cas 5711-61-5, 2-AMINO-5-(4-METHOXYPHENYL)-1,3,4-OXADIAZOLE

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Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety
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.
Han, Xu,Liu, Xin Hua,Ma, Duo,Yu, Yun Long,Zhang, Zhao Yan
p. 344 - 360
(2021/01/06)

Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide
A series of N-(substituted benzothiazole-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a-i) and substituted-[3-((5-phenyl-1,3,4-oxadiazole-2-yl)imino)indolene-2-one] (5a-f) were designed, synthesized fulfilling the structural requirement of pharmacophore and evaluated for anticonvulsant activities using maximal electroshock test (MES), subcutaneous pentylenetetrazole (scPTZ) seizures and neurotoxicity by motor impairment model in mice. The most active compoundN-(5-chlorobenzo[d]thiazol-2-yl)-2-(2,3-dioxoindolin-1-yl)acetamide (4a) has shown significant anticonvulsant activity against both MES and scPTZ screens and emerged as most effective anticonvulsant compound with median dose of 35.7 mg/kg (MES ED50), 88.15 mg/kg (scPTZ ED50) and toxic dose (TD50) was found to be > 500mg/kg. In silico studies including molecular docking study was carried to establish the molecular interaction of potent compound (4a) in both Na+ channel and GABAA receptors. The prediction of pharmacokinetic parameters and distance mapping of compounds were also performed to establish the drug likeness property.
Akhtar, Md Jawaid,Debnath, Biplab,Grover, Gourav,Nath, Rajarshi,Pathania, Shelly,Shahar Yar, M.
(2020/12/25)

SSAO INHIBITOR
The present invention provides an SSAO inhibitor and an application thereof in preparing a drug for treating a disease related to SSAO. In particular, the present invention provides a compound shown in formula (IV) and a pharmaceutically acceptable salt thereof.
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Paragraph 0383; 0384; 0386

(2020/04/02)

Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo
Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.
Naclerio, George A.,Abutaleb, Nader S.,Li, Daoyi,Seleem, Mohamed N.,Sintim, Herman O.
p. 11934 - 11944
(2020/11/26)

Synthesis of N-pyrimidin[1,3,4]oxadiazoles and N-pyrimidin[1,3,4]-thiadiazoles from 1,3,4-oxadiazol-2-amines and 1,3,4-thiadiazol-2-amines via Pd-catalyzed heteroarylamination
An efficient and practical procedure was developed to prepare various N-pyrimidin[1,3,4]oxadiazole and thiadiazole scaffolds using a Buchwald-type coupling. The products of this reaction are otherwise difficult to access and could be used as building bloc
Yan, Longjia,Deng, Minggao,Chen, Anchao,Li, Yongliang,Zhang, Wanzheng,Du, Zhi-yun,Dong, Chang-zhi,Meunier, Bernard,Chen, Huixiong
supporting information
p. 1359 - 1362
(2019/04/25)

Spiro-heterocycles containing 1,3,4-oxadiazole: A convenient synthesis of 3-(5- Substitutedphenyl-l,3,4-oxadiazole-2-yl)-5,8-dithiaspiro[3,4]-octan-2-onesand 1,4-dithia-6-azaspiro[4,4]-nonan-7-ones
A new series of novel 3-(5-substituted phenyl-l,3,4-oxadiazole-2-yl)-5,8-dithiaspiro [3,4]-octan-2-ones and l,4-dithia-6- azaspiro[4,4]nonan-7-ones have been synthesized from a common intermediate, in good yields. These compounds have been screened for th
Tiwari, Shailendra,Singh, Kamal Pratap,Pathak, Poonam,Ahmad, Akeel
p. 1060 - 1064
(2019/05/22)

Efficient synthesis of novel conjugated 1,3,4-oxadiazole-peptides
We were interested in the design and synthesis of novel bioisosteric analogues of leuprolide acetate containing the oxadiazole moiety at the C- or N-terminal of the peptide. An efficient approach for the synthesis of 2-amino-1,3,4-oxadiazoles through the reaction of hydrazide with ammonium thiocyanate and desulfurization reaction of the thiosemicarbazides using different coupling reagents was employed. These compounds are bioisosteres of the amide bond. Furthermore, the coupling of 2-amino-1,3,4-oxadiazoles at the C-terminal of leuprolide analogues was carried out, using a coupling reagent in the solution phase. On the other hand, the addition of a 2-amino-1,3,4-oxadiazole to the N-terminal of the peptide sequence was carried out through the reaction of the 2-amino-1,3,4-oxadiazole with succinic anhydride that led to the formation of a carboxylic acid moiety. Addition of the synthesized oxadiazole containing carboxylic acid to the peptide sequence was performed using a coupling reagent and on the surface of the resin. The synthesized peptides containing the oxadiazole moiety at the C- or N-terminal of the peptide sequence are peptidomimetics of leuprolide acetate. All of the synthesized peptides were purified using preparative HPLC and their structures were confirmed using HR-MS (ESI).
Golmohammadi, Farhad,Balalaie, Saeed,Hamdan, Fatima,Maghari, Shokoofeh
p. 4344 - 4351
(2018/03/21)

Ultrasound-assisted synthesis of 2-amino-1,3,4-oxadiazoles through NBS-mediated oxidative cyclization of semicarbazones
A ultrasound-assisted oxidative cyclization of semicarbazones using N-bromosuccinimide in the presence of sodium acetate was established providing efficient and rapid access to a variety of 2-amino-1,3,4-oxadiazoles. Moreover, the new synthetic protocol provides a simple procedure utilizing a safer oxidizing system that affords the target products in high regioselectivity, satisfactory yields, and elevated purities.
Borsoi, Ana Flávia,Coldeira, Mateus Emanuel,Pissinate, Kenia,Macchi, Fernanda Souza,Basso, Luiz Augusto,Santos, Diógenes Santiago,Machado, Pablo
p. 1319 - 1325
(2017/07/12)

Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity
A series of novel tetrahydropyrazolopyridone derivatives containing 1,3,4-triazole, triazolylmethyl, and partially saturated heterocyclic moieties as P2 binding element was designed, synthesized, and evaluated in vitro for anticoagulant activity in human and rabbit plasma. All compounds showed moderate to significant potency, and compounds 15b, 15c, 20b, 20c, and 22b were further examined for their inhibitory activity against human FXa in vitro. While compounds 15c and 22b were tested for rat venous thrombosis in vivo. The most promising compound 15c, with an IC50 (FXa) value of 0.14?μM and 98% inhibition rate, warranted further investigation as an FXa inhibitor.
Sun, Xiaoqing,Hong, Zexin,Liu, Moyi,Guo, Su,Yang, Di,Wang, Yong,Lan, Tian,Gao, Linyu,Qi, Hongxia,Gong, Ping,Liu, Yajing
p. 2800 - 2810
(2017/04/18)

A 2-amino-5-substituted -1, 3, 4-oxadiazoles and its preparation method and application
The invention relates to 2-amido-5-substituted-1,3,4-oxadiazole as well as a preparation method and application thereof. The preparation method comprises the following steps: adding semicarbazone, manganese dioxide and pyridine into a reaction vessel, rea
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Paragraph 0069-0070; 0071

(2017/01/12)

Inhibitors of ribosome rescue arrest growth of francisella tularensis at all stages of intracellular replication
Bacteria require at least one pathway to rescue ribosomes stalled at the ends of mRNAs. The primary pathway for ribosome rescue is trans-translation, which is conserved in >99% of sequenced bacterial genomes. Some species also have backup systems, such as ArfA or ArfB, which can rescue ribosomes in the absence of sufficient trans-translation activity. Small-molecule inhibitors of ribosome rescue have broad-spectrum antimicrobial activity against bacteria grown in liquid culture. These compounds were tested against the tier 1 select agent Francisella tularensis to determine if they can limit bacterial proliferation during infection of eukaryotic cells. The inhibitors KKL-10 and KKL-40 exhibited exceptional antimicrobial activity against both attenuated and fully virulent strains of F. tularensis in vitro and during ex vivo infection. Addition of KKL-10 or KKL-40 to macrophages or liver cells at any time after infection by F. tularensis prevented further bacterial proliferation. When macrophages were stimulated with the proinflammatory cytokine gamma interferon before being infected by F. tularensis, addition of KKL-10 or KKL-40 reduced intracellular bacteria by >99%, indicating that the combination of cytokine-induced stress and a nonfunctional ribosome rescue pathway is fatal to F. tularensis. Neither KKL-10 nor KKL-40 was cytotoxic to eukaryotic cells in culture. These results demonstrate that ribosome rescue is required for F. tularensis growth at all stages of its infection cycle and suggest that KKL-10 and KKL-40 are good lead compounds for antibiotic development.
Goralski, Tyler D. P.,Dewan, Kalyan K.,Alumasa, John N.,Avanzato, Victoria,Place, David E.,Markley, Rachel L.,Katkere, Bhuvana,Rabadi, Seham M.,Bakshi, Chandra Shekhar,Keiler, Kenneth C.,Kirimanjeswara, Girish S.
supporting information
p. 3276 - 3282
(2016/07/06)

Photocatalytic oxidative heterocyclization of semicarbazones: An efficient approach for the synthesis of 1,3,4-oxadiazoles
Abstract A highly efficient eosin Y catalyzed oxidative heterocyclization of semicarbazones was established under visible-light photoredox catalysis using CBr4 as a bromine source. The protocol renders a rapid, mild, and efficient access to val
Kapoorr, Ritu,Singh, Sachchida N.,Tripathi, Shubhangi,Yadav, Lal Dhar S.
supporting information
p. 1201 - 1206
(2015/06/02)

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
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.
Niu, Pengfei,Kang, Jinfeng,Tian, Xianhai,Song, Lina,Liu, Hongxu,Wu, Jie,Yu, Wenquan,Chang, Junbiao
p. 1018 - 1024
(2015/01/30)

A Highly Efficient Diversification of 2-Amino/Amido-1,3,4-oxadiazole and 1,3,4-Thiadiazole Derivatives via Reagent-Based Cyclization of Thiosemicarbazide Intermediate on Solid-Phase
A 2-amino/amido-1,3,4-oxadiazole and 1,3,4-thiadiazole library has been constructed on solid-phase organic synthesis. The key step on this solid-phase synthesis involves the preparation of polymer-bound 2-amino-1,3,4-oxadiazole and 1,3,4-thiadiazole core
Yang, Seung-Ju,Choe, Ji-Hye,Abdildinova, Aizhan,Gong, Young-Dae
p. 732 - 741
(2015/12/23)

Synthesis and antitubercular activity of 2-(1H-pyrrol-1-Yl)-5- substituted-1,3,4-oxadiazoles
A series of 2-(1H-pyrrol-1-yl)-5-substituted-1,3,4-oxadiazole derivatives were prepared and evaluated for their antitubercular activity. These derivatives were synthesized by the reaction of 5-substituted-1,3,4-oxadiazol-2-amines (4a-j) with 2,5- dimethoxytetrahydrofuran in dried acetic acid. Structures of the newly synthesized compounds were confirmed on the basis of physico-chemical and spectral data. All the synthesized compounds were screened for their antitubercular activity using microplate almar blue assay (MABA) method. Compounds have shown moderate to good antitubercular activity against M. tuberculosis H37Rv microorganism.
Joshi, Shrinivas D.,Dixit, Sheshagiri R.,More, Uttam A.,Kulkarni, Venkatrao H.
p. 137 - 140
(2019/01/21)

Novel limonene and citral based 2,5-disubstituted-1,3,4-oxadiazoles: A natural product coupled approach to semicarbazones for antiepileptic activity
Two novel series of N4-(5-(2/3/4-substituted-phenyl)-1,3,4- oxadiazol-2-yl)-N1-(2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene) semicarbazide and N4-(5-(2/3/4-substituted-phenyl)-1,3,4-oxadiazol-2- yl)-N1-(3,7-dimethylocta-3,6-dienylidene)-semicarbazide were synthesized to meet structural prerequisite indispensable for anticonvulsant activity. The anticonvulsant activities of the compounds were investigated using maximal electroshock seizure (MES), subcutaneous pentylenetrtrazole (scPTZ) and subcutaneous strychnine (scSTY) models. The rotorod test was conducted to evaluate neurotoxicity. Some of the selected active compounds were subjected to GABA assay to confirm their mode of action. The outcome of the present investigations proved that the four binding sites pharmacophore model is vital for anticonvulsant activity. The efforts were also made to establish structure-activity relationships among test compounds.
Rajak, Harish,Singh Thakur, Bhupendra,Singh, Avineesh,Raghuvanshi, Kamlesh,Sah, Anil Kumar,Veerasamy, Ravichandran,Sharma, Prabodh Chander,Singh Pawar, Rajesh,Kharya, Murli Dhar
p. 864 - 868
(2013/02/25)

Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS)
A mild, convenient, and efficient one-pot synthesis of amino-1,3,4- oxadiazoles is described. In situ preparation of various thiosemicarbazides by the reaction of different carboxylic acid hydrazides with trimethylsilyl isothiocyanate (TMSNCS), followed by cyclodesulfurization of thiosemicarbazides under basic conditions in the presence of I2/KI resulted in 2-amino-1,3,4-oxadiazoles in high yields (79-94%).
Guda, Dinneswara Reddy,Cho, Hyeon Mo,Lee, Myong Euy
p. 7684 - 7687
(2013/07/11)

A Facile microwave assisted synthesis and spectral analysis of 2-amino-5-substituted phenyl-1,3,4-oxadiazoles
An efficient synthesis for the preparation of some 2-amino-5-substituted phenyl-1,3,4-oxadiazoles by using both conventional and microwave method have been devised. The obtained results revealed that, microwave assisted technique is efficient, eco-friendl
Kumar, Sanjeev,Yadav, Sneha,Jadon, Sudha,Kumar, Vipin,Khedr, Abdalla M.,Gupta, Kishan C.
p. 1845 - 1848
(2013/06/27)

Synthesis and in vitro antitumor activity of 1,3,4-oxadiazole derivatives based on benzisoselenazolone
A series of novel 1,3,4-oxadiazole derivatives based on benzisoselenazolone has been prepared and tested for antiproliferative activity in vitro against the cells of human cancer cell lines: SSMC-7721 (human liver cancer cell), MCF-7 (human breast cancer cell) and A549 (human lung cancer cell). All the compounds obtained exhibited antiproliferative activity and showed selective cytotoxicity against different cancer cells. Compounds 7d and 7i showed significant antiproliferative activities against MCF-7 cells, with IC50 values of 1.07 and 1.76/μM respectively. Compound 7d were found to be the most potent compound against SSMC-7721 cells, with IC50 values 4.46/μM.
Luo, Zhen-Hua,He, Shuang-Yan,Chen, Bao-Quan,Shi, Yan-Ping,Liu, Yu-Ming,Li, Cai-Wen,Wang, Qiu-Sheng
experimental part
p. 887 - 891
(2012/08/14)

Microwave assisted synthesis and spectral analysis of schiff bases derived from 2-amino-5-aryl-1,3,4-oxadiazoles
Microwave assisted synthesis of new Schiff bases derived from 2-amino-5-substituted aryl-1,3,4-oxadiazoles with substituted aromatic aldehyde have been carried out. The chemical structures of the prepared Schiff bases have been investigated by analytical
Kumar, Sanjeev,Yadav, Sneha,Jadon, Sudha,Kumar, Vipin,Khedr, Abdalla M.,Gupta, Kishan C.
p. 1833 - 1836
(2013/07/05)

Facile method for the conversion of semicarbazones/thiosemicarbazones into azines (Under Microwave Irradiation) and oxadiazoles (By Grinding)
In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase. Taylor &Francis Group, LLC.
Chattopadhyay, Gautam,Ray, Partha Sinha
experimental part
p. 2607 - 2614
(2011/08/07)

2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors
The enzymatic inhibition of histone deacetylase activity has come out as a novel and effectual means for the treatment of cancer. Two novel series of 2-[5-(4-substitutedphenyl)-[1,3,4]-oxadiazol/thiadiazol-2-ylamino] -pyrimidine-5-carboxylic acid (tetrahydro-pyran-2-yloxy)-amides were designed and synthesized as novel hydroxamic acid based histone deacetylase inhibitors. The antiproliferative activities of the compounds were investigated in vitro using histone deacetylase inhibitory assay and MTT assay. The synthesized compounds were also tested for antitumor activity against Ehrlich ascites carcinoma cells in Swiss albino mice. The efforts were also made to establish structure-activity relationships among synthesized compounds. The results of the present studying indicates 2,5-disubstituted 1,3,4-oxadiazole/thiadiazole as promising surface recognition moiety for development of newer hydroxamic acid based histone deacetylase inhibitor.
Rajak, Harish,Agarawal, Avantika,Parmar, Poonam,Thakur, Bhupendra Singh,Veerasamy, Ravichandran,Sharma, Prabodh Chander,Kharya, Murli Dhar
supporting information; scheme or table
p. 5735 - 5738
(2011/10/09)

Design and synthesis of some novel 3-[5-(4-substituted) phenyl- 1,3,4-oxadiazole-2yl]-2-phenylquinazoline-4(3H)-ones as possible anticonvulsant agent
A novel series 7(a-f) 3-[5-(4-substituted) phenyl- 1,3,4-oxadiazole-2yl]-2 phenylquinazoline-4(3H)-ones have been synthesized and screened for its anticonvulsant and neurotoxic activity. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight 2,3-disubstitutedquinazolin- 4(3H)-ones were examined in the maximal electroshock induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ) induced seizure models in mice. Spectroscopic data were consistent with the structure of newly synthesized compounds. The neurotoxicity was assessed using the rotorod method. In the prepared series, 7a was found to be active in the MES screen at 0.5 h, whereas 7f showed anticonvulsant activity at both 0.5 and 4 h. Springer Science+Business Media, LLC 2010.
Gupta, Anjali,Kashaw, Sushil K.,Jain, Neha,Rajak, Harish,Soni, Abhishek,Stables
experimental part
p. 1638 - 1642
(2012/06/05)

Synthesis, anticonvulsant and neurotoxic activity of some new 2,5-disubstituted-1,3,4-oxadiazoles
Two novel series 2a-2d (2Z)-N-[5-(4-substituted) phenyl-1,3,4-oxadiazol-2- yl]-2-[(2Z)-3,7-dimethylocta- 2,6-dien-1-ylidene]hydrazinecarboxamide and 1a-1d 5-(4-substituted)phenyl-N-[(1Z,2Z)-3,7-dimethylocta-2,6- dien-1-ylidene]-1,3,4- oxadiazol-2-amine have been synthesized and screened for their anticonvulsant and neurotoxic activity. After i.p. injection to mice at doses of 30, 100 and 300 mg/kg body weight 2,5-disubstituted-1,3,4- oxadiazole analogues were examined in the maximal electroshock induced seizures (MES) and subcutaneous metrazole (ScMET) induced seizure models in mice. Amongst all the compounds, 1a-1d and 2a-2d, one compound 1a exhibited activity at 100 mg/kg body weight at 0.5 and 4 h in ScMET, respectively. Compound 2b showed anticonvulsant activity at 100 mg/kg without activity in ScMET and neurotoxicity. The neurotoxicity was assessed by rotorod method, and all compounds (except 1a) were found to be safe at maximum administered dose. Springer Science+Business Media, LLC 2010.
Jain, Neha,Kashaw, Sushil K.,Agrawal,Gupta, Anjali,Soni, Abhishek
experimental part
p. 1696 - 1703
(2012/06/16)

Synthesis, antibacterial evaluation and QSAR studies of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolone derivatives
A series of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolones (I-XXI) were synthesized using an appropriate synthetic route and characterized by elemental and spectral analysis. The antibacterial activities of all the synthesized compounds were e
Kumar, Rajnish,Kumar, Ashwani,Jain, Sandip,Kaushik, Darpan
experimental part
p. 3543 - 3550
(2011/10/19)

Anticonvulsant and sedative-hypnotic activity of some novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones
A few novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones were synthesized and evaluated for anticonvulsant, neurotoxicity, sedative-hypnotic, and phenobarbitone-induced hypnosis potentiation test. After i.p. injection to mice at doses of 30, 100, and 300 mg/kg body weight derivatives were examined in the maximal electroshock-induced seizures (MES) and subcutaneous pentylenetetrazole (scPTZ)-induced seizure models in mice. Spectroscopic data were consistence with the newly synthesized compounds. The neurotoxicity was assessed using the Rotorod method. Out of 15 compounds only 7e and 7o showed anticonvulsant activity at various doses in one or more test models. All except 7d, 7m, and 7n exhibited significant sedative-hypnotic activity via actophotometer screen. Central nervous system (CNS)-depressant activity screened with the help of the forced swim method resulted into some potent compounds. No percentage increase in the sleeping time was observed in any of the synthesized compounds evaluated by the phenobarbitone-induced hypnosis potentiation test. On the basis of experimental data, it can be concluded that synthesized compounds possessed relatively better sedative-hypnotic and CNS-depressant activities.
Kashaw, Sushil K.,Gupta, Vivek,Kashaw, Varsha,Mishra,Stables,Jain
experimental part
p. 250 - 261
(2011/01/12)

A novel electroorganic synthesis of some 2-amino-5-substituted-1,3,4- oxadiazoles at the platinum electrode
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
Singh, Sushma,Kumar, Sanjeev,Sharma, Laxmi Kant,Singh
experimental part
p. 734 - 738
(2010/07/15)

Synthesis and antimicrobial activity of some new 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2- styrylquinazoline-4(3H)-ones
Several 3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2-yl]-2-styryl quinazoline-4(3H)-one were synthesized and screened for antibacterial activity against Staphylococcus aureus , Bacillus subtilis, Pseudomonas aeruginosa, and Escherichia coli and antifungal activity against Aspergillus niger and Fusariumoxysporum by the serial dilution technique. Compounds were prepared by reacting corresponding 2-methtyl quinazolinone and 4-subustituted benzaldehydes in glacial acetic acid. Physicochemical and spectral data were consistent with newly synthesized compounds. The prepared compounds were compared with previously synthesized 2-methyl-3-[5-(4-substituted)phenyl-1,3,4-oxadiazole-2- yl]-quinazoline-4(3H)-ones for antimicrobial activity. The present study revealed that styryl moiety at the second position of 4(3H) quinazolinone marginally increased the biological activity and exhibited better antibacterial than antifungal activities.
Gupta, Vivek,Kashaw, Sushil K.,Jatav, Varsha,Mishra, Pradeep
p. 205 - 211
(2008/12/22)

Synthesis and evaluation of antimicrobial and anticonvulsant activities of some new 3-[2-(5-aryl-1,3,4-oxadiazol-2-yl/4-carbethoxymethylthiazol-2-yl)imino- 4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-ones and investigation of their
In the present study, 20 new compounds having 3-[2-(5-aryl-1,3,4-oxadiazol- 2-yl) imino-4-thiazolidinon-5-ylidene]-5-substituted/nonsubstituted 1H-indole-2-one (I-XII) and 3-[2-(4-carbethoxymethylthiazol-2-yl)imino-4- thiazolidinon-5-ylidene]-5-substitute
Altintas, Handan,Ates, Oeznur,Uydes-Dogan, B. Soenmez,Alp, F. Ilkay,Kaleli, Deniz,Oezdemir, Osman,Birteksoez, Seher,Oetuek, Guelten,Satana, Dilek,Uzun, Meltem
p. 239 - 248
(2007/10/03)

Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant
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.
Rivera, Nelo R.,Balsells, Jaume,Hansen, Karl B.
p. 4889 - 4891
(2007/10/03)

Synthesis and bioevaluation of some novel nucleosides as antiherptic agents
N1-(5-Aryl-1,3,4-oxadiazolo-2-yl)-ureas on cyclocondensation with CS2/KOH afford 2-aryl-1,3,4-oxadiazole[3,2-a]-s-triazine-5,7-(6H) dithione nucleobase which on glycosylation with different sugars gives nucleoside analogues.
Chauhan, Deepa,Chauhan,Singh,Bajpai,Joshi
p. 215 - 218
(2007/10/03)

Antifungal activity of new 1,3,4-oxadiazolo[3,2-a]-s-triazine-5,7-diones and their 5-thioxo-7-ones
N1- and N3-(4-fluorophenyl) ureas (III a-e) were cyclocondensed with ethyl chloroformate and CS2/ KOH to yield 2-aryl-6-(4-fluorophenyl)-1,3,4-oxadiazolo[3,2-a]-s-triazine-5,7-diones (IVa-e) and their 5-thioxo-7-ones (Va-e
Mishra, Atma R.,Singh, Shailendra,Wahab, Abdul
p. 5465 - 5468
(2007/10/03)

Synthesis and antibacterial activity of 5-aryl-2- [(α-chloro-α-phenylacetyl/α- bromopropionyl)amino]-1,3,4-oxadiazoles and 2-[(5-aryl-1 ,3,4-oxadiazol-2-yl)imino]-5-phenyl/methyl-4-thiazolidinones
Reaction of 5-aryl-2-amino-1,3,4-oxadiazoles (B(I-VI)), obtained by the oxydative cyclization of aromatic aldehyde semicarbazones (A(I-VI)), with α-chloro-α-phenylacetyl chloride and a-bromopropionyl bromide yielded 5-aryl-2-[(α-chloro-α-phenylacetyl)amino]-1,3,4-oxadiazoles (Ia-VIa) and 5-aryl-2-[(α-bromopropionyl)amino]-1, 3,4-oxadiazoles (VIIa-XIIa), respectively. Furthermore, Ia-XIIa were refluxed with ammonium thiocyanate to give 5-phenyl/methyl-2-[(5-aryl-1,3,4-oxadiazol-2-yl)imino]-4-thiazolidinones (It-XIIt). All compounds were tested for antibacterial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Pseudomonas aeruginosa. They were all found to possess significant activity against S. aureus with MIC values ranging from 0.24 to 125 μg/ml. LD50 of compounds chosen as prototypes are estimated.
Ates, Oeznur,Kocabalkanlr, Ayse,Sanis, Guelten Oetuek,Ekinci, Ahmet C.,Vidin, Aylin
p. 1134 - 1138
(2007/10/03)

Photochemical Behaviour of Some 1,2,4-Oxadiazole Derivatives
The photochemical behaviour of some 1,2,4-oxadiazole derivatives in methanol has been studied at 254 nm.On irradiation, 3-amino- (or 3-methylamino-) 5-aryl-1,2,4-oxadiazoles underwent a ring photoisomerization to 1,3,4-oxadiazoles, probably through a 'rin
Buscemi, Silvestre,Cicero, Maria G.,Vivona, Nicolo,Caronna, Tullio
p. 1313 - 1316
(2007/10/02)

Synthesis and Biological Activity of 2-Substituted 6-Carbethoxy-5(H)-oxo-1,3,4-oxadiazolopyrimidines
Several 2-substituted 6-carbethoxy-5(H)-oxo-1,3,4-oxadiazolopyrimidines (4) have been synthesised by the reaction of 5-substituted 2-amino-1,3,4-oxadiazoles (1) with diethyl ethoxymethylenemalonate (2).These compounds have been screened for their p
Murty, M. S. R.,Ramalingam, T.,Diwan, P. V.,Sattur, P. B.
p. 293 - 294
(2007/10/02)

CONVERSION OF 2-AMINO-5-R-PHENYL-1,3,4-OXADIAZOLES INTO 3-R-PHENYL-5-ALKOXY-1,2,4-TRIAZOLES
2-Amino-5-R-phenyl-1,3,4-oxadiazoles have been shown to isomerize in alcoholic potassium hydroxide solution to 3-R-phenyl-5-alkoxy-1,2,4-triazoles.The dissociative ionization of 3-R-phenyl-5-alkoxy-1,2,4-triazoles and 3-R-phenyl-1,2,4-triazolin-5-ones has
Alekseeva, V. Ya.,Boitkov, Yu. A.,Viktorovskii, I. V.,V'yunov, K. A.
p. 1258 - 1261
(2007/10/02)

Synthesis and Mass Spectral Studies of Some New 1,3,4-Oxadiazoles
Some new 1,3,4-oxadiazoles have been synthesized in good yields from the reaction of aldehyde semicarbazones with bromine in presence of acetic acid and sodium acetate.The reaction proceeds through the formation of nitrilimine intermediate which on cycliz
Bansal, R. K.,Bhagchandani, G.
p. 277 - 279
(2007/10/02)