- Design and synthesis novel amide derivatives containing an 1,3,4-oxadiazole moiety as potential antibacterial agents
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To find new antibacterial agents, 25 novel amide derivatives containing an 1,3,4-oxadiazole moiety were designed and synthesized, and their antibacterial activity against Xanthomonas oryzae pv. oryzicola (Xoc) and Xanthomonas oryzae pv. oryzae (Xoo) were tested. Interestingly, all target compounds showed excellent antibacterial activities against Xoc and Xoo. The EC50 values of compounds 1–25 against Xoc and Xoo were 1.2–4.0?mg/L and 0.5–2.3?mg/L, respectively, which were significantly superior to those of the thiodiazole copper (95.1 and 89.0?mg/L) and bismerthhibol (73.8 and 68.8?mg/L). For example, the EC50 values of compound 16 against Xoc and Xoo were 1.7 and 0.5?mg/L, respectively. Meanwhile, the curative and protection activity of compound 16 against rice bacterial leaf blight were 42.4% and 42.1%, respectively, which were superior to the control of jiahuangxianjunzuo (34.1% and 32.6%) and thiodiazole copper (33.0% and 27.1%). In addition, compound 16 might suppress the cell growth of Xoo by inhibiting the production of extracellular polysaccharide, the formation of biofilm, changes the cell membrane permeability, and cell surface morphology.
- Chen, Jixiang,Chen, Yifang,Luo, Xin,Wang, Yu,Xing, Zhifu
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supporting information
(2022/02/17)
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- ANTIBIOTICS EFFECTIVE FOR GRAM-NEGATIVE PATHOGENS
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Disclosed herein are antibacterial compounds that accumulate in Gram-negative bacteria, methods of preparing the compounds, and methods of using the compounds to inhibit or kill microbes, and methods of treating microbial infections, such as Gram-negative
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Page/Page column 53; 54; 66; 69
(2019/10/04)
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- IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
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What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons; R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons; L1 and L2 are the same or different, each a linear alkylene of 1 to 20 carbons or a linear alkenylene of 2 to 20 carbons; X1 is S or O; R3 is a linear or branched alkylene consisting of 1 to 6 carbons; and R4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.
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Paragraph 0029; 0487-0491
(2018/07/04)
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- IONIZABLE CATIONIC LIPID FOR RNA DELIVERY
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What is described is a compound of formula I consisting of a compound in which R1 is a branched chain alkyl consisting of 10 to 31 carbons;R2 is a linear alkyl, alkenyl, or alkynyl consisting of 2 to 20 carbons, or a branched chain alkyl consisting of 10 to 31 carbons;L1 and L2 are the same or different, each a linear alkane of 1 to 20 carbons or a linear alkene of 2 to 20 carbons;X1 is S or O;R3 is a linear or branched alkylene consisting of 1 to 6 carbons; andR4 and R5 are the same or different, each a hydrogen or a linear or branched alkyl consisting of 1 to 6 carbons; or a pharmaceutically acceptable salt thereof.
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Paragraph 0529; 0530; 0531; 0532; 0533
(2018/07/05)
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- BICYCLIC AMINES AS NOVEL JAK KINASE INHIBITORS
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The present invention relates to a compound according to formula (I) wherein R1 represents alkyl; n is 1 or 2; R2 is selected from the group consisting of hydrogen, cyano, -SO2Ra, -SO2NRbR
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Page/Page column 42
(2018/08/12)
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- New reagent for the introduction of Boc protecting group to amines: Boc-OASUD
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A new reagent, tert-butyl (2,4-dioxo-3-azaspiro [5,5] undecan-3-yl) carbonate (Boc-OASUD) for the preparation of N-Boc-amino acids is described. The Boc-OASUD reacts with amino acids and their esters at room temperature in the presence of a base and gives N-Boc-amino acids and their esters in good yields and purity. Introduction of the Boc group takes place without racemization. The Boc-OASUD, being a solid and more stable, is a better alternative to di-tert-butyl dicarbonate which is low melting and has to be dispensed in plastic containers than glass because of its poor stability.
- Maheswara Rao, B. Leela,Nowshuddin, Shaik,Jha, Anjali,Divi, Murali K.,Rao
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supporting information
p. 2127 - 2132
(2017/10/31)
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- Facile synthesis of hexahydropyrazino[2,3-e]pyrazines from 3-aminomethyl-1,2,4-triazoles
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The cyclocondensation of aminomethyl-1,2,4-triazoles and glyoxal gives hexahydropyrazino[2,3-e]pyrazines in good yields. 1H and 13C NMR spectra of the title compounds are described and the molecular structure of 4a,5,6,10a,11,12-hexa
- Khomenko, Dmytro M.,Doroschuk, Roman O.,Trachevskii, Vladimir V.,Shova, Sergiu,Lampeka, Rostyslav D.
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p. 990 - 992
(2016/02/18)
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- Synthesis of N-propynyl analogues of peptide nucleic acid (PNA) monomers and their use in the click reaction to prepare N-functionalized PNAs
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Application of the click reaction for coupling a 2-(2-aminoethoxy)ethoxy (AEE) function to thyminyl, cytosinyl and adeninyl peptide nucleic acid (PNA) monomer analogues bearing a N-propynyl group, in place of the original N-2-aminoethyl moiety, has been explored. The N-propynyl PNA analogues were prepared from glycine ethyl ester hydrochloride and the structure of the thyminyl derivative was confirmed by X-ray diffraction. These monomers were employed in click reactions with Boc-protected AEE azide to afford the corresponding triazolyl-linked PNA-AEE conjugates in yields ranging from 64 to 76%. [1,4]-Regiochemistry was verified from a NOESY correlation experiment.
- Howarth, Nicola M.,Ricci, Jennyfer
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experimental part
p. 9588 - 9594
(2011/12/14)
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- Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles
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Combinatorial cyclizations of imidates and hydrazides with methylene linked R groups, generated from the corresponding nitriles and carboxylic acids, respectively, provided a large library of 3,5-dimethylene substituted 1,2,4- trizoles. 2011 Bentham Science Publishers Ltd.
- Woodard, Scott S.,Jerome, Kevin D.
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experimental part
p. 132 - 137
(2012/04/18)
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- Efficient and selective cleavage of the t-butoxycarbonyl group from di-t-butylimidodicarbonate using catalytic bismuth(III) bromide in acetonitrile
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Di-t-butylimidodicarbonates can be chemoselectively and efficiently deprotected to the corresponding mono-BOC-protected amines in high yields using a catalytic amount of bismuth(III) bromide in acetonitrile at room temperature. This method is mild and compatible with the presence of a wide range of functional and other protecting groups in the substrates, such as TBDMS, MOM and mono-BOC or Cbz-protected amines, etc. The method has advantages of ease of operation and use of nontoxic and inexpensive catalyst.
- Zheng, Jianlong,Yin, Biaolin,Huang, Wenming,Li, Xiaopeng,Yao, Hequan,Liu, Zhaogui,Zhang, Jiancun,Jiang, Sheng
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scheme or table
p. 5094 - 5097
(2009/12/01)
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- Palladium-catalysed enantioselective α-hydroxylation of β-ketoesters
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Highly enantioselective α-hydroxylation of cyclic and acyclic 1,3-ketoesters can be achieved with up to 98% ee using a dicationic palladium(ii) catalyst and dimethyldioxirane as oxidant.
- Smith, Alexander M.R.,Billen, Denis,Hii, King Kuok
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supporting information; experimental part
p. 3925 - 3927
(2010/01/06)
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- Environmentally benign N-Boc protection under solvent- and catalyst-free conditions
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A practical and highly efficient method for the protection of amines to their corresponding N-Boc derivatives is reported. In the absence of any solvent and catalyst, the present strategy works well for a series of electron-deficient and electron-rich aromatic amines as well as some sterically hindered substrates. Georg Thieme Verlag Stuttgart.
- Jia, Xueshun,Huang, Qing,Li, Jian,Li, Shaoyu,Yang, Qiushi
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p. 806 - 808
(2007/12/26)
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- Novel stereoselective synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine from glycine ethyl ester
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Asymmetric synthesis of all four diastereomers of 3a-methyl-pyrrolo[3,4-c]piperidine is described herein. The key steps in this synthesis are the highly diastereoselective hydrogenation of an alkenyl nitrile through a hydroxyl-directed or sterically contr
- Kim, Sung-Gon,Lee, Sang Ho,Park, Tae-Ho
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p. 5023 - 5026
(2008/02/10)
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- Glycosylated foldamers to probe the carbohydrate-carbohydrate interaction
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The synthesis of a triglycosylated helical foldamer based on a combination of cyclopentyl- and pyrrolidinyl-based amino acids is described. This structure is stable in water, maintaining as it does a series of carbohydrate units in proximity to one another, and represents the basis of a new approach to the study of carbohydrate-carbohydrate interactions. Copyright
- Simpson, Graham L.,Gordon, Andrew H.,Lindsay, David M.,Promsawan, Netnepa,Crump, Matthew P.,Mulholland, Keith,Hayter, Barry R.,Gallagher, Timothy
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p. 10638 - 10639
(2007/10/03)
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- A highly chemoselective Boc protection of amines using sulfonic-acid-functionalized silica as an efficient heterogeneous recyclable catalyst
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A facile and versatile method for the chemoselective Boc protection of amines has been developed by a treatment with (Boc)2O in the presence of sulfonic-acid-functionalized silica as a catalyst. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic), aromatic, and heteroaromatic amines; primary and secondary amines; aminols, amino-esters; and sulfonamides. The catalyst works under heterogeneous conditions and can be recycled.
- Das, Biswanath,Venkateswarlu, Katta,Krishnaiah, Maddeboina,Holla, Harish
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p. 7551 - 7556
(2008/02/08)
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- Large scale synthesis of 1,2,4- and 1,3,4-oxadiazole carboxylates
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Disclosed are efficient and scalable processes for preparing 1,2,4- and 1,3,4-oxadiazole carboxylates from readily available starting materials.
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- Solution phase synthesis of esters within a micro reactor
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A range of techniques are demonstrated for the solution phase synthesis of esters within an EOF-based borosilicate glass micro reactor, including the use of mixed anhydrides and the in situ preparation of acyl halides.
- Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.,Pombo-Villar, Esteban
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p. 10173 - 10179
(2007/10/03)
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- Molecular discrimination of N-protected amino acid esters by a self-assembled cylindrical capsule: spectroscopic and computational studies.
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A self-assembled, cylindrical capsule was used to bind N-alpha-protected amino acid esters. The reversible encapsulation was studied using NMR spectroscopy in deuterated mesitylene solution and by computer-aided molecular modeling. BOC-L-alanine alkyl est
- Hayashida, Osamu,Sebo, Lubomir,Rebek Jr., Julius
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p. 8291 - 8298
(2007/10/03)
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- Mechanistic studies on prolyl-4-hydroxylase: The vitamin C requiring uncoupled oxidation
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A deuteriated substrate for the human type I prolyl-4-hydroxylase was synthesized and its V/K deuterium isotope effect was determined to be 3.4 ± 0.2. The isotope effect was attributed to the uncoupled oxidation. A dehydroproline containing tetrapeptide was also found to stimulate the uncoupled oxidation. (C) 2000 Elsevier Science Ltd. All rights reserved.
- Wu, Min,Moon, Hong-sik,Pirskanen, Asta,Myllyharju, Johanna,Kivirikko, Kari I.,Begley, Tadhg P.
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p. 1511 - 1514
(2007/10/03)
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- Synthesis and pharmacological profile of a series of 2,5-substituted-N,N-dimethyltryptamine derivatives as novel antagonists for the vascular 5-HT1B-like receptor
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The coronary 5-HT1B-like receptor has been implicated in vasospasm and it is postulated that a 5-HT1B-like antagonist may block the detrimental action of 5-HT whilst not interfering with normal blood vessel function. The synthesis and pharmacological profile of a novel series of 2-(N-heteroaryl)carboxamido-5-substituted-N,N-dimethyltryptamine derivatives as silent (as judged by the inability of angiotensin II to unmask 5-HT1B-like receptor mediated agonist activity in the rabbit femoral artery), competitive and selective 5-HT1B-like receptor antagonists is described. Modifications to the 2-carboxamido sidechain as well as the 5-ethylene linked heterocycle are explored. N-Furfuryl-5-[2-(N-phthalimido)ethyl]-3-[2-(dimethylamino)ethyl]-1H-indole-2- carboxamide (34) was discovered which fulfilled our in vitro selection criteria and which had a favourable pharmacokinetic profile. Compound 34 showed good affinity (pKB = 7.38) for the vascular 5-HT1B-like receptor and greater than 125 fold selectivity over α1-adrenoceptor affinity. The selectivity of 34 and related compounds for the 5-HT1B-like receptor over other receptor subtypes is discussed and a mode of binding for this class of compound to a pharmacophore model is proposed. The Royal Society of Chemistry 1999.
- Moloney, Gerard P.,Martin, Graeme R.,Mathews, Neil,Hobbs, Heather,Dodsworth, Susan,Sang, Pang Yih,Knight, Cameron,Maxwell, Miles,Glen, Robert C.
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p. 2713 - 2723
(2007/10/03)
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- A facile new method for selective deprotection of N- (tertbutoxycarbonyl)-protected carboxamides with Yb(OTf)3 supported on silica gel
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A selective new method for the deprotection of N-Boc carboxamides was achieved by using Yb(OTf)3 supported on silica gel trader solvent-free conditions.
- Kotsuki, Hiyoshizo,Ohishi, Takeshi,Araki, Tomohiro,Arimura, Koji
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p. 4869 - 4870
(2007/10/03)
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- New facile alkoxycarbonylating agent, alkyl pyrazole-1-carboxylates. The preparation and the utilities
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Alkyl pyrazole-1-carboxylates (2), which were readily prepared from alkyl chloroformate or carbazate in good yields, were provided as the new facile alkoxycarbonylating agents toward the Grignard reagents for the synthesis of one carbon higher carboxylic esters. Also amines were alkoxycarbonylated by 2 to produce the corresponding urethanes even in an aqueous medium. Benzyl 3,5-dimethylpyrazole-1-carboxylate (2d) could be utilized for the Cbz-protection of amino acids and esters in good yield without any racemization.
- Kashima, Choji,Tsuruoka, Shiro,Mizuhara, Saori
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p. 14679 - 14688
(2007/10/03)
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- Synthesis of 1,2,4-Oxadiazole-, 1,3,4-Oxadiazole-, and 1,2,4-Triazole-Derived Dipeptidomimetics
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Three series of heterocyclic dipeptidomimetics have been synthesized.The compounds were designed as amino acid-glycine mimetics containing 1,2,4-oxadiazole, 1,3,4-oxadiazole, and 1,2,4-triazole ring systems, useful as building blocks in the synthesis of m
- Borg, Susanna,Estenne-Bouhtou, Genevieve,Luthman, Kristina,Csoeregh, Ingeborg,Hesselink, Willy,Hacksell, Uli
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p. 3112 - 3120
(2007/10/02)
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- Preparation of 3-pyrrolidone and 4-perhydroazepinone
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Efficient multigram preparations of 3-pyrrolidone by sequential Michael addition and Dieckmann condensation, and of 4-perhydroazepinone by ring expansion have been achieved.
- Roglans,Marquet,Moreno-Manas
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p. 1249 - 1258
(2007/10/02)
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- SYNTHESIS OF AMINO ACID ESTERS BY PAPAIN
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A wide range of N-Boc-amino acid esters were synthesized from N-Boc-amino acids and alcohol using papain as catalyst.Suitable biphasic reaction mixtures were found for most amino acids to achieve high yield of ester synthesis.With N-Boc-L-aspartic and glutamic acids only the α carbonyl group esterified, without racemisation.
- Cantacuzene, D.,Pascal, F.,Guerreiro, C.
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p. 1823 - 1826
(2007/10/02)
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