• Bulletin of the Korean Chemical Society
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• v.27 no.9
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• pp.1371-1376
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• 2006

BACE 1 ($\beta$-secretase), a membrane bound aspartic protease, is a key enzyme in the process of amyloid precursor protein (APP) into A$\beta$ peptide which is considered to play a causative role in Alzheimers Disease (AD). Here, we reported the synthesis and inhibitory activity of optically active 3-amino-4-aryl-piperidines.

• Archives of Pharmacal Research
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• v.17 no.2
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• pp.66-70
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• 1994

The condensation reactions of hippuric acid and tis furyl derivative with salicyladehydes or that of salicylhippuric acid analogues with furadehyde led to the comesponding oxazoles. These wre subsequently treated with hydrazine hydrate, hydroxylamine or subjected to alkaline hydrolysis to yield new o-hydroxyaryl or salicyl containing derivatives. 5-Substituted salicylanilides were treated with piperidine and formaldehyde in a Mannich type reaction affording the corresponding 3-(N-piperidinomethyl) salicylanilides. It was noticed that the presence of an electron donating group in in position 3 in the salicylanilide moiety decrease the mollusicidal activity.

• Bulletin of the Korean Chemical Society
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• v.30 no.7
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• pp.1531-1534
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• 2009

(2S,3R)-3-Hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyridine 8, an important precursor for the synthesis of polyhydroxylated piperidine azasugars, has been prepared from L-serine. Highly stereoselective nucleophilic addition to amino aldehyde 5 gave the corresponding allylic alcohol 6 which proceeded to give dihydro-2H-piridine 7a via a Grubbs II catalyzed RCM. Stereoselective H-bond directed epoxidation of allylic alcohol led to the oxiranyl alcohol 9 which was easily converted to L-deoxyaltronojirimycin by regioselective ring opening.

• Bulletin of the Korean Chemical Society
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• v.34 no.7
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• pp.2023-2028
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• 2013

A kinetic study is reported for the nucleophilic substitution reactions of phenyl Y-substituted-phenyl carbonates (5a-5k) with piperidine in 80 mol % $H_2O$/20 mol % DMSO at $25.0{\pm}0.1^{\circ}C$. The plots of $k_{obsd}$ vs. [piperidine] for the reactions of substrates possessing a strong electron-withdrawing group (EWG) in the leaving group (i.e., 5a-5i) are linear and pass through the origin. In contrast, the plots for the reactions of substrates bearing a weak EWG or no substituent (i.e., 5j or 5k) curve upward, indicating that the electronic nature of the substituent Y in the leaving group governs the reaction mechanism. Thus, it has been suggested that the reactions of 5a-5i proceed through a stepwise mechanism with a zwitterionic tetrahedral intermediate (i.e., $T^{\pm}$) while those of 5j and 5k proceed through a stepwise mechanism with two intermediates (i.e., $T^{\pm}$ and its deprotonated form $T^-$). The slope of the Br${\o}$nsted-type plot for the second-order rate constants (i.e., $k_N$ or $Kk_2$) changes from -0.41 to -1.89 as the leaving-group basicity increases, indicating that a change in the rate-determining step (RDS) occurs. The reactions of 5a-5k with piperidine result in larger $k_1$ values than the corresponding reactions with ethylamine.

• Bulletin of the Korean Chemical Society
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• v.28 no.8
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• pp.1353-1357
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• 2007

Second-order rate constants (kN) have been determined spectrophotometrically for reactions of Y-substituted phenyl 2-furoates (1a-h) with piperidine and morpholine in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 oC. The Brønsted-type plot exhibits a downward curvature for the reactions with strongly basic piperidine but is linear for the reactions with weakly basic morpholine. The slope of the curved Brønsted-type plot changes from -1.25 to ?0.28 as the pKa of the conjugate acid of the leaving aryloxides decreases. The pKa at the center of the Brønsted curvature, defined as pKa°, was determined to be 6.4. The aminolysis of 1a-h has been concluded to proceed through a stepwise mechanism on the basis of the curved Brønsted-type plot. The reactions of Ysubstituted phenyl cinnamates (2a-g) with piperidine resulted in a curved Brønsted-type plot with a pKa° values of 6.4. However, the curved Brønsted-type plot has been suggested to be not due to a change in the RDS but due to a normal Hammond effect of a concerted mechanism, since the Brønsted-type plot for the corresponding reactions with morpholine results in also a curved Brønsted-type plot with a pKa° values of 6.1. The furoates with a basic leaving group (i.e., 1b-g) are less reactive than the corresponding cinnamates (i.e., 2b-g). The k2/ k-1 ratios for the reactions of 1b-h are much smaller than unity, which has been suggested to be responsible for their low reactivity.

• Archives of Pharmacal Research
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• v.29 no.1
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• pp.34-39
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• 2006

The antispasmodic and vasodilator activities of a newly synthesized piperidine derivative (1-(4'fluorophenacyl)-4-hydroxy-4-phenyl-piperidinium chloride) were studied in vitro. The test compound exhibited a dose-dependent relaxant effect on the spontaneous and $K^+$ (75 mM)-induced contractions of isolated rabbit jejunum with respective $EC_{50}$ values of 0.01 mM(0.01-0.02, 95% CI) and 0.30 mM (0.17-0.56). The $Ca^{++}$ channel blocking (CCB) activity was confirmed when the test compound (0.1-0.2 mM) shifted the $Ca^{++}$ dose-response curves to the right, similar to that produced by verapamil ($0.1-1.0{\mu}M$), a standard CCB. In the isolated rabbit aorta, the test compound showed a dose-dependent vasodilator effect on $K^+$ (75 mM)-induced contractions with an $EC_{50}$ value of 0.08 mM (0.02-0.26) while also suppressed the norepinephrine ($1{\mu}M$) control peak responses with $EC_{50}$ value of 0.08 mM (0.05-0.13, n=5). When tested in Langendorff perfused rabbit heart preparation, the test compound exhibited a negligible inhibitory effect on the rate or force of atrial and ventricular contractions when tested up to 5 mM. The results show smooth muscle-selective relaxant effect of the test compound on intestinal and vascular preparations mediated possibly via blockade of voltage and receptor-operated $Ca^{++}$ channels.

• Journal of the Korean Chemical Society
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• v.36 no.3
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• pp.446-452
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• 1992

The rates of hydrolysis of aryl phenylacetates have been measured in the presence of piperidine in 80% acetonitrile-20% water(v/v). For the electron withdrawing substituents of leaving group, the hydrolysis is catalyzed by a general base and the Hammett $\rho_{LG}$ and Bronsted value $\beta$ are 5.28 and -2.72 at $30^{\circ}C$, respectively. These high senstivities of Hammett and Bronsted values are $E1_{C}B$ mechanism. But in the electron donating ones, the hydrolysis is catalyzed by a specific base and $B_{AC}2 mechanism is predominated. $pK_{SH}'s of phenylacetic acid ester and rate constants of hydrolysis $k_1$, $k_{-1)$, $k_2$ were calculated.

• Korean Chemical Engineering Research
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• v.49 no.5
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• pp.657-663
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• 2011

Structure directing agent(SDA) containing piperidine moiety such as piperidine(PI), 2-methylpiperidine (MPI), 2,6-dimethylpiperidine(DMPI) and 2,2,6,6,-tetramethylpiperidine(TMPI), respectively has been utilized to synthesize aluminophosphate zeolite using hydrothermal method. The gel composition was $1.0Al_2O_3:1.0P_2O_5:0.76SDA:45H_2O$ and the hydrothermal heating was performed in an oven at 443 K and for 7 days at static mode. The obtained zeolitic material contained a lamellar structure when PI was used as the SDA. With a progressive increase of the SDA size, various structures of aluminophosphate including AlPO-5 of AFI structure were obtained. The aluminophosphate of SAS structure was formed when the largest TMPI was utilized as the SDA, which was confirmed by the Rietveld refinement. The result of $^{27}Al$ and $^{31}P$ MAS NMR of the sample suggested that Al and P were incorporated into the framework of the aluminophosphate.

• Korean Journal of Food Science and Technology
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• v.29 no.3
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• pp.446-451
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• 1997

The primary alcohol groups of four kinds of polysaccharides (com starch, rice starch, sweet potato starch, and cellulose), with different structures and water solubilities, were oxidized to carboxyl groups using 2,2,6,6-tetramethyl-1-piperidine oxoammonium ion (TEMPO) at $25^{\circ}C$. The optimum pH, TEMPO content, and NaBr content for the TEMPO/hypobromite-catalyzed oxidation of the polysaccharides were $10.5{\sim}11.0$, 10 mmol/mol primary alcohol, and 0.49 mmol/mol primary alcohol, respectively. The oxidation degree for the primary alcohol group was more than 90% for all four kinds of the polysaccharides. The oxidation process greatly increased the water solubility of the polysaccharides. Water-insoluble polysaccharide such as cellulose became water-soluble to the extent of 8.42% (w/v). And also, the polysaccharides with very low water solubility (less than 0.10% (w/v)) such as com starch, rice starch, and sweet potato starch had high water solubility of approximately 45%(w/v). The gel-forming abilities with calcium ion were determined. The oxidized polysaccharides are new anionic polymers with unique structures that could have application as gums, gels, and films.

• Bulletin of the Korean Chemical Society
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• v.26 no.3
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• pp.477-480
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• 2005