- 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, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety
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A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.
- Cui, Peng-Lei,Zhang, Di,Guo, Xiu-Min,Ji, Shu-Jing,Jiang, Qing-Mei
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p. 1754 - 1762
(2021/04/09)
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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 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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- 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
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Paragraph 0036-0038
(2017/01/12)
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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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- 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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- Electrochemical synthesis of 2-amino-5-substituted-1,3,4-oxadiazole derivatives and evaluation of antibacterial activity
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Some new 2-amino-5-substituted-1,3,4-oxadiazoles have been synthesized at platinum electrode through the electrochemical oxidation of semicarbazone at room temperature and studied for their antibacterial activity. This is an environmentally benign method in the field of electroorganic synthesis under controlled potential electrolysis in an undivided cell. The electrolysis have been carried out in the acetonitrile solvent and lithium perchlorate is used as a supporting electrolyte. Two platinum plates are used as working as well as counter electrode and saturated calomel electrode as the reference electrode. These compounds have been characterized by microanalyses, IR, Mass, 1H NMR and 13C NMR spectral data. All the compounds have been evaluated for their antibacterial activity against Klebsilla penumoniae, Escherichia coli, Streptococcus aureus and Shigella dysenteriea at 25 and 50 ppm concentrations.
- Kumar, Sanjeev,Pandey
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p. 252 - 258
(2013/05/09)
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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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- 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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- Synthesis, antibacterial evaluation and QSAR studies of 7-[4-(5-aryl-1,3,4-oxadiazole-2-yl)piperazinyl] quinolone derivatives
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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
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experimental part
p. 3543 - 3550
(2011/10/19)
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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)
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- Studies on biologically active heterocycles: Part X - Synthesis of 2-amino-4-[5-(2-chlorophenyl)-1,3,4-oxa/thiadiazol}-2-yl]6-aryl/substituted aryl-7-oxo-6,7-dihydrothiazolo[4,5-d]pyrimidine-5(H)-thiones as probable bioactive compounds
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A series of new 2-amino-4-[5-{(2-chlorophenyl)-1,3,4-oxadiazolo}-2-yl]-6-aryl/ substituted-aryl-7-oxo-6,7-dihydrothia zolo[4,5-d]pyrimidine-5(H)-thiones 8a-h and 2-amino-4-[5-(2-chlorophenyl)-1,3,4-thiadiazol-2-yl]-6-aryl/ substituted-aryl-7-oxo-6,7-dihydrothiazolo[4,5-d]pyrimidine-5(H)-thiones 9a-h have been synthesized from 3-[5-(2-chlorophenyl)-1,3,4-oxa/thiadiazol-2-yl]-l-aryl/ substituted-arylthiobarbituric acid 6, 7 which in turn are prepared from N-aryl/substituted-aryl, N-5-[(2-chlorophenyl)-1,3,4-oxa/thiadiazol-2-yl]thioureas 4, 5 on treatment with malonic acid, acetyl chloride and thiourea respectively in the presence of chlorine. All the newly synthesized compounds have been characterized by their elemental analysis, physical and spectroscopic data. These substituted oxa/thiadiazolthiones are screened for their fungitoxic and antibacterial properties.
- Hazarika,Kataky
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p. 255 - 257
(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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