• Title/Summary/Keyword: Heterocyclic compounds

Search Result 142, Processing Time 0.025 seconds

Syntheses and Central Nervous Depressant Activities of Piperine Derivatives (V) (피페린 유도체의 합성 및 중추 억제작용에 관한 연구(V) -Methylenedioxyphenylalkenoic Acid Amide 유도체-)

  • 도경삼;임중기;우경식;이은방
    • YAKHAK HOEJI
    • /
    • v.30 no.4
    • /
    • pp.163-168
    • /
    • 1986
  • Thirteen compounds were synthesized by condensing the N-heterocyclic amines (piperidine, pyrrolidine, morpholine) and secondary aliphatic amines (dimethylamine, diethylamine) with 3,4-methylenedioxyphenylalkenoic acid chlorides for developing CNS depressants. Among them, N, N-diethyl-3,4-methylenedioxycinnamamide (IX) and N, N-dimethyl-5-(3,4-methylenedioxyphenyl)-2, 4-pentadienoic acid amicle (XII) exhibited strong activity in antagonism against pentylenetetrazole-induced convulsion, strychnine-induced convulsion and maximal electroshock seizure. N, N-Dimethyl-3, 4-methylenedioxycinnamide (VIII) showed more potent activity in antagonism against strychnine-induced convulsion and maximal electroshock seizure and in the prolongation of hexobarbital sleeping time.

  • PDF

Benzoin Condensation Reactions of 5-Membered Heterocyclic Compounds Catalyzed by Thiazolium Salts

  • Chang Kiu Lee;Jin Soon Gong;Sin Kwan Seog;Jong-Gab Jun
    • Bulletin of the Korean Chemical Society
    • /
    • v.14 no.1
    • /
    • pp.29-31
    • /
    • 1993
  • Benzoin condensation reactions of furfurals and thiophenecarboxaldehydes in the presence of substituted benzyl and alkyl thiazolium salts were examined in order to improve the yield of the reaction and to examine the effect of the electronic nature of the catalysts. Thiophene derivatives gave thenils as the major products in low yields while furan derivatives gave only furoins in moderate to high yields.

Synthesis of Selenoflavonoids

  • Kim, Dong-Myung;Jeong, Jin-Hyun
    • Proceedings of the PSK Conference
    • /
    • 2003.10b
    • /
    • pp.182.1-182.1
    • /
    • 2003
  • Flavonoids with oxygen atoms are known to have potent biological effect.They have been studied long as major antioxidants which protect cell membranes. Recent medical surveys show that increased intake of selenium decreases the risk of breast, colon, lung and prostrate cancer by preventing free radical generation. The flavonoids, isoflavonoids, and coumarins which form the bulk of these compounds are very polar and have limited use as drugs which have to pass through BBB(Brain Blood Barrier)The non-polar property is increased by exchange oxygen to selenium as a part of heterocyclic compound. (omitted)

  • PDF

Liquid Membrane Permeation of Nitrogen Heterocyclic Compounds Contained in Model Coal Tar Fraction

  • Kim, Su-Jin;Kang, Ho-Cheol;Kim, Yong-Shik;Jeong, Hwa-Jin
    • Bulletin of the Korean Chemical Society
    • /
    • v.31 no.5
    • /
    • pp.1143-1148
    • /
    • 2010
  • We investigated the separation of nitrogen heterocyclic compound (NHC) contained in a model coal tar fraction comprising four kinds of NHC [indole (In), quinoline (Q), iso-quinoline (iQ), quinaldine (Qu)], three kinds of bicyclic aromatic compound (BAC) [1-methylnaphthalene (1MN), 2-methylnaphthalene (2MN), dimethylnaphthalene (DMN) mixture with ten structural isomers (DMNs; regarded as one component)], biphenyl (Bp) and phenyl ether (Pe) by liquid membrane permeation (LMP). A batch-stirred tank was used as the permeation unit. An aqueous solution of saponin and n-hexane were used as the liquid membrane and the outer oil phase, respectively. Yield and selectivity of individual NHC was much larger than that of BAC, Bp and Pe. Increasing the initial mass fraction of the saponin to the membrane solution ($C_{sap,0}$) and the initial volume fraction of O/W emulsion to total liquid in a stirred tank (${\phi}_{OW,0}$) resulted in deteriorating the yield of individual NHC, but increasing the stirring speed (N) resulted in improving the yield of each NHC. With increasing $C_{sap,0}$, the selectivity of each NHC based on DMNs increased. Increasing ${\phi}_{OW,0}$ and N resulted in decreasing the selectivity of individual NHC based on DMNs. At an experimental condition fixed, the sequence of the yield and selectivity in reference to DMNs for each NHC was Q > Qu = iQ > In. Furthermore, we compared LPM method with methanol extraction method in view of the separation efficiency (yield, selectivity) of NHC.

Volatile Flavor Compounds in Pen Shell By-product Hydrolysate (키조개 부산물 단백질 가수분해물의 휘발성 향기성분에 관한 연구)

  • Cha, Yong-Jun;Kim, Eun-Jeong
    • Korean Journal of Food Science and Technology
    • /
    • v.27 no.6
    • /
    • pp.964-971
    • /
    • 1995
  • Volatile flavor compounds and free amino acids in untreated and hydrolysate pen shell by-product produced with APL 440 protease were compared by vacuum simultaneous steam distillation-solvent extraction/gas chromatography/mass spectrometry. A total of 109 volatile flavor compounds were detected in hydrolysate (65 compounds) or the 109 volatile flavor compounds were detected in untreated pen shell by-product (88). These compounds were composed of aldehydes(16), ketones(17), alcohols(31), nitrogen containing compounds (16), aromatic hydrocarbon compounds(8), esters(3), and miscellaneous compounds (17). Levels of aldehydes and aromatic hydrocarbons decreased after hydrolysis, whereas levels of nitrogen containing compounds increased 3 times than in untreated pen shell by-product. Taurine, known to be having a physiological function, was accounted for 31.25% of total amino acids in hydrolysate.

  • PDF

Ring Flipping of Seven-membered and Eight-membered Dithienodisila-heterocycles

  • Lee, In-Sook;Kwak, Young-Woo;Ghosh, Manikkumer;Ohshita, Joji;Choi, Cheol-Ho
    • Bulletin of the Korean Chemical Society
    • /
    • v.29 no.2
    • /
    • pp.377-380
    • /
    • 2008
  • Ground state structures and ring flipping transition states of eight- and seven-membered silicon containing heterocyclic compounds such as dithienodisilacyclooctatriene and oxadithienodisilacycloheptadiene derivatives, respectively have theoretically been investigated. Although the bithienylene moiety of the derivatives does not change the ground state structures, they significantly increase the ring flipping barrier by 13-17 kcal/mol in the case of the eight-membered rings (2, 3, and 4) in comparison with that of silicon containing heterocyclic compound 6, chosen as a model. The same moiety increases the flipping barrier of seven-membered ring (5) is only slightly (3.3 kcal/mol) in comparison with that of model compound 7. Hence, it has been concluded that not only the existing ring strain of eight-membered ring but also the bithienylene moiety collectively increases the ring flipping barrier so as to prevent such conformational changes explaining anomalous NMR behaviour of dithienodisilacyclooctatriene derivatives (2-4). In contrast, the effect of substituents R1 and R2 at the olefinic carbons of the eight-membered ring on the flipping barrier turned out to be mild.

A Selective Oxidation of Tetraline by Chromium (VI) Compounds (I) (Cr (VI) 촉매에 의한 Tetraline 의 선택적 산화반응 (I))

  • Sun-Kun Bae;Sang-Bong Lee;Dae-Chul Park;Kyu-Wan Lee
    • Journal of the Korean Chemical Society
    • /
    • v.33 no.1
    • /
    • pp.106-112
    • /
    • 1989
  • Liquid phase oxidation of tetralin with clean air were carried out utilizing complexes composed of various heterocyclic base and CrO$_3$ in N,N-dialkylamides. In the CrO$_3$-N,N-dialkylacetamide complex catalyzed oxidations of tetralin at 90$^{\circ}$C, the maximum conversion of tetralin to the products and selectivity of ${\alpha}$-tetralone were 35.2% and 96.1%, respectively. Under this condition, however, negligible amount of ${\alpha}$-tetralol was determined.

  • PDF

Synthesis and Characterization of Aluminum and Gallium Complexes of Heterocyclic Thiosemicarbazones. Crystal Structures of $Me_2M[SC_4H_3CHNNC(S)SCH_3$] (M=Al, Ga)

  • 강영진;유병우;강상욱;고재정;강승주
    • Bulletin of the Korean Chemical Society
    • /
    • v.19 no.1
    • /
    • pp.63-67
    • /
    • 1998
  • The synthesis and characterization of the monomeric group 13 heterocyclic thiosemicarbazone complexes $Me_2M[SC_4H_3CHNNC(S)SCH_3]$ (M=Al (2), Ga (3)) are described. Compounds 2-3 were prepared using $MMe_3$ (M=Al, Ga) in toluene with 2-thiophenecarboxaldehyde-S-methyldithiocarbazat e under anaerobic conditions. These complexes have been characterized by $^1H\;NMR,\; ^{13}C\; NMR$, elemental analyses, and single-crystal X-ray diffraction. 2 crystallizes in the monoclinic space group $P2_1/c$ with unit cell parameters a=10.2930(5) Å, b=18.564 (1) Å, c=7.3812(6) Å, V=1347.9(2) Å3, $D_{calc}=1.342\; gcm^{-3}$ for Z=4, 9281 reflections with $I_o<3{\sigma}\;(I_o),$ R1=0.0500 and wR2=0.0526. 3 crystalizes in the orthorhombic space group $P_{bca}$ with unit cell parameters a=13.340(3) Å, b=19.9070(5) Å, c=11.3690(2) Å, $V=2673.88(9)\;{\AA}^3$, $D_{calc}=1.511\; gcm^{-3}$ for Z=8, 17004 reflections with $I_o>3{\sigma}\;(I_o),$, R1=0.0480 and wR2=0.0524. Compound 3 is a monomeric gallium compound with a weak interaction between the pendant thiophene and the gallium center.

Hygrolansamycins A-D, O-Heterocyclic Macrolides from Streptomyces sp. KCB17JA11

  • Jang, Jun-Pil;Lee, Byeongsan;Heo, Kyung Taek;Oh, Tae Hoon;Lee, Hyeok-Won;Ko, Sung-Kyun;Hwang, Bang Yeon;Jang, Jae-Hyuk;Hong, Young-Soo
    • Journal of Microbiology and Biotechnology
    • /
    • v.32 no.10
    • /
    • pp.1299-1306
    • /
    • 2022
  • Six ansamycin derivatives were isolated from the culture broth of Streptomyces sp. KCB17JA11, including four new hygrolansamycins A-D (1-4) and known congeners divergolide O (5) and hygrocin C (6). Compounds 1-5 featured an unusual six-membered O-heterocyclic moiety. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The structures of 1-4 were elucidated using NMR and HRESIMS experiments, and the absolute configuration was established by the Mosher's method. Compound 2 exhibited mild cytotoxicity against five cancer cell lines with IC50 values ranging from 24.60 ± 3.37 µM to 49.93 ± 4.52 µM.

Synthesis and Antiproliferative Potency within Anticonvulsant of Novel Bichalcone Derivatives

  • Mansour, Eman;El-Badry, Yaser A.;El-Tokhy, Afaf;Ayyad, Rezed;Abd-Rabou, Ahmed A.
    • Journal of the Korean Chemical Society
    • /
    • v.64 no.1
    • /
    • pp.7-18
    • /
    • 2020
  • An efficient and facile procedure has been developed for the synthesis of novel bichalcone derivatives (4a, 4b). The key step contains the solvent-free aldol synthesis of bichalcones based on quinones. Bichalcones (4a, 4b) were used as precursors for the synthesis of some interesting heterocyclic compounds like, diazepines (5a, 5b), pyrazolo-pyrimidines (7a, 7b), and pyrazoline derivatives (8a, 8b). Moreover, new thioxopyrimidine derivatives (9a, 9b) were furnished and used as a functionalizing agent to produce the triazole-pyrimidines (11, 12) and the carbonitrile derivative (14). All the synthesized compounds were fully characterized using physical and spectral data like, FT-IR, 1H NMR, 13C NMR, and MS. Bichalcones (4a, 4b) and diazepines (5a, 5b) were screened for their anticonvulsant activity, where compounds (4a, 5a, and 5b) revealed potent anticonvulsant activity compared to diazepam. On the other hand, some of the prepared compounds were screened for their antiproliferative activity and they showed significant cytotoxic effects on most of the cancer cell lines with regard to broad spectrum antitumor activity.