Topiramate heterocyclic analogues: synthesis and spectroscopic characterization

被引:3
|
作者
Martins Alho, Miriam A. [1 ]
D'Accorso, Norma [1 ]
机构
[1] UBA, FCEN, Dept Quim Organ, Ctr Invest Hidratos Carbono,CIHIDECAR,CONICET, Intendente Guiraldes 2160,Ciudad Univ,C1428EGA, Buenos Aires, DF, Argentina
关键词
Topiramate; D-fructose; heterocyclic rings; spectroscopic data; DERIVATIVES; INHIBITORS; CURRENTS;
D O I
10.3998/ark.5550190.0012.712
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we describe the synthesis of a set of heterocyclic analogues of topiramate as possible therapeutic agents for epileptic seizure treatment. The new compounds and their precursors were characterized by physical, as well as spectroscopic techniques. We verified that the preferential conformation in solution of the carbohydrate ring is twist-boat. The stereochemistry of the new asymmetric centre, generated during the heterocyclizations, was proposed using NOESY experiment. These novel compounds could help to elucidate the mechanism of action of the commercial drug used for this disease.
引用
收藏
页码:136 / 148
页数:13
相关论文
共 50 条
  • [41] Synthesis, Characterization and Biological Evaluations of Ciprofloxacin Carboxamide Analogues
    Sultana, Najma
    Arayne, Muhammad Saeed
    Rizvi, Syeda Bushra Shakeb
    Haroon, Urooj
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2011, 32 (02): : 483 - 488
  • [42] Synthesis, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues
    Sherif, Salah Hamza
    Gebreyohannes, BerihuTekluu
    JOURNAL OF CHEMISTRY, 2018, 2018
  • [43] Efficient Synthesis of 9-Aminophenanthrenes and Heterocyclic Analogues by Electrocyclization of Biaryl Keteniminium Salts
    Quinodoz, Pierre
    Kolleth, Amandine
    Dagoneau, Dylan
    Yoshimura, Masahiko
    Mendez, Lucia Reyes
    Joigneaux, Mylene
    Staiger, Roman
    Horber, Robin
    Sulzer-Mosse, Sarah
    Cesaretli, Aybike Bekar
    Yezer, Ulfet Karadeniz
    Catak, Saron
    De Mesmaeker, Alain
    HELVETICA CHIMICA ACTA, 2022, 105 (11)
  • [44] Design, synthesis and biological profile of heterocyclic benzimidazole analogues as prospective antimicrobial and antiproliferative agents
    Tahlan, Sumit
    Kumar, Sanjiv
    Ramasamy, Kalavathy
    Lim, Siong Meng
    Shah, Syed Adnan Ali
    Mani, Vasudevan
    Pathania, Ranjana
    Narasimhan, Balasubramanian
    BMC CHEMISTRY, 2019, 13 (1)
  • [45] Synthesis and Characterization of Novel Heterocyclic Compounds Containing the Benzoxazine Ring by 7-Hydroxycoumarin
    Ali-Asgari, S.
    Moradi, M.
    Maskani, E.
    Mirtamizdoust, B.
    CHEMISTRY OF NATURAL COMPOUNDS, 2017, 53 (06) : 1028 - 1030
  • [46] Synthesis, characterization and antimicrobial screening of hybrid molecules containing quinoline, pyrimidine and morpholine analogues
    Desai, N. C.
    Rajpara, K. M.
    Joshi, V. V.
    Vaghani, H. V.
    Satodiya, H. M.
    JOURNAL OF CHEMICAL SCIENCES, 2013, 125 (02) : 321 - 333
  • [47] Synthesis and Spectroscopic Characterization of Metal Complexes of Rosuvastatin
    Tabassum, Arman
    Arayne, Muhammad Saeed
    Sultana, Najma
    INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH, 2017, 51 (01) : 102 - 109
  • [48] Synthesis, spectroscopic and electrochemical characterization of secnidazole esters
    Shahid, Hafiz Abdullah
    Jahangir, Sajid
    Hanif, Muddasir
    Xiong, Tianrou
    Muhammad, Haji
    Wahid, Sana
    Yousuf, Sammer
    Qureshi, Naseem
    JOURNAL OF MOLECULAR STRUCTURE, 2017, 1149 : 792 - 802
  • [49] Synthesis and Spectroscopic Characterization of the First Mixed Six- and Seven-Membered Heterocyclic Boron Compounds With Intramolecular N→B Bond
    Goyal, Sunita
    Mishra, Shashank
    Singh, Anirudh
    MAIN GROUP METAL CHEMISTRY, 2009, 32 (02) : 55 - 63
  • [50] Some Reactions with Indane-1,3-dione: A Facile Synthesis of Pentacycline Heterocyclic Analogues
    Abdelrazek, Fathy M.
    Metz, Peter
    Jaeger, Anne
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (07) : 1939 - 1945