Recent Advances in the Chemistry of 1,2,4-Oxadiazoles

被引:67
作者
Pace, Andrea [1 ]
Buscemi, Silvestre [1 ]
Piccionello, Antonio Palumbo [1 ]
Pibiri, Ivana [1 ]
机构
[1] Univ Palermo, Dipartimento Sci & Tecnol Biol Chim & Farmaceut, Palermo, Italy
来源
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 116 | 2015年 / 116卷
关键词
1,2,4-Oxadiazoles; Fluorinated heterocycles; Materials; Pharmaceuticals; Photochemistry; Rearrangements; BIPOLAR HOST MATERIALS; PROTIC IONIC LIQUIDS; ONE-POT SYNTHESIS; 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES; SIDE-CHAIN; BUILDING-BLOCKS; NEMATIC PHASE; DEEP-BLUE; OXADIAZOLES; DERIVATIVES;
D O I
10.1016/bs.aihch.2015.05.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,2,4-Oxadiazoles experienced an almost 80-year long period of scientific lethargy before they tickled the curiosity of chemists. The study of chemical and photochemical reactivity of 1,2,4-oxadiazoles opened the way to a series of applications in heterocyclic synthesis. Today, 1,2,4-oxadiazoles are known in medicinal chemistry for their use as bioisosters of esters and amides. Furthermore, fluorinated 1,2,4-oxadiazoles have been applied in materials science either by themselves or for the targeted modification of polymers and macromolecules. Overall, the synthesis of 1,2,4-oxadiazoles can be planned to fine-tune their properties for featured applications. Their versatility, either as starting synthons or as target compounds, has boosted the number of studies involving 1,2,4-oxadiazoles in the last decade. This review presents a selection of 1,2,4-oxadiazoles applications in materials science and medicinal chemistry.
引用
收藏
页码:85 / 136
页数:52
相关论文
共 142 条
[1]   Synthesis and Characterization of 1,2,4-Oxadiazole-Based Deep-Blue and Blue Color Emitting Polymers [J].
Agneeswari, Rajalingam ;
Tamilavan, Vellaiappillai ;
Hyun, Myung Ho .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2014, 35 (02) :513-517
[2]   New Peptides with Metal Binding Abilities and Their Use as Drug Carriers [J].
Allam, Anas ;
Maigre, Laure ;
Alimi, Mickael ;
de Sousa, Rodolphe Alves ;
Hessani, Assia ;
Galardon, Erwan ;
Pages, Jean-Marie ;
Artaud, Isabelle .
BIOCONJUGATE CHEMISTRY, 2014, 25 (10) :1811-1819
[3]   1,2,4-and 1,3,4-Oxadiazole Synthesis by Palladium-Catalyzed Carbonylative Assembly of Aryl Bromides with Amidoximes or Hydrazides [J].
Andersen, Thomas L. ;
Caneschi, Wiliam ;
Ayoub, Ali ;
Lindhardt, Anders T. ;
Couri, Mara R. C. ;
Skrydstrup, Troels .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (14-15) :3074-3082
[4]   Studies in chemotherapy. VI. Sulfanilamido heterocycles [J].
Anderson, GW ;
Faith, HE ;
Marson, HW ;
Winnek, PS ;
Roblin, RO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1942, 64 :2902-2905
[5]   Screening and hit evaluation of a chemical library against blood-stage Plasmodium falciparum [J].
Avery, Vicky M. ;
Bashyam, Sridevi ;
Burrows, Jeremy N. ;
Duffy, Sandra ;
Papadatos, George ;
Puthukkuti, Shyni ;
Sambandan, Yuvaraj ;
Singh, Shivendra ;
Spangenberg, Thomas ;
Waterson, David ;
Willis, Paul .
MALARIA JOURNAL, 2014, 13
[6]   Design of fluorescent materials for chemical sensing [J].
Basabe-Desmonts, Lourdes ;
Reinhoudt, David N. ;
Crego-Calama, Mercedes .
CHEMICAL SOCIETY REVIEWS, 2007, 36 (06) :993-1017
[7]   NEW SUBSTANCES OF POSSIBLE CHEMOTHERAPEUTICAL VALUE .1. [J].
BERGMANN, ED ;
BENDAS, H ;
DAVILLA, U .
JOURNAL OF ORGANIC CHEMISTRY, 1953, 18 (01) :64-69
[8]   Zinc(II)-Mediated Nitrile-Amidoxime Coupling Gives New Insights into H+-Assisted Generation of 1,2,4-Oxadiazoles [J].
Bolotin, Dmitrii S. ;
Kulish, Kirill I. ;
Bokach, Nadezhda A. ;
Starova, Galina L. ;
Gurzhiy, Vladislav V. ;
Kukushkin, Vadim Yu .
INORGANIC CHEMISTRY, 2014, 53 (19) :10312-10324
[9]   Design, synthesis, and evaluation of Phe-Gly mimetics: Heterocyclic building blocks for pseudopeptides [J].
Borg, S ;
Vollinga, RC ;
Labarre, M ;
Payza, K ;
Terenius, L ;
Luthman, K .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (21) :4331-4342
[10]   Oxadiazoles in Medicinal Chemistry [J].
Bostrom, Jonas ;
Hogner, Anders ;
Llinas, Antonio ;
Wellner, Eric ;
Plowright, Alleyn T. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (05) :1817-1830