Synthesis of New 5-Substituted Hydantoins and Symmetrical Twin-Drug Type Hydantoin Derivatives

被引:20
作者
Fujisaki, Fumiko [1 ]
Aki, Hatsumi [1 ]
Naito, Ayumi [1 ]
Fukami, Enko [1 ]
Kashige, Nobuhiro [1 ]
Miake, Fumio [1 ]
Sumoto, Kunihiro [1 ]
机构
[1] Fukuoka Univ, Fac Pharmaceut Sci, Jonan Ku, Fukuoka 8140180, Japan
关键词
hydantoin; regioselective; antibacterial activity; isothermal titration calorimetry; bivalent twin-drug; sulfated glycosaminoglycan; ANTIBACTERIAL ACTIVITY; CHEMICAL-PROPERTIES; 5-DIALKYLAMINOMETHYLHYDANTOINS; OXAZOLIDINONES;
D O I
10.1248/cpb.c14-00017
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
In connection with our studies on hydantoin derivatives, a conventional regioselective chemical transformation of 5-methylene hydantoins 4a-c to 5-aminomethyl-substituted hydantoins 5-10 or to 5-amino-5-methyl-disubstituted hydantoins 11-14 is described. Synthesis of bivalent twin-drug type hydantoin derivatives 19-24 and the binding property of a bivalent symmetrical hydantoin derivative 24b to sulfated glycosaminoglycans are also described.
引用
收藏
页码:429 / 438
页数:10
相关论文
共 27 条
  • [1] SYNTHESIS, CHEMICAL PROPERTIES, AND BIOLOGICAL EVALUATIONS OF SOME TWIN-DRUG TYPE C2-SYMMETRICAL DERIVATIVES
    Fujisaki, Fumiko
    Usami, Haruka
    Nakashima, Saya
    Nishida, Sho
    Fujioka, Toshihiro
    Kashige, Nobuhiro
    Miake, Fumio
    Sumoto, Kunihiro
    HETEROCYCLES, 2013, 87 (03) : 665 - 675
  • [2] PREPARATION AND ANTIBACTERIAL EVALUATION OF SOME SYMMETRICAL TWIN-DRUG TYPE BIVALENT MOLECULES
    Fujisaki, Fumiko
    Furutachi, Makoto
    Fujiwara, Ryou
    Okabe, Miriko
    Aki, Hatsumi
    Kashige, Nobuhiro
    Miake, Fumio
    Sumoto, Kunihiro
    HETEROCYCLES, 2015, 91 (08) : 1668 - 1677
  • [3] REACTION OF 5-METHYLENEHYDANTOINS AND THEIR CHEMICAL MODIFICATION TO TWIN-DRUG TYPE SYMMETEICAL MOLECULES
    Fujisaki, Fumiko
    Fujiwara, Ryou
    Okabe, Miriko
    Naito, Ayumi
    Fukami, Enko
    Aid, Hatsumi
    Kashige, Nobuhiro
    Miake, Fumio
    Sumoto, Kunihiro
    HETEROCYCLES, 2014, 89 (12) : 2745 - 2759
  • [4] Synthesis and biological evaluation of 5-substituted derivatives of benzimidazole
    Vasic, Vesna P.
    Penjisevic, Jelena Z.
    Novakovic, Irena T.
    Sukalovic, Vladimir V.
    Andric, Deana B.
    Kostic-Rajacic, Sladana V.
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2014, 79 (03) : 277 - 282
  • [5] Synthesis of new 5-substituted hydantoins from 2-alkoxy-1-cyano-1-trimethylsiloxypropenes
    N. A. Keiko
    T. A. Kuznetsova
    N. V. Vchislo
    Yu. A. Chuvashev
    L. I. Larina
    M. G. Voronkov
    Russian Journal of General Chemistry, 2007, 77 : 2145 - 2149
  • [6] Synthesis and Antibacterial Activity of 3-(Morpholinopyridyl)-5-substituted Isoxazole Derivatives
    Du, Guangjian
    Chen, Dongliang
    Lu, Ruijiong
    Wang, Xiaojun
    Yan, Ming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (10) : 1575 - 1581
  • [7] Synthesis, properties, and reactions of 5-substituted derivatives of 2,3-diphenylquinoxaline [1]
    Salon, J
    Milata, V
    Chudík, M
    Prónayovaá, N
    Lesko, J
    Seman, M
    Belicová, A
    MONATSHEFTE FUR CHEMIE, 2004, 135 (03): : 283 - 291
  • [8] Synthesis and antibacterial activity of 1β-methyl-2-(5-substituted thiazolo pyrrolidin-3-ylthio)carbapenem derivatives
    Oh, CH
    Cho, HW
    Baek, D
    Cho, JH
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2002, 37 (09) : 743 - 754
  • [9] Synthesis and antibacterial activity of 1β-methyl-2-(5-substituted imidazolino pyrrolidin-3-ylthio)carbapenem derivatives
    Oh, CH
    Lee, CS
    Lee, JS
    Cho, JH
    ARCHIV DER PHARMAZIE, 2003, 336 (11) : 504 - 509
  • [10] A facile synthesis of novel 5-substituted pyridine 2 carboxamide derivatives and their biological evaluation and 3D QSAR studies
    Dharman, Prabu
    Babu, Visagamoorthy
    Basha, K. Anver
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2019, 66 (04) : 415 - 426