7659-06-5Relevant academic research and scientific papers
Synthesis of a Series of Novel 2-Amino-5-substituted 1,3,4-oxadiazole and 1,3,4-thiadiazole Derivatives as Potential Anticancer, Antifungal and Anti-bacterial Agents
Do, tuoi thi Hong,Dong, Nguyen Hanh,Vo, Duy Duc,pham, Em canh,truong, tuyen Ngoc
, p. 558 - 573 (2022/03/09)
Objective: The objective of the present study was to prepare the 5-substituted 2-amino-1,3,4-oxadiazole and 2-amino-1,3,4-thiadiazole derivatives and evaluate their potential anticancer, antibac-terial and antifungal activities. Methods: Twenty-seven derivatives were synthesized by iodine-mediated cyclization of semicarba-zones or thiosemicarbazones obtained from condensation of semicarbazide or thiosemicarbazide and aldehydes. The structures were confirmed by1H-NMR,13C-NMR and MS spectra. The antibacterial and antifungal activities were evaluated by diffusion method and the anticancer activities were evaluated by MTT assay. Results: Twenty-seven derivatives have been synthesized in moderate to good yields. A number of derivatives exhibited potential antibacterial, antifungal and anticancer activities. Conclusion: Compounds (1b, 1e and 1g) showed antibacterial activity against Streptococcus faecal-is, MSSA and MRSA with MIC value ranging between 4 to 64 μg/mL. Compound (2g) showed anti-fungal activity against Candida albicans (8 μg/mL) and Aspergillus niger (64 μg/mL). Compound (1o) exhibited high cytotoxic activity against HepG2 cell line (IC50 value 8.6 μM) which is compara-ble to the activity of paclitaxel, and is non-toxic on LLC-PK1 normal cell line. The structure activity relationship and molecular docking study of the synthesized compounds have also been reported.
Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds
Pallesen, Jakob S.,Narayanan, Dilip,Tran, Kim T.,Solbak, Sara M. ?.,Marseglia, Giuseppe,S?rensen, Louis M. E.,H?j, Lars J.,Munafò, Federico,Carmona, Rosa M. C.,Garcia, Anthony D.,Desu, Haritha L.,Brambilla, Roberta,Johansen, Tommy N.,Popowicz, Grzegorz M.,Sattler, Michael,Gajhede, Michael,Bach, Anders
, p. 4623 - 4661 (2021/05/07)
Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.
Direct C-C Bond Cleavage of 1,3-Dicarbonyl Compounds as a Single-Carbon Synthon: Synthesis of 2-Aryl-4-quinolinecarboxylates
Zhou, You,Zhao, Peng,Wang, Li-Sheng,Yu, Xiao-Xiao,Huang, Chun,Wu, Yan-Dong,Wu, An-Xin
, p. 6461 - 6465 (2021/08/23)
A novel [2 + 1 + 3] cyclization reaction for the synthesis of 2-aryl-4-quinolinecarboxylates from aryl methyl ketones, arylamines, and 1,3-dicarbonyl compounds has been established. This metal-free process achieved the C-C bond cleavage of 1,3-dicarbonyl compounds directly as a single-carbon synthon. The reaction is highly efficient and has good substrate compatibility while operating under mild conditions. This method has good practicability and successfully realized the synthesis of bioactive molecules.
Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety
Han, Xu,Liu, Xin Hua,Ma, Duo,Yu, Yun Long,Zhang, Zhao Yan
, p. 344 - 360 (2021/01/06)
Based on previous studies, 66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 50 = 6.41 μM). In addition, clear structure–activity relationships were summarised, indicating that the substitution of the methoxy group and the position, type and number of the substituents on the phenyl ring had significant effects on telomerase activity. Among them, compound A33 showed considerable inhibition against telomerase. Flow cytometric analysis showed that compound A33 could arrest MGC-803 cell cycle at G2/M phase and induce apoptosis in a concentration-dependent way. Meanwhile, Western blotting revealed that this compound could reduce the expression of dyskerin, which is a fragment of telomerase.
Synthesis of 2-amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via sequential condensation and I2-mediated oxidative C-O/C-S bond formation
Niu, Pengfei,Kang, Jinfeng,Tian, Xianhai,Song, Lina,Liu, Hongxu,Wu, Jie,Yu, Wenquan,Chang, Junbiao
, p. 1018 - 1024 (2015/01/30)
2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.
A convenient synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using iodine and Oxone
Shinde, Vikas N.,Ugarkar, Bheemarao G.,Ghorpade, Sandeep R.
, p. 53 - 54 (2013/04/10)
A convenient methodology has been developed for the synthesis of substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using catalytic amount of iodine/KI in the presence of Oxone as a bulk oxidant. This offers the adv
A novel electroorganic synthesis of some 2-amino-5-substituted-1,3,4- oxadiazoles at the platinum electrode
Singh, Sushma,Kumar, Sanjeev,Sharma, Laxmi Kant,Singh
experimental part, p. 734 - 738 (2010/07/15)
The electroorganic synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles from semicarbazone has been carried out at platinum electrode. This is an environmentally benign electroorganic reaction done under controlled potential electrolysis in an undivided c
Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant
Rivera, Nelo R.,Balsells, Jaume,Hansen, Karl B.
, p. 4889 - 4891 (2007/10/03)
A scalable synthesis of 5-substituted-2-amino-1,3,4-oxadiazoles via oxidation of a thiosemicarbazide precursor is described. The thiosemicarbazide intermediates are easily accessed from the corresponding acid chlorides. Oxidative cyclization using 1,3-dibromo-5,5-dimethylhydantoin as the primary oxidant, in the presence of potassium iodide, gives a variety of oxadiazoles in good yields. This methodology utilizes a commercially inexpensive and easily handled oxidant.
Oxidation of 2-amino-5-aryl-1,3,4-oxadiazole by sodium periodate: A kinetic study
Pradhan, Banasova,Misro,Padhy, Arun Kumar
, p. 898 - 900 (2007/10/03)
Kinetics of oxidation of a few 2-amino-5-aryl-1,3,4-oxadiazoles by sodium periodate in aqueous acetic acid-HClO4 medium have been studied. The reaction follows a first order rate each with respect to oxidant and substrate concentration. A suita
