- Imidazole hydrochloride promoted synthesis of 3,5-disubstituted-1,2,4-oxadiazoles
-
Imidazole hydrochloride as an additive promotes the reaction of amidoximes and DMA derivatives to generated 3,5-disubstituted-1,2,4-oxadiazoles in low to excellent yields without the use of coupling reagents, oxidants, strong acids or bases and other additives.
- Wang, Xuetong,Wang, Yin,Liu, Xiaoling,He, Tingshu,Li, Lingli,Wu, Huili,Zhou, Shangjun,Li, Dan,Liao, Siwei,Xu, Ping,Huang, Xing,Yuan, Jianyong
-
supporting information
(2021/10/14)
-
- NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N?O bond formation
-
A reaction involving an efficient NBS-mediated oxidative N?O bond formation has been established for the synthesis of 1,2,4-oxadiazoles from readily accessible N-acyl amidines. The features of this synthetic method include simplicity of operation, mild re
- Li, Ertong,Wang, Manman,Wang, Zhen,Yu, Wenquan,Chang, Junbiao
-
p. 4613 - 4618
(2018/07/31)
-
- One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Using Catalytic System NaOH?DMSO
-
One-pot convenient process was developed for the production of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with anhydrides or acyl chlorides in a system NaOH?DMSO. The reaction proceeds at room temperature with high yields.
- Pankrat’eva,Sharonova,Tarasenko,Baikov,Kofanov
-
p. 1250 - 1255
(2018/10/24)
-
- Fragmentation of GW4064 led to a highly potent partial farnesoid X receptor agonist with improved drug-like properties
-
Abstract The ligand activated transcription factor farnesoid X receptor (FXR) is a crucial regulator of several metabolic and inflammatory pathways and its activation by agonistic ligands seems a valuable therapeutic approach for many disorders. Most known non-steroidal FXR agonists however, have limitations that hinder their clinical development and novel FXR ligands are required. Evaluation of the co-crystal structures of the widely used FXR agonist GW4064 and related compounds in complex with the FXR ligand binding domain indicated that their disubstituted isoxazole moiety is especially relevant for FXR activation. By investigation of GW4064-fragments missing the aromatic tail, we discovered a highly potent and soluble partial FXR agonist (14, ST-1892) as well as a fluorescent FXR ligand (15) as potential pharmacological tool.
- Flesch, Daniel,Gabler, Matthias,Lill, Andreas,Gomez, Roberto Carrasco,Steri, Ramona,Schneider, Gisbert,Stark, Holger,Schubert-Zsilavecz, Manfred,Merk, Daniel
-
p. 3490 - 3498
(2015/08/03)
-
- Mild and efficient one-pot synthesis of 3,5-disubstituted 1,2,4-oxadiazoles from nitriles mediated by K 3PO 4
-
Potassium phosphate, K3PO4, has been proved to be a cheap, strong, and efficient reagent for the one-pot synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from nitriles and acid chlorides under mild conditions. [Supplementary material
- Movassagh, Barahman,Talebsereshki, Farzaneh
-
supporting information
p. 188 - 194
(2013/12/04)
-
- Antikinetoplastid activity of 3-aryl-5-thiocyanatomethyl-1,2,4-oxadiazoles
-
A series of 5-thiocyanatomethyl- and 5-alkyl-3-aryl-1,2,4-oxadiazoles were synthesized and evaluated for their activity against kinetoplastid parasites. Formation of the oxadiazole ring was accomplished through the reaction of benzamidoximes with acyl chlorides, while the thiocyanate group was inserted by reacting the appropriate 5-halomethyl oxadiazole with ammonium thiocyanate. The thiocyanate-containing compounds possessed low micromolar activity against Leishmania donovani and Trypanosoma brucei, while the 5-alkyl oxadiazoles were less active against these parasites. 3-(4-Chlorophenyl)-5-(thiocyanatomethyl)-1, 2,4-oxadiazole (compound 4b) displayed modest selectivity for L. donovani axenic amastigote-like parasites over J774 macrophages, PC3 prostate cancer cells, and Vero cells (6.4-fold, 3.8-fold, and 9.1-fold, respectively), while 3-(3,4-dichlorophenyl)-5-(thiocyanatomethyl)-1,2,4-oxadiazole (compound 4h) showed 30-fold selectivity against Vero cells but was not selective against PC3 cells. In a murine model of visceral leishmaniasis, compound 4b decreased liver parasitemia caused by L. donovani by 48% when given in five daily i.v. doses at 5mg/kg and by 61% when administered orally for 5days at 50mg/kg. These results indicate that aromatic thiocyanates hold promise for the treatment of leishmanial infections if the selectivity of these compounds can be improved.
- Cottrell, Denise M.,Capers, Jeffrey,Salem, Manar M.,DeLuca-Fradley, Kate,Croft, Simon L.,Werbovetz, Karl A.
-
p. 2815 - 2824
(2007/10/03)
-
- Electrochemical oxidation of substituted amide oximes and 4,5-dihydro-1,2,4-oxadiazoles
-
The electrooxidation of several substituted amide oximes to yield the corresponding nitriles, alcohols, and imidate was successfully carried out. The reaction products were dependent on the substituents. Additionally, 4,5-dihydro-1,2,4-oxadiazoles derived from amide oximes were electro-oxidized to afford 1,2,4-oxadiazoles in good yields.
- Okimoto, Mitsuhiro,Takahashi, Yukio
-
p. 427 - 428
(2007/10/03)
-
- Rearrangement Reactions of Aziridinylbenzaldoximes
-
Reactions of 2,2-dimethylaziridine with benzohydroximoyl chlorides [ArC(Cl)=NOH] give aziridinyl-benzaldoximes 1. It has been found that the aziridine ring in these compounds undergoes ring opening in hydrogen chloride-dioxane solution to give (Z)-N-hydro
- Johnson, James E.,Nwoko, Delphine,Hotema, Martha,Sanchez, Natalia,Alderman, Reidun,Lynch, Vincent
-
p. 1583 - 1592
(2007/10/03)
-
- SYNTHESIS AND THERMOLYSIS OF SOME N-HYDROXIMOYL- AND N-HYDRAZONOYLAZOLES
-
The reactions of nitrile oxides or nitrile imines with pyrazole, imidazole, 1,2,3- and 1,2,4-triazole or tetrazole derivatives yield the appropriate N-hydroximoyl- or N-hydrazonoylazoles.Thermolysis of 1-hydroximoyltetrazoles, depending on the nature of the substituents in the tetrazole ring, yields 1,2,4-oxadiazoles or 5-amino-1,2,4-oxadiazoles upon hydrazoic acid or nitrogen evolution.Under similar conditions, 1-hydrazonoyltetrazoles give 1,2,4-triazoles or 5-amino-1,2,4-triazoles while 2-hydrazonoyltetrazoles decompose to the dihydro-1,2,4,5-tetrazine derivatives.
- Plenkiewicz, Jan,Zdrojewski, Tadeusz
-
p. 675 - 710
(2007/10/02)
-