Synthesis and Pharmacological Evaluation of Some Novel Thebaine Derivatives: N-(Tetrazol-1H-5-yl)-6,14-endoethenotetrahydrothebaine Incorporating the 1,3,4-Oxadiazole or the 1,3,4-Thiadiazole Moiety

被引：18
|
作者：
Yavuz, Serkan [1 ]
Unal, Yusuf [2 ]
Pamir, Ozgur [1 ]
Yilmazer, Demet [3 ]
Kurtipek, Omer [2 ]
Kavutcu, Mustafa [4 ]
Arslan, Mustafa [4 ]
Ark, Mustafa [5 ]
Yildirir, Yilmaz [1 ]
机构：
[1] Gazi Univ, Fac Sci, Dept Chem, TR-06500 Ankara, Turkey
[2] Gazi Univ, Fac Med, Dept Anesthesiol & Reanimat, TR-06500 Ankara, Turkey
[3] Diskapi Yildirim Bayezit Res & Educ Hosp, Dept Pathol, Ankara, Turkey
[4] Gazi Univ, Fac Med, Dept Clin Biochem, TR-06500 Ankara, Turkey
[5] Gazi Univ, Fac Pharm, Dept Pharmacol, TR-06500 Ankara, Turkey
来源：
ARCHIV DER PHARMAZIE | 2013年 / 346卷 / 06期
关键词：
Analgesic activity; Oxadiazole; Tetrazole; Thebaine; Thiadiazole; ANALGESICS;
D O I：
10.1002/ardp.201200451
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
In this study, we synthesized some novel N-(tetrazol-1H-5-yl)-6,14-endoethenotetrahydrothebaine 7-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives as potential analgesic agents. The structures of the compounds were established on the basis of their IR, 1H NMR, 13C NMR, 2D NMR, and high-resolution mass spectral data. The analgesic activity was evaluated by a rat-hot plate test model and a rat tail-flick model. Compound 12 showed analgesic activity higher than that of morphine. In addition to a histopathological and biochemical evaluation, the LD50 dose for the most active compound 12 was determined.
引用
收藏
页码：455 / 462
页数：8
相关论文
共 50 条
  • [21] Synthesis and antibacterial activities of 1,3,4-thiadiazole, 1,3,4-oxadiazole and 1,2,4-triazole derivatives of 5-methylisoxazole
    Hui, XP
    Zhang, LM
    Zhang, ZY
    Wang, Q
    Wang, F
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1999, 38 (09): : 1066 - 1069
  • [22] Synthesis, characterization, antimicrobial, and pharmacological evaluation of some 2, 5-disubstituted sulfonyl amino 1,3,4-oxadiazole and 2-amino-disubstituted 1,3,4-thiadiazole derivatives
    Pal, Dilipkumar
    Tripathi, Rohit
    Pandey, Desh Deepak
    Mishra, Preety
    JOURNAL OF ADVANCED PHARMACEUTICAL TECHNOLOGY & RESEARCH, 2014, 5 (04) : 196 - 201
  • [23] SYNTHESIS OF 1,3,4-OXADIAZOLE AND 1,3,4-THIADIAZOLE AMINO DERIVATIVES CONTAINING FRAGMENTS OF SPATIALLY-HINDERED PHENOL
    KOSHELEV, VN
    KELAREV, VI
    KUATBEKOV, AM
    POLIVIN, YN
    SHALKAROV, SI
    IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA I KHIMICHESKAYA TEKHNOLOGIYA, 1993, 36 (08): : 60 - 66
  • [24] Synthesis and bioactivities of novel 1,3,4-oxadiazole derivatives containing 1,2,3-thiadiazole moiety
    Sun, Guo-Xiang
    Yang, Ming-Yan
    Sun, Zhao-Hui
    Wu, Hong-Ke
    Liu, Xing-Hai
    Wei, Yun-Yang
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2014, 189 (12) : 1895 - 1900
  • [25] Synthesis and Antimicrobial Evaluation of Some 1,3,4-Thiadiazole Derivatives
    Shashikant, Pattan R.
    Desai, N. S.
    Rabara, P. A.
    Bukitgar, A. A.
    Wakale, V. S.
    INDIAN JOURNAL OF PHARMACEUTICAL EDUCATION AND RESEARCH, 2008, 42 (04) : 314 - 318
  • [26] Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives
    Manjunatha, K.
    Poojary, Boja
    Lobo, Prajwal L.
    Fernandes, Jennifer
    Kumari, N. Suchetha
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (11) : 5225 - 5233
  • [27] 1,3,4-Oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole derivatives as potential antibacterial agents
    Othman, Adil A.
    Kihel, Mebrouk
    Amara, Sarah
    ARABIAN JOURNAL OF CHEMISTRY, 2019, 12 (07) : 1660 - 1675
  • [28] Synthesis and Antitumor Activity Evaluation of Novel Echinatin Derivatives with a 1,3,4-Oxadiazole Moiety
    Tian, Xing
    Sun, Zihan
    Zhong, Ye
    Yang, Huali
    Cheng, Maosheng
    Liu, Yang
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2024, 25 (04)
  • [29] Synthesis and pharmacological evaluation of condensed heterocyclic 6-substituted 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole and 1,3,4-oxadiazole derivatives of isoniazid
    Gilani, Sadaf J.
    Khan, Suroor A.
    Siddiqui, Nadeem
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (16) : 4762 - 4765
  • [30] Synthesis and Nematicidal Activity of Novel 1,3,4-Oxadiazole (Thiadiazole) Thioether Derivatives Containing Trifluorobuten Moiety
    Chen, Xuewen
    Gan, Xiuhai
    Chen, Jixiang
    Chen, Yongzhong
    Wang, Yanjiao
    Hu, Deyu
    Song, Baoan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (09) : 2343 - 2351
12345