- Design, Synthesis, and Synergistic Activity of Eight-Membered Oxabridge Neonicotinoid Analogues
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Insecticide synergists are sought-after due to their potential in improving the pesticide control efficacy with a reduced dose of an active ingredient. We previously reported that a cis-configuration neonicotinoid (IPPA08) exhibited specific synergistic activity toward neonicotinoid insecticides. In this study, we synthesized a series of structural analogues of IPPA08 by converting the pyridyl moiety of IPPA08 into phenyl groups, via facile double-Mannich condensation reactions between nitromethylene compounds and glutaraldehyde. All of the oxabridged neonicotinoid compounds were found to increase the toxicity of imidacloprid against Aphis craccivora. Notably, compound 25 at 0.75 mg/L lowered the LC50 value of imidacloprid against A. craccivora by 6.54-fold, while a 3.50-fold reduction of the LC50 value was observed for IPPA08. The results of bee toxicity test showed that compound 25 display selectivity in its effects on imidacloprid toxicity against the honey bee (Apis mellifera L.). In summary, replacing the pyridyl ring with a phenyl ring was a viable approach to obtain a novel synergist with oxabridged moiety for neonicotinoid insecticides.
- Zhang, Xiao,Wang, Yiping,Xu, Zhiping,Shao, Xusheng,Liu, Zewen,Xu, Xiaoyong,Maienfisch, Peter,Li, Zhong
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p. 3005 - 3014
(2021/04/09)
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- Low emission epoxy resin composition
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An epoxy resin composition, the curing components of which contain at least one amine of formula (I) and optionally at least one amine A which is, in particular, an adduct of a polyamine and an epoxide. The amine for formula (I) is used in particular in the form of a reaction product of the reductive alkylation of 1,2-ethylenediamine and an aldehyde or ketone. The epoxy resin composition is used in particular as a low-emission, room-temperature-curing epoxy-resin coating. It is characterised by good processibility, quick curing, high hardness, a nice surface and a low tendency to yellowing.
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Paragraph 0224-0229
(2021/09/01)
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- A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)
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The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)
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Paragraph 0104; 0105
(2018/04/03)
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- Design, synthesis and antimycobacterial activity of novel imidazo[1,2-a]pyridine-3-carboxamide derivatives
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We report herein the design and synthesis of “novel imidazo [1,2-a]pyridine-3-carboxamides (IPAs)” bearing a variety of different linkers, based on the structure of IMB-1402 discovered in our lab. Results reveal that 2,6-dimethyl-N-[2-(phenylamino)ethyl] IPAs with an electron-donating group on the benzene ring as a potent scaffold. Compounds 26g and 26h have considerable activity (MIC: 0.041–2.64 μM) against drug-sensitive/resistant MTB strains, and they have acceptable safety indices against MTB H37Rv with the SI values of 4395 and 1405, respectively. Moreover, N-[2-(piperazin-1-yl)ethyl] moiety was also identified as a potentially alternative linker (compound 31), opening a new direction for further SAR studies.
- Lv, Kai,Li, Linhu,Wang, Bo,Liu, Mingliang,Wang, Bin,Shen, Weiyi,Guo, Huiyuan,Lu, Yu
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p. 117 - 125
(2017/06/05)
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- Highly enantioselective synthesis of 2,3-dihydro-1 H-imidazo[2,1-a isoindol-5(9b H)-ones via catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization
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Highly enantioselective catalytic asymmetric intramolecular cascade imidization-nucleophilic addition-lactamization of N1-alkylethane-1,2-diamine with methyl 2-formylbenzoate catalyzed by a chiral phosphoric acid represents the first efficient method for the preparation of medicinally interesting chiral 2,3-dihydro-1H-imidazo[2,1-a]isoindol-5(9bH)-ones with high yields and excellent enantioselectivities. This strategy has been shown to be quite general toward various methyl 2-formylbenzoates.
- He, Yuwei,Cheng, Chuyu,Chen, Bin,Duan, Kun,Zhuang, Yue,Yuan, Bo,Zhang, Meisan,Zhou, Yougui,Zhou, Zihong,Su, Yu-Jun,Cao, Rihui,Qiu, Liqin
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p. 6366 - 6369
(2015/01/16)
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- Structure-activity relationships of novel substituted naphthalene diimides as anticancer agents
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Novel 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) derivatives were synthesized and evaluated for their antiproliferative activity on a wide number of different tumor cell lines. The prototypes of the present series were derivatives 1 and 2 characterized by interesting biological profiles as anticancer agents. The present investigation expands on the study of structure-activity relationships of prototypes 1 and 2, namely, the influence of the different substituents of the phenyl rings on the biological activity. Derivatives 3-22, characterized by a different substituent on the aromatic rings and/or a different chain length varying from two to three carbon units, were synthesized and evaluated for their cytostatic and cytotoxic activities. The most interesting compound was 20, characterized by a linker of three methylene units and a 2,3,4-trimethoxy substituent on the two aromatic rings. It displayed antiproliferative activity in the submicromolar range, especially against some different cell lines, the ability to inhibit Taq polymerase and telomerase, to trigger caspase activation by a possible oxidative mechanism, to downregulate ERK 2 protein and to inhibit ERKs phosphorylation, without acting directly on microtubules and tubuline. Its theoretical recognition against duplex and quadruplex DNA structures have been compared to experimental thermodynamic measurements and by molecular modeling investigation leading to putative binding modes. Taken together these findings contribute to define this compound as potential Multitarget-Directed Ligands interacting simultaneously with different biological targets.
- Milelli, Andrea,Tumiatti, Vincenzo,Micco, Marialuisa,Rosini, Michela,Zuccari, Guendalina,Raffaghello, Lizzia,Bianchi, Giovanna,Pistoia, Vito,Fernando Díaz,Pera, Benet,Trigili, Chiara,Barasoain, Isabel,Musetti, Caterina,Toniolo, Marianna,Sissi, Claudia,Alcaro, Stefano,Moraca, Federica,Zini, Maddalena,Stefanelli, Claudio,Minarini, Anna
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supporting information
p. 417 - 428
(2013/01/15)
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- Design, synthesis, and bioactivity of cyanonitrovinyl neonicotinoids as potential insecticides
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A series of cyanonitrovinyl neonicotinoids were designed and synthesized via five steps in about 35% overall yields. All compounds were structurally characterized by 1H nuclear magnetic resonance (NMR), 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS), and single-crystal X-ray diffraction analysis of 2-[1-[(6-chloropyridin-3-yl)methyl] -2-imidazolidinylidene]-2-nitroacetonitrile revealed that the double bond is (E)-configured. The preliminary agriculture bioassay indicated that one compound exhibited moderate insecticidal activity against pea aphid. Springer-Verlag 2010.
- Wang, Kewei,Qian, Xuhong,Cui, Jingnan
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scheme or table
p. 1117 - 1122
(2012/06/18)
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- Synthesis and selected properties of N-substituted pyrrolo[2,1-c]-1,3- diazacycloalkano[1,2-a]pyrazinones
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The reactions of methyl α-(2-formyl-1H-pyrrol-1-yl)carboxylates with N-substituted aliphatic 1,2-, 1,3-, and 1,4-diamines afford new pyrrole-containing heterocyclic systems: 1,2,3,10b-tetrahydroimidazo[1,2-a] pyrrolo[2,1-c]pyrazin-5(6H)-ones, 1,3,4,11b-tetrahydro-2H-pyrrolo[2′, 1′:3,4]pyrazino[1,2-a]pyrimidin-6(7H)-ones, and 1,2,3,4,5,12b-hexahydro- pyrrolo[2′,1′:3,4]pyrazino[1,2-a][1,3]diazepin-7(8H)-ones. The reduction of these compounds with different reagents was studied.
- Mokrov,Likhosherstov,Lezina,Gudasheva,Bushmarinov,Antipin, M. Yu.
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experimental part
p. 1254 - 1266
(2011/02/23)
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- Robust and electron-rich cis-palladium(II) complexes with phosphine and carbene ligands as catalytic precursors in Suzuki coupling reactions
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A new imidazolinium ligand precursor [L2H]Cl (2) was prepared in 86 % yield. Compared with its imidazolium counterpart, [L1H]Cl (1), 2 is very sensitive to moisture and can undergo ring-opening reactions very readily. Palladium complexes with the ring-opened products from imidazolinium salts were isolated and characterized by X-ray crystallography. Theoretical studies confirmed that the imidazolinium salt has a higher propensity for the ring-opening reaction than the imidazolium counterpart. New mixed phosphine/carbene palladium complexes, Cis-[PdCl2(L)(PR3)] (L = L1 and L2; R = Ph. Cy). were successfully prepared. These complexes are highly robust as revealed by variable-temperature NMR spectroscopic studies and thermal gravimetric analysis. The structural and electronic properties of the new complexes on varying the carbene group (imidazol-2-ylidene group (unsaturated carbene) vs. imidazolin-2-ylidene (saturated carbene)) and the phosphine group (PPh3 vs. PCy 3) were studied in detail by X-ray crystallography, X-ray photoelectron spectroscopy, and theoretical calculations. The catalytic study reveals that Cis-[PdCl2(L2)-(PCy3)] is a competent PdII precatalyst for Suzuki coupling reactions, in which unreactive aryl chlorides can be applied as substrates.
- Liao, Chuang-Yi,Chan, Kai-Ting,Tu, Cheng-Yi,Chang, Yu-Wei,Hu, Ching-Han,Lee, Hon Man
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body text
p. 405 - 417
(2009/09/28)
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- One step from nitro to oxime: a convenient preparation of unsaturated oximes by the reduction of the corresponding vinylnitro compounds
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A series of novel unsaturated oximes were conveniently prepared from the corresponding vinylnitro compounds by reduction with SnCl2·2H2O. The structures of the oximes were characterized by 1H and 13C NMR, IR and HRMS, and X-ray crystallography analysis of 1-(6-chloro-pyridin-3-ylmethyl)-4,5-dihydro-1H-imidazole-2-carbaldehyde oxime 2a reveals that, the hydroxyl group is arranged in a trans configuration. Some evidences from a brief investigation suggest that these oximes seem to be formed by reduction of the aci form of nitro aliphatic compounds.
- Wang, Kewei,Qian, Xuhong,Cui, Jingnan
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experimental part
p. 10377 - 10382
(2010/02/27)
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- Design, synthesis, and insecticidal activities of novel analogues of neonicotinoids: Replacement of nitromethylene with nitroconjugated system
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To replace nitromethylene pharmacophore with a nitroconjugated system, a series of novel neonicotinoid analogues bearing five-membered aromatic heterocycles were designed and synthesized. Bioassays indicated that some of the synthesized compounds exhibited higher insecticidal activities than imidacloprid against cowpea aphids (Aphis craccivora), armyworm (Pseudaletia separate Walker), Nephotettix bipunctatus (Fabricius), and small brown rice planthopper (Laodelphasx striatellus). Exhilaratingly, the activity levels of derivatives 13a and 13j rivaled that of imidacloprid.
- Shao, Xusheng,Li, Zhong,Qian, Xuhong,Xu, Xiaoyong
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scheme or table
p. 951 - 957
(2010/04/05)
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- Design, synthesis, and evaluation of unsymmetrical difluoro-boron complexes with imidazoline as potential fungicides
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A series of unsymmetrical difluoroboron (BF2) complexes with pyridine and imidazoline were synthesized by reaction of new chelating ligands (arylmethyl-imidazolidinylidene)-pyridin-2-yl-amine with boron trifluoride diethyl etherate. All the ligands and BF2 complexes were structurally characterized by IR, HRMS, 1H, 13C, 11B, and 19F NMR,indicating the bidentate complexation of imidazoline nitrogen and the pyridine nitrogen to the boron center. Evaluation of agricultural bioactivities showed that some of the BF2 complexes exhibited moderate fungicidal activities, and most of the BF2 complexes exhibited higher activities than the none-BF2 complexed substrates.
- Wang, Kewei,Cui, Jingnan,Xie, Lijuan,Qian, Xuhong
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experimental part
p. 418 - 424
(2010/08/05)
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- Competitive amide hydrolysis in mono- and diformylated ethylenediamines
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Alkaline hydrolysis of formylated ethylenediamines of the general structure R1-N(X)-CH2CH2-N(CHO)-R2 (R 1, R2 = H, benzyl, benzoyl; X = H, CHO) was studied in mild conditions. Breaking of the N-C amide bonds took place easily for HN-CHO or (benzoyl)N-CHO, hardly for (benzyl)N-CHO, and did not occur at all for N-COPh. Generally speaking, the various amide bonds underwent hydrolysis according to the following qualitative order of increasing reactivity: PhCO-N(H or alkyl)(alkyl or CHO) ?HCO-N(alkyl)2 1H- and 13C-NMR features of all compounds of interest are presented and discussed. Hindered rotation about the C-N amide bond(s) caused E/Z isomerism in mono- and diformylated derivatives.
- Petride, Horia,Costan, Oana,Florea, Cristina,Udrea, Silvia
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p. 245 - 253
(2007/10/03)
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- Unnatural multidentate metal ligating α-amino acids
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A family of penta- and hexadentate metal ligating α-amino acids, suitably protected for Fmoc solid-phase chemistry, has been prepared. These residues incorporate the mono-amides of ethanolaminetriacetic acid, ethylenediaminetriacetic acid, and ethylenediaminetetraacetic acid as side chains. Side chains are tethered varying distances (n) from the Cα-carbon to allow metal binding events to occur at distinct distances from the peptide backbone. These residues are designed to allow the facile installation of metal chelates along a peptide backbone.
- Micklitsch, Christopher M.,Yu, Qian,Schneider, Joel P.
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p. 6277 - 6280
(2007/10/03)
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- METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE
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PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.
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Page/Page column 7
(2010/02/11)
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- Aspartyl protease inhibitors
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The present invention provides compounds having the formula: wherein R1, R′, R2, R3, R3′, R4, X1, X2 and X3 are as defined herein, and pharmaceutical compositions thereof. The present invention also provides methods of inhibiting proteases, more specifically aspartyl proteases. In certain embodiments, compounds inhibit BACE (β-site APP-cleaving enzyme), and thus are useful in the treatment or prevention of a disease characterized by β-amyloid deposits in the brain (including, but not limited to, Alzheimer's Disease). The present invention also provides methods for preparing compounds of the invention.
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- ASPARTYL PROTEASE INHIBITORS
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The present invention provides compounds having formula (I): wherein R’, R0, R1, X1, R2, R3, R3’, X2, X3, and R4 are as defined herein, and pharmaceuticals compositions thereof. The present invention also provides methods of inhibiting proteases, more specially aspartyl proteases. In certain embodiments, compounds inhibit BACE (β-site APP-cleaving enzyme), and thus are useful in the treatment or prevention of a disease characterized by β-amyloid deposits in the brain (including, but not limited to, Alzheimer’s Disease). The present invention also provides methods for preparing compounds of the invention.
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Page 226-230
(2010/02/05)
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- Monofunctionalised EDTA, DTPA and TTHA derivatives and their use in medical diagnosis and therapy
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The invention relates to new monofunctionalized ethylenediaminetetraacetic acid, diethylenetriaminepentaacetic acid and triethylenetetraaminehexaacetic acid derivatives, their production and their use for the production of pharmaceutical agents.
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- Synthesis and superoxide dismutase activity of novel iron complexes
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We have previously shown that the Fe(II) tetrakis-N,N,N′,N′-(2-pyridylmethyl)ethylenediamine complex (Fe(II)TPEN) has high superoxide dismutase (SOD) activity, using the xanthine-xanthine oxidase-cytochrome c method (cyt. c method) [J. Biol. Chem. 264 (1989) 9243-9249]. X-ray analysis showed that Fe(II)TPEN has two different coordination structures, one in which Fe(II) is coordinated with six nitrogens of TPEN and one in which Fe(II) is coordinated with five nitrogens of TPEN and one oxygen of sulfate anion as the counter anion [Chem. Pharm. Bull. 48 (2000) 223-230]. To investigate the relationship between these two structures and SOD activity, we synthesized novel Fe(II) complexes of TPEN analogues and measured their SOD activity by the cyt. c method. The Fe(II) tetrakis-N,N,N′,N′-(2-pyridylmethyl)trimethylenediamine complex (Fe(II)TPTN) and the Fe(II) tris(2-pyridylmethyi)triazacyclononane complex (Fe(II)TPTCN) had no SOD activity (IC50 = > 100 μM), probably because these two complexes have undistorted steric structure with no easily substituted ligand. On the other hand, other Fe(II) complexes with unsaturated coordination or an easily substituted ligand had high SOD activity (IC50 = 0.4-20 μM). The results indicate that the substitution reaction of a ligand with superoxide or the coordination of superoxide is essential for Fe(II)TPEN analogue complexes to have SOD activity. Moreover, we examined the effect of steric hindrance of the ligands on the SOD activity and the stability of the iron complexes to oxygen.
- Tamura, Masakazu,Urano, Yasuteru,Kikuchi, Kazuya,Higuchi, Tsunehiko,Hirobe, Masaaki,Nagano, Tetsuo
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p. 586 - 592
(2007/10/03)
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- Method and apparatus for sunless tanning
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Apparatus for simulating skin tanning comprises a receptacle containing a fluid comprising dihydroxyacetone, a receptacle containing a fluid comprising a secondary polyamine, and dispensing means for simultaneously or sequentially providing desired amounts of dihydroxyacetone and polyamine.
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- 2-(Trifluoromethyl)piperazine: synthesis and characterization using NMR and X-ray photoelectron spectroscopy
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The synthesis of 2-(trifluoromethyl)piperazine (1) is reported. 1H NMR spectroscopy shows that in the chair-type piperazine ring the CF3 group occupies an equatorial position.X-ray photoelectron spectroscopy of solid 1 reveals that the CF3 group induces a secondary (β) chemical shift of 1.5 eV on the C 1s core binding energy of its nearest neighbour carbon atom.The results are supported by semi-empirical PM3 and HAM/3 calculations.
- Jenneskens, Leonardus W.,Mahy, Jan,Berg, Ellen M. M. de Brabander-van.,Hoef, Ineke van der,Lugtenburg, Johan
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- Phosphoric amides. Part 11. Intramolecular reactivity of phosphorotriamidates
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Five N-(2-chloroethyl)phosphorotriamidates, (RNH)2P(O)NHCH2CH2Cl, have been synthesized, and their behavior under strongly basic conditions was studied.For N-alkyl derivatives (R = Me, PhCH2), base-promoted intramolecular displacement of chloride yielded the N-phosphorylated aziridine, (RNH)2P(O)NC2H4, as the exclusive cyclization product.For N-aryl derivatives (R = Ar), both the aziridine and the 1,3,2-diazaphospholidine, RNHP(O)NHCH2CH2NR, products could be obtained in comparable yields.The N-aromatic cyclic products are mutually interconvertible; 1,3,2-diazaphospholidines rearrange to the corresponding aziridines upon treatment with base, while bromide ions catalyze the reverse isomerization. Key words: phosphoramidates acidity, N-phosphorylated aziridines - 1,3,2-diazaphospholidines isomerization, 1,3 vs. 1,5 cyclization.
- Bauermeister, Siegelinde,Modro, Agnes M.,Modro, Tom A.,Zwierzak, Andrzej
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p. 811 - 816
(2007/10/02)
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- Some Benzyl-Substituted Imidazoles, Triazoles, Tetrazoles, Pyridinethiones, and Structural Relatives as Multisubstrate Inhibitors of Dopamine β-Hydroxylase. 4. Structure-Activity Relationships at the Copper Binding Site
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Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine β-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor.Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously.The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity.An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitor potency.In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced.Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.
- Kruse, Lawrence I.,Kaiser, Carl,DeWolf, Walter E.,Finkelstein, Joseph A.,Frazee, James S.,et al.
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p. 781 - 789
(2007/10/02)
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- 1-aralkyl-2-mercaptoimidazolines as DBH inhibitors
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Disclosed are novel substituted 3-aralkylimidazolines of the structure. STR1 processes for their preparation, intermediates useful in their preparation, pharmaceutical compositions containing them and their use in therapy in particular as dopamine-β-hydroxylase inhibitors.
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- Substituted sulfonamidobenzamides and method of treating arrhythmias
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Novel substituted sulfonamidobenzamides are described as useful antiarrhythmic agents. Their use in the treatment of cardiac arrhythmias, especially re-entrant arrhythmias, via the prolongation of the action potential of cardiac tissue is provided. Pharmaceutical formulations containing such compounds are also disclosed.
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- CATALYTIC ALKYL GROUP EXCHANGE REACTION OF PRIMARY AND SECONDARY AMINES.
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It has been shown that primary and secondary amines undergo alkyl group exchange reactions upon treatment with palladium catalyst as depicted in an operationally simple and efficient reaction which provides a convenient method for synthesis of unsymmetrical amines. The application of the reaction for the preparation of various substituted amines and heterocyclic compounds such as hexahydropyrimidine tetrahydropyrimidine, imidazolidine, and imidazoles is described. The preparation of polyamines such as H//2N(CH//2)//mNH(CH//2)//nNH//2 (10) and H//2N(CH//2)//lNH(CH//2)//mNH(CH//2)//nNH//2 (l-n, equals 2,3; 11) is readily performed by the appadium-catalyzed reactions of azetidine (6) and aziridine (7) via azetine (9) and azirine intermediates. The mechanism the palladium-catalyzed reaction has been extensively studied on the carbonylation, racemization, and deuteurium-exchange reaction of (S)-( minus )- alpha -phenylethylamine (17).
- Murahashi,Yoshimura,Tsumiyama,Kojima
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p. 5002 - 5011
(2007/10/02)
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