203268-83-1Relevant articles and documents
Synthesis and Evaluation of Antimicrobial Activity of New Imides and Schiff Bases Derived from Ethyl-4-Amino Benzoate
Ahmed, Wurood S.,Al-Bayati, Redha I.,Razzak Mahmood, Ammar A.
, p. 2477 - 2486 (2020)
A series of disubstituted 1,3,4-oxadiazole derivatives, including: imides and Schiff bases, was achieved from the starting material, ethyl-4-aminobenzoate, which was converted to the corresponding 4-aminobenzohydrazide (1), by its reaction with hydrazine hydrate in absolute ethanol. Two oxadiazole parent nuclei had been synthesized from (1), the first nucleus 5-(4-aminophenyl)-1,3,4-oxadiazol-2-amine(2), and the second is 5-(4-aminophenyl)-1,3,4-oxadiazole-2-thione (3). Compound (2) obtained from stirring methanolic solution of (1) with cyanogen bromide(CNBr) and sodium bicarbonate (NaHCO3) at RT. While compound (3) was synthesized by refluxing of (1) with CS2 in the presence of (KOH), the produced potassium salt of hydrazide underwent cyclization by acidification with 10% HCl. Meanwhile, the cyclic imides derivatives (4-6) and (10-12) were synthesized by thermal fusion of (2) or (3) with acid anhydrides, while Schiffs bases derivatives (7-9) and (13-15) were synthesized by a conventional method involved refluxing of (2) or (3) with different aromatic aldehydes, in acidic medium (using glacial acetic acid). The new derivatives had been tested against three Gram-positive bacteria (Staphylococcus aureus, Micrococcus luteus, and Bacillus pumilus) and two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli) and two fungal species: (Saccharomyces cerevisiae and Candida albicans). Among the synthesized derivatives, compound (15) displayed a moderate to potent antibacterial activity, against different (Gram - positive and Gram-negative) bacteria, and also showed a slight to moderate antifungal activity.
Microwave synthesis and antibacterial activities of some imidazolidine derivatives containing 1, 3, 4-oxadiazole moiety
Abood, Zeid Hassan,Ali, Hayder Raheem,Qabel, Hussein Ali,Rasheed, Osama Hameed
, p. 546 - 550 (2018)
5-(4-Aminophenyl)-2-thiol-1, 3, 4-oxadiazole (1) was synthesized via the reaction of carbon disulfide with 4-aminobenzoyl hydrazide in presence of potassium hydroxide in absolute ethanol. Compound 1 was converted to the corresponding diazonium salt which
Synthesis of four liquid crystals and study of alkyl chain effect on the nematic range for application in GC
Tafer,Benalia,Djedid,Bouchareb,Al-dujaili
, p. 10 - 19 (2018)
Four liquid crystals (LCs) compounds which contain the 1,3,4-oxadiazole group were synthesized and characterized with spectroscopic techniques (IR, 1H- and 13C NMR), their thermal properties were analyzed by the Differential Scanning Calorimetry (DSC) and the polarizing microscope (POM). A comparative study of the mesomorphic properties of these LCs and three other compounds which have already been used as a stationary phase in gas chromatography (GC) was carried out. These compounds have the same main nucleus. LCs V1, LC1, LC2 and LC3 gave a nematic (N) phase to the heating, LCs V2 and V3 recorded smectic A (SmA) and N phases. However, the range (N) has disappeared in V4.
Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker
Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi
, (2021/05/17)
A class of pleuromutilin derivatives containing 1, 3, 4-oxadiazole were designed and synthesized as potential antibacterial agents against Methicillin-resistant staphylococcus aureus (MRSA). The ultrasound-assisted reaction was proposed as a green chemistry method to synthesize 1, 3, 4-oxadiazole derivatives (intermediates 85–110). Among these pleuromutilin derivatives, compound 133 was found to be the strongest antibacterial derivative against MRSA (MIC = 0.125 μg/mL). Furthermore, the result of the time-kill curves displayed that compound 133 could inhibit the growth of MRSA in vitro quickly (- 4.36 log10 CFU/mL reduction). Then, compound 133 (- 1.82 log10 CFU/mL) displayed superior in vivo antibacterial efficacy than tiamulin (- 0.82 log10 CFU/mL) in reducing MRSA load in mice thigh model. Besides, compound 133 exhibited low cytotoxicity to RAW 264.7 cells. Molecular docking studies revealed that compound 133 was successfully localized in the binding pocket of 50S ribosomal subunit (ΔGb = -10.50 kcal/mol). The results indicated that these pleuromutilin derivatives containing 1, 3, 4-oxadiazole might be further developed into novel antibiotics against MRSA.
Design and synthesis of quinoxaline-1,3,4-oxadiazole hybrid derivatives as potent inhibitors of the anti-apoptotic Bcl-2 protein
Ono, Yukari,Ninomiya, Masayuki,Kaneko, Daiki,Sonawane, Amol D.,Udagawa, Taro,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
, (2020/09/09)
Quinoxaline is one of the privileged heterocyclic fragments for drug molecules. Quinoxaline anticancer drug candidates XK469 and CQS exhibit antiproliferative and proapoptotic properties against various cancers. Based on their chemical structures, we therefore synthesized a series of quinoxaline-1,3,4-oxadiazole hybrids and assessed their anticancer potential on human leukemia HL-60 cells. Although these hybrids exerted significant inhibition of HL-60 cell proliferation, they showed high cytotoxicity on human normal cells (WI-38). Utilizing information from molecular modelling of the hybrids to the anti-apoptotic Bcl-2 protein, we added substructures including phenyl, piperazine, piperidine, and morpholine rings to their frameworks. The designed quinoxaline-1,3,4-oxadiazole hybrid derivatives successfully induced apoptotic response on HL-60 cells with low toxicity on WI-38 cells. Furthermore, RT-PCR analysis demonstrated that these derivatives predominantly inhibit Bcl-2 expression. Our findings highlight the great potential for the development of synthetic quinoxaline-1,3,4-oxadiazole hybrid derivatives as proapoptotic anticancer agents.
