1,2,4-and 1,3,4-Oxadiazoles as Scaffolds in the Development of Antiparasitic Agents

被引:76
|
作者
Pitasse-Santos, Paulo [1 ]
Sueth-Santiago, Vitor [2 ]
Lima, Marco E. F. [1 ]
机构
[1] Univ Fed Rural Rio de Janeiro, Dept Quim, BR-465,Km 7, BR-23897000 Seropedica, RJ, Brazil
[2] Inst Fed Educ Ciencia Tecnol & Rio de Janeiro, Rua Jose Augusto Pereira Santos S-N, BR-24425004 Sao Goncalo, RJ, Brazil
关键词
drug design; bioisosterism; heterocyclic drugs; anti-infective drugs; BIOLOGICAL EVALUATION; TRYPANOSOMA-CRUZI; ANTILEISHMANIAL AGENTS; CATALYZED SYNTHESIS; MOLECULAR DOCKING; ANTIFUNGAL AGENTS; IN-VITRO; DERIVATIVES; OXADIAZOLE; HETEROCYCLES;
D O I
10.21577/0103-5053.20170208
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this review, we present the potential use of the heterocyclic oxadiazole rings in the design and synthesis of new drugs to treat parasitic infections. We intend to compare herein all the four isomeric forms of oxadiazole rings as well as discuss the differences and similarities between them. In addition, we discuss aspects on their reactivity that justify the great importance of both 1,2,4- and 1,3,4-oxadiazoles isomers when compared with their other two isomers. Although some oxadiazole isomers satisfy Huckel's rule, there are differences concerning their aromaticity, which have a great impact on the possible interactions of the oxadiazole ring with biological receptors. The set of works selected from the literature and discussed herein points out the oxadiazole core as an important and versatile scaffold in the development of new chemical entities potentially useful as antiparasitic drugs.
引用
收藏
页码:435 / 456
页数:22
相关论文
共 50 条
  • [41] PREPARATION OF POLY(1,3,4-OXADIAZOLES)
    VARMA, IK
    GEETHA, CK
    INDIAN JOURNAL OF CHEMISTRY SECTION A-INORGANIC BIO-INORGANIC PHYSICAL THEORETICAL & ANALYTICAL CHEMISTRY, 1978, 16 (04): : 352 - 353
  • [42] Synthesis and bioassay of a new class of disubstituted 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles
    Sekhar, Mangali Madhu
    Yamini, Gudi
    Divya, Kuppi Reddy Gari
    Padmavathi, Venkatapuram
    Padmaja, Adivireddy
    MEDICINAL CHEMISTRY RESEARCH, 2019, 28 (07) : 1049 - 1062
  • [43] HYDROXYLAMINE DERIVATIVES AS POTENTIAL ANTIMALARIAL AGENTS .3. 1,2,4-OXADIAZOLES
    HYNES, JB
    GRATZ, RF
    JOURNAL OF MEDICINAL CHEMISTRY, 1972, 15 (11) : 1198 - &
  • [44] Synthesis of pyridazinone-substituted 1,3,4-thiadiazoles,-1,3,4-oxadiazoles and-1,2,4-triazoles
    Zou, XJ
    Jin, GY
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (04) : 993 - 996
  • [45] SYNTHESIS OF PHOSPHORYLATED 1,3,4-OXADIAZOLES
    SHISHKIN, VE
    ZOTOV, YL
    NO, BI
    ZHURNAL OBSHCHEI KHIMII, 1977, 47 (11): : 2623 - 2623
  • [46] One-potCuAAC synthesis of (1H-1,2,3-triazol-1-yl)methyl-1,3,4/1,2,4-oxadiazoles starting from available chloromethyl-1,3,4/1,2,4-oxadiazoles
    Pokhodylo, Nazariy T.
    Savka, Roman D.
    Shyyka, Olga Ya.
    Obushak, Mykola D.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (07) : 2969 - 2976
  • [47] Synthesis and Antioxidant Activity of Styrylsulfonylmethyl 1,3,4-Oxadiazoles, Pyrazolyl/Isoxazolyl-1,3,4-oxadiazoles
    Reddy, Guda Mallikarjuna
    Muralikrishna, Akkarapalli
    Padmavathi, Venkatapuram
    Padmaja, Adivireddy
    Tilak, Thandaiah Krishna
    Rao, Chippada Appa
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (12) : 1291 - 1297
  • [48] Synthesis of certain 1,3,4-oxadiazoles as potential antitubercular and antimicrobial agents
    Dhol, SR
    Bhimani, AS
    Khunt, RC
    Parikh, AR
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 15 (01) : 63 - 64
  • [49] Synthesis of 1,2,4-oxadiazoles (a review)
    Kayukova L.A.
    Pharmaceutical Chemistry Journal, 2005, 39 (10) : 539 - 547
  • [50] NEW PATH TO 1,2,4-OXADIAZOLES
    BUZYKIN, BI
    KHARITONOVA, OA
    ZHURNAL OBSHCHEI KHIMII, 1993, 63 (11): : 2635 - 2636