Synthesis, Structure, and Antiradical Activity of New Methano[1,3]Thiazolo[2,3-d][1,3,5]Benzoxa-Diazocine Derivatives

被引:12
|
作者
Kulakov, I. V. [1 ]
Talipov, S. A. [2 ]
Shulgau, Z. T. [3 ]
Seilkhanov, T. M. [4 ]
机构
[1] Omsk FM Dostoevskii State Univ, Omsk 644077, Russia
[2] Inst Bioorgan Chem, Tashkent 100125, Uzbekistan
[3] Ctr Life Sci Inc, Astana 010000, Kazakhstan
[4] Sh Ualikhanov Kokshetau State Univ, Kokshetau 020000, Kazakhstan
关键词
2H-2,6-methano[1,3,5]benzoxadiazocines; salicylic aldehyde; thiourea; Biginelli reaction; intramolecular heterocyclization; X-ray structural analysis; ONE-POT SYNTHESIS; BIGINELLI DIHYDROPYRIMIDINE SYNTHESIS; MICROWAVE IRRADIATION; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; CONDENSATION; EFFICIENT; CHEMISTRY;
D O I
10.1007/s10593-014-1613-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 2,6-methano[1, 3, 5]benzoxadiazocines, obtained in Biginelli reaction, with chloroacetic acid derivatives produced previously unknown tricyclic methano[1,3]thiazolo[2,3-d][1,3,5]benz-oxadiazocines, the structure of which was proved by (1)De NMR spectroscopy and X-ray structural analysis. The methano[1,3]thiazolo[2,3-d][1,3,5]benzoxadiazocines showed no antiradical activity in contrast to the starting 2,6-methano[1,3,5]benzoxadiazocines.
引用
收藏
页码:1478 / 1486
页数:9
相关论文
共 50 条
  • [41] Design and synthesis of pyrido[2,3-d]pyrimidine derivatives for a novel PAC1 receptor antagonist
    Takasaki, Ichiro
    Watanabe, Ai
    Okada, Takuya
    Kanayama, Daisuke
    Nagashima, Ryota
    Shudo, Miyu
    Shimodaira, Ayaka
    Nunomura, Kazuto
    Lin, Bangzhong
    Watanabe, Yurie
    Gouda, Hiroaki
    Miyata, Atsuro
    Kurihara, Takashi
    Toyooka, Naoki
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2022, 231
  • [42] Synthesis and in vitro Evaluation of 1,2,4-Triazolo[1,5-a][1,3,5]triazine Derivatives as Thymidine Phosphorylase Inhibitors
    Bera, Hriday
    Dolzhenko, Anton V.
    Sun, Lingyi
    Gupta, Sayan Dutta
    Chui, Wai-Keung
    CHEMICAL BIOLOGY & DRUG DESIGN, 2013, 82 (03) : 351 - 360
  • [43] Synthesis and antifungal activities of 3,5-diphenyl-7-amino-[1,3]-thiazolo[3,2-a]pyrimidine-6-nitrile derivatives
    Borthakur, Susanta Kumar
    Kalita, Pabitra Kumar
    Borthakur, Sukanya
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (03) : 1261 - 1265
  • [44] Facile Route to Novel Pyrazolo[3,4-d]pyrimidine, Imidazo[1,2-b] pyrazole, Pyrazolo[3,4-d][1,2,3]triazine, Pyrazolo[1,5-c][1,3,5]triazine and Pyrazolo[1,5-c][1,3,5]thiadiazine Derivatives
    Bondock, Samir
    Tarhoni, Abd El-Gaber
    Fadda, Ahmed A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (02) : 346 - 351
  • [45] Novel Route for the Synthesis of 5-(4-Hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dimethyl-1H-chromeno[2,3-d]pyrimidine-2,4(3H,5H)-diones
    Dige, Nilam C.
    Mahajan, Prasad G.
    Dhokale, Ramdas K.
    Chinchkar, Sarika M.
    Patil, Mayuri, V
    Pore, Dattaprasad M.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2019, 51 (06) : 553 - 565
  • [46] Design, Synthesis and Antiviral Evaluation of New N-(4)-(benzo[d][1,3]-dioxol-5-yl)thiosemicarbazone Derivatives
    Abbas, Samir Y.
    Tohamy, Wael M.
    Basyouni, Wahid M.
    El-Bayouki, Khairy A. M.
    Dawood, Reham M.
    El-awady, Mostafa K.
    Sroor, Farid M.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2021, 64 (07): : 3791 - 3800
  • [47] A facile one-pot synthesis of new thieno-[2,3-d]pyrimidine-2,4(1H,3H)-dione derivatives
    A.Davoodnia
    H.Behmadi
    A.Zare Bidaki
    M.Bakavoli
    N.Tavakoli Hoseini
    Chinese Chemical Letters, 2007, (10) : 1163 - 1165
  • [48] In Vitro Cytotoxicity of Methano[1,2,4]Triazolo-[1,5-C][1,3,5]Benzoxadiazocine Derivatives and Their Effects on Nitrite and Prostaglandin E2 (PGE2) Levels
    Dogan, Inci Selin
    Gumus, Mustafa Kemal
    Gorobets, Nikolay Yu
    Reis, Rengin
    Orak, Duygu
    Sipahi, Hande
    Sari, Suat
    Chebanov, Valentyn A.
    PHARMACEUTICAL CHEMISTRY JOURNAL, 2022, 56 (06) : 769 - 776
  • [49] In Vitro Cytotoxicity of Methano[1,2,4]Triazolo-[1,5-C][1,3,5]Benzoxadiazocine Derivatives and Their Effects on Nitrite and Prostaglandin E2 (PGE2) Levels
    İnci Selin Doğan
    Mustafa Kemal Gümüş
    Nikolay Yu. Gorobets
    Rengin Reis
    Duygu Orak
    Hande Sipahi
    Suat Sari
    Valentyn A. Chebanov
    Pharmaceutical Chemistry Journal, 2022, 56 : 769 - 776
  • [50] Synthesis of chiral 2(5H)-furanone derivatives with 1,3-butadiyne structure
    Huo, Jing-Pei
    Xiong, Jin-Feng
    Mo, Guang-Zhen
    Peng, Pai
    Wang, Zhao-Yang
    RESEARCH ON CHEMICAL INTERMEDIATES, 2013, 39 (09) : 4321 - 4335