- In Silico Study and In Vitro Evaluation of Novel Synthesized Quinolone Derivatives Having Five-Membered Heterocyclic Moieties
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Infectious diseases are caused by pathogens, such as viruses, bacteria, fungi, and parasites. Quinolones work by inhibition of bacterial topoisomerase IV and/or gyrase, a group of oxadiazole derivatives were incorporated into C7 piperazine ring of Gatiflo
- Naser, Noor H.,Raauf, Ayad M. R.,Sheehan, Mustafa R.
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p. 215 - 225
(2022/02/14)
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- Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety
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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
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p. 344 - 360
(2021/01/06)
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- Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking studies of 2-amino-1,3,4-oxadiazole derivatives
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Background: In the recent past, we have synthesized and reported different derivatives of oxadiazoles as potential α-glucosidase inhibitors, keeping in mind, the pharmacological aspects of oxadiazole moiety and in continuation of our ongoing research on the chemistry and bioactivity of new heterocyclic compounds. Methods: 1,3,4-Oxadiazole derivatives (1-14) have been synthesized and characterized by different spectroscopic techniques such as1 H-,13 C-NMR and HREI-MS. Results: The synthetic derivatives were screened for α-glucosidase inhibitory potential. All compounds exhibited good inhibitory activity with IC50 values ranging between 0.80 ± 0.1 to 45.1 ± 1.7 μM in comparison with the standard acarbose having IC50 value 38.45 ± 0.80 μM. Conclusion: Thirteen compounds 1-6 and 8-14 showed potential inhibitory activity as compared to the standard acarbose having IC50 value 38.45 ± 0.80 μM, however, only one compound 7 (IC50 = 45.1 ± 1.7 μM) was found to be less active. Compound 14 (IC50 = 0.80 ± 0.1 μM) showed promising inhibitory activity among all synthetic derivatives. Molecular docking studies were also conducted for the active compounds to understand the ligand-enzyme binding interactions.
- Ullah, Hayat,Rahim, Fazal,Taha, Muhammad,Hussain, Raffaqat,Wadood, Abdul,Nawaz, Mohsan,Wahab, Zainul,Kanwal,Khan, Khalid M.
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p. 724 - 734
(2020/08/19)
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- Synthesis of indole-tethered [1,3,4]thiadiazolo and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids as anti-pancreatic cancer agents
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New indole-tethered [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (8a-j) and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids (9a-e) were synthesized using [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with indole-ketenes. All molecul
- Gummidi, Lalitha,Kerru, Nagaraju,Awolade, Paul,Raza, Asif,Sharma, Arun K.,Singh, Parvesh
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- Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo
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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.
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p. 11934 - 11944
(2020/11/26)
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- Synthesis and antitubercular activity of new N-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]-(nitroheteroaryl)carboxamides
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Nitro-substituted heteroaromatic carboxamides 1a-e were synthesized and tested against three Mycobacterium tuberculosis cell lines. The activities can be explained in terms of the distribution of the electronic density across the nitro-substituted heteroaromatic ring attached to the amide group. 1,3,5-Oxadiazole derivatives 1c-e are candidates for the development of novel antitubercular agents. Ongoing studies are focused on exploring the mechanism by which these compounds inhibit M. tuberculosis cell growth.
- Martínez, Roberto,Nieves Zamudio, Gladys J.,Pretelin-Castillo, Gustavo,Torres-Ochoa, Rubén O.,Medina-Franco, José L.,Espitia Pinzón, Clara I.,Silva Miranda, Mayra,Hernández, Eugenio,Alanís-Garza, Blanca
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- Synthesis, in vitro and in silico Anti-Proliferative Studies of Novel Piperiene-Oxadiazole and Thiadiazole Analogs
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Piperine is a component of pepper which has earlier been reported as anticancer active compound. This work is emphasized on the design and synthesis of new hybrid piperine analogs by coupling piperine with the amine group of oxadiazoles and thiadiazoles.
- Amperayani,Parimi
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p. 2301 - 2307
(2020/01/08)
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- Synthesis and amelioration of inflammatory paw edema by novel benzophenone appended oxadiazole derivatives by exhibiting cyclooxygenase-2 antagonist activity
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Ten new 2(4-hydroxy-3-benzoyl) benzamide-5-phenyl-1,3,4-oxadiazole derivatives (10a–j) were synthesized by coupling 3-benzoyl-4-hydroxybenzoic acid (5) with 2-amino-5-phenyl-1,3,4-oxadiazoles (9a–j). The structures of these compounds were confirmed by IR, 1H, 13C NMR, and mass spectra, and also by elemental analyses. The anti-inflammatory activity of the compounds 10a–j were investigated by screening them against human red blood cells (HRBC) in-vitro. The results reveal that among this series, compound 10j with hydroxy substituent, particularly at the ortho position of the phenyl ring attached to the 5th carbon atom of the oxadiazole ring possess significant membrane stabilizing activity in comparison with the control. Further, in-vivo chick chorioallantoic membrane (CAM) and rat corneal anti-angiogenesis assays were performed to assess the effect of compound 10j on endothelial cell migration. This confirmed that compound 10j inhibits the proliferation of endothelial cells. Anti-inflammatory studies detected the amelioration of carrageen induced rat hind paw edema. Further in-vivo and in-silico approaches revealed the inhibition of inflammatory marker enzyme cyclooxygenase-2 (Cox-2) and myleoperoxidase (MPO). The study reports that the compound 10j effectively act against the inflammatory mediated anti-angiogenic disorders which could be translated into a new drug in future.
- Puttaswamy, Naveen,Malojiao, Vikas H.,Mohammed, Yasser Hussein Eissa,Sherapura, Ankith,Prabhakar,Khanum, Shaukath Ara
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p. 1446 - 1455
(2018/05/22)
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- 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
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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
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p. 1060 - 1064
(2019/05/22)
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- Ultrasound-assisted synthesis of 2-amino-1,3,4-oxadiazoles through NBS-mediated oxidative cyclization of semicarbazones
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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
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p. 1319 - 1325
(2017/07/12)
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- A 2-amino-5-substituted -1, 3, 4-oxadiazoles and its preparation method and application
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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
- -
-
Paragraph 0069-0070; 0077
(2017/01/12)
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- From Sphingosine Kinase to Dihydroceramide Desaturase: A Structure-Activity Relationship (SAR) Study of the Enzyme Inhibitory and Anticancer Activity of 4-((4-(4-Chlorophenyl)thiazol-2-yl)amino)phenol (SKI-II)
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The sphingosine kinase (SK) inhibitor, SKI-II, has been employed extensively in biological investigations of the role of SK1 and SK2 in disease and has demonstrated impressive anticancer activity in vitro and in vivo. However, interpretations of results u
- Aurelio, Luigi,Scullino, Carmen V.,Pitman, Melissa R.,Sexton, Anna,Oliver, Victoria,Davies, Lorena,Rebello, Richard J.,Furic, Luc,Creek, Darren J.,Pitson, Stuart M.,Flynn, Bernard L.
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p. 965 - 984
(2016/02/23)
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- Expeditious Synthesis, Antimicrobial and Antimalarial Activities of Novel Heterocycles Bearing Imidazole-oxadiazole Based Hybrid Pharmacophores
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A facile synthesis of 2-substituted-5-amino-oxadiazole derivatives has been achieved by refluxing/sonicating a mixture of semicarbazide with various aromatic acids in conc. sulphuric acid alone. The isolated products were further condensed with p-dimethyl
- Balaji,Bhatt,Jha
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p. 587 - 591
(2016/11/17)
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- 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
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p. 1018 - 1024
(2015/01/30)
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- Photocatalytic oxidative heterocyclization of semicarbazones: An efficient approach for the synthesis of 1,3,4-oxadiazoles
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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.
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supporting information
p. 1201 - 1206
(2015/06/02)
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- Synthesis and antitubercular activity of 2-(1H-pyrrol-1-Yl)-5- substituted-1,3,4-oxadiazoles
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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.
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p. 137 - 140
(2019/01/21)
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- Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS)
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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
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p. 7684 - 7687
(2013/07/11)
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- A convenient synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using iodine and Oxone
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A convenient methodology has been developed for the synthesis of substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using catalytic amount of iodine/KI in the presence of Oxone as a bulk oxidant. This offers the adv
- Shinde, Vikas N.,Ugarkar, Bheemarao G.,Ghorpade, Sandeep R.
-
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- Novel limonene and citral based 2,5-disubstituted-1,3,4-oxadiazoles: A natural product coupled approach to semicarbazones for antiepileptic activity
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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
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p. 864 - 868
(2013/02/25)
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- Synthesis and in vitro antitumor activity of 1,3,4-oxadiazole derivatives based on benzisoselenazolone
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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
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p. 887 - 891
(2012/08/14)
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- 2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors
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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
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p. 5735 - 5738
(2011/10/09)
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- 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
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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
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p. 1638 - 1642
(2012/06/05)
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- Synthesis, anticonvulsant and neurotoxic activity of some new 2,5-disubstituted-1,3,4-oxadiazoles
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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
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p. 1696 - 1703
(2012/06/16)
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- Facile method for the conversion of semicarbazones/thiosemicarbazones into azines (Under Microwave Irradiation) and oxadiazoles (By Grinding)
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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
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experimental part
p. 2607 - 2614
(2011/08/07)
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- Anticonvulsant and sedative-hypnotic activity of some novel 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2-styrylquinazoline-4(3H)-ones
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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
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experimental part
p. 250 - 261
(2011/01/12)
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- A novel electroorganic synthesis of some 2-amino-5-substituted-1,3,4- oxadiazoles at the platinum electrode
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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
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experimental part
p. 734 - 738
(2010/07/15)
-
- Synthesis and local anesthetic activity of some novel N-[5-(4-Substituted) phenyl-1,3,4-oxadiazol-2-yl]-2-(substituted)-acetamides
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A novel series of acetamides carrying substituted-1,3,4-oxadiazole moiety were synthesized from reaction of 5-aryl-2-chloroacetamido-1,3,4-oxadiazoles with different secondary amines. The local anesthetic potential of the compounds was investigated using
- Rajak, Harish,Kharya, Murli Dhar,Mishra, Pradeep
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experimental part
p. 247 - 261
(2009/04/04)
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- Synthesis and antimicrobial activity of some new 3-[5-(4-substituted) phenyl-1,3,4-oxadiazole-2yl]-2- styrylquinazoline-4(3H)-ones
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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
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p. 205 - 211
(2008/12/22)
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- Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant
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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.
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p. 4889 - 4891
(2007/10/03)
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- 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
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p. 239 - 248
(2007/10/03)
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- Synthesis and bioevaluation of some novel nucleosides as antiherptic agents
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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
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p. 215 - 218
(2007/10/03)
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- Oxidation of 2-amino-5-aryl-1,3,4-oxadiazole by sodium periodate: A kinetic study
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Kinetics of oxidation of a few 2-amino-5-aryl-1,3,4-oxadiazoles by sodium periodate in aqueous acetic acid-HClO4 medium have been studied. The reaction follows a first order rate each with respect to oxidant and substrate concentration. A suita
- Pradhan, Banasova,Misro,Padhy, Arun Kumar
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p. 898 - 900
(2007/10/03)
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- Antifungal activity of new 1,3,4-oxadiazolo[3,2-a]-s-triazine-5,7-diones and their 5-thioxo-7-ones
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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
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p. 5465 - 5468
(2007/10/03)
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- Syntheses and characterization of 2-amino-5-aryl-1,3,4-oxadiazoles containing trifluoroethoxy groups
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In order to develop an effective synthetic route to 2-amino-5-aryl-1,3,4-oxadiazoles containing trifluoroethoxy groups, a novel intermediate 2-amino-5-[4-(2′,2′,2′-trifluoroethoxy)-phenyl]-1,3,4- oxadiazole was prepared and its structure was confirmed by
- Zhang, Rong,Qian, Xuhong,Li, Zhong
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- Synthesis and antimicrobial activity of some 5-aryl-2-[(N,N-disubstituted thiocarbamoylthio)acylamino]-1,3,4-oxadiazoles
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In this study, a number of novel 5-aryl-2-[(N,N-disubstituted thiocarbamoylthio)acylamino]-1,3,4-oxadiazole derivatives were synthesized by the reaction of potassium salts of N,N-disubstituted dithiocarbamoic acids with 2-[(α-chloro-α-phenylacetyl/α-bromo
- Ates, Oeznur,Kocabalkanli, Ayse,Cesur, Nesrin,Oetuek, Guelten
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p. 541 - 544
(2007/10/03)
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- 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
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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
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p. 1134 - 1138
(2007/10/03)
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- A new route for the convenient synthesis of imidazo[2,1-b]-1,3,4-oxadiazoles and their fungitoxicity
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5-Aryl-1-arylideneamino-1,3,4-oxadiazoles (4a-f) react with trichloroacetic acid with the evolution of carbon dioxide to furnish 5-aryl-2-[(1-aryl-2,2,2-trichloroethyl)amino]-1,3,4-oxadiazoles (6a-f), which undergo ring closure with primary arylamines to
- Yadav,Saigal, Sandhya,Shukla, Supriya
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p. 385 - 387
(2007/10/03)
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- Photochemical Behaviour of Some 1,2,4-Oxadiazole Derivatives
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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
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p. 1313 - 1316
(2007/10/02)
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- Synthesis and Biological Activity of 2-Substituted 6-Carbethoxy-5(H)-oxo-1,3,4-oxadiazolopyrimidines
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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.
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p. 293 - 294
(2007/10/02)
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- CONVERSION OF 2-AMINO-5-R-PHENYL-1,3,4-OXADIAZOLES INTO 3-R-PHENYL-5-ALKOXY-1,2,4-TRIAZOLES
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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.
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p. 1258 - 1261
(2007/10/02)
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- Synthesis and Mass Spectral Studies of Some New 1,3,4-Oxadiazoles
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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.
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p. 277 - 279
(2007/10/02)
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