detection limit for $Hg^{2+}$ ions and potential applicability for detecting aqueous $Hg^{2+}$ ions.

• Journal of Integrative Natural Science
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• v.8 no.3
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• pp.204-208
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• 2015

Pyrazole, ${\beta}$-lactam, salicidine, pyren and oxazole derivatives exhibit a broad spectrum of biological activities such as antimicrobial, anti-inflammatory and antitumor activities. With growing application on their synthesis and bioactivity, chemists and biologists in recent years have considerable attention on the research of these derivatives. In the view of potential importance of these derivatives, we have crystallized few of the derivatives and its report has been published. The present study focuses on docking studies of these derivatives against COX-2 enzyme. Docking studies using Schrodinger's GLIDE reveals that these derivatives shows better binding energy and score in the defined active site. These results may provide a guiding role to design a lead molecule which may reduce inflamation.

• Bulletin of the Korean Chemical Society
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• v.14 no.4
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• pp.524-526
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• 1993

• Archives of Pharmacal Research
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• v.22 no.6
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• pp.624-628
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• 1999

A formal asymmetric synthesis of Mugineic acid was accomplished from cis-2-butene-1,4-diol throughcatalytic Sharpless epoxidation oxidations and doupling reaction.

• Journal of Integrative Natural Science
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• v.9 no.2
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• pp.94-102
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• 2016

The crystal structure of the potential active 6-ethoxy-3-phenyl-5a,9a-dihydro-3H-chromen[4,3-c][1,2]oxazole-3a(4H)-carbonitrile ($C_{19}H_{15}N_2O_3$) has been determined from single crystal X-ray diffraction technique. The title compound crystallizes in the monoclinic space group C2/c with unit cell dimension a= 29.3026(9) ${\AA}$, b= 6.7695(2) ${\AA}$ and c= 19.7597(6) ${\AA}$ [${\alpha}= 90^{\circ}$, ${\beta}= 125.709(10)^{\circ}$ and ${\gamma}= 90^{\circ}$]. Single crystals suitable for X-ray diffraction were obtained by slow evaporation method, the isoxazole and six membered pyran rings adopts envelope conformation. The crystal packing of the molecules is stabilized by the weak $C-H{\ldots}N$ hydrogen bond interaction.

• 한국정보디스플레이학회:학술대회논문집
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• 2003.07a
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• pp.174-177
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• 2003

We report four new phosphorescent iridium(III} complexes with 2,4-diphenyl-1,3-oxazole [$Ir(24dpo)_3$], 2,5-diphenyl-1,3-oxazole [$Ir(25dpo)_3$], 2-(3-thienyl) pyridine [$Ir(3thpyh)_3$] and [Ir(3thpy)2(acac)]. Three of them demonstrate good photophysical properties to be used as dopants to organic polymer matrix or to be used "as is" without a host matrix to fabricate OLEDs. Green and yellow light emission was observed for the photoluminescence: 569/525, 549/498 nm and 557,604/533 (solid state/$CH_2Cl_2$ solution) for $Ir(24dpo)_3$, $Ir(3thpyh)_3$ and $Ir(3thpyh)_2$acac respectively. Room temperature luminescent lifetimes are 2.5 and 1.8 ${\mu}s$ and quantum efficiencies 37 and 53%for $Ir(24dpo)_3$ and $Ir(3thpyh)_3$. The complexes are stable in air and sublimable at low pressure without considerable decomposition. Comparison of physicochemical properties of the reported iridium(III) cyclometalated compounds with that known from literature is carried out.