- Growth mechanisms of 2D organic assemblies generated from dialkylated melaminium derivatives: The length difference of the two alkyl chains that matters
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This research is aimed to understand the growth mechanisms for self-assembly of dialkylated melamine derivatives. The dialkylated melamine derivatives with different alkyl chains (Mela-m-n) are able to self-assemble with hydrochloric acid in dichloromethane to form 2D organic assemblies, exhibiting similar lamellar structures as Mela-n·HCl with identical alkyl chains. The most interesting finding is that the growth mechanism of Mela-n·HCl with identical alkyl chains is revealed to be layer growth, while Mela-m-n·HCl with asymmetric alkyl chains adopts a spiral growth mechanism. The asymmetric alkyl chains in Mela-m-n may lead to the formation of dislocation, which is responsible for the spiral growth mechanism.
- Xu, Jun,Wu, Guanglu,Wang, Zhiqiang,Zhang, Xi
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- Synthesis and structural study of 4,6-diazido-2-(2,2,2-trinitroethylamino)-1,3,5-triazine
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A method for synthesis of 2-(2,2,2-trinitroethylamino)-4,6-diazido-1,3,5-triazine from 2-amino-4,6-diazido-1,3,5-triazine was elaborated. The molecular and crystal structures of this compound were studied using X-ray diffraction analysis.
- Shastin,Korepin,Aliev,Korchagin,Glushakova,Malygina,Kosilko,Lodygina,Lagodzinskaya,Aldoshin
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- Nitrogen-rich salts based on energetic nitroaminodiazido[1,3,5]triazine and Guanazine
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Highly dense nitrogen-rich ionic compounds are potential high-performance energetic materials for use in military and industrial venues. Guanazinium salts with promising energetic anions and a family of energetic salts based on nitrogen-rich cations and the 6-nitroamino-2,4-diazido[1,3,5]triazine anion (NADAT) were prepared and fully characterized by elemental analysis, IR spectroscopy, 1Ha NMR and 13Ca NMR spectroscopy, and differential scanning calorimetry (DSC). The crystal structures of neutral NADAT (2) and its biguanidinium salt 5 were determined by single-crystal X-ray diffraction (2: orthorhombic, Pnma; 5: monoclinic, P21). Additionally, the isomerization behavior of 2 in solution was investigated by proton-decoupled 13C and 15N NMR spectroscopy. All the new salts exhibit desirable physical properties, such as relatively high densities (1.63-1.78a ga cm-3) and moderate thermal stabilities (Td = 130-196°C for 3-10 and 209-257°C for 11-15). Theoretical performance calculations (Gaussiana 03 and Cheetaha 5.0) gave detonation pressures and velocities for the ionic compounds 3-15 in the range of 21.0-30.3a GPa and 7675-9048a ma s-1, respectively, which makes them competitive energetic materials. Bang boom bang: Nitrogen-rich salts based on nitroamino-diazido-s-triazine and guanazine exhibit high density, good thermal stabilities, and positive calculated heats of formation (see scheme). Predicted detonation pressures (21.0-30.3a GPa) and detonation velocities (7675-9048a ma s-1) suggest that these salts have potential as insensitive energetic materials.
- Huang, Yangen,Zhang, Yanqiang,Shreeve, Jean'Ne M.
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- Hierarchical organization of a robust porphyrin cage self-assembled by hydrogen bonds
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Porphyrins appended with four rigid hydrogen bonding motifs on the meso positions were synthesized and self-assembled into a cofacial cage with four complementary bis(decyl)melamine units in dry solvents. The hydrocarbon chains on the melamine mediate the formation of nanofilms on surfaces as the solvent slowly evaporates.
- Singh, Sunaina,Aggarwal, Amit,Farley, Christopher,Hageman, Brian A.,Batteas, James D.,Drain, Charles Michael
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- A PROCESS FOR THE PREPARATION OF UV ABSORBERS
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The presently claimed invention relates to a novel, highly efficient and general process for the preparation of UV absorbers.
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(2020/07/25)
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- Microwave assisted synthesis, docking and antimalarial evaluation of hybrid PABA-substituted 1,3,5-triazine derivatives
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A series of novel PABA-substituted 1,3,5-triazine derivatives were developed via microwave assisted synthesis and subsequently tested for antimalarial activity against chloroquine sensitive 3D7 strain of Plasmodium falciparum using chloroquine as standard. Antimalarial screening result showed that synthesized compounds exhibited IC50 in the range of 4.46 to 79.72 μg mL?1. Among the tested compounds, 4c and 4f showed significant antimalarial activity with low binding energies (BE) -172.32 and 160.41 kcal mol?1 via interacting with Arg122 through the involvement of COOH of the phenyl linked to 1,3,5-triazine. In conclusion, these core scaffolds can be used for future antimalarial drug development.
- Adhikari, Nayana,Kashyap, Ankita,Shakya, Anshul,Ghosh, Surajit Kumar,Bhattacharyya, Dibya Ranjan,Bhat, Hans Raj,Singh, Udaya Pratap
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p. 2389 - 2399
(2020/03/24)
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- Design and development of 1,3,5-triazine-thiadiazole hybrids as potent adenosine A2A receptor (A2AR) antagonist for benefit in Parkinson's disease
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Various studies showed adenosine A2A receptors (A2ARs) antagonists have profound therapeutic efficacy in Parkinsons Disease (PD) by improving dopamine transmission, thus being active in reversing motor deficits and extrapyramidal symptoms related to the disease. Therefore, in the presents study, we have showed the development of novel 1,3,5-triazine-thiadiazole derivative as potent A2ARs antagonist. In the radioligand binding assay, these molecules showed excellent binding affinity with A2AR compared to A1R, with significant selectivity. Results suggest, compound 7e as most potent antagonist of A2AR among the tested series. In docking analysis with A2AR protein model, compound 7e found to be deeply buried into the cavity of receptor lined via making numerous interatomic contacts with His264, Tyr271, His278, Glu169, Ala63, Val84, Ile274, Met270, Phe169. Collectively, our study demonstrated 1,3,5-triazine-thiadiazole hybrid as a highly effective scaffold for the design of new A2A antagonists.
- Agnihotri, Amol Kumar,Bhat, Hans Raj,Giri, Sabeena,Masih, Anup,Pandey, Nidhi,Shrivastava, Jitendra Kumar,Singh, Saumya,Singh, Udaya Pratap
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- Design, synthesis and biological evaluation of novel ureido benzenesulfonamides incorporating 1,3,5-triazine moieties as potent carbonic anhydrase IX inhibitors
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A series of novel ureido benzenesulfonamides incorporating 1,3,5-triazine moieties were obtained by reacting 4-isocyanato-benzenesulfonamide (2) with 2-amino-4,6-dicholoro-1,3,5-triazine (4). The 4-(3-(4,6-dichloro-1,3,5-triazin-2-yl)ureido) benzenesulfonamide (5) was subsequently derivatized by reaction with various nucleophiles such as, morpholine, ammonia, methyl amine, dimethyl amine, and piperidine. The ureido benzenesulfonamides incorporating triazinyl moieties were investigated as inhibitors of four selected physiologically relevant human carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, namely, hCA I, II, IX, and XII which are involved in various diseases such as glaucoma, epilepsy, obesity and cancer. The membrane-bound tumor-associated isoform hCA IX was potently inhibited with these compounds with Kis in the range of 0.91–126.2 nM. Specifically, compound 7j showed great potency against hCA IX with sub-nanomolar Ki of 0.91 nM. Since hCA IX is a validated drug target for anticancer agents, these isoform-selective and potent inhibitors may be considered of interest for further medicinal/pharmacologic studies.
- Lolak, Nabih,Akocak, Suleyman,Bua, Silvia,Supuran, Claudiu T.
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p. 117 - 122
(2018/10/20)
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- The surprising pairing of 2-aminoimidazo[1,2-a][1,3,5]triazin-4-one, a component of an expanded DNA alphabet
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Synthetic biologists demonstrate their command over natural biology by reproducing the behaviors of natural living systems on synthetic biomolecular platforms. For nucleic acids, this is being done stepwise, first by adding replicable nucleotides to DNA, and then removing its standard nucleotides. This challenge has been met in vitro with `six-letter' DNA and RNA, where the Watson–Crick pairing `concept' is recruited to increase the number of independently replicable nucleotides from four to six. The two nucleobases most successfully added so far are Z and P, which present a donor–donor–acceptor and an acceptor–acceptor–donor pattern, respectively. This pair of nucleobases are part of an `artificially expanded genetic information system' (AEGIS). The Z nucleobase has been already crystallized, characterized, and published in this journal [Matsuura et al. (2016). Acta Cryst. C72, 952–959]. More recently, variants of Taq polymerase have been crystallized with the pair P:Z trapped in the active site. Here we report the crystal structure of the nucleobase 2-aminoimidazo[1,2-a][1,3,5]triazin-4-one (trivially named P) as the monohydrate, C5H5N5O·H2O. The nucleobase P was crystallized from water and characterized by X-ray diffraction. Interestingly, the crystal structure shows two tautomers of P packed in a Watson–Crick fashion that cocrystallized in a 1:1 ratio.
- Laos, Roberto,Lampropoulos, Christos,Benner, Steven A.
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- Design, discovery, modelling, synthesis, and biological evaluation of novel and small, low toxicity s-triazine derivatives as HIV-1 non-nucleoside reverse transcriptase inhibitors
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A set of top-ranked compounds from a multi-objective in silico screen was experimentally tested for toxicity and the ability to inhibit the activity of HIV-1 reverse transcriptase (RT) in cell-free assay and in cell-based assay using HIV-1 based virus-like particles. Detailed analysis of a commercial sample that indicated specific inhibition of HIV-1 reverse transcription revealed that a minor component that was structurally similar to that of the main compound was responsible for the strongest inhibition. As a result, novel s-triazine derivatives were proposed, modelled, discovered, and synthesised, and their antiviral activity and cellular toxicity were tested. Compounds 18a and 18b were found to be efficient HIV-1 RT inhibitors, with an IC50 of 5.6 ± 1.1 μM and 0.16 ± 0.05 μM in a cell-based assay using infectious HIV-1, respectively. Compound 18b also had no detectable toxicity for different human cell lines. Their binding mode and interactions with the RT suggest that there was strong and adaptable binding in a tight (NNRTI) hydrophobic pocket. In summary, this iterative study produced structural clues and led to a group of non-toxic, novel compounds to inhibit HIV-RT with up to nanomolar potency.
- Viira, Birgit,Selyutina, Anastasia,García-Sosa, Alfonso T.,Karonen, Maarit,Sinkkonen, Jari,Merits, Andres,Maran, Uko
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p. 2519 - 2529
(2016/05/09)
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- N-Methylmelamines: Synthesis, Characterization, and Physical Properties
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N-Methylmelamines have recently gained importance as valuable compounds for manufacturing modified melamine formaldehyde resins and other polymer building blocks. A great advantage of these polymers is the reduction of the carcinogenic formaldehyde. Selecting the polymerization processes (e.g., substance polymerization, polymerization in solution) and controlling the polymerization reaction and properties of these novel materials requires knowledge of the properties of the individual melamine derivatives used as new building blocks. All possible permutations of N-methylmelamines were prepared, and reaction progress was monitored by GC/MS. 2,4,6-Tris(dimethylamino)-1,3,5-triazine was prepared to complete the series; this is, however, also a possible byproduct in various synthesis routes. The reaction conditions were optimized to obtain high yields of each derivative with the highest possible purity. The substances were characterized by NMR and IR spectroscopy, mass spectrometry, elemental analysis, and single-crystal X-ray diffraction. In addition, physical properties, such as solubility, melting points, and pKb values, were determined. The number of amino-, methylamino-, and dimethylamino groups has a significant effect on these properties. In summary, we found that by increasing the number of amino- and methylamino groups, solubility and pKb increase. With increasing number of amino groups, the compounds tend to form hydrogen bonds, and thus, the melting point shifts to higher temperature ranges where they start to decompose.
- List, Manuela,Puchinger, Helmut,Gabriel, Herbert,Monkowius, Uwe,Schwarzinger, Clemens
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p. 4066 - 4075
(2016/06/09)
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- Sulfonamide-1,3,5-triazine-thiazoles: Discovery of a novel class of antidiabetic agents: Via inhibition of DPP-4
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Dipeptidyl peptidase-4 (DPP-4) inhibitors are a novel class of antidiabetic drugs used for treating type 2 diabetes mellitus. In the present study, a novel hybrid sulphonamide-1,3,5-triazine-thiazole derivatives were synthesized and characterized by 1H-NMR, 13C-NMR, FT-IR, mass spectroscopy and elemental analysis. The result showed that among the tested compounds, 8c was found to be a more potent inhibitor of DPP-4 (2.32 nM) than the alogliptin standard. Moreover, molecular docking results showed that ligand 8c was efficiently docked into the active site of the catalytic triad of Ser630, Asp708 and His740, encompassing both the S1 and S2 pocket with a CDOCKER interaction energy of 57.80. The in vitro results were further substantiated by in vivo blood glucose lowering effects in experimental subjects. The results of the investigation showed that compound 8c exhibited concentration-dependent improvement of glucose tolerance in ICR after oral administration. It has been also found that compound 8c (30 mg kg-1) showed a reduction in the area under the curve from 0 to 120 min [(AUC) 0-120 min] to 37.46%, which was found to be approximately similar to the hypoglycemic profile of alogliptin (standard). The activity of compound 8c was also investigated in STZ-induced diabetic rats where it showed a dose-dependent decrease in blood glucose levels together with an improvement in insulin levels probably via inhibition of DPP-4. The effect of compound 8c was also investigated on the lipid profile and antioxidant enzyme system.
- Gao, Hai-De,Liu, Peng,Yang, Yang,Gao, Fang
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p. 83438 - 83447
(2016/11/09)
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- Dioxouranium complexes with pentadentate s-triazine Schiff base ligands: Synthesis, crystal structure and optical properties
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Using the reactions of 2,4-dihydrazino-(R)-s-triazine (R – methoxy (DHMT)) with salicylaldehyde and o-vanillin ligands 2,4-Bis(2-hydroxybenzylidenehydrazino)-6-methoxy-s-triazin (L1) and 2,4-Bis(2-hydroxy-3-methoxybenzylidenehydrazino)-6-methoxy-s-triazin (L2) were obtained. Using the reaction of 2,4-dihydrazino-(R)-s-triazine (R – amino (DHAT)) with o-vanillin ligand 2,4-Bis(2-hydroxy-3-methoxybenzylidenehydrazino)-6-amino-s-triazine (L3) was obtained. By the reactions of the prepared ligands, derivatives of hydrazo-s-triazine, with uranyl acetate or nitrate, three new complexes were prepared. X-ray diffraction shows that the UO22+ion is in a pentagonal bipyramidal coordination environment. Two oxygen atoms of the UO22+ion occupy the axial positions and three atoms of nitrogen and two atoms of oxygen construct the equatorial plane. The uranyl(VI) complexes were characterized by single-crystal X-ray diffraction, UV–vis, fluorescence and IR spectroscopy. Thermal stabilities of the complexes were investigated using thermogravimetric analysis.
- Pavelek, Lubomír,Ladányi, Vít,Ne?as, Marek,Vallová, Silvie,Wichterle, Kamil
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- Hybrid 4-Aminoquinoline-1,3,5-triazine Derivatives: Design, Synthesis, Characterization, and Antibacterial Evaluation
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A series of novel 4-aminoquinoline 1,3,5-triazine derivatives were synthesized and characterized by FTIR, 1H-NMR, 13C-NMR, MS, and elemental analysis. The antibacterial activities of synthesized compounds were tested against three Gram-positive bacteria, namely Bacillus subtilis (NCIM-2063), Bacillus cereus (NCIM-2156), and Staphylococcus aureus (NCIM-2079), and four Gram-negative bacteria, namely Proteus vulgaris (NCIM-2027), Proteus mirabilis (NCIM-2241), Escherichia coli (NCIM-2065), and Pseudomonas aeruginosa (NCIM-2036), using ciprofloxacin as reference standard drug. Results showed compound 9a and 9e as potent antibacterial agents against all bacterial strains except Bacillus cereus (NCIM-2156).
- Pathak,Thakur,Bhat,Singh
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p. 1108 - 1113
(2015/08/06)
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- Hydrogen Bonded non-covalent synthesis by reaction of porphyrin appended calix[4]arene with 5,5-diethylbarbituric acid in solution
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Calix[4]arene, diametrically substituted at the upper rim, with two porphyrin appended melamine units spontaneously form well-defined double rosette in the presence of 5,5-diethylbarbituric acid. This assembly consists of nine components which utilize 36 hydrogen bonds and are quite stable in apolar solvents of up to 10-4 M concentration. The formation of assembly between porphyrin appended calix[4]arene and diethylbarbiturate has been broadly studied by UV-visible, fluorescence and 1H NMR spectroscopic techniques. The stoichiometries of proposed aggregates have been analyzed by facile titration of calixarene and barbital. Furthermore, the MALDI-TOF mass measurement is found fully compatible with the observed stoichiometries. Graphical abstract: [Figure not available: see fulltext.]
- Bisht, Tanuja,Garg, Bhaskar,Chauhan, Shive Murat Singh
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p. 103 - 111
(2014/03/21)
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- Ribonucleoside analogs with novel hydrogen bonding patterns
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This invention relates to nucleoside, nucleotide, and oligonucleotide analogs that incorporate non-standard nucleobase analogs, defined to be those that present a pattern of hydrogen bonds to a paired nucleobase analog in a complementary strand that is different from the pattern presented by adenine, guanine, cytosine, and thymine. The invention is specifically concerned with nucleotide analogs that present the donor-donor-acceptor, hydrogen bonding patterns on pyrimidine analogs, and especially those that are analogs of ribonucleotides, including protected ribonucleotides suitable for phosphoramidite-based synthesis of RNA. The heterocycles on these nucleoside analogs are aminopyridones that have electron withdrawing groups attached to the position analogous to the 5-position of the ring in standard pyrimidines, including nitro, cyano, and carboxylic acid derivatives.
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- NOVEL COMPOUNDS AS RESPIRATORY STIMULANTS FOR TREATMENT OF BREATHING CONTROL DISORDERS OR DISEASES
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The present invention includes compositions that are useful in the treatment of breathing control diseases or disorders in a subject in need thereof. The present invention also includes a method of treating a respiratory disease or disorder in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a pharmaceutical formulation of the invention, The present invention further includes a method of preventing destabilization or stabilizing breathing rhythm in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of a pharmaceutical formulation of the invention.
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(2012/06/16)
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- Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones
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Conditions for selective substitution for one chlorine atom in 2-(R,R-amino)-4,6-dichloro-1,3,5-triazines with a hydroxide ion were elaborated. Spectral and calculation methods showed that the products formed are in the lactam form, i.e., have the structure of 4-chloro-6-(R,R- amino)-1,3,5-triazin-2(1H)-ones.
- Bakharev,Gidaspov,Parfenov,Ulyankina,Zavodskaya,Selezneva,Suponitskii,Sheremetev
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- Identification of novel adenosine A2A receptor antagonists by virtual screening
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Virtual screening was performed against experimentally enabled homology models of the adenosine A2A receptor, identifying a diverse range of ligand efficient antagonists (hit rate 9%). By use of ligand docking and Biophysical Mapping (BPM), hits 1 and 5 were optimized to potent and selective lead molecules (11-13 from 5, pKI = 7.5-8.5, 13- to >100-fold selective versus adenosine A1; 14-16 from 1, pKI = 7.9-9.0, 19- to 59-fold selective).
- Langmead, Christopher J.,Andrews, Stephen P.,Congreve, Miles,Errey, James C.,Hurrell, Edward,Marshall, Fiona H.,Mason, Jonathan S.,Richardson, Christine M.,Robertson, Nathan,Zhukov, Andrei,Weir, Malcolm
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supporting information; experimental part
p. 1904 - 1909
(2012/05/19)
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- Discrete assembly of synthetic peptide-DNA triplex structures from polyvalent melamine-thymine bifacial recognition
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We have designed a 21-residue α-peptide that simultaneously recognizes two decadeoxyoligothymidine (dT10) tracts to form triplexes with a peptide-DNA strand ratio of 1:2. The synthetic peptide side chain displays 10 melamine rings, which provide a bifacial thymine-recognition interface along the length of the 21-residue peptide. Recognition is selective for thymine over other nucleobases and drives the formation of ternary peptide· [dT10]2 complexes as well as heterodimeric peptide· [dT10C10T10] hairpin structures with triplex stems.
- Zeng, Yingying,Pratumyot, Yaowalak,Piao, Xijun,Bong, Dennis
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supporting information; experimental part
p. 832 - 835
(2012/03/07)
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- Biophysical mapping of the adenosine A2A receptor
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A new approach to generating information on ligand receptor interactions within the binding pocket of G protein-coupled receptors has been developed, called Biophysical Mapping (BPM). Starting from a stabilized receptor (StaR), minimally engineered for thermostability, additional single mutations are then added at positions that could be involved in small molecule interactions. The StaR and a panel of binding site mutants are captured onto Biacore chips to enable characterization of the binding of small molecule ligands using surface plasmon resonance (SPR) measurement. A matrix of binding data for a set of ligands versus each active site mutation is then generated, providing specific affinity and kinetic information (KD, kon, and k off) of receptor-ligand interactions. This data set, in combination with molecular modeling and docking, is used to map the small molecule binding site for each class of compounds. Taken together, the many constraints provided by these data identify key protein-ligand interactions and allow the shape of the site to be refined to produce a high quality three-dimensional picture of ligand binding, thereby facilitating structure based drug design. Results of biophysical mapping of the adenosine A2A receptor are presented.
- Zhukov, Andrei,Andrews, Stephen P.,Errey, James C.,Robertson, Nathan,Tehan, Benjamin,Mason, Jonathan S.,Marshall, Fiona H.,Weir, Malcolm,Congreve, Miles
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supporting information; experimental part
p. 4312 - 4323
(2011/09/20)
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- Chemoselective polycondensation of 2-amino-4,6-dichloro-1,3,5-triazine with aromatic diamines
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Chemoselective polycondensation of 2-amino-4,6-dichloro-1,3,5-triazine (ADCT) was investigated with various aromatic diamines such as 4,4′-oxydianiline (ODA), 9,9-bis(4-aminophenyl)fluorene (BAFL), 4,4′-(hexafluoropropane-2,2-diyl)dianiline (BisAF), and bis(4-aminophenyl)sulfone (SODA) in the presence of potassium carbonate as a base. High-molecular weight perfectly linear polyguanamines (Mn μ 46000) were successfully obtained for the polycondensation of ADCT with BisAF, while the polycondensation of ADCT with BAFL afforded branched polyguanamines with a degree of branching of from 0.02 to 0.17.
- Shibasaki, Yuji,Koizumi, Takanori,Nishimura, Naoya,Oishi, Yoshiyuki
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supporting information; experimental part
p. 1132 - 1134
(2011/11/30)
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- Novel functionalized melamine-based nitroheterocycles: Synthesis and activity against trypanosomatid parasites
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Human African trypanosomiasis (HAT), caused by the protozoan parasite Trypanosoma brucei spp., is a major health problem in sub-Saharan Africa. New drugs are urgently required for the disease. Selective uptake of toxic compounds into trypanosomes has been achieved by exploiting plasma membrane transporters. For example, the P2 aminopurine transporter, along with other transporters, selectively concentrates melamine and benzamidine moieties into trypanosomes. We have previously reported the use of the melamine motif to selectively target nitrofuran to the trypanosome. In this paper we report the further investigation of the structure activity relationships and the effect of the introduction of different functionalized substituents onto the melamine unit. Most of the compounds tested in vitro for their trypanocidal activity showed activities in the submicromolar range against T. b. rhodesiense. The Royal Society of Chemistry 2009.
- Baliani, Alessandro,Peal, Valerie,Gros, Ludovic,Brun, Reto,Kaiser, Marcel,Barrett, Michael P.,Gilbert, Ian H.
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supporting information; experimental part
p. 1154 - 1166
(2009/05/30)
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- PROCESS FOR PREPARATION OF DISODIUM STILBENEDISULFONATES
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The present invention relates to a process for preparing sodium benzenesulf onate, more specifically, to a process for preparing sodium benzenesulfonate, which comprises the steps of a) reacting 2-X-4, 6-dichloro-l, 3, 5-triazine with a benzenesulf onic acid, 2, 2- (1, 2-ethenediyl) bis [5-amino] - disodium salt to produce a mixture; b) adding cyanuric chloride to the mixture from a); c) adding the compound, XH to the mixture from b) to produce a benzenesulf onic acid, 2,2'- (1, 2-ethenediyl) bis [5- (4-X-β-chloro-l, 3, 5-triazine-2- yl) amino] disodium salt; and d) separating and purifying the product to obtain the final benzenesulf onic acid, 2, 2'- (1,2- ethenediyl) bis [5- (4-X-β-chloro-l, 3, 5-triazin-2-yl) amino] - disodium salt [wherein, X represents an organic substituent].
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(2009/03/07)
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- Visualization of various supramolecular assemblies of oligo(para- phenylenevinylene)-melamine and perylene bisimide
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A melamine derivative has been covalently equipped with two oligo(para-phenylenevinylene) (OPV) chromophores. This procedure yields a bifunctional molecule with two hydrogen-bonding arrays available for complementary binding to perylene bisimide derivatives. Depending on the solvent, hydrogen-bonded trimers, tetramers, and dimers on a graphite surface are observed for pure OPV-melamine by using scanning tunneling microscopy (STM). Upon the addition of perylene bisimide, linear tapes of perylene bisimide, 12-membered rosettes that consist of alternating hydrogenbonded OPV-melamine and perylene bisimide moieties are visualized. These results provide direct evidence for the possible modes of hydrogen bonding within a supramolecular co-assembly in solution. Subsequently, the optical properties of pure OPV-melamine and co-assemblies with a perylene bisimide derivative were characterized in solution. In an apolar solvent, OPV-melamine self-assembles into chiral superstructures. Disassembly into molecularly dissolved species is reversibly controlled by concentration and tempera-ture. Complementary hydrogen bonding to a perylene bisimide derivative in an apolar solvent yields multicomponent, π-stacked dye assemblies of enhanced stability that are characterized by fluorescence quenching of the constituent chromophores. Titration experiments reveal that a mixture of hydrogen-bonded oligomers is present in solution, rather than a single discrete assembly. The solution experiments are consistent with the STM results, which revealed various supramolecular assemblies. Our system is likely not to be optimally programmed to obtain a discrete co-assembled structure in quantitative yield.
- Hoeben, Freek J. M.,Zhang, Jian,Lee, Cameron C.,Pouderoijen, Maarten J.,Wolffs, Martin,Wuerthner, Frank,Schenning, Albertus P. H. J.,Meijer,De Feyter, Steven
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p. 8579 - 8589
(2009/09/30)
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- Design and synthesis of a series of melamine-based nitroheterocycles with activity against trypanosomatid parasites
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The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T. brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T. cruzi against which various nitro heterocycles are already registered for use.
- Baliani, Alessandro,Bueno, Gorka Jimenez,Stewart, Mhairi L.,Yardley, Vanessa,Brun, Reto,Barrett, Michael P.,Gilbert, Ian H.
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p. 5570 - 5579
(2007/10/03)
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- Hierarchical Self-Organization of Perylene Bisimide - Melamine Assemblies to Fluorescent Mesoscopic Superstructures
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A series of three perylene tetracarboxylic acid bisimide dyes 3a-c bearing phenoxy substituents at the four bay positions of the perylene core were synthesized and their complexation behavior to complementary ditopic dialkyl melamines 8a-c was investigated. Binding constants and Gibbs binding energies for the hydrogen bonds between the imide and the complementary melamine moiety have been determined in several solvents by NMR and UV/Vis titration experiments with monotopic model compounds 5 and 9. The effects of the solvent polarity and specific solvent-solute interactions on the degree of polymerization of (3-8)n are discussed, and a general formula to estimate the chain length of [AA-BB]n nylon-type supramolecular polymers is derived. In addition to the formation of a hydrogen-bonded supramolecular chain, π-π interactions were observed for perylene bisimide - melamine assemblies 3b·8b and 3b8c in aliphatic solvents. The orthogonal nature of hydrogen bonding and π-π interactions leads to three-dimensional growth yielding large-sized aggregates already in dilute solution. On suitable substrates, densely intertwined networks of nano-to mesoscopic strands are formed which have been investigated by electron microscopy, confocal fluorescence microscopy and optical polarization microscopy. The high fluorescence and excellent photostability of these superstructures is promising for future studies on energy migration and artificial light harvesting at the nano- and mesoscopic length scale.
- Wuerthner, Frank,Thalacker, Christoph,Sautter, Armin,Schaertl, Wolfgang,Ibach, Wolfram,Hollricher, Olaf
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p. 3871 - 3886
(2007/10/03)
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- Novel inhibitors of Erm methyltransferases from NMR and parallel synthesis
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The Erm family of methyltransferases confers resistance to the macrolide-lincosamide-streptogramin type B (MLS) antibiotics through the methylation of 23S ribosomal RNA. Upon the methylation of RNA, the MLS antibiotics lose their ability to bind to the ribosome and exhibit their antibiotic activity. Using an NMR-based screen, we identified a series of triazinecontaining compounds that bind weakly to ErmAM. These initial lead compounds were optimized by the parallel synthesis of a large number of analogues, resulting in compounds which inhibit the Erm-mediated methylation of rRNA in the low micromolar range. NMR and X-ray structures of enzyme/inhibitor complexes reveal that the inhibitors bind to the S- adenosylmethionine binding site on the Erm protein. These compounds represent novel methyltransferase inhibitors that serve as new leads for the reversal of Erm-mediated MLS antibiotic resistance.
- Hajduk, Philip J.,Dinges, Jürgen,Schkeryantz, Jeffrey M.,Janowick, David,Kaminski, Michele,Tufano, Michael,Augeri, David J.,Petros, Andrew,Nienaber, Vicki,Zhong, Ping,Hammond, Rachel,Coen, Michael,Beutel, Bruce,Katz, Leonard,Fesik, Stephen W.
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p. 3852 - 3859
(2007/10/03)
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- Process for making 2-amino-4, 6-dialkoxy-1, 3, 5-triazines
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A method is provided for making ammelide ethers, such as a 2-amino-4,6-dialkoxy-1,3,5-triazine. A 2-amino-4,6-dihalo-1,3,5-triazine (ADXT) is synthesized in the presence of an aromatic organic solvent, and reaction is effected directly between the (ADXT) synthesis mixture and an alkali metal C(1-4) alkoxide and C(1-4) alkanol, including contact through a static mixer. These ammelide ethers are useful as intermediates for making N-phenylsulfonyl-N-triazinylureas, which have herbicidal and growth regulating properties.
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- Triazine derivatives for enhancing antitumor activity
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2,4,6-Triaminotriazine derivatives as potentiators of chemotherapeutic agents in the treatment of cancer.
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- Design of organic structures in the solid state: Molecular tapes based on the network of hydrogen bonds present in the cyanuric acid-melamine complex
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This paper describes the single-crystal X-ray structures of 1:1 complexes between seven N,N′-bis(4-X-phenyl)melamines (X = H, F, Cl, Br, I, CH3, and CF3) and 5,5-diethylbarbituric acid. These complexes crystallize as infinite tapes having components joined by triads of hydrogen bonds; the tapes pack with their long axes parallel. The crystalline architecture of these complexes - parallel tapes - serves as a structurally constrained framework with which to study physical-organic relationships between the structures of the crystals and the molecules of which they are composed. The complex with X = Br exists in polymorphic forms. One of the polymorphs is isomorphous to the X = Cl complex; the other is related to the X = I complex.
- Zerkowski, Jonathan A.,MacDonald, John C.,Seto, Christopher T.,Wierda, Derk A.,Whitesides, George M.
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p. 2382 - 2391
(2007/10/02)
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- New penicillin derivatives
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New penicillin derivatives have been synthesized by condensation of mono-substituted cyanuric chlorides (3) with 6-aminopenicillanic acid (2), and screened for their antibacterial activity against S. aureus, E. coli, K. pneumonae, S. typhi and P. aeruginosa at 500 μg/ml concentration.Compounds 4a and 4d are inactive while compound 4c is active against all the tested micro-organisms.
- Adure, A. S.,Shelar, A. R.
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p. 759 - 760
(2007/10/02)
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- Herbicidal fluoroethoxy triazines
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Specific fluoroethoxy pyrimidines and triazines are useful as general or selective preemergent and postemergent herbicides. Ortho-ethoxy and ortho-propoxy substituted benzenesulfonamides, such as 2-ethoxy-N-[[4-methoxy-6-(2,2,2-trifluoroethyoxy)-1,3,5-triazin-2-yl]aminocarboxy]benzenesulfonamide and N-[[4-methoxy-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]aminocarbonyl]-2-propoxybenzenesulfonamide, and their agriculturally suitable salts show preemergent and postemergent herbicial utility in corn.
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- N-(2,4-dihalo-S-triazin-6-yl)-ureas and process for their manufacture
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A process for the manufacture of N-(2,4-dihalo-s-triazin-6-yl)-ureas of the formula SPC1 Wherein X represents halogen, R represents alkyl, aryl or hydrogen and Y represents hydrogen or the sulphonic acid group, which comprises reacting a dihalo-amino-s-triazine of the formula SPC2 Wherein X and R have the meanings assigned to them hereinbefore, with chloro-sulphonylisocyanate and hydrolysing the resulting reaction product. The compounds of the formula (1) are suitable as starting products for the manufacture of reactive dyes, fluorescent whiteners or agro - chemicals.
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