- Synthesis and analgesic profile of novel N-containing heterocycle derivatives: Arylidene 3-phenyl-1,2,4-oxadiazole-5-carbohydrazide
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This paper describes recent results of a research program aimed at the synthesis and pharmacological evaluation of new heterocyclic N-acylhydrazone (NAH) compounds, belonging to the arylidene (3-phenyl)-1,2,4-oxadiazolyl-5- carboxyhydrazide (8a-p) series.
- Leite, Lucia Fernanda C.C.,Ramos, Mozart N.,Da Silva, Joao Bosco P.,Miranda, Ana L.P.,Fraga, Carlos A.M.,Barreiro, Eliezer J.
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- 1,2,4-Oxadiazole ring–containing pyridylpyrazole-4-carboxamides: Synthesis and evaluation as novel insecticides of the anthranilic diamide family
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Herein, we describe the preparation of pyridylpyrazole-4-carboxamides containing a 1,2,4-oxadiazole ring as novel anthranilic diamide derivatives and compare their insecticidal activities to that of chlorantraniliprole, a well-established potent insectici
- Khallaf, Abdalla,Liu, Hui,Wang, Ping,Zhu, Hongjun,Zhuo, Shuping
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- Discovery of 1,2,4-oxadiazole derivatives as a novel class of noncompetitive inhibitors of 3-hydroxykynurenine transaminase (HKT) from Aedes aegypti
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The mosquito Aedes aegypti is the vector of arboviruses such as Zika, Chikungunya, dengue and yellow fever. These infectious diseases have a major impact on public health. The unavailability of effective vaccines or drugs to prevent or treat most of these
- Guido, Rafael V. C.,Leal, Laylla L. L.,Maciel, Larissa G.,Oliveira, Andrew A.,Rom?o, Tatiany P.,Silva-Filha, Maria Helena N. L.,Soares, Thereza A.,dos Anjos, Janaína V.
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Read Online
- Boron tribromide mediated debenzylation of benzylamino and benzyloxy groups
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The treatment of 2(or 4)-benzylamino substituted quinolines, 9-benzylaminoacridine, 2-benzylaminopyridine, a 4-benzyloxyquinoline, and an N-benzyloxyamidine with BBr3 yields the corresponding amino or hydroxy substituted compounds. The scope and limitations of this novel reaction are discussed.
- Paliakov, Ekaterina,Strekowski, Lucjan
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Read Online
- Synthesis and Biological Screening of Novel 5-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole Derivatives
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A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole (6a-o) have been synthesized by a cyclocondensation reaction of ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate (3a-c) with aryl imidoxime (5a-e). The newly synthesize
- Agrawal, Brijmohan R.,Farooqui, Mazahar,Khandebharad, Amol U.,Kulkarni, Pravin S.,Sarda, Swapnil R.
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p. 209 - 215
(2022/01/06)
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- Synthesis, spectroscopic characterization and DNA/HSA binding studies of (phenyl/naphthyl)ethenyl-substituted 1,3,4-oxadiazolyl-1,2,4-oxadiazoles
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Two new series of conjugated arylethenyl-1,3,4-oxadiazolyl-1,2,4-oxadiazoles were obtained and spectroscopically characterized in terms of UV-Vis absorption, fluorescence and interaction with CT-DNA and Human Serum Albumin (HSA) biomolecules. Phenyl- and 1-naphthyl-bearing examples were analysed, and the spectroscopic properties of its substitution series were compared, showing extensive conjugation in all compounds and absorption differences due to both the aryl-ethenyl subunit and substituted phenyl/phenylene at the 1,2,4-oxadiazole side. Strong binding interactions of the obtained compounds with CT-DNA and moderate HSA-association capability were observed spectroscopically, and further docking studies were performed. This journal is
- Mayer, Joao C. P.,Acunha, Thiago V.,Rodrigues, Oscar E. D.,Back, Davi F.,Chaves, Otavio A.,Dornelles, Luciano,Iglesias, Bernardo A.
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p. 471 - 484
(2021/01/11)
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- Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine
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Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.
- Wu, Weiping,Fan, Shuaixin,Li, Tielei,Fang, Lili,Chu, Benfa,Zhu, Jin
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supporting information
p. 5652 - 5657
(2021/08/01)
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- Novel 1,2,4-oxadiazole derivatives as selective butyrylcholinesterase inhibitors: Design, synthesis, and biological evaluation
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Alzheimer’s disease (AD) is a progressive mental disorder that brings a huge economic burden to the healthcare systems. During this illness, acetylcholine levels in the cholinergic systems gradually diminish, which results in severe memory loss and cognitive impairments. Moreover, Butyrylcholinesterase (BuChE) enzyme participates in cholinergic neurotransmission regulation by playing a prominent role in the latter phase of AD. In this study, based on donepezil, which is an effective acetylcholinesterase (AChE) inhibitor, a series of 1,2,4-oxadiazole compounds were designed, synthesized and their inhibitory activities towards AChE and BuChE enzymes were evaluated. Some structures exhibited a higher selectivity rate towards BuChE in comparison to donepezil. Notably, compound 6n with an IC50 value of 5.07 μM and an SI ratio greater than 19.72 showed the highest potency and selectivity towards BuChE enzyme. The docking result revealed that compound 6n properly fitted the active site pocket of BuChE enzyme, and formed desirable lipophilic interactions and hydrogen bonds. Moreover, according to in silico ADME studies, these compounds have proper potential for being developed as new oral anti-Alzheimer’s agents.
- Akbarzadeh, Tahmineh,Hariri, Roshanak,Nazari, Maryam,Rezaee, Elham,Tabatabai, Sayyed Abbas
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p. 907 - 921
(2021/06/09)
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- Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators
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Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py
- Xiao, Zhihong,Peng, Yajun,Zheng, Bifeng,Chang, Qi,Guo, Yating,Chen, Zhuo,Li, Qianbin,Hu, Gaoyun
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- One-pot synthesis of 1,2,4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation
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A series of sulfur- and selenium-bearing, amino acid-derived 1,2,4-oxadiazoles were obtained by a simple procedure. The method consists of EDC-promoted coupling of chalcogen amino acid derivatives with arylamidoximes in acetone, followed by solvent removal and microwave irradiation in water medium. Influence of amidoxime substituents, of the chalcogen atom and of the amino acid side chain is discussed. The results showed this to be a fast, easy and effective method to obtain these compounds, with good functional-group tolerance, potentially favouring future applications in organic synthesis.
- Wolf, Lucas,Mayer, Jo?o C.P.,Quoos, Natália,Sauer, André C.,Schwab, Ricardo S.,Rodrigues, Oscar E.D.,Dornelles, Luciano
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supporting information
(2021/06/06)
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- Catalyst-free, one-pot strategy to access 3-substituted-5-amino-1,2,4-thiadiazoles in water
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A protocol has been devised for the synthesis of 3-substituted 5-amino-1,2,4-thiadiazoles utilizing isothiocyanates, amidoximes and water as an eco-friendly solvent. The strategy involves consecutive C?N and S?N bonds formation in a one-pot reaction under
- Nagaraju, Chaithra,Ashok, Swarup Hassan,Narayana, Yatheesh,Nagarakere, Sandhya C.,Kempegowda, Mantelingu,Kanchugarkoppal, Rangappa S.
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p. 3610 - 3619
(2021/10/14)
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- Convenient one-pot synthesis of 1,2,4-oxadiazoles and 2,4,6-triarylpyridines using graphene oxide (GO) as a metal-free catalyst: Importance of dual catalytic activity
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A convenient and efficient process for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 2,4,6-triarylpyridines has been described using an inexpensive, environmentally benign, metal-free heterogeneous carbocatalyst, graphene oxide (GO). GO plays a dual role of an oxidizing agent and solid acid catalyst for synthesizing 1,2,4-oxadiazoles and triarylpyridines. This dual catalytic activity of GO is due to the presence of oxygenated functional groups which are distributed on the nanosheets of graphene oxide. A broad scope of substrate applicability and good sustainability is offered in this developed protocol. The results of a few control experiments reveal a plausible mechanism and the role of GO as a catalyst was confirmed by FTIR, XRD, SEM, and HR-TEM analysis.
- Basak, Puja,Dey, Sourav,Ghosh, Pranab
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p. 32106 - 32118
(2021/12/02)
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- Design, Synthesis, and Pesticidal Activities of Pyrimidin-4-amine Derivatives Bearing a 5-(Trifluoromethyl)-1,2,4-oxadiazole Moiety
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It is important to discover new pesticides with new modes of action because of the increasing evolution of pesticide resistance. In this study, a series of novel pyrimidin-4-amine derivatives containing a 5-(trifluoromethyl)-1,2,4-oxadiazole moiety were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Bioassays indicated that the 29 compounds synthesized possessed excellent insecticidal activity against Mythimna separata, Aphis medicagini, and Tetranychus cinnabarinus and fungicidal activity against Pseudoperonospora cubensis. Among these pyrimidin-4-amine compounds, 5-chloro-N-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)-6-(1-fluoroethyl)pyrimidin-4-amine (U7) and 5-bromo-N-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)-6-(1-fluoroethyl) pyrimidin-4-amine(U8) had broad-spectrum insecticidal and fungicidal activity. The LC50 values were 3.57 ± 0.42, 4.22 ± 0.47, and 3.14 ± 0.73 mg/L for U7, U8, and flufenerim against M. separata, respectively. The EC50 values were 24.94 ± 2.13, 30.79 ± 2.21, and 3.18 ± 0.21 mg/L for U7, U8, and azoxystrobin against P. cubensis, respectively. The AChE enzymatic activity testing revealed that the enzyme activities of compounds U7, U8, and flufenerim are 0.215, 0.184, and 0.184 U/mg prot, respectively. The molecular docking results of compounds U7, U8, and flufenerim with the AChE model demonstrated the opposite docking mode between compound U7 or U8 and positive control flufenerim in the active site of AChE. The structure-activity relationships are also discussed. This work provided excellent pesticide for further optimization. Density functional theory analysis can potentially be used to design more active compounds.
- Cheng, Long,Liu, Xing-Hai,Wen, Yong-Hui,Wu, Ning-Jie,Xu, Tian-Ming
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p. 6968 - 6980
(2021/07/19)
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- SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
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A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
- Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
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p. 17288 - 17292
(2020/05/18)
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- Entry into (E)-3-(1,2,4-oxadiazol-5-yl)acrylic acids via a one-pot ring-opening/ring-closing/retro-Diels-Alder reaction sequence
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A simple and convenient one-pot method is reported for the synthesis of (E)-3-(3-aryl(heteroaryl, alkyl)-1,2,4-oxadiazole-5-yl)acrylic acids utilizing readily accessible or commercially available substituted benzamidoximes and inexpensive exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride. The method is based on the reaction of amidoximes with the anhydride in a basic medium at RT followed by an acid-catalyzed retro-Diels-Alder reaction. The observed stereoselective heterocyclization/retro-Diels-Alder cascade process is suitable for the synthesis of a wide range of substituted (E)-1,2,4-oxadiazole-5-ylacrylic acids featuring electron donating and electron withdrawing groups on the aryl moiety, as well as heteroaryl or alkyl substituents at position 3 of the 1,2,4-oxadiazole ring (42–79%; 15 examples).
- Presnukhina, Sofia,Tarasenko, Marina,Baykov, Sergey,Smirnov, Sergey N.,Boyarskiy, Vadim P.,Shetnev, Anton,Korsakov, Mikhail K.
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supporting information
(2019/12/27)
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- Synthesis and Evaluation of Antibacterial Activity of 1,2,4-Oxadiazole-Containing Biphenylcarboxylic Acids
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Abstract: A one-pot method for the synthesis of biphenylcarboxylic acids containing 1,2,4-oxadiazole ring in the NaOH–DMSO system was developed. The results of in vitro experiments showed that the synthesized compounds exhibit antibacterial activity against susceptible strains of E. coli and S. aureus.
- Baikov, S. V.,Presnukhina, S. I.,Shetnev, A. A.,Tarasenko, M. V.
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p. 1611 - 1619
(2020/10/15)
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- Synthesis and evaluation of new 1,2,4-oxadiazole based trans- acrylic acid derivatives as potential PPAR-alpha/gamma dual agonist
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Diabetes is a ubiquitously a metabolic disorder and life-threatening disease. Peroxisome proliferator-activated receptors (PPARs) belong to the class of nuclear receptors which acts as transcription factors to regulate lipid and glucose metabolism. PPAR alpha/gamma dual agonists tend to corroborate the functions of both thiazolidinediones and fibrates and they hold substantial promise for ameliorating the type 2 diabetic treatments and providing potential therapeutic diabetic interventions. New 1,2,4-oxadiazole based trans- acrylic acid derivatives compounds possessing aryl/methylene linker in between pharmacophore head and lipophilic tail for dual PPAR-alpha/gamma agonists are studied. AutoDock Vina used for potential PPAR alpha/gamma dual agonists and 6 compounds 9a, 9g, 9 m, 9n, 9o, and 9r were identified comparable to PPAR gamma agonist Pioglitazone on the basis of their affinity scores and further their in-silico toxicity and in-silico ADME properties. The selected compounds showed better-calculated lipophilicity (iLogP) was found to be 0.92 to 3.19. Compound 9n and 9a were found to be most potent on both PPAR alpha and gamma receptors with EC50 of 0.07 ± 0.0006 μM, 0.06 ± 0.0005 μM and 0.781 ± 0.008 μM, 3.29 μM ± 0.03 respectively as better to pioglitazone having EC50 of 32.38 ± 0.2 and 38.03 ± 0.13 for both receptors. The in-vivo evaluation found to reduce the plasma glucose level and total cholesterol level significantly in diabetic rats compared to pioglitazone at 5 mg/kg/day dose for 7 days of treatment. Thus, trans- acrylic acid derivatives can be further developed as oral therapeutic agents for diabetic interventions as PPAR alpha/gamma dual agonists.
- Bhat, Sana,Bhat, Zahid Rafiq,Gupta, Jeena,Kaur, Jaskiran,Kaur, Paranjeet,Khatik, Gopal L.,Khurana, Navneet,Kumar, Rajan,Kumar, Rakesh,Tikoo, Kulbhushan
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- Synthesis of Some Azamacrocycles Bearing 1,2,4-Oxadiazole and 1,2,3-Triazole Moieties
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Abstract: A tetraazacrown ether,4,9-di(prop-2-yn-1-yl)-1,4,9,12-tetraazacyclohexadecane-2,11-dione, bearingpropargyl groups on two nitrogens was synthesized starting from1,4,9,12-tetraazacyclohexadecane-2,11-dione and subjected to 1,3-cycloadditionreactio
- ?zer, B.,Dürüst, Y.
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p. 698 - 705
(2020/06/01)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of formula (I): (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 55-56
(2020/05/21)
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- Synthesis and Anticancer Activity of Novel Actinonin Derivatives as HsPDF Inhibitors
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Human mitochondrial peptide deformylase (HsPDF) is responsible for removing the formyl group from N-terminal formylmethionines of newly synthesized mitochondrial proteins and plays important roles in maintaining mitochondria function. It is overexpressed
- Hu, Liu,Cai, Xing,Dong, Suzhen,Zhen, Yongjia,Hu, Jidi,Wang, Shenjun,Jiang, Jingwen,Huang, Jiawu,Han, Yuqiao,Qian, Yu,Yuan, Yanqiu,Hu, Wenhao
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p. 6959 - 6978
(2020/08/14)
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- FUNGICIDAL OXADIAZOLES
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Disclosed are compounds of Formula 1, including all geometric and stereoisomers, tautomers, N-oxides, and salts thereof, wherein R1, R2, A, L and J are as defined in the disclosure. Also disclosed are compositions containing the comp
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Paragraph 0364-0366
(2020/12/01)
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- NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI
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The present invention discloses a compound of formula (I), wherein, R1, L1,A, k, L2, W, L4, R5, R8 and R9 are as defined in the detailed description. The present invention furthe
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Page/Page column 74
(2020/10/21)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of formula (I), wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 76
(2019/02/02)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of Formula (I), wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 68-69
(2019/06/09)
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- One-pot synthesis of 3,5-diaryl substituted-1,2,4-oxadiazoles using gem -dibromomethylarenes
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1,2,4-Oxadiazole is one of the most promising heterocyclic ring systems in medicinal chemistry. In the present paper, we report the method for an efficient one-pot synthesis of 3,5-diaryl substituted 1,2,4-oxadiazoles using a two-component reaction of gem-dibromomethylarenes with amidoximes in good yields. In this method, gem-dibromomethylarenes are used as benzoic acid equivalents for the efficient synthesis of aryl-substituted 1,2,4-oxadiazoles. It is anticipated that this methodology will have versatile applications in the practical syntheses of various molecules of both medicinal and material chemistry importance.
- Vinaya, Kambappa,Chandrashekara, Ganganahalli K.,Shivaramu, Prasanna D.
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p. 690 - 696
(2019/09/06)
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- HETEROCYCLIC COMPOUNDS AS FUNGICIDES
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The present invention relates to novel heterocyclic compound of Formula (I), (I) wherein, Het, L1, A, L2 and R12 are as defined in the detailed description, for use as fungicides.
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Page/Page column 67; 68
(2019/10/01)
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- Convenient entry to N-pyridinylureas with pharmaceutically privileged oxadiazole substituents via the acid-catalyzed C[sbnd]H activation of N-oxides
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Pyridine-N-oxides bearing a pharmacophoric oxadiazole moiety could be C[sbnd]H functionalized via the acid-catalyzed reaction with dialkylcyanamides, providing access to hitherto undescribed pyridine-2-yl substituted ureas, which have potential as “lead-l
- Geyl, Kirill,Baykov, Sergey,Tarasenko, Marina,Zelenkov, Lev E.,Matveevskaya, Vladislava,Boyarskiy, Vadim P.
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supporting information
(2019/09/12)
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- Synthesis and Biological Evaluation of Sigma-1 (σ1) Receptor Ligands Based on Phenyl-1,2,4-oxadiazole Derivatives
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In this study, a series of phenyl-1,2,4-oxadiazole derivatives were synthesized and evaluated for anti-allodynic activity. Structure–activity relationship studies identified 1-{4-[3-(2,4-dichlorophenyl)-1,2,4-oxadiazol-5-yl]butyl}piperidine (39) with excellent affinity for the σ1 receptor and selectivity for the σ2 receptor, with poor activity to other central nervous system neurotransmitter receptors and transporters associated with pain. Compound 39 exhibited dose-dependent efficacy in suppressing the formalin-induced flinching and attenuating mechanical allodynia in chronic constriction injury-induced neuropathic rats. These results suggest that compound 39 exerts potent antihyperalgesic activity and could be considered as a promising candidate for treating neuropathic pain.
- Cao, Xudong,Yao, Zhongyuan,Dou, Fei,Zhang, Yifang,Qiu, Yinli,Zhao, Song,Xu, Xiangqing,Liu, Xin,Liu, Bi-Feng,Chen, Yin,Zhang, Guisen
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- Development of hydroxamate-based histone deacetylase inhibitors containing 1,2,4-oxadiazole moiety core with antitumor activities
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Histone deacetylases (HDACs) has proved to be promising target for the development of antitumor drugs. In this study, we reported the design and synthesis of a class of novel hydroxamate-based bis-substituted aromatic amide HDAC inhibitors with 1,2,4-oxadiazole core. Most newly synthesized compounds displayed excellent HDAC1 inhibitory effects and significant anti-proliferative activities. Among them, compounds 11a and 11c increased acetylation of histone H3 and H4 in dose-dependent manner. Furthermore, 11a and 11c remarkably induced apoptosis in HepG2 cancer cells. Finally, the high potency of compound 11a was rationalized by molecular docking studies.
- Yang, Feifei,Shan, Peipei,Zhao, Na,Ge, Di,Zhu, Kongkai,Jiang, Cheng-shi,Li, Peifeng,Zhang, Hua
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 64-65
(2019/02/02)
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- A Straightforward and High-Yielding Synthesis of 1,2,4-Oxadiazoles from Chiral N-Protected α-Amino Acids and Amidoximes in Acetone-Water: An Eco-Friendly Approach
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A straightforward and high-yielding methodology for the synthesis of a high structural diversity of 1,2,4-oxadiazoles from different chiral N-protected α-amino acids and amidoximes under microwave (MW) irradiation is described herein. This greener approac
- Sauer, André C.,Wolf, Lucas,Quoos, Natália,Rodrigues, Mariele B.,Braga, Ant?nio L.,Rodrigues, Oscar E. D.,Dornelles, Luciano
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of the formula (I): (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 62
(2019/02/02)
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- FUNGICIDAL COMPOSITIONS
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A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopatho
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Page/Page column 68
(2019/01/16)
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- Efficient Synthesis of Functionalized Indene Derivatives via Rh(III)-Catalyzed Cascade Reaction between Oxadiazoles and Allylic Alcohols
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A highly efficient rhodium(III)-catalyzed synthesis of novel functionalized indene derivatives has been achieved via C?H activation/intramolecular aldol condensation. This cascade reaction is an atom economical protocol which could be further applied to build more complex compounds. (Figure presented.).
- Zhang, Jing,Sun, Jun-Shu,Xia, Ying-Qi,Dong, Lin
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supporting information
p. 2037 - 2041
(2019/03/28)
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- Oxadiazole Derivatives as Dual Orexin Receptor Antagonists: Synthesis, Structure–Activity Relationships, and Sleep-Promoting Properties in Rats
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The orexin system plays an important role in the regulation of wakefulness. Suvorexant, a dual orexin receptor antagonist (DORA) is approved for the treatment of primary insomnia. Herein, we outline our optimization efforts toward a novel DORA. We started our investigation with rac-[3-(5-chloro-benzooxazol-2-ylamino)piperidin-1-yl]-(5-methyl-2-[1,2,3]triazol-2-ylphenyl)methanone (3), a structural hybrid of suvorexant and a piperidine-containing DORA. During the optimization, we resolved liabilities such as chemical instability, CYP3A4 inhibition, and low brain penetration potential. Furthermore, structural modification of the piperidine scaffold was essential to improve potency at the orexin 2 receptor. This work led to the identification of (5-methoxy-4-methyl-2-[1,2,3]triazol-2-ylphenyl)-{(S)-2-[5-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-3-yl]pyrrolidin-1-yl}methanone (51), a potent, brain-penetrating DORA with in vivo efficacy similar to that of suvorexant in rats.
- Brotschi, Christine,Roch, Catherine,Gatfield, John,Treiber, Alexander,Williams, Jodi T.,Sifferlen, Thierry,Heidmann, Bibia,Jenck, Francois,Bolli, Martin H.,Boss, Christoph
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supporting information
p. 1257 - 1270
(2019/06/17)
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- A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement
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A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.
- Zhang, Guofu,Zhao, Yiyong,Ding, Chengrong
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supporting information
p. 7684 - 7688
(2019/08/30)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of the Formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Paragraph 0510; 0512; 0513; 0514
(2019/12/08)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 68-69
(2019/11/12)
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- COMPOUNDS AND USES THEREOF
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The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.
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Page/Page column 92
(2018/05/17)
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- Structure-activity and structure-property relationships of novel Nrf2 activators with a 1,2,4-oxadiazole core and their therapeutic effects on acetaminophen (APAP)-induced acute liver injury
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The antioxidant function induced by Nrf2 protects the liver from damage. We found a novel Nrf2 activator named compound 25 via structural modification of compound 1 we previously reported. In vitro, compound 25 induced Nrf2 transport into the nucleus and protected hepatocyte L02 cells from APAP-induced cytotoxicity via activating the Nrf2-ARE signaling pathway. In vivo, 25 exhibited therapeutic effects in a mouse model of acute liver injury induced by acetaminophen (APAP) by up-regulating Nrf2-dependent antioxidases and down-regulating liver injury markers in serum. Together, these results indicated that 25 is a potent Nrf2/ARE activator both in vitro and in vivo. The drug-like properties of compound 25 further revealed its potential for development as a therapeutic drug against acute liver injury.
- Xu, Li-Li,Wu, Yu-Feng,Wang, Lei,Li, Cui-Cui,Li, Li,Di, Bin,You, Qi-Dong,Jiang, Zheng-Yu
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p. 1376 - 1394
(2018/09/13)
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- Facile room-temperature assembly of the 1,2,4-oxadiazole core from readily available amidoximes and carboxylic acids
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A one-pot ambient-temperature procedure for the synthesis of 3,5-disubstituted-1,2,4-oxadiazoles from amidoximes and carboxylic acids under superbase-promoted conditions is reported.
- Sharonova, Tatyana,Pankrat'eva, Vitalina,Savko, Polyna,Baykov, Sergey,Shetnev, Anton
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supporting information
p. 2824 - 2827
(2018/06/13)
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- An efficient synthesis and antimicrobial evaluation of 5-alkenyl- and 5-styryl-1,2,4-oxadiazoles
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The cyclodehydration of O-acylamidoximes at room temperature in the superbase system KOH/DMSO represents a simple and efficient way to 5-alkenyl- and 5-styryl-1,2,4-oxadiazoles. This method is suitable for the preparation of 5-(4-vinylphenyl)-1,2,4-oxadia
- Tarasenko, Marina,Sidneva, Vera,Belova, Alexandra,Romanycheva, Anna,Sharonova, Tatyana,Baykov, Sergey,Shetnev, Anton,Kofanov, Eugeniy,Kuznetsov, Mikhail A.
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supporting information
p. 458 - 470
(2019/03/07)
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- 1, 2, 4-oxadiazole incorporated ketoprofen analogues in search of safer non-steroidal anti-inflammatory agents: Design, syntheses, biological evaluation and molecular docking Studies
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Background: Improving the gastrointestinal safety profile of Non-Steroidal Anti- Inflammatory Drugs (NSAIDs) is an important goal. An important strategy to develop NSAIDs with minimal Gastrointestinal (GI) toxicity is to target the COX-2 isoform with a se
- Ranjan, Chanda,Kumar, Jagdish,Sharma, Kalicharan,Akhter, Mymoona,Siddiqui, Anees A.,Chawla, Gita
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p. 590 - 601
(2018/06/06)
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- Pharmacophore requirements for HIV-1 reverse transcriptase inhibitors that selectively “Freeze” the pre-translocated complex during the polymerization catalytic cycle
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Reverse transcriptase (RT) is responsible for replicating the HIV-1 genome and is a validated therapeutic target for the treatment of HIV infections. During each cycle of the RT-catalyzed DNA polymerization process, inorganic pyrophosphate is released as the by-product of nucleotide incorporation. Small molecules were identified that act as bioisosteres of pyrophosphate and can selectively freeze the catalytic cycle of HIV-1 RT at the pre-translocated stage of the DNA- or RNA-template-primer-enzyme complex.
- Lacbay, Cyrus M.,Menni, Michael,Bernatchez, Jean A.,G?tte, Matthias,Tsantrizos, Youla S.
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p. 1713 - 1726
(2018/02/27)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of Formula (I): wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 53
(2018/04/21)
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- FUNGICIDAL COMPOSITIONS
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A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopatho
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Page/Page column 68
(2018/10/30)
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- FUNGICIDAL COMPOSITIONS
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A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.
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Page/Page column 84
(2018/10/25)
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- Focused microwave irradiation-assisted synthesis of N-cyclohexyl-1,2,4-oxadiazole derivatives with antitumor activity
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A facile synthesis of 3,5-disubstituted 1,2,4-oxadiazole derivatives under focused microwave irradiation (FMWI) is reported. Arylamidoximes 1a–i and dicyclohexylcarbodiimide (DCC) were carried out in DMF under FMWI to obtain 1,2,4-oxadiazoles 2a–i in 61–8
- de Oliveira, Valentina Nascimento Melo,dos Santos, Franciane Gon?alves,Ferreira, Vanessa Pinheiro Gon?alves,Araújo, Héverton Mendes,do ó Pessoa, Cláudia,Nicolete, Roberto,de Oliveira, Ronaldo Nascimento
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p. 2522 - 2532
(2018/10/15)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as pesticides, especially as fungicides.
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Page/Page column 63; 64
(2019/01/05)
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- FUNGICIDAL COMPOSITIONS
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A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopatho
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Page/Page column 64; 65
(2019/01/04)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as fungicides.
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Page/Page column 62; 63
(2017/05/30)
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- MICROBIOCIDAL OXADIAZOLE DERIVATIVES
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Compounds of the formula (I) wherein the substituents are as defined in claim 1, useful as a pesticides, especially as fungicides.
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Page/Page column 60
(2017/07/14)
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