- 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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- Photoinduced molecular rearrangements. Some comments on the ring-photoisomerization of 1,2,4-oxadiazoles into 1,3,4-oxadiazoles
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The ring-photoisomerization of 3-amino- and 3-methylamino-5-phenyl-1,2,4-oxadiazoles into the corresponding 2-amino- and 2-methylamino-5-phenyl-1,3,4-oxadiazoles has been reinvestigated by examining the effect of a base on the photoreaction. On irradiatin
- Buscemi,Pace,Vivona,Caronna
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- Synthesis of N,N-Disubstituted 3-amino- 1,2,4-triazoles
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A general method for the synthesis of N,N-disubstituted 3-amino-l,2,4-triazoles 5 from di(benzotriazolyl)methanimines 1 and 1′, hydrazine and substituted hydrazines is developed. The desired compounds were prepared regioselectively under mild conditions b
- Katritzky, Alan R.,Rogovoy, Boris V.,Vvedensky, Vladimir Y.,Kovalenko, Katherine,Steel, Peter J.,Markov, Victor I.,Forood, Behrouz
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- Chlorination and subsequent cyclization to 1,3,4-oxadiazoles of N1-acyl-N3-cyanoguanidines and rerated compounds
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N1-Acyl-, N1-alkoxycarbonyl-, and N1-(N,N-dialkylcarbamoyl)guanidines bearing electron-withdrawing cyano or sulfonyl group at the N3-position were found to provide corresponding rearranged products, 1,3,4-oxadiazoles, when these guanidines were chlorinated by sodium hypochlorite followed by treating with base. Assignments of obtained compounds were accomplished by means of some reactions such as acid hydrolysis, alkoholysis, and catalytic hydrogenations, and of MS spectra.
- Suyama, Takayuki,Hasegawa, Tadashi,Oda, Motokazu,Tomaru, Masahiko,Ohkoshi, Hiroyuki
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- N,N-dialkyl-N′-chlorosulfonylchloroformamidines in heterocyclic synthesis. II. Thiazolo-, thiadiazolo-, and oxadiazolo-fused [1,2,4,6]thiatriazine dioxides
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N,N-dialkyl-N′-chlorosulfonylchloroformamidines 1 were treated with 2-aminothiazoline, 2-aminothiazoles, 2-aminobenzothiazoles, 2-amino-1,3,4- thiadiazoles, and 2-amino-1,3,4-oxadiazoles to give a 6,7-dihydrothiazolo[3,2-b] [1,2,4,6]thiatriazine dioxide 3
- Fallon, Gary D.,Francis, Craig L.,Johansson, Katarina,Liepa, Andris J.,Woodgate, Ruth C. J.
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- Synthesis and anticonvulsant evaluation of indoline derivatives of functionalized aryloxadiazole amine and benzothiazole acetamide
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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.
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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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- 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 of 1,3,4-oxadiazoles as selective T-type calcium channel inhibitors
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– Neuropathic pain, epilepsy, insomnia, and tremor disorder may arrive from an increase of intracellular Ca2+ concentration through a dysfunction of T-type Ca2+ channels. Thus, T-type calcium channels could be a target in drug discovery for the treatments of neuropathic pain and epilepsy. From rational drug design approach, a group of 2,5-disubstituted 1,3,4-oxadiazole molecules was synthesized and their selective T-type channel inhibitions were evaluated. The synthetic strategy consists of a short sequence of three reactions: (i) condensation of thiosemicarbazide with acid chlorides; (ii) ring closing by 1,3-dibromo-5,5-dimethylhydantoin; and (iii) coupling with various acid chlorides. 5-Chloro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)thiophene-2-carboxamide (11) was found to selectively inhibit T-type Ca2+ channel over Na+ and K+ channels in mouse dorsal root ganglion neurons and/or human embryonic kidney (HEK)-293 cells and to suppress seizure-induced death in mouse model. Consequently, compound 11 is a useful probe for investigation of physiologic and pathophysiologic roles of the T-channel, and provides a basis to develop a novel therapeutic to treat chronic neuropathic and inflammatory pains.
- Zhang, Man,Zou, Bende,Gunaratna, Medha J.,Weerasekara, Sahani,Tong, Zongbo,Nguyen, Thi D.T.,Koldas, Serkan,Cao, William S.,Pascual, Conrado,Xie, Xinmin Simon,Hua, Duy H.
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p. 145 - 164
(2020/02/04)
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- CF3-, OCF3-, SCF3- AND SF5-CONTAINING ANTIBACTERIAL AGENTS
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The present invention generally relates to compounds as a new antibiotic to treat various infections, including infections caused by methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-intermediate and vancomycin-resistant S. aureus (VISA and VRSA respectively) vancomycin-resistant Enterococcus faecalis (VRE), and Clostridioides difficile. Pharmaceutical compositions and methods for treating those infection diseases are within the scope of this invention.
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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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- 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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- Myricetin derivative containing amide-oxadiazole and preparation method and application of myricetin derivative
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The invention discloses a myricetin derivative containing amide-oxadiazole and a preparation method and application of the myricetin derivative. General formula (A) is as shown in specification, wherein R is alkyl consisting of 1-6 carbon atoms, alkoxy co
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Paragraph 0027-0030
(2019/04/02)
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- Efficient synthesis of novel conjugated 1,3,4-oxadiazole-peptides
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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
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p. 4344 - 4351
(2018/03/21)
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- Preparation method and application of 1,3,4-thiadiazole (oxadiazole)-phenazine-1-formamide compound
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The invention discloses a 1,3,4-thiadiazole (oxadiazole)-phenazine-1-formamide compound. The structure of the compound is as shown in a formula (I), wherein R is at least one of hydrogen, halogen, nitryl, hydroxyl and alkyl or alkoxy of which the carbon a
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Paragraph 0051; 0052
(2018/04/26)
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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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- Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity
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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
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p. 2800 - 2810
(2017/04/18)
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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 0032-0034
(2017/01/12)
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- A turn-on lanthanide complex chemosensor for recognition of lead(ii) based on the formation of nanoparticles
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A functional amide-type pincer ligand was designed and synthesized, which could effectively capture Tb3+ ions to form a phosphorescence complex-based chemosensor Tb-1. The chemosensor could further coordinate with Pb2+ ions and display a turn-on phosphorescence response. This sensing process was analyzed in detail by steady-state luminescence spectroscopy, time-resolved luminescence spectroscopy, electron microscopy and dynamic light scattering, which suggest that the formation of Pb2+-induced hydroxide nanoclusters can adjust the optical signal of the external luminescence compound by embedment and fixation of Tb3+ complexes. Furthermore, Tb-1 could effectively eliminate the signal interference from the short-lived fluorescence and improve the signal-to-noise ratio to increase the accuracy of the detection for Pb2+. An understanding of the recognition mechanism of the Tb3+ complex-based chemosensor and the application of the characteristic spectra of lanthanide ions might be able to provide more opportunities to develop highly selective optical chemosensors.
- Xu, Benhua,Tang, Xiaoliang,Zhou, Ji'An,Chen, Wanmin,Liu, Haile,Ju, Zhenghua,Liu, Weisheng
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supporting information
p. 18859 - 18866
(2016/12/09)
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- Oxidazol- gland glucoside compounds as inhibitors of TyrRS and its preparation and use
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Oxadiazole-adenosine compounds have a structural general formula as shown in the specification. The compounds have better inhibition and killing effects on various germs, part of compounds have higher bacteriostatic activity than positive control penicillin G, kamamycin and ketoconazole, and the compounds can be used for preparing anti-infective drugs. The invention discloses preparation methods of the oxadiazole-adenosine compounds and anti-pathogen microbial activity.
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- Oxidazol- myo- glucoside compounds as inhibitors of TyrRS and its preparation and use
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A structural general formula of oxadiazole and inosine type compounds is as the following formal. The oxadiazole and inosine type compounds have a good role in restraining and killing multiple germs and a part of compounds are high in bacteriostatic activity compared with positive control penicillin G, kalamycin and ketoconazole and can be used for preparing anti-infective drugs. The invention discloses a preparation method and the pathogenic microorganism resistant activity.
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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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- Novel agonists of benzodiazepine receptors: Design, synthesis, binding assay and pharmacological evaluation of 1,2,4-triazolo[1,5-a]pyrimidinone and 3-amino-1,2,4-triazole derivatives
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Agonists of benzodiazepine (BZD) binding site in GABA receptors are widely used in clinical practice. In spite of their benefits they have several side effects, so synthesis of new agonists of these receptors to get more specific effect and better profile
- Faizi, Mehrdad,Dabirian, Sara,Tajali, Hamed,Ahmadi, Fatemeh,Rezaee, Elham,Shahhosseini, Soraya,Tabatabai, Sayyed Abbas
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p. 480 - 487
(2015/01/30)
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- 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
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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
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p. 732 - 741
(2015/12/23)
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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
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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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- O -iodoxybenzoic acid mediated oxidative desulfurization initiated domino reactions for synthesis of azoles
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A systematic exploration of thiophilic ability of o-iodoxybenzoic acid (IBX) for oxidative desulfurization to trigger domino reactions leading to new methodologies for synthesis of different azoles is described. A variety of highly substituted oxadiazoles, thiadiazoles, triazoles, and tetrazoles have been successfully synthesized in good to excellent yields, starting from readily accessible thiosemicarbazides, bis-diarylthiourea, 1,3-disubtituted thiourea, and thioamides.
- Chaudhari, Pramod S.,Pathare, Sagar P.,Akamanchi, Krishnacharaya G.
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experimental part
p. 3716 - 3723
(2012/06/16)
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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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- A Facile microwave assisted synthesis and spectral analysis of 2-amino-5-substituted phenyl-1,3,4-oxadiazoles
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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.
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p. 1845 - 1848
(2013/06/27)
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- Microwave assisted synthesis and spectral analysis of schiff bases derived from 2-amino-5-aryl-1,3,4-oxadiazoles
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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.
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p. 1833 - 1836
(2013/07/05)
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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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- 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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- 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)
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- Dicyanomethylene compounds and heterocyclization of acylthiosemicarbazides
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(Chemical Equation Presented) (1,3-Dioxo-2,3-dihydro-1H-inden-2-ylidene) propanedinitrile (1, in ethyl acetate solution), 3-(dicyanomethylene)-2-indolone (2, in ethanol/piperidine solution) and 7,7′,8,8′- tetracyanoquinodimethane (3, in pyridine solution)
- Hassan, Alaa A.,Mourad, Aboul-Fetouh E.,Abou-Zeid, Ashraf H.
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p. 323 - 328
(2008/09/20)
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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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- General facile synthesis of 2,5-diarylheteropentalenes
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Palladium-catalyzed cross-coupling reactions of various heteropentalene derivatives were systematically studied. A general three-step synthesis of 2,5-diarylheteropentalenes involving two Suzuki or Negishi couplings and a regiospecific bromination was developed. Nonsymmetrical 2,5-diaryl-furans, thiophenes, pyrroles, 1,3-thiazoles, 1,3-oxazoles, 1,3,4-thiadiazoles, and 1,3,4-oxadiazoles were prepared in 31-67% isolated yield (three steps).
- Vachal, Petr,Toth, Leslie M.
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p. 7157 - 7161
(2007/10/03)
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- Formation of nitrogen-containing heterocycles using di(imidazole-1-yl)methanimine
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A mild and efficient synthesis of five- and six-membered nitrogen containing heterocyclic compounds, in which di(imidazole-1-yl)methanimine serves as a one-carbon source, is reported.
- Wu, Yong-Qian,Limburg, David C.,Wilkinson, Douglas E.,Hamilton, Gregory S.
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p. 191 - 193
(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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