- Lipid membrane adhesion and fusion driven by designed, minimally multivalent hydrogen-bonding lipids
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Cyanuric acid (CA) and melamine (M) functionalized lipids can form membranes that exhibit robust hydrogen-bond driven surface recognition in water, facilitated by multivalent surface clustering of recognition groups and variable hydration at the lipid-water interface. Here we describe a minimal lipid recognition cluster: three CA or M recognition groups are forced into proximity by covalent attachment to a single lipid headgroup. This trivalent lipid system guides recognition at the lipid-water interface using cyanurate-melamine hydrogen bonding when incorporated at 0.1-5 mol percent in fluid phospholipid membranes, inducing both vesicle-vesicle binding and membrane fusion. Fusion was accelerated when the antimicrobial peptide magainin was used to anchor trivalent recognition, or when added exogenously to a preassembled lipid vesicle complex, underscoring the importance of coupling recognition with membrane disruption in membrane fusion. Membrane apposition and fusion were studied in vesicle suspensions using light scattering, FRET assays for lipid mixing, surface plasmon resonance, and cryo-electron microscopy. Recognition was found to be highly spatially selective as judged by vesicular adhesion to surface patterned supported lipid bilayers (SLBs). Fusion to SLBs was also readily observed by fluorescence microscopy. Together, these studies indicate effective and functional recognition of trivalent phospholipids, despite low mole percentage concentration, solvent competition for hydrogen bond donor/acceptor sites, and simplicity of structure. This novel designed molecular recognition motif may be useful for directing aqueous-phase assembly and biomolecular interactions.
- Ma, Mingming,Gong, Yun,Bong, Dennis
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Read Online
- A novel dithiourea and its response to metal ions
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The synthesis, characterization, and its response to metal ions of a novel thiourea N,N′-diethoxycarbonyl-N″,N?-(1,2-ethylidene) dithiourea was reported. The results show that this dithiourea with new structure can react with Cu2+ and Ni2+ separately, and has a best selectivity to Fe3+ ions. Bench-scale flotation tests were also carried out, verifying it has higher copper flotation recovery and better selectivity to sulfide ores containing Cu compared with universal collectors.
- Yuan, Lu,Zhong, Hong,Li, Li Qing,Xiao, Jing Jing
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- Visualized detection of melamine in milk by supramolecular hydrogelations
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We reported a visualized detection system for melamine based on supramolecular dydrogelations.
- Zhang, Jianwu,Ou, Caiwen,Shi, Yang,Wang, Ling,Chen, Minsheng,Yang, Zhimou
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Read Online
- Synthesis and reaction with metal ions of a new thionocarbamate
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The synthesis and research of a novel thionocarbamate N,N′-diethoxy- carbonyl-O,O′-(1,4-butylidene) dithionocarbamate which contains two ester and two thioamide groups are reported. This compound was characterized by elemental analysis, UV spectrum, infrared spectrum, mass spectrum, and 1H NMR and 13C NMR spectroscopy. Additionally, the metal ion-collector interaction in organic solution was put into practice. The results of UV spectroscopic analysis showed that this dithionocarbamate with a new structure exhibited a stronger complex ability with Cu2+ than with Ni2+ or Fe3+. Furthermore, infrared spectroscopic analysis implicated that this dithionocarbamate binds to Cu2+ through both the C=O and C=S groups. Bench-scale flotation tests were also carried out, verifying that it has a higher copper flotation recovery and better selectivity to sulfide ores containing Cu compared with universal collectors. Springer Science+Business Media B.V. 2011.
- Yuan, Lu,Zhong, Hong
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- Fusion reactions of N-heterocyclic moieties to thiopyrano[4′,3′:4,5]thieno[2,3-d]pyrimidines
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Derivatives of the novel heterocyclic parent systems imidazolo[1,2-a]thiopyrano[4′,3′:4,5]thieno[2,3-d]-pyrimidine (B) and thiopyrano[4′,3′:4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidine (C) have been synthesized by fusing pyrimidine moieties to 2-amino-4,7-dihydro-5H-thieno[2,3-c]thiopyran-3-car-boxylic acid ethyl ester (1) and -3-carbonitrile (10), followed by cyclization reactions of the title intermediates A thus obtained.
- Ahmed, Essam K.,Froehlich, Johannes,Sauter, Fritz
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- Structural, Hirshfeld surface and in?vitro cytotoxicity evaluation of five new N-aryl-N’-alkoxycarbonyl thiocarbamide derivatives
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Five new compounds, N-(2, 4-dichlorophenyl)-N’-(methoxycarbonyl) thiocarbamide (1), N-(2, 4-dichlorophenyl)-N’-(ethoxycarbonyl) thiocarbamide (2), N-(2, 4-dichlorophenyl)-N’-(2, 2, 2-trichloroethoxycarbonyl) thiocarbamide (3), N-(2,4-dichlrophenyl)-N’-(pentoxycarbonyl) thiocarbamide (4) and N-(4-nitrophenyl)-N’-(pentoxycarbonyl) thiocarbamide (5), have been synthesized by the reaction of various alkoxy chloroformates with 2, 4-dichloroaniline/4-nitroaniline.The molecular structures of the compounds were elucidated by using spectroscopic methods (FT-IR, 1H and 13C NMR) and single-crystal X-ray structure analysis of compounds 2 and 5. Antiperiplanar orientation of C = O and C = S group across C–N bonds of thiocarbamide core may be due to the presence of intramolecular (N–H···O–C) hydrogen bond in the crystal structure of both the compounds. The presence of intermolecular interactions (C–H···S, C–H···O and N–H···S) in the molecular structure of the compounds has been studied in detail using Hirshfeld surfaces and their associated two-dimensional fingerprint plots. In vitro cytotoxicity screening of the synthesized compounds evaluated on a panel of seven human cancer cell lines (cervical carcinoma (2008, C13*), colorectal (HT29 and HCT116) and ovarian carcinoma (A2780, A2780/CP and IGROV-1)) demonstrated significant inhibitory properties.
- Pandey, Sunil K.,Pratap, Seema,Rai, Sunil K.,Marverti, Gaetano
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Read Online
- Weak interaction and supramolecular structure of N-ethoxycarbonyl-N′- arylthiourea
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Two kinds of N-ethoxycarbonyl-N′-arylthiourea were synthesized, and their structure was determined by X-ray diffraction. There are inter-and intramolecular hydrogen bonds in these compounds. In the crystals, the compounds were assembled to one-dimensional catenulate supramolecular structure by intermolecular hydrogen bonds. Copyright Taylor & Francis Group, LLC.
- Lin, Qi,Wei, Tai-Bao,Zhang, You-Ming
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Read Online
- Preparation process of alkoxycarbonyl thiourea
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The invention relates to a preparation process of alkoxycarbonyl thiourea. The process comprises the following steps: 1, preparing alkoxycarbonyl isothiocyanate by using chloroformate and thiocyanateas raw materials; and 2, adding an aqueous solution of an amine compound to the bottom of a reaction kettle, slowly dropwise adding the alkoxycarbonyl isothiocyanate prepared in the step 1, controlling the dropwise adding temperature at 0-50 DEG C, continuously heating to 60-90 DEG C after the dropwise adding is completed, and standing for layering to obtain an organic phase product. According tothe preparation process of the alkoxycarbonyl thiourea, the feeding mode is changed, and production operation control is better facilitated; the heat release rate of the alkoxycarbonyl thiourea synthesis reaction is favorably reduced; safe production is facilitated; and no flammable and explosive organic solvent with high cost and large pollution is used. The process is simple to operate, and is more beneficial to industrial production control operation, so that safe production of the alkoxycarbonyl thiourea is realized.
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Paragraph 0025-0026; 0028-0029
(2021/01/24)
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- Synthetic method of 1,3,4-thiadiazole derivative
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The invention discloses a synthetic method of a 1,3,4-thiadiazole derivative. The method comprises the following steps: (1) using hydrazine hydrate as a raw material, under the action of a catalyst, reacting with acid, to obtain a hydrazide compound I; (2) using alkyl chloroformate and thiocyanate to react in a condition of a solvent, to obtain an isothiocyanate compound II; (3) in a reaction system of the isothiocyanate compound II, adding solution containing the compound I, reacting to obtain solution containing a compound III; (4) processing the solution of the compound III by dehydrating,neutralizing, and washing, to obtain a compound IV; (5) in the conditions of an acid-binding agent and a solvent, adding alkyl halide or sulfuric acid diester into the compound IV, reacting to obtaina compound V; and (6) enabling the compound V to perform an amination reaction with primary amine, to obtain the 1,3,4-thiadiazole derivative VI. The preparation method has the advantages of green andno pollution, simple and convenient operation, higher yield, mild reaction condition and the like.
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Paragraph 0031; 0033
(2018/12/05)
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- Synthesis, crystal structure and herbicidal activity of a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds
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With the aim of obtaining efficient, safe and environmentally friendly green herbicide, a series of [1,2,4]triazolo[1,5-a]pyrimidine-2-sulfonamide compounds (8a-8f) were synthesized by reacting 2-amino-5,7-(bis-substituted)- 1,2,4-triazolo[1,5-a]pyrimidine (4a and 4b) with 2-substituted-6-trifluoromethyl-benzenesulfonyl chloride (7a-7c). And their structures were characterized by H-NMR, C-NMR, HRMS, FTIR, single-crystal X-ray diffraction, elemental analysis. Moreover, their herbicidal activities against six species of weeds were evaluated. Three target compounds such as 8a, 8c and 8e, exhibited significant postemergence herbicidal activity against some common dicotyledons and monocotyledons under different concentrations. The structure and activity relationship is discussed based on the herbicidal performances of the compounds with different substituents. The investigation results indicated that the above structures could serve as lead compounds for the development of new herbicides.
- Ma, Yi-Chao,Yu, Ying-Hui,Hou, Guang-Feng,Huang, Ji-Han,Gao, Jin-Sheng
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p. 829 - 843
(2016/07/06)
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- Triazolopyrimidinylsulfonamide compound, composition containing compound, and application of compound
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The invention discloses a triazolopyrimidinylsulfonamide compound having a structural formula shown in the description, a composition containing the compound, and an application of the compound. X1, X2, B1, B2, R1, R2, R3, R4 and R5 in the formula are as defined in the description. The triazolopyrimidinylsulfonamide compound has high growth inhibition activity on multiple broadleaf weeds and grassy weeds, has no obvious drug effects on corn, rice, cotton, wheat and other crops, also has the advantages of good crop safety, few synthesis steps, simple method and low preparation cost, and is suitable for large-scale industrial production.
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Paragraph 0073-0074
(2016/11/21)
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- 2-amino -5,8-disubstituted [1, 2, 4] triazolo [1,5-c] pyrimidine method for synthesizing environmental protection
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A disclosed environment-friendly synthetic method for 2-amino-5,8-disubstituted-[1,2,4]triazole[1,5-c]pyrimidine comprises performing thiocyanation reaction on a chloroformate and a thiocyanate to obtain a thiocyanatoformate of a formula III compound; performing condensation reaction on the thiocyanatoformate and a formula IV compound to obtain a formula V compound; and performing a ring-closure reaction on the formula V compound under the effect of a hydroxylamine salt and a sodium alkoxide to obtain a formula I compound. The method provided by the invention employing routine raw material, is low in production cost and suitable for industrialized production, is short in reaction route, mild in reaction conditions and easily-controllable in reaction process, and does not generate various high-pollution wastewater during synthesis and is in favor of environment protection. Additionally, the synthetic route is shown in the specification.
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Paragraph 0021; 0022; 0023
(2017/03/08)
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- PROCESS FOR PREPARING ALKOXYCARBONYL ISOTHIOCYANATE
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Provided herein are processes for the preparation of alkoxycarbonyl isothiocyanates from alkyl chloroformates and thiocyanates in toluene by controlling the amounts of water and catalyst.
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Page/Page column
(2014/04/18)
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- Development of a scalable synthesis of a vascular endothelial growth factor receptor-2 kinase inhibitor: Efficient construction of a 6-etherified [1,2,4]triazolo[1,5-a]pyridine-2-amine Core
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A practical and scalable synthesis of the vascular endothelial growth factor receptor-2 (VEGFR-2) kinase inhibitor 1 has been developed. The key features of the process development include facile preparation of the key raw material 3-amino-4- fluorophenol, chemoselective nucleophilic aromatic substitution of 5-chloro-2-nitropyridine with phenol, a safe one-pot synthesis of a substituted urea using an isothiocyanate generated in situ from inexpensive materials, and improvement of the yield of acylation in the end game. The optimized six-step synthesis afforded 1·H2O in 54% overall yield, twice as much as the yield of the original synthesis, without chromatographic purification. In addition, a robust recrystallization procedure to afford the desired crystal form of 1 was also developed.
- Ishimoto, Kazuhisa,Fukuda, Naohiro,Nagata, Toshiaki,Sawai, Yasuhiro,Ikemoto, Tomomi
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p. 122 - 134
(2014/05/20)
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- PYRIMIDO- PYRIDAZINONE COMPOUNDS AND USE THEREOF
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The present application provides novel pyrimido-pyridazinone compounds and methods for preparing and using these compounds. These compounds are useful in treating inflammation in patients by administering one or more of the compounds to a patient. In one embodiment, the novel pyrimido-pyridazinone compound is of Formula (I) and R1 and R2 are defined herein.
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Page/Page column 28; 29; 46; 47
(2013/03/26)
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- A highly selective colorimetric sensor for Hg2+ based on nitrophenyl-aminothiourea
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A simple and highly selective colorimetric sensor (L1) bearing thiosemicarbazide moiety as binding site and nitrophenyl moiety as signal group were synthesized. Sensor L1 showed great colorimetric single selectivity and high sensitivity for mercury cation in DMSO and DMSO/H2O binary solutions. When Hg2+ was added to the DMSO solution of L1, dramatic color change from brown to colorless was observed. While the cations Ca 2+, Mg2+, Cd2+, Fe3+, Co 2+, Ni2+, Cu2+, Zn2+, Pb 2+, Ag+ and Cr3+ could not cause any distinct interferer toward the recognition process for Hg2+. The detection limit is allowable to 5.0 × 10-6 and 1.0 × 10 -7 M level of Hg2+ according to visual color change and UV-vis change, respectively. The recognition mechanism of the sensor toward mercury cation was evaluated in DMSO solutions by UV-vis and 1H NMR. The sensor selectively sense Hg2+ via the formation of a stable 1:1 complex through C=S and C=O group with Hg2+. When these complex bonds formed, the sensor carried out an ICT transition induced color change.
- Liu, Juan,Yu, Mei,Wang, Xi-Cun,Zhang, Zhang
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experimental part
p. 245 - 249
(2012/06/04)
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- Pyridazine derivatives and related compounds, part 221: Synthesis, reactions, and insecticidal activity of 3-amino-5,6-diaryl-1h-pyrazolo[3,4-c] pyridazines
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Starting with 3-amino-5,6-diaryl-1H-pyrazolo[3,4-c]pyridazine, the syntheses of thiourea derivatives, dithiocarbamates, ethyl carbamate, phosphoranylidene amino, and substituted acetamido derivatives are described. The products were screened for their insecticidal activity against Mucsa, domestica, and Aphid, Macrosiphum pisi. Supplemental materials are available for this article. Go to the publisher′s online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
- Deeb, Ali,Mourad, Elsayed,Elenany, Diaa
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experimental part
p. 222 - 231
(2010/06/16)
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- BICYCLIC HETEROARYL COMPOUNDS AND THEIR USE AS KINASE INHIBITORS
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Phosphatidylinositol (PI) 3-kinase inhibitor compounds, their pharmaceutically acceptable salts, and prodrugs thereof; compositions of the new compounds, either alone or in combination with at least one additional therapeutic agent, with a pharmaceutically acceptable carrier; and uses of the new compounds, either alone or in combination with at least one additional therapeutic agent, in the prophylaxis or treatment of proliferative diseases characterized by the abnormal activity of growth factors, protein serine/threonine kinases, and phospholipid kinases.
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Page/Page column 72
(2009/03/07)
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- Intra- and intermembrane pairwise molecular recognition between synthetic hydrogen-bonding phospholipids
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Multivalency and preorganization are fundamental aspects of molecular recognition at the lipid membrane-water interface and can render weak monomeric binding interactions selective and robust; this concept is important throughout biology, biotechnology, and materials science. Though hydrogen bonding is typically weakened in water, intramembrane hydrogen bonding between native lipids has been well-studied and is thought to contribute to lipid bioactivity and membrane function. We hypothesized that avidity and preorganization effects at the lipid-water interface could overcome solvent competition and allow for selective hydrogen-bond recognition between small, unstructured components. We have found that electrostatically identical vesicular membranes composed of cyanuric acid and melamine functionalized phospholipids 1 and 2 undergo selective apposition, fusion and adhesion in suspension and on solid support, indicating that their well-known low-dielectric hydrogen bonding properties translate effectively to the lipid-water interface. This work is notable and of general interest given the few detailed studies of aqueous phase hydrogen-bonding systems; we have extensively characterized this system, gaining structural, functional, and thermodynamic data. Furthermore, we have found that the designed lipid-lipid headgroup interactions result in dramatic alteration of the lipid phase morphology, providing insight into the coupling of molecular interactions with assembly state. As such, this work contributes to our understanding of fundamental phenomena such as molecular recognition at the lipid-water interface membrane chemistry and further illustrates the general possibility of designing selective hydrogen-bonding adhesive interactions from simple starting materials at other polar-apolar interfaces; this could have numerous materials and biotechnological applications. Copyright
- Ma, Mingming,Paredes, Angel,Bong, Dennis
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supporting information; experimental part
p. 14456 - 14458
(2009/02/08)
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- ANTIBACTERIAL AGENTS
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The present invention is directed to a new class of triazolopyridine derivatives, to their use as antimicrobials, and to pharmaceuticals containing these compounds.
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Page/Page column 20-21
(2008/06/13)
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- Efficient and novel synthesis of N-Aryl-N'-ethoxycarbonylthiourea and arene-bis-ethoxycarbonylthiourea derivatives catalyzed by TMEDA
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A series of N-aryl-N'-ethoxycarbonyl thioureas and arene-bis- ethoxycarbonylthiourea derivatives have been synthesized in good to excellent yields under the TMEDA catalyzed conditions at room temperature.
- Wei, Tai-Bao,Lin, Qi,Zhang, You-Ming,Wang, Hai
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p. 2205 - 2213
(2007/10/03)
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- TMEDA-catalyzed synthesis of N-aryl-N′-ethoxycarbonyl thiourea and arene (or polymethylene)-bis-ethoxycarbonylthiourea derivatives
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A novel and efficient method for synthesis ethoxycarbonyl isothiocyanate and ethoxycarbonyl thioureas catalyzed by TMEDA is reported. A series of N-aryl-N′-ethoxycarbonyl thioureas and arene (or polymethylene)-bis- ethoxycarbonyl thiourea derivatives have been synthesized in good-to-excellent yields via this method at room temperature.
- Lin, Qi,Zhang, You-Ming,Gao, Li-Ming,Wei, Tai-Bao,Wang, Hai
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p. 2051 - 2057
(2007/10/03)
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- Microwave promoted efficient synthesis of N-aryl-N′-ethoxycarbonyl thioureas under solvent-free and phase-transfer catalysis conditions
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A series of N-aryl-N′-ethoxycarbonyl thioureas 3a-j were synthesised under microwave irradiation, phase transfer catalysis and solvent-free conditions.
- Lin, Qi,Zhang, You-Ming,Wei, Tai-Bao,Wang, Hai
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p. 298 - 299
(2007/10/03)
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- Stability Constants of N-Ethoxycarbonyl-N-thiourea Complexes with some Transition Metal Ions. Synthesis and Characterisation of Copper(II) and Cobalt(II) Complexex
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The formation constants of N-ethoxycarbonyl-N-thiourea (2) and N-ethoxycarbonyl-N-thiourea (3) with 3d-transition metals (CuII, NiII, CoII, MnII and ZnII) have been determined in 70percent (v/v) ethanol-water medium.The formation constants both K1 and K2 follow the order: MnII II II II II.Complexes of CuII and CoII with ligand have been characterised by analytical, electrical conductivity, magnetic, ir and uv spectral data.The ligands form biscomplexes ML2, where L is uninegatively charged an the binding sites are oxygen and sulphur atoms.
- Ibrahim, Mohamed K.A.,El-Hadi, Afkar K. Abd,Darwish, Faiza M.
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p. 671 - 674
(2007/10/02)
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- Synthesis, antineoplastic and anthelmintic activities of N-alkyloxycarbonyl-N'-(4-benzyloxy-2-nitrophenyl)thioureas as prodrugs of (6-benzyloxy-1H-benzimidazol-2-yl)carbamic acid ester
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N-Methoxycarbonyl-N'-(4-benzyloxy-2-nitrophenyl)thiourea (7) has been synthesised as a potential prodrug of (6-benzyloxy-1H-benzimidazol-2-yl)carbamic acid methyl ester (9).Biological activities of the compounds 7-10 have been evaluated against Ehrlich ascites carcinoma, ascaris and hymenolepis infected animals.Ethyl carbamates (8,10) show poor activity and compounds 7 and 9 are well tolerated in acute toxicity study.The intestinal bacterial flora E. coli can cyclise the compound 7 to 9.
- Bera, Tanmoy,Belsare, D. P.
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p. 370 - 372
(2007/10/02)
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- Preparation of Ethoxycarbonyl Isothiocyanate Using a Pyridine or Quinoline Catalyst
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A process for the preparation of ethoxycarbonyl isothiocyanate using pyridine or quinoline as a catalyst in an aqueous medium is presented.This process leads to high yields of the desired product with only trace amounts of the thiocyanate being formed.Reaction of ethoxycarbonyl isothiocyanate, prepared in situ, with nucleophiles can be carried out in with yields and purity.
- Lewellyn, Morris E.,Wang, Samuel S.,Strydom, Peter J.
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p. 5230 - 5231
(2007/10/02)
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- Reaction of Hydrazidoyl Halides with Thiocyanate Anion: Synthesis of Thiadiazolines and Thiadiazoloquinazoline
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Hydrazidoyl chlorides (1a-d) react with potassium thiocyanate to give 5-imino-Δ2-1,3,4-thiadiazoline derivatives (4a-d).The corresponding N-acetyl-, N-benzoyl- and N-ethoxycarbonyl-thiadiazolines (5, 6 and 7) have been obtained via 1,3-dipolar cycloaddition of 1d to acetyl isothiocyanate, benzoyl isothiocyanate and ethoxycarbonyl isothiocyanate or via acylation reaction of compound 4d with acetyl chloride, benzoyl chloride and ethyl chloroformate.Compound 1e, however, on reaction with potassium thiocyanate furnishes directly the thiadiazoloquinazoline (8).Condensation of 4a with α-halogenketones and isothiocyanates gives N-alkylderivatives (9-11) and thioureas (12-14) respectively.Compound 4c on treatment with nitrous acid followed by reduction gives hydrazine derivative (16) via the intermediate 15.Bromination of 4b furnishes 17 which on reaction with cyanide ion furnishes the corresponding cyanoacetyl derivative (18).
- Ibrahim, Mohamed Kamal Ahmed
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p. 120 - 122
(2007/10/02)
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- Novel process of alkoxy and aryloxy isothiocyanate preparation
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Alkoxy and aryloxy isothiocyanates are produced by the reaction of a haloformate and an alkali or alkaline earth metal thiocyanate in the presence of water and a catalyst comprising a six membered mononuclear or ten membered fused polynuclear aromatic, heterocyclic compound having 1 or 2 nitrogen atoms as the only hetero atoms in the ring.
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- Synthesis of Heterocyclically Substituted-4-Piperidinyl-1,4-dihydropyridines by Ring Closure Reactions at a N-Acylthioamide- or at a N-Acylisothioamide-Side-Group
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A series of 4-(2'-methylenepiperidin-4'-yl)-1,4-dihydropyridines with a heterocyclic substituent at the methylene group is prepared by reaction of the nonsubstituted compound 1 with benzoylisothiocyanate or ethoxycarbonylisothiocyanate to the N-benzoylthioamide 2 or the N-ethoxycarbonylthioamide 3, transformation of 2 into the isothioamide 4 by S-methylation, and subsequent ring closure of 2, 3 or 4 with hydrazine, methylhydrazine, phenylhydrazine, 1,2-diaminoethane, 1,2- and 1,3-diaminopropane, o-diaminobenzene and o-aminophenol.
- Pragst, F.,Liebscher, J.,Boche, E.,Koeppel, H.
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p. 383 - 390
(2007/10/02)
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- Process for the production of isothiocyanate derivatives
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Derivatives of alkoxy, aryloxy and alkene isothiocyanates are produced by the reaction of a haloformate, an alkali, alkaline earth metal, lead or ammonium thiocyanate and a compound having the formula R1 YH wherein R1 is alkyl, aryl or alkoxy, Y is oxygen, sulfur or NR2 and R2 is hydrogen or R1, in the presence of a solvent or water and a catalyst.
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- Cyanothioacetamide in Heterocyclic Synthesis: A New Approach for the Synthesis of 2-Pyridothione and 2-Pyridazinothione Derivatives
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Cyanothioacetamide (1) undergoes self condensation to give 4,6-diamino-3-cyano-2-pyridothione (2).The latter was utilised in synthesis of pyridopyrazole, pyridopyrimidine, bis-(pyridothione derivatives) through reaction with hydrazine hydrate, ethoxycarbonyl isothiocyanate and cinnamonitrile derivatives.Also 1 undergoes self dimerisation to give 13, the latter form the pyridazine derivative on coupling with benzenediazonium chloride. - Key words: Heterocyclic Synthesis, Cyanothioacetamide, Pyridazine Derivatives
- Mohareb, R. M.,Fahmy, S. M.
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p. 105 - 109
(2007/10/02)
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- 1,3-Oxazines and Related Compounds. IX. Alkylation, Acylation, and Cleavage Reaction of 6-Methyl-4-oxo-2-thioxo-3,4-dihydro-2H-1,3-oxazine
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Alkylation of the title compound (2) with alkyl halides in the presence of Et3N proceeded exclusively on the sulfur atom to give the alkyl-1,3-oxazine derivatives.Acylation with acyl chlorides took place regioselectively on the nitrogen atom, giving the N-acyl derivatives. 1,3-Oxazine 2 was found to undergo cleavage of the ring into acetylketene and thiocyanic acid.Hence, treatment of 2 with alkyl halides in the presence of K2CO3 gave alkyl thiocyanates; treatment with active methylene compounds afforded γ-pyrone derivatives.N-Acyl derivatives of 2 also underwent thermal cleavage of the ring, leading to the corresponding acyl isothiocyanates.Keywords - 2-thioxo-4-oxo-1,3-oxazine; acetylketene; thiocyanic acid; acyl isothiocyanate; alkyl thiocyanate; acylation; alkylation; substituted γ-pyrone.
- Yamamoto, Yutaka,Morita, Yasuo
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p. 2957 - 2962
(2007/10/02)
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- Activated Nitriles in Heterocyclic Syntheses, I. Novel Synthesis of Pyrrolones and 1,2,4-Triazol-3-oyl nitriles
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The behaviour of 4-benzylidene-2-oxazolin-5-one (2) and of 4-phenylazo-2-oxazolin-5-one (3) toward a variety of active methylene reagents is reported.Cleavage of the oxazolin-5-one ring was observed in most cases.A variety of new, otherwise, difficult accessible, azolyl derivatives could be prepared. - Keywords: Heterocyclic Synthesis, Pyrrolones
- Elmoghayar, Mohamed Rifaat Hamza,Ibrahim, Mohamed Kamal Ahmed,Ramiz, Mahmoud Mohamed Mahfouz,Elnagdi, Mohamed Hilmy
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p. 764 - 768
(2007/10/02)
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- Activated Nitriles in Heterocyclic Synthesis. A Novel Synthesis of 1,2,4-Triazol-3-oyl Nitriles
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Synthesis of 1,2,4-triazoloyl nitriles via reaction of 4-phenylhydrazono-2-phenyl-2-oxazolin-5-one and 4-phenylhydrazono-2-ethoxy-2-thiazolin-5-one with active methylene nitriles was accomplished.Some of the chemical properties of the nitriles obtained are reported.
- Nada, Afaf,Elfahham, Hassan Attia,Mohamed, Nadia Ragab,Elnagdi, Mohamed Hilmy
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p. 1457 - 1459
(2007/10/02)
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- Synthesis of N-acyl-1,3-oxathiol-2-imines
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A facile synthesis of N-acyl-1,3-oxathiol-2-imines, 7, is reported.It comprises the reaction of O-alkyl acylcarbamothioates, 4, with 2-chloroketones in the presence of alcoholic sodium alkoxide.The resulting O-alkyl-S-substituted-N-acylcarbonimidothiates, 6, undergo cyclization with elimination of alcohol, spontaneously, or upon heating in boiling toluene to form 7.
- Kulka, Marshall
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p. 1557 - 1559
(2007/10/02)
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- Oxalyl Isothiocyanates and Carbonyl Halogenide Isothiocyanates
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Preparations of ethoxalyl isothiocyanate (1), oxalyl diisothiocyanate (3), oxalyl chloride isothiocyanate (4), and oxalyl bromide isothiocyanate (16) are described.Thermal decarbonylation of 4 and 16 leads to carbonyl chloride isothiocyanate (7) and carbonyl bromide isothiocyanate (17), resp.Some reactions of the new oxalyl and carbonyl pseudohalogenides are given.Trichloromethyl isothiocyanate (13) is obtained from trichloromethyl isocyanide dichloride (12).
- Bunnenberg, Rolf,Jochims, Johannes C.
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p. 1746 - 1751
(2007/10/02)
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- Synthesis of a Triazole Homo-C-nucleoside
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The present paper describes a totally synthetic triazole homo-C-nucleoside.One sequence directed toward this compound started by reducing dimethyl cis-2,5-dihydrofuran-2,5-dicarboxylate to cis-2,5-bis(hydroxymethyl)-2,5-dihydrofuran with lithium borohydride.The diol could be converted to the dimesyl derivative, the ditosylate, or the cyclic sulfite.None of these compounds reacted with cyanide ion to form the 2-(cyanomethyl) derivative or to form 2,5-bis(cyanomethyl)-2,5-dihydrofuran.This first approach was put aside at this point, so that the planned conversion of the cyclic sulfite by oxidation to the corresponding cyclic sulfate was left untried.The second sequence, which was brought to completion, made use of 2,3,4,4-tetrachloro-8-oxabicycloocta-2,6-diene as the starting material.This with lithium aluminum hydride plus lithium hydride yielded 3-chloro-8-oxabicycloocta-2,6-diene, which on hydroxylation with hydrogen peroxide and osmium tetraoxide gave 3-chloro-exo-cis-6,7-dihydroxy-8-oxabicyclooct-2-ene and by combination with acetone 3-chloro-exo-cis-6,7-(isopropylidenedioxy)-8-oxabicyclooct-2-ene.Ozonolysis in methanol solution followed directly by borohydride reduction produced methyl 2,3-O-isopropylidene-β-ribofuranosylacetate.Condensation of the corresponding lactone with aminoguanidine formed 3--5-amino-1,2,4-triazole, and finally acid hydrolysis removed the protective isopropylidene group and yielded the desired homo-C-nucleoside, 3-(β-ribofuranosylmethyl)-5-amino-1,2,4-triazole hydrochloride.Several derivatives of the above-mentioned lactone carrying different functions on the carbon next to the carbonylgroup were also prepared.
- Gensler, Walter J.,Chan, Sum,Ball, David B.
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p. 3407 - 3415
(2007/10/02)
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- Process for preparing 1,2,4-triazole derivatives
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1,2,4-TRIAZOLE DERIVATIVES WHICH HAVE PARTICULAR IMPORTANCE AS INTERMEDIATES FOR, E.G., THE PREPARATION OF ACTIVE SUBSTANCES FOR PEST CONTROL, CORRESPONDING TO THE FORMULA STR1 wherein R1 represents an unsubstituted or substituted alkyl, alkenyl, or alkynyl, naphthyl, benzyl, phenylethyl, STR2 or phenylpropyl radical, or a mono or polycyclic cycloalkyl radical which can be bound by way of an alkylene bridge member, or a substituted phenyl radical, And new processes for the preparation of compounds of the formula STR3 wherein R represents hydrogen, an optionally substituted alkyl, alkenyl or alkynyl radical, an optionally substituted phenyl, naphthyl, benzyl, phenylethyl or phenylpropyl radical, a mono- or polycyclic cycloalkyl radical which can be bound by way of an alkylene bridge member and/or be substituted by alkyl, or a partially hydrogenated naphthyl radical, which processes are performed by addition to a hydrazine of the formula or to a hydrazone of the formula STR4 wherein R has the above given meaning, R1 represents hydrogen or lower alkyl and R2 represents lower alkyl, of an alkoxy-carbonyl-isothiocyanate of the formula and subsequent closure of the triazole ring in the resulting thiosemicarbazide of the formula STR5 by the splitting-off of an alkanol (alkyl--OH), are disclosed.
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- Fungicidal compositions containing bisthioureido-benzenes and methods for use thereof
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Fungicidal compositions are provided containing as the active constituent compounds having the formula: STR1 wherein each of R and R1 represents a member of the group consisting of alkyl containing from 1 to 12 carbon atoms, alkyl containing from 1 to 2 carbon atoms substituted with halogen, methoxy or phenyl, alkenyl containing 2 to 3 carbon atoms, alkynyl containing 2 to 3 carbon atoms, aryl containing not more than 10 carbon atoms, aryl containing not more than 10 carbon atoms substituted with halogen or methyl; each X represents halogen, nitro or methyl; n represents an integer from 0 to 3; and Y represents oxygen or sulfur, with the proviso that when Y represents sulfur, each R and R1 represents alkyl containing 1 to 12 carbon atoms. These compounds may be prepared in accordance with the following equation: STR2 wherein R, R1, X, Y and n are as stated above. These compounds have broad fungicidal activity with very low mammalian toxicity.
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- Bis-thioureido-benzenes, preparation and uses thereof
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Compounds having the formula: STR1 wherein each of R and R1 represents a member of the group consisting of alkyl containing from 1 to 12 carbon atoms, alkyl containing from 1 to 2 carbon atoms substituted with halogen, methoxy or phenyl, alkenyl containing 2 to 3 carbon atoms, alkynyl containing 2 to 3 carbon atoms, aryl containing not more than 10 carbon atoms, aryl containing not more than 10 carbon atoms substituted with halogen or methyl; each X represents halogen, nitro or methyl; and n represents an integer from 0 to 3. These compounds may be prepared in accordance with the following equation: STR2 wherein R, R1, X and n are as stated above. These compounds have broad fungicidal activity with very low mammalian toxicity.
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- Treatment of helminth infections with substituted phenyl-thiourea derivatives
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Benzene derivatives of the formula:- STR1 wherein R is an aliphatic hydrocarbon group of 1 to 4 carbon atoms optionally substituted by halogen or alkoxy, R1 is hydrogen or methyl, R2 is hydrogen, halogen, alkyl, alkanoylamino optionally substituted by cycloalkyl of 3 to 6 carbon atoms, alkoxycarbonylamino, alkanoyl, benzoyl or N-methylmethanesulphonylamino, and Y is primary amino or substituted amino, possess anthelmintic and anti-viral activity. New compounds within that formula possess fungicidal properties.
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- 2,3-Bis-(3-acyl-2-thioureido)-pyridines
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New 2,3-bis(3-acyl-2-thioureido)-pyridines having anthelmintic activity are prepared by reacting a diaminopyridine with acylthiocyanates.
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- Uses of Anthranilic Acid for the Synthesis of Dihydroquinazolin Derivatives with Antitumor, Antiproliferative and Pim-1 kinase Activities
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The reaction of anthranilic acid with ethoxycarbonylisothiocyanate gave the ethyl 4-oxo-2-thioxo-1,2-dihydroquina-zoline-3(4H)-carboxylate (4). The reaction of compound 4 with hydrazine hydrate and α-halocarbonyl derivatives was found to give either hydrazono or S-alkylated products. Heterocyclization reactions of some of the S-alkylated derivatives 8 and 12 were carried out to afford thiazole, pyran and pyridine derivatives. The cytotoxicity of the newly synthesized compounds towards the six cancer cell lines NUGC, DLD-1, HA22T, HEPG-2, HONE-1 and MCF-7 showed that compounds 6, 8, 13, 19c–f, 21b-f, 24a and 24c with the highest cytotoxicity. The c-Met kinase inhibition for some of the selected compounds showed that compounds 8, 13, 19d, 21e, 21f and 24a were the most active compounds. Screening toward tyrosine kinases revealed that compounds 13, 21e and 24a exhibit the highest inhibitions and therefore their molecular modeling was described. In addition, compounds 13 and 24a showed the highest activities towards Pim-1 kinase.
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