• Title/Summary/Keyword: hydantoin derivatives

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Synthesis and Screening of Cyclooxygenase Activity of Hydantoin and 2-Thiohydantoin Derivatives (Hydantoin 및 2-Thiohydantoin 유도체의 합성과 사이클로옥시게나제 활성 검색)

  • 신혜순;최희전;권순경
    • YAKHAK HOEJI
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    • v.48 no.2
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    • pp.141-146
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    • 2004
  • Selective COX-2 inhibitors were expected to retain anti-inflammatory activity by inhibition of prostaglandin production with reduction of gastric and renal side effect associated with non-steroidal anti-inflammatory drugs. This study reported the syntheses of novel 2-thiohydantoin and hydantoin derivatives which have the structure of 5-membered heterocyclic ring substituted with two aryl groups, phenyl group at 5-position and p-sulfamylphenyl or p-methoxyphenyl group at 1-position. These synthetic compounds showed significant COX-2 activities in vitro screening. Among them, 5-phenyl-2-thiohydantoin and hydantoin substituted with benzyl group at 3-position, compounds 5 and 8, could be considered as lead compounds with $IC_{50}$/=13.13∼18.78 $\mu\textrm{g}$/$m\ell$ for the development of COX-2 inhibitors.

Synthesis and Antitumor Evaluation of 3-(2-Chloroethyl)-hydantoins from Some Amino Acids (아미노산으로부터 3-(2-Chloroethyl) hydantoin들의 합성과 그들의 항암작용 평가)

  • 김정균;윤이규;고영심;윤웅찬;박무영;문경호
    • YAKHAK HOEJI
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    • v.27 no.4
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    • pp.309-314
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    • 1983
  • Six hydantoin derivatives, 3-(2-chloroethyl) hydantoin (6a), 3-(2-chloroethyl)-5-isopropylhydantoin (6b), 3-(2-chloroethyl)-5-isobutylhydantoin (6c), 3-(2-chloroetbyl)5-(2-butyl) hydantoin (6d), 3-(2-chloroethyl)-5-benzylhydantoin (6e), 3-(2-chloroethyl)-5-(indolyl-3-methyl) hydantoin (6f), were prepared by the treatment of the corresponding salt of amino acids with 2-chloroethyl isocyanate in cold water, followed by refluxing in concentrated HCl solution. Anticancer activity of the synthesized hydantoin derivatives were examined on murine leukemia L1210 cells growing in Fischer medium. Among them, 3-(2-chloroethy)-5-isobutyl-hydantoin (6c) showed substantially low $ED_{50}$ value of $9.6{\mu}g/ml$.

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Synthesis of 5-Aslkylthio (or sulfonyl) methyl-5-m-methoxy-phenylhydantion-3-acetic Acid Derivatives

  • Kwon, Soon-Kyoung;Park, Muoung-Suk;Nam, Young-Ju
    • Archives of Pharmacal Research
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    • v.16 no.4
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    • pp.322-326
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    • 1993
  • For the development of new antinflammatory and analgesic drugs, new 5-alkylthio (or sulfonyl) methyl-5-m-methoxyphenylhydantoin-3-acetic acid derivatives(alkyl; ethyl, propyl, butyl) were prepared. The 5,5 -disubstituted hydantoins which were used as starting materials, were prepared acording to Bucherer-Berg method. The reaction of ethyl chloroacelate with these compounds gave 3-acetate and the subsequent hydrolysis with dilute sodium hydroxide resulted in hydantoin 3-acetate and the subsequent hydrolysis with dilute sodium hydroxide resulted in hydantoin 3-acetic acid derivatives. Through the same procedure of equivalent hydroxide resulted in hydantoin 3-acetic acid derivatives. Through the same procedure of equivelent hydantions or the oxidation of 5-alkylthiohydantoin ocmpounds described above, 5-alkylsulfonylme-thyl-5-m-methoxyphenylhydantoin-30acetic acid derivatives were also synthesized.

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A New Synthesis of Hydantoin derivatives by the Reaction of Unnatural Amino acids with Potassium Isocyanate

  • Park, Hae-Sun;Choi, Hee-Jeon;Kwon, Soon-Kyoung;Park, Myoung-Sook
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.339.1-339.1
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    • 2002
  • Since two selective COX-2 inhibitors. celecoxib and rofecoxib, showed good biological activity as antiinflammatory agents. many medicinal chemists are interested in specific COX-2 inhibitors. The distinguished feature of these drugs is that the 5-membered heterocycle ring is substituted with two aryl groups. Therefore, in this study, we designed a new hydantoin derivatives via the reaction of unnatural amino acids as selective COX-2 inhibitors, In systematically steps. 5-phenyl-1 (or substituted) hydantoin derivatives were prepared through esterification. bromination, C-N bond formation, cyclization from phenyl acetic acid. Particularly. a novel hydantoin ring was converted from unnatural amino acids with potassium isoyanate. In last step. the final analogs were synthesized the substitution at 3-position with alkyl reagents.

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Microwave Assisted Rapid Synthesis of Novel Optically Active Poly(amide-imide)s Based on N-Trimellitylimido-L-Leucine Diacid Chloride and Hydantoin Derivatives

  • Faghihi, Khalil
    • Macromolecular Research
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    • v.12 no.3
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    • pp.258-262
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    • 2004
  • We have developed facile and rapid polycondensation reactions of N-trimellitylimido-L-leucine diacid chloride 1 with eight different derivatives of hydantoin compounds 2a-h, in the presence of a small amount of a polar organic medium, such as Ο-cresol, by using a domestic microwave oven. The polycondensation reactions proceeded rapidly-they were complete within 7-9 min-to produce a series of novel optically active poly(amide-imide)s (3a-h) in high yield with inherent viscosities of 0.33-0.51 dL/g. We characterized the resulting poly(amide-imide)s by elemental analysis, thermal gravimetric analysis (DSC, TGA, and DTG), and FTIR spectroscopy, and by measuring their viscosities, specific rotations, and solubilities. All of the polymers were soluble at room temperature in polar solvents such as N ,N-dimethylacetamide, N,N-dimethylformamide, dimethylsulfoxide, tetrahydrofuran, and N-methyl-2-pyrrolidone.

Elimination Reaction of $\alpha$-Diethaylaminoacetophenone in the Formation of Hydantoin Derivatives (히단토인 유도체 형성에 있어서 $\alpha$-Diethaylaminoacetophenone의 탈이반응)

  • 권순경
    • YAKHAK HOEJI
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    • v.22 no.4
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    • pp.215-218
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    • 1978
  • It is known that hydantoin derivative can be synthesized according to the method of Bucherer-Bergs, which employs the interaction of the carbonyl compounds with potassium cyanide and ammonium carbonate in dilute alcohol solution. In a converting study of .alpha.-dietylaminoacetophenone with KCN and ($NH_{4})_{2}CO_{3}$ to hydantoin, the attempted 5-diethylaminomethyl-5-phenylhydantoin was not formed. In this reaction diethylaminomethly group was unexpectedly eliminated and 5-phenylhydantoin was obtained, instead of the anticipated compound.

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Synthesis and Herbicidal Activities of Hydantoin Derivatives Possessing Amide Subgroup (아미드 치환체를 갖는 히단토인계 화합물의 합성과 제초활성 연구)

  • Ko, Young-Kwan;Chung, Keun-Hoe;Ryu, Jae-Wook;Woo, Jae-Chun;Koo, Dong-Wan;Choi, Jung-Sub;Kim, Jun-Young;Kim, Tae-Joon;Kwon, Oh-Yeon;Chung, Bong-Jin;Kim, Dae-Whang
    • The Korean Journal of Pesticide Science
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    • v.10 no.2
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    • pp.153-156
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    • 2006
  • As an ongoing research program for the development of environmentally friendly new herbicide, several hydantoin derivatives 5a - 5i possessing amide subgroup were synthesized and shown to have interesting herbicidal activities exhibiting symptoms as Protoporphyrinogen IX oxidase inhibitor under postemergence upland greenhouse screening. Among derivatives tested, compound 5h showed superior herbicidal activity against upland problem weed, digitaria sanguinalis and aeschynomene indica to reference compound fluthiacet-methyl.

Synthesis of New Salicylamide Derivatives with Evaluation of Their Antiinflammatory, Analgesic and Antipyretic Activities

  • Fahmy, H.H.;Soliman, G.A.
    • Archives of Pharmacal Research
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    • v.24 no.3
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    • pp.180-189
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    • 2001
  • A new series of pyridazine, pyrazoles, pyrazolidine-3,5-dione, Semicarbazide, thiosemicarbazides, hydantoin, thiohydantoins, 1,2,4-triazoles, S-triazolo[3,4-b]-1,3,4-thiadiazoles incorporated indirectly into salicylamide moiety at position 2 were synthesized. Also the synthesis of novel series of 3-salicylamido-2-hydroxypropyl-amino derivatives were prepared. Several of these compounds were screened for antiinflammatory, analgesic, antipyretic and ulcerogenic activities.

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