Synthesis and anti-bacterial, anti-fungal activity of novel 1,2,4-oxadiazole (original) (raw)
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Synthesis of some novel 1, 3, 4-oxadiazole and its anti-bacterial and anti-fungal activity
2011
Research on 1, 3, 4-oxadiazole and their synthetic analogs have revealed a variety of pharmacological activities including anti-microbial, anti-tubercular and insecticidal agents. Some of these compounds have also analgesic, anti-inflammatory, anti-cancer, anti-HIV agent, anti-parkinsonian and anti-proliferative agent. It was our interest to make novel derivatives of the titled compounds and evaluate the anti-bacterial and anti-fungal activities. 1, 3, 4-oxadiazole and its derivatives were obtained from 6-phenyl-2-substituted quinoline-4-carbohydrazide and a mixture of carbon disulphide and potassium hydroxide. Elemental analysis, IR, 1H-NMR, and mass spectral data established identification of the compounds. Products were evaluated for their antimicrobial activity using cup plate method1. Some of the obtained compounds showed the interesting antimicrobial activity.
International Journal of Research in Pharmacy and Pharmaceutical Sciences
A new series of some pyridine condensed oxadiazole derivatives were prepared by reacting pyridine derivative with various aromatic carboxylic acids. In the present work 9 different 2, 5-disubstituted 1, 3, 4 oxadiazole derivatives (3a-i) were synthesized. Pyridine 4-carboxylic acid (Nicotinic acid) is converted into methyl pyridine 4-carboxlate by esterification. Pyridine 4-carboxlate is converted to pyridine 4-carbohydrazide (Isoniazid) by treating with hydrazine hydrate. Pyridine 4-carbohydrazide is converted to 2, 5-disubstituted 1, 3, 4 oxadiazole derivatives by treating with different types of aromatic carboxylic acids in the presence of POCl3. Confirmation of the chemical structure of the synthesized compounds was substantiated by TLC, IR, 1H NMR, and MS spectroscopy. All the synthesized compounds were tested for in-vitro antibacterial (against Escherichia coli, Bacillus subtilis, Staphylococcus aureus) and antifungal activity (against Aspergillus niger). 5e, 5i, 5b, 5d showed...
Synthesis, Antibacterial and Antifungal Activity of 2,5- Disubstituted-1,3,4-oxadiazole Derivatives
International Journal of PharmTech Research
In the present article synthesis and evaluation for antibacterial and antifungal activity of a new series of 2,5-disubstituted-1,3,4-oxadiazole derivatives is described. 2,5-disubstituted-1,3,4-oxadiazole derivatives were synthesized by the reaction of quinolinyl hydrazone derivatives with dichloromethane. The compounds (6a-h) were characterized by IR, NMR, and mass spectroscopy. All the synthesized compounds were screened for their antimicrobial activity. The antimicrobial results reveal that among the synthesized compounds 6b and 6f showed excellent antibacterial and antifungal activity. The compounds 6c, 6d and 6e did not show antifungal activity against the Colletotrichum capsici.
Synthesis, antimicrobial activity and cytotoxicity of novel oxadiazole derivatives
Journal of Enzyme Inhibition and Medicinal Chemistry, 2012
In the present study, 5-substituted-1,3,4-oxadiazolin-2-thiones (1a-b) were synthesized via the ring closure reactions of appropriate acid hydrazides with carbon disulphide. N-(Benzothiazol-2-yl)-2-[[5-substituted-1,3,4-oxadiazol-2-yl] sulfanyl]acetamide derivatives (3a-j) were obtained by the nucleophilic substitution reactions of 5-substituted-1,3,4-oxadiazolin-2-thiones (1a-b) with N-(benzothiazol-2-yl)-2-chloroacetamides. The chemical structures of the compounds were elucidated by IR, 1 H NMR, 13 C NMR and FAB +-MS spectral data and elemental analyses. The synthesized compounds were screened for their antimicrobial activities against Micrococcus luteus, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus, Escherichia coli, Listeria monocytogenes and Candida albicans. All compounds except compound 3h exhibited the highest antibacterial activity against P. aeruginosa. Among all compounds (3a-j), the compounds bearing 4-methoxyphenoxymethyl moiety on oxadiazole ring (3a-e) exhibited the highest inhibitory activity against C. albicans. Although compound 3j did not possess 4-methoxyphenoxymethyl moiety on oxadiazole ring, this derivative also exhibited the same level of anti-candidal activity. The compounds were also investigated for their cytotoxic effects using MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Compound 3a exhibited the highest cytotoxic activity, whereas compound 3g possessed the lowest cytotoxic activity against NIH/3T3 cells.
2012
Heterocyclic systems are one of the most important classes of organic compounds present in nature or synthesized in laboratory. These compounds possess an array of biological activities and are employed in the treatment of commonly occurring diseases. This has been the backbone for medicinal chemists to impart interest for synthesizing some novel derivatives of possible high biological activity. In the last few decades, the chemistry of five-membered heterocyclic rings has received considerable attention owing to their synthetic and effective biological importance. One such class of compound is oxadiazole. The synthesis of novel oxadiazole derivatives and investigation of their chemical and biological behaviour have gained more importance in recent decades for medicinal, agricultural and industrial point of view. The oxadiazole chemistry has been developed extensively and is still developing. Presently there are a number of drugs used clinically which comprise oxadiazole moiety in association with various heterocyclic rings such as furamizole, nosapidil and tiodazosin. The present review deals with various method of preparation, chemistry, therapeutic potential of oxadiazole derivatives and special emphasis is given on recently reported oxadiazole analogues possessing antimicrobial activity.
Synthesis and evaluation of antimicrobial activity of novel 1,3,4-oxadiazole derivatives
2011
In attempt to find new pharmacologically active molecules, we report here the synthesis and in vitro antimicrobial activities of various novel 1,3,4-oxadiazole containing 5-phenyltetrazole. The Schiff bases were obtained by condensation 2-(5-phenyl-1H-tetrazol-1-yl)acetohydrazide with various aromatic aldehydes. Cyclocondensation of Schiff’s bases with acetic anhydride results in 1,3,4-oxadiazole derivatives. The structures of the newly synthesized 1,3,4-oxadiazole were confirmed by FT-IR, 1H NMR and mass spectral data. The antimicrobial activity was determined by MIC method. All the compounds exhibited weak to potent antimicrobial activity. Some derivatives bearing a methoxy group exhibited very good antimicrobial activity at conc. of 62.5 µg/mL.
Synthesis and antimicrobial activity of some 1,3,4-oxadiazole derivatives
Six new 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-thione, 2-amino-5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole, 5-(1-/ 2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-one derivatives have been synthesized from 1-and/or 2-naphthol. The structures of the compounds were confirmed by IR and 1 H NMR spectral data and microanalysis. The antimicrobial properties of the compounds were investigated against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa, Candida albicans, C. krusei and C. parapsilosis using microbroth dilution method. 2-Amino-5-(2-naphthyloxymethyl)-1,3,4-oxadiazole and 5-(2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-one show significantly (32 mg/ml), compounds 5-(1-/2-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-thione, 2-amino-5-(1-naphthyloxymethyl)-1,3,4-oxadiazole and 5-(1-naphthyloxymethyl)-1,3,4-oxadiazole-2(3H)-one moderately (64 mg/ml) active against C. krusei. All the compounds were active against S. aureus, E. coli, P. aeruginosa, C. albicans, and C. parapsilosis at 64-256 mg/ml concentration.
European Journal of Medicinal Chemistry, 2010
In present investigation a series of 28 oxadiazole analogues (AB1eAB28) were subjected to molecular properties prediction, drug-likeness by Molinspiration (Molinspiration, 2008) & MolSoft (MolSoft, 2007 softwares, lipophilicity and solubility parameters using ALOGPS 2.1 program. Out of 28 analogues only 16 were chosen on the basis of Lipinski "Rule of Five" (Ro5) for the synthesis and antimicrobial screening as oral bioavailable drugs/leads. Maximum drug-likeness model score (1.22) was found to be of compound AB13. Selected compounds (AB1eAB2), (AB5eAB9), (AB12eAB16), (AB18eAB21) were synthesized and characterized by IR, NMR and mass spectral analysis followed by antibacterial and antifungal screening. It was observed that compounds showed moderate to good antibacterial activity, but their antifungal activity was somewhat moderate. Compounds AB13 and AB20 showed pronounced activity against all bacterial and fungal strains. We had noticed that compounds (AB13, AB20) bearing OH group at one of the phenyl ring of oxadiazole exhibited good antimicrobial properties and their drug-likeness model score were also predicted maximum among the series.