• Title/Summary/Keyword: Amide compound

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Central Nervous Depressant Activity of 5-Phenyl-2, 4-pentadienoic Acid Amide Derivatives (5-Phenyl-2, 4-Pentadienoic Acid Amide 유도체의 중추 억제작용에 관한 연구)

  • 조태순;임중기;신용회;신대희
    • YAKHAK HOEJI
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    • v.31 no.1
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    • pp.19-24
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    • 1987
  • In order to find out the pharmacologically active but less toxic compounds than piperine, the actions of several amide derivatives of 5-phenyl-2, 4-pentadienoic acid on the CNS depressant activities were examined. The nine amide derivatives were investigated by using ICR mice as an experimental amimals on acute toxicities, anticonvulsant, sedative, analgesic and antipyretic effects. In the case of acute toxicities, all derivatives were weaker than piperine except compound III. Compound I showed strong anticonvulsant activity. On the other hand, compound I, III and IV significantly prolonged the sleeping time induced by hexobarbital in mice. Compound I, III and IV exhibited better analgesic effect than aspirin while compound II, V, VII and IX showed similar antipyretic activity to aspirin.

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Synthesis of Novel Kojic Acid Derivatives and Their Tyrosinase Inhibitory Activities (새로운 코직산 유도체의 합성과 티로시나제 저해활성)

  • 김지연;임세진
    • YAKHAK HOEJI
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    • v.43 no.1
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    • pp.28-32
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    • 1999
  • Four derivatives of kojic acid were synthesized and their inhibitory activities against tyrosinase were evaluated. The C-2 hydroxymethyl and C-7 hydroxyl of kojic acid were replaced by carboxylate and amine, respectively. These derivatives were coupled to L-phenylalanine, producing two amide compounds. The carboxylate derivative (3), its amide compound (5), and the amine derivative (7) were weak inhibitors. The amide compound (9) where amine derivative (7) coupled to L-phenylalanine showed strong inhibitory activity ($IC_{50}=24.6{\;}{\mu}M$) comparable to kojic acid.

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NF-κB Activation and PPAR Transactivational Effects of a New Aliphatic Acid Amide from Pericarps of Zanthoxylum piperitum

  • Yang, Seo Young;Tai, Bui Huu;Song, Seok Bean;Li, Wei;Yan, Xi Tao;Sun, Ya Nan;Nguyen, Phuong Thao;Kim, Young Ho
    • Bulletin of the Korean Chemical Society
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    • v.35 no.8
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    • pp.2361-2366
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    • 2014
  • A new aliphatic acid amide, ZP-amide F (1), and eight known compounds, including bungeanumamide A (2), tumuramide C (3), ZP-amide A (4), ZP-amide B (5), ZP-amide D (6), hyperin (7), quercitrin (8), and (-)-sesamin (9), were isolated from pericarps of Zanthoxylum piperitum. The effects of these compounds on $TNF{\alpha}$-induced NF-${\kappa}B$ activation and transactivational activity of PPARs, including $PPAR{\alpha}$, $PPAR{\beta}({\delta})$ and $PPAR{\gamma}$ subtypes, were evaluated. Compounds 7 and 9 exhibited potent inhibitory effects on $TNF{\alpha}$-induced NF-${\kappa}B$ activation with $IC_{50}$ values of 5.50 and $8.10{\mu}M$, respectively. Aliphatic acid amide compounds 3, 4 and 6 displayed enhanced effects on PPAR transactivational activity with $EC_{50}$ values of 47.12, 19.13 and $12.02{\mu}M$, respectively. Among them, compound 4 demonstrated an increase in $PPAR{\alpha}$ transactivational activity, compound 3 showed a moderate increase on all PPAR subtypes, whereas compound 6 displayed weak PPAR transactivational activity.

Synthesis of a New 4-(Pyridin-3-yl)pyrimidine Derivatives for Anticancer Activity

  • Jung, Se-Jin;El-Deeb, Ibrahim Mustafa;Lee, So-Ha
    • Journal of the Korean Applied Science and Technology
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    • v.26 no.1
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    • pp.29-37
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    • 2009
  • This study is focused on the synthesis of urea and amide derivatives particularly, since the amide moiety is an essential binding group at the binding site. Urea derivatives 3-7 and 13-14 were obtained by reaction of 2-aminopyrimidines and other amines with diverse isocyanates in pyridine as a solvent under reflux. The urea derivatives were obtained in low yield because of the highly electron deficient nature of the amino group of the 2-aminopyrimidine. Amide derivatives 8-10 were obtained in moderate yields by reaction of compound 1 with aryl chloride derivatives. Also, arylamine 11 was synthesized by Buchwald-Hartwig amination in moderate yields. Most of the compound did not show good activity against A375P melanoma cells, compared with Sorafenib as control compound.

Synthesis, Characterization and Antimicrobial Activity of Bifunctional Sulfonamide-Amide Derivatives

  • Abbavaram, Babul Reddy A.;Reddyvari, Hymavathi R.V.
    • Journal of the Korean Chemical Society
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    • v.57 no.6
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    • pp.731-737
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    • 2013
  • A convenient synthesis of bifunctional sulfonamide-amide derivatives was reported. Amide coupling of 4-methyl benzoic acid 1 followed by reaction with chlorosulfonic acid produce ethyl-4-(3-(chlorosulfonyl)-4-methylbenzoyl)piperazine-1-carboxylate 4. The resulted compound on further treatment with various anilines produces the title sulfonamide-amide derivatives 5a-n. The configurations of these compounds were established by elemental analysis, IR, $^1H$ NMR, mass spectra, and by their preparation from the corresponding 4-methyl benzoic acid 1 and chlorosulfonic acid. All these new compounds demonstrate significant in vitro antibacterial and antifungal activities against all bacterial and fungal strains.

A Novel 3D Polypseudo-rotaxane Metal-organic Framework Based on a Flexible Bis-pyridyl-bis-amide Ligand

  • Wang, Xiu-Li;Han, Na;Lin, Hong-Yan;Xu, Chuang;Luan, Jian;Liu, Guo-Cheng
    • Bulletin of the Korean Chemical Society
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    • v.33 no.11
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    • pp.3793-3796
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    • 2012
  • A novel 3D compound $\{[Cu(L)(H_2O)_4][Cu_2(SIP)_2(L)_2]\}{\cdot}2H_2O$ (1) (L = N,N-bis(4-pyridinecarboxamide)-1,4-butane, SIP = 5-sulfoisophthalate) is hydrothermally synthesized. X-ray diffraction analysis reveals that compound 1 is composed of 2D anionic $[Cu_2(SIP)_2(L)_2]_n{^{2n-}}$ double-layers and discrete 1D cationic $[CuL(H_2O)_4]_n{^{2n+}}$ polymeric chains, which represents a rare 3D polypseudo-rotaxane MOF from intercalation of 1D and 2D framework. In addition, the luminescent property and electrochemical behavior of compound 1 have been investigated.

The Crystal Structure of One Natural Compound Cyclo-(1,10-Docandiamino-11,20-Docanedioic) Amide (1,12-Diazacyclodocosane-2,11-Dione)

  • Wei, Wan-Xing;Pan, Yuan-Jiang
    • Bulletin of the Korean Chemical Society
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    • v.23 no.11
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    • pp.1527-1530
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    • 2002
  • 1,12-diazacyclodocosane-2,11-dione was first isolated from a plant Phyllanthus niruri Linn. Its structure has been determined by means of spectroscopy methods and X-ray crystallography. Two peptide groups in the big ring (lactam) are the main factors influencing intermolecular contacts. The hydrogen-bond interaction of these hydrophilic groups is observed in the crystal structure. Meanwhile, C-H···O hydrogen bonds in molecules contribute to the formation of the whole crystal. These two kinds of hydrogen-bond form six- member rings among molecules. This compound crystallizes in the triclinic space group P-1 with a= 9.588(1) $\AA$, b= $9.850(1)\AA$, c = $11.810(1)\AA$, $\alpha=$ 68.18(1)$^{\circ}C$ , $\beta=$ 84.98(1), $\gamma$ = 86.03(1)$^{\circ}C$ , V = $1030.66(17)\AA3$ , Z = 2. A disorder of five-member carbon chain in the whole ring is observed in the title compound. The bond angle 105.8(4) is determined for a extreme configuration C(14)-C(15)-C(16), and 117.7(10) for another extreme configuration C(14')-C(15')-C(16'). In this crystal, two molecules are tied each other by short intermolecular hydrogen bonds, the oxygen atom being tied by hydrogen bond to nitrogen atom of another two molecules. The NMR and IR spectral data coincides to the structure of the compound.

Analysis of Beauvericin and Unusual Enniatins Co-Produced by Fusarium oxysporum FB1501 (KFCC 11363P)

  • Song Hyuk-Hwan;Ahn Joong-Hoon;Lim Yoong-Ho;Lee Chan
    • Journal of Microbiology and Biotechnology
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    • v.16 no.7
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    • pp.1111-1119
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    • 2006
  • Beauvericins and enniatins are cyclohexadepsipeptides exhibiting various biological activities on animal systems, including humans. Fusarium oxysporum FB1501 (KFCC 11363P) that produces four different cyclohexadepsipeptides was isolated from soil in Korea and the structures of the four cyclohexadepsipeptides elucidated by HPLC, MS, IR, and NMR analyses. The molecular weights for compounds 1,2,3, and 4 were determined to be 654.5, 784.5, 668.6, and 682.5, respectively, on the basis of ESI-MS measurements. The IR spectra for all the compounds exhibited absorptions for ester $(1,733-1,743\;cm^{-1})$ and amide $(1,649-1,655\;cm^{-1})$ bonds that were very similar to those for beauvericin and enniatins with ester and amide absorptions. The results of the NMR analysis $(^{1}H,\;^{13}C,\;135-DEPT,\;COSY,\;HMQC,\;and\;HMBC;\;in\;COCl_{3})$ revealed that compounds 1,3, and 4 consisted of $_{L}-N-methyl\;valine$ (N-MeVal), $_{D}-{\alpha}-hydroxyisovaleic\;acid$ (Hiv), and 2-hydroxy-3-methylpentanoic acid (Hmp) residues (compound 1: three N-MeVal residues, two Hiv residues, and one Hmp residue; compound 3: three N-MeVal residues, one Hiv, and two Hmp residues; compound 4: three N-MeVal residues and three Hmp residues). Therefore, the compounds were identified as enniatin H (compound 1), enniatin I (compound 3), and enniatin MK1688 (compound 4). Compound 2 was analyzed as beauvericin according to 1D and 2D NMR analyses. This study is the first report related to the co-production of beauvericin with other unusual enniatins, such as enniatin H, enniatin I, and enniatin MK1688, by Fusarium oxysporum.

Development of Novel Small Chemical Inhibitors for Lck SH Domain with in vitro T-cell Inhibitory Activity

  • Park, See-Hyoung;Kang, Mi-Ae;Shim, Hyeong-Soo;Cho, Hyeong-Jin;Won, Jong-Hwa;Lee, Keun-Hyeung
    • Bulletin of the Korean Chemical Society
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    • v.27 no.9
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    • pp.1353-1358
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    • 2006
  • We investigated in vitro T-cell inhibitory activity and bioavailability of small chemical inhibitors for Lck SH2 domain, which had a different scaffold such as an amide bond, reduced amide bond, N-methyl amide bond, thioamide bond, and urethane bond. Each of these compounds, with its particular scaffold, showed a different logP value, stability against serum enzyme, stability in buffer solution, and in vitro T-cell inhibitory activity. Overall results indicated that the SH2 inhibitor containing urethane bond can be a new lead compound because of its superior bioavailability, potent in vitro T-cell inhibitory activity, and facile synthesis.

Synthesis and Cytotoxic Activity of (R)-(-)-PGME Amide of Diterpene Acid

  • Lim, Jin-A;Yook, Chan-Nam;You, Il-Soo;Oh, Hyun-Ju;Kim, Myung-Ju;Baek, Seung-Hwa
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.19 no.2
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    • pp.520-523
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    • 2005
  • (R)-(-)-PGME amide of diterpene acid (2) was assigned the absolute configuration from NMR correlation experiments. The compound (2) was tested for its growth inhibitory effects against tumor cell lines by the MTT method.