62382-85-8Relevant articles and documents
Expedient discovery for novel antifungal leads: 1,3,4-Oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment
Wang, Xiaobin,Chai, Jianqi,Kong, Xiangyi,Jin, Fei,Chen, Min,Yang, Chunlong,Xue, Wei
, (2021/08/03)
Developing novel fungicide candidates are intensively promoted by the rapid emergences of resistant fungi that outbreak on agricultural production. Aiming to discovery novel antifungal leads, a series of 1,3,4-oxadiazole derivatives bearing a quinazolin-4(3H)-one fragment were constructed for evaluating their inhibition effects against phytopathogenic fungi in vitro and in vivo. Systematically structural optimizations generated the bioactive molecule I32 that was identified as a promising inhibitor against Rhizoctonia solani with the in vivo preventative effect of 58.63% at 200 μg/mL. The observations that were captured by scanning electron microscopy and transmission electron microscopy demonstrated that the bioactive molecule I32 could induce the sprawling growth of hyphae, the local shrinkage and rupture on hyphal surfaces, the extreme swelling of vacuoles, the striking distortions on cell walls, and the reduction of mitochondria numbers. The above results provided an indispensable complement for the discovery of antifungal lead bearing a quinazolin-4(3H)-one and 1,3,4-oxadiazole fragment.
Synthesis and biological evaluations of some new oxadiazole–piperidine hybrid derivatives as antioxidant agents
Al-Ghorbani, Mohammed M. Abdullah
, p. 379 - 384 (2018/09/29)
A series of some new 1,3,4-oxadiazole-2-thiol derivatives (6a-h) containing cyclic secondary amine such as piperidine ring was expeditiously synthesized by alkylation of 1,3,4-oxadiazol-2-thiol derivatives with chloroethyl piperidine hydrochloride. The 1,3,4-oxadiazole-2-thiols were effectively synthesized by cyclization reaction of acid hydrazide derivatives with carbon disulfide. The target compounds 6a-h were preliminarily screened for in vitro antioxidant activities using various in vitro antioxidant assays including 2,2′-diphenyl-1-picrylhydrazyl, nitric oxide, and hydrogen peroxide methods. The results showed that the compounds exhibited promising antioxidant property in the three methods at 50, 75, and 100 μM. Among the tested compounds, the compounds 6a and 6b having chloro substituent in the benzene ring displayed greater radical scavenging activity.
Synthesis and antibacterial evaluation of new sulfone derivatives containing 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole moiety
Su, Shihu,Zhou, Xia,Liao, Guoping,Qi, Puying,Jin, Linhong
, (2017/01/24)
Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1-5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45-1.86 μg/mL against X. oryzae and 1.97-20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.
2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as preparation method and application thereof
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Paragraph 0056, (2017/04/03)
The invention discloses 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives as well as a preparation method and an application thereof. The 2,5-substituent-1,3,4-oxadiazole (thiadiazole) thioether derivatives have the general formula (I) shown in the following specification, wherein R1 represents as 4-chlorphenyl, 4-fluorophenyl, 4-methylphenyl, 4-methoxyphenyl, 4-nitrophenyl, 4-cyano-3,5-difluorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, 4-t-butylphenyl, 2-fluorophenyl and other substituents; R2 represents methyl, ethyl, 4-chlorobenzyl, 2,4-dichlorobenzyl, 4-trifluoromethoxy, benzyl, 4-fluorobenzyl, 4-chlorobenzyl and other substituents; X represents O or S. The compound can be used as a pesticide for killing crop nematode and inhibiting bacterial diseases of crops.
Synthesis of oxadiazole-morpholine derivatives and manifestation of the repressed CD31 Microvessel Density (MVD) as tumoral angiogenic parameters in Dalton's Lymphoma
Al-Ghorbani, Mohammed,Vigneshwaran,Ranganatha, V. Lakshmi,Prabhakar,Khanum, Shaukath Ara
, p. 136 - 146 (2015/06/02)
A series of oxadiazole derivatives possessing morpholine 6a-l were synthesized by nucleophilic substitution reaction of key intermediates [1,3,4]-oxadiazole-2-thiol derivatives 5a-l with 4-(2-chloroethyl) morpholine. Compounds 6a-l were evaluated for their in vitro and in vivo antitumor potential in Dalton's Lymphoma Ascites (DLA) tumor cells. Among 6a-l series, compound 6a with concentration ～8.5 μM have shown extensive cytotoxicity in vitro and 85% reduction in tumor volume in vivo, attributing an excellent anti-proliferative capability towards the cancer cells. Compound 6a has extensively inhibited the Microvessel Density (MVD) or tumoral neovasculature which was evident from the CD31 immuno staining and peritoneal H&E staining. The major reason for the antiproliferative activity of compound 6a was due to the repression of tumor vasculature.
Synthesis, Structural Analysis, and Screening of Some Novel 5-Substituted Aryl/Aralkyl-1,3,4-Oxadiazol-2-Yl 4-(Morpholin-4-Ylsulfonyl)Benzyl Sulfides As Potential Antibacterial Agents
Aziz-Ur-Rehman,Gul, Samreen,Abbasi, Muhammad Athar,Nafeesa, Khadija,Akhtar, Muhammad Nadeem,Ahmad, Irshad,Afzal, Saira
, p. 1045 - 1055 (2015/08/04)
A series of new 5-substituted aryl/aralkyl-1,3,4-oxadiazol-2-yl 4-(morpholin-4-ylsulfonyl)benzyl sulfides 6a-k were synthesized by converting multifarious aryl/aralkyl organic acids 1a-k successively into corresponding esters 2a-k, hydrazides 3a-k, and 5-substituted aryl/aralkyl-1,3,4-oxadiazole-2-thiols 4a-k. Finally, the target compounds, 6a-k were prepared by stirring 5-substituted-1,3,4-oxadiazole-2-thiols with 4-(4-(bromomethyl)phenylsulfonyl) morpholine (5) in the presence of N,N-dimethylformamide (DMF) and sodium hydride (NaH). The structures of the newly synthesized compounds were elucidated by spectroscopic techniques. In addition, the antibacterial activity of all the synthesized compounds was investigated in vitro against Gram-positive and Gram-negative bacteria by using ciprofloxacin as reference standard drug and the results showed that some of the tested compounds possessed good antibacterial activity.
Synthesis and evaluation of antibacterial and antifungal activities of some novel 2,5-disubstituted-1,3,4-oxadiazoles
Joshi,Unale,Parkale,Nadagouda,Gadaginamath,Ashalata
, p. 319 - 322 (2013/09/24)
4-Chlorophenoxy acetic acid 2 was prepared by the condensation of phenol with monochloroacetic acid. Compound 2 was refluxed with ethanol in the presence of HCI gas yielding ethyl (4-chlorophenoxy) acetate 3. Compound 3 was refluxed with hydrazine hydrate in ethanol which produced 2-(4-chlorophenoxy) acetohydrazide 4. Compound 5a was synthesized by refluxing 2-(4-chlorophenoxy) acetohydrazide 4 with carbon disulfide and KOH in the presence of ethanol. Compound 5a on condensation with pbenzoquinone yielded 2-({4-[(4-chlorophenoxy) methyl]-1,3-4-oxadiazole-2-yl} sulfanyl) benzene-1,4-diol 5b. Oxadiazoles 6a-d were prepared by reacting substituted phenoxy acetic acids with 2-(4-chlorophenoxy) acetohydrazide 4 in the presence of POCI3. Further Schiff bases were synthesized by the reaction of substituted aldehydes with 2-(4-chlorophenoxy) acetohydrazide 4 in presence of ethanol. These Schiff bases on reaction with acetic anhyd gave the corresponding 3-acetyl-2,3-dihydro 1,3,4-oxadiazoles 7ad. Synthesized compounds were characterized on the basis of spectral and analytical data. All the compounds were screened for antimicrobial activity.
Synthesis, Characterization, Spectral and Antifungal Properties of Some 5-Substituted-1,3,4-oxadiazole-2-thiones and Their Mannich Bases
Holla, B. Shivarama,Kalluraya, Balakrishna,Nath, S. C.
, p. 549 - 557 (2007/10/02)
A series of 5-substituted aryloxymethyl-1,3,4-oxadiazole-2-thione (3a-e) and their Mannich bases 4-8 are synthesized and subjected to fungitoxic screening.The structures of these compounds are established on the basis of elemental analysis 1H-n.m.r. and mass spectral data.The mass spectral fragmentation pathways of these compounds are discussed.
