203268-83-1

Upstream product

• 75-15-0 carbon disulfide 
• 5351-17-7 4-aminobenzohydrazide 
• 85106-57-6 C₈H₈N₃OS₂^(1-)*K⁽¹⁺⁾ 
• 23269-70-7 N-(4-(5-mercapto-1,3,4-oxadiazol-2-yl)phenyl)acetamide 
• 41764-73-2 N-[4-(hydrazinecarbonyl)phenyl]acetamide 
• 17012-22-5 methyl 4-acetamidobenzoate 
• 619-45-4 4-methoxycarbonyl aniline 
• 150-13-0 4-amino-benzoic acid 
• 94-09-7 p-aminoethylbenzoate 

Downstream Products

• 870537-61-4 5-[(4-styrylmethine)amino]phenyl-1,3,4-oxadiazol-2-thiol 
• 1260218-09-4 4-(5-((2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl)thio)-1,3,4-oxadiazol-2-yl)aniline 

Relevant academic research and scientific papers

Synthesis and Evaluation of Antimicrobial Activity of New Imides and Schiff Bases Derived from Ethyl-4-Amino Benzoate

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.

Synthesis and mesomorphic behavior of two new homologous series containing azobenzene and 1,3,4-oxadiazole units

Two new nonsymmetrical mesogenic homologous series of terminal substituent ether (series [Vn]) and carboxy (series [VIn]) incorporating azobenzene and 1,3,4-oxadiazole group were synthesized. Both series have been All compounds thus isolated were purified and characterized by elemental analysis, Fourier Transform Infrared Spectroscopy, 1H NMR, along with thermal analysis and texture observation using Differential Scanning Calorimetry (DSC) and Polarizing Optical Microscopy (POM), respectively. All compounds of the first series exhibited liquid crystalline properties. The homologues [V1]-[V3] display a nematic mesophase, the compounds [V4]-[V7] exhibit a dimorphism behavior, nematic (N) and smectic A (SmA) mesophases, the compounds [V8] and [VI9] display enantiotropic smectic A and C (SmA and SmC) phases and the last homologue [V12] exhibits only a smectic C mesophase. All compounds of the second series [VIn] also show mesomorphic behavior, the compounds [VI1]-[VI3] and [VI5] display the nematic mesophase, the homologue [VI7] exhibits dimorphism behavior, nematic, and smectic A (SmA). The mesomorphic behavior has been analyzed in terms of structural property relationships.

Microwave synthesis and antibacterial activities of some imidazolidine derivatives containing 1, 3, 4-oxadiazole moiety

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 and characterization of some 5-substituted 2-thiol/thione-1,3,4-oxadiazoles

5-(4-Aminophenyl)-2-thiol-1,3,4-oxadiazole (1) was synthesized via the reaction of carbon disulfide with 4-aminobenzoyl hydrazide. Compound 1 was converted to the corresponding diazonium salt which was introduced in coupling reaction with sodium phenoxide as coupling reagent to give azo-oxadiazole derivative containing aldehyde group 2. The resulting aldehyde 2 was then introduced in acid-catalyzed condensation reactions with both 2-aminobenzothiazole and 2-amino-5-mercapto-1,3,4-thiadiazole to obtain the oxadiazolicimines 3a and 3b, respectively. Treatment of the resulting imines 3a and 3b with each succinic acid, maleic acid, phthalic acid and 3-nitrophthalic anhydrides, respectively, under (2+5) cycloaddition conditions afforded eight new oxadiazoles substituted with 1,3-oxazepane and 1,3-oxazepine moieties 4a-d and 5a-d, respectively. The resulting imines 3a and 3b were also treated with sodium azide under (2+3) cycloaddition conditions to obtain two new oxadiazoles containing tetrazole moiety 4e and 5e, respectively. The newly synthesized oxadiazoles might have some biological, pharmaceutical and medicinal applications.

Synthesis of four liquid crystals and study of alkyl chain effect on the nematic range for application in GC

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

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.

Pleuromutilin derivative with 1, 3, 4-oxadiazole side chain and preparation and application thereof

The invention belongs to the field of medicinal chemistry, and particularly relates to a pleuromutilin derivative with a 1, 3, 4-oxadiazole side chain and preparation and application thereof The pleuromutilin derivative with the 1, 3, 4-oxadiazole side chain is a compound shown in a formula 2 or a pharmaceutically acceptable salt thereof, and a solvent compound, an enantiomer, a diastereoisomer and a tautomer of the compound shown in the formula 2 or the pharmaceutically acceptable salt thereof or a mixture of the solvent compound, the enantiomer, the diastereoisomer and the tautomer in any proportion, including a racemic mixture. The pleuromutilin derivative has good antibacterial activity, is especially suitable for being used as a novel antibacterial agent for systemic system infection of animals or human beings, and has good water solubility.

Design and synthesis of quinoxaline-1,3,4-oxadiazole hybrid derivatives as potent inhibitors of the anti-apoptotic Bcl-2 protein

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.

Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach

Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.

Design, synthesis, and biological evaluation of new challenging thalidomide analogs as potential anticancer immunomodulatory agents

Thalidomide and its analogs are immunomodulatory drugs that inhibit the production of certain inflammatory mediators associated with cancer. In the present work, a new series of thalidomide analogs was designed and synthesized to obtain new effective antitumor immunomodulatory agents. The synthesized compounds were evaluated for their cytotoxic activities against a panel of four cancer cell lines (HepG-2, HCT-116, PC3 and MCF-7). Compounds 33h, 33i, 42f and 42h showed strong potencies against all tested cell lines with IC50 values ranging from 14.63 to 49.90 μM comparable to that of thalidomide (IC50 values ranging from 32.12 to 76.91 μM). The most active compounds were further evaluated for their in vitro immunomodulatory activities via estimation of human tumor necrosis factor alpha (TNF-α), human caspase-8 (CASP8), human vascular endothelial growth factor (VEGF), and nuclear factor kappa-B P65 (NF-κB P65) in HCT-116 cells. Thalidomide was used as a positive control. Compounds 33h and 42f showed a significant reduction in TNF-α. Furthermore, compounds 33i and 42f exhibited significant elevation in CASP8 levels. Compounds 33i and 42f inhibited VEGF. In addition, compound 42f showed significant decrease in levels of NF-κB p65. Moreover, apoptosis and cell cycle tests of the most active compound 42f, were performed. The results indicated that compound 42f significantly induce apoptosis in HCT-116 cells and arrest cell cycle at the G2/M phase.