- Synthesis and Antifungal Activity of Substituted 2-Aryl Benzimidazoles Derivatives
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Benzimidazole fungicides were among the early systemic fungicides developed and used for controlling a wide variety of plant diseases. During the course of our screening process for active compounds, two 2-aryl benzimidazoles derivatives bearing sulfoxide group (6b and 6c) have been demonstrated to exhibit good inhibition activity against high-resistant isolate of Botrytis cinerea compared with carbendazim, and the inhibition rates are up to 46.67% and 51.11% at the concentration of 10 μg/mL, which might be considered as the active framework for the discovery of novel fungicide to high-resistant isolate of B. cinerea.
- Huang, Daye,Qiu, Fang,Zhang, Zhigang,Shi, Liqiao,Cao, Chunxia,Ke, Shaoyong
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Read Online
- Iridium-catalyzed direct C-H amidation of anilines with sulfonyl azides: Easy access to 1,2-diaminobenzenes
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An Ir(iii)-catalyzed regioselective C-H amidation of anilines with sulfonyl azides is described. The developed protocol has good compatibility with diverse functional groups, efficiently providing the monoamidated products with good to excellent yields un
- Wang, Lianhui,Yang, Zi,Yang, Mengqi,Zhang, Rongyi,Kuai, Changsheng,Cui, Xiuling
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Read Online
- Selectivity of the complexation reactions of four regioisomeric methylcamphorquinoxaline ligands with gold(III): X-ray, NMR and DFT investigations
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Reported are the synthesis, spectral and structural characteristics of new quinoxaline-related regioisomeric ligands L1-L4 (1,x,11,11-tetramethyl-1,2,3,4-tetrahydro-1,4-methanophenazine, x = 7, 8, 9 and 6, respectively) and their mononuclear Au(III) complexes (1-4). Fusion of the camphor moiety to the quinoxaline core made two N-atoms of quinoxaline nonequivalent while the introduction of a methyl-substituent at positions 6-9 enabled a tuning of coordination properties of L1-L4. Gold(III) complexes 1-4 and ligands L1-L4 have been studied in detailed by 1D and 2D NMR and the structures of 1-4 have been determined by X-ray crystallography. The results of these analyses revealed a regiospecific coordination of Au(III) to the sterically less hindered N-5 atom (spatially close to the non-substituted bridgehead carbon) of L1-L3, and to N-10 (spatially close to the methyl-substituted bridgehead carbon) of L4. The results of DFT calculations shed light on disparate coordination modes of L1-L4 toward the AuCl3 fragment and explain formation of single coordination products in high yield.
- Gli?i?, Biljana D.,Hoffmann, Marcin,Warzajtis, Beata,Gen?i?, Marija S.,Blagojevi?, Polina D.,Radulovi?, Niko S.,Rychlewska, Urszula,Djuran, Milo? I.
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- Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
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The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
- Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
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supporting information
p. 9355 - 9360
(2021/07/19)
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- METALLOENZYME INHIBITOR COMPOUNDS
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Provided are compounds having metalloenzyme modulating activity, and methods of treating diseases, disorders or symptoms thereof mediated by such metalloenzymes.
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Page/Page column 45
(2020/07/25)
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- 2-Aminopyrimidine Derivatives as New Selective Fibroblast Growth Factor Receptor 4 (FGFR4) Inhibitors
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A series of 2-aminopyrimidine derivatives were designed and synthesized as highly selective FGFR4 inhibitors. One of the most promising compounds 2n tightly bound FGFR4 with a Kd value of 3.3 nM and potently inhibited its enzymatic activity with an IC50 value of 2.6 nM, but completely spared FGFR1/2/3. The compound selectively suppressed proliferation of breast cancer cells harboring dysregulated FGFR4 signaling with an IC50 value of 0.38 μM. Furthermore, 2n exhibited extraordinary target specificity in a Kinome-wide screen against 468 kinases, with S(35) and S(10) selectivity scores of 0.01 and 0.007 at 1.0 μM, respectively.
- Mo, Cheng,Zhang, Zhang,Guise, Christopher P.,Li, Xueqiang,Luo, Jinfeng,Tu, Zhengchao,Xu, Yong,Patterson, Adam V.,Smaill, Jeff B.,Ren, Xiaomei,Lu, Xiaoyun,Ding, Ke
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supporting information
p. 543 - 548
(2017/05/19)
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- Potent, Selective, and Cell Active Protein Arginine Methyltransferase 5 (PRMT5) Inhibitor Developed by Structure-Based Virtual Screening and Hit Optimization
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PRMT5 plays important roles in diverse cellular processes and is upregulated in several human malignancies. Besides, PRMT5 has been validated as an anticancer target in mantle cell lymphoma. In this study, we found a potent and selective PRMT5 inhibitor by performing structure-based virtual screening and hit optimization. The identified compound 17 (IC50 = 0.33 μM) exhibited a broad selectivity against a panel of other methyltransferases. The direct binding of 17 to PRMT5 was validated by surface plasmon resonance experiments, with a Kd of 0.987 μM. Kinetic experiments indicated that 17 was a SAM competitive inhibitor other than the substrate. In addition, 17 showed selective antiproliferative effects against MV4-11 cells, and further studies indicated that the mechanism of cellular antitumor activity was due to the inhibition of PRMT5 mediated SmD3 methylation. 17 may represent a promising lead compound to understand more about PRMT5 and potentially assist the development of treatments for leukemia indications.
- Mao, Ruifeng,Shao, Jingwei,Zhu, Kongkai,Zhang, Yuanyuan,Ding, Hong,Zhang, Chenhua,Shi, Zhe,Jiang, Hualiang,Sun, Dequn,Duan, Wenhu,Luo, Cheng
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p. 6289 - 6304
(2017/08/02)
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- A O-phenylenediamine and its derivatives of the preparation method
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The invention relates to a method for synthesizing organic compounds, and provides a method for preparing o-phenylenediamine and a derivative of o-phenylenediamine, for solving the problems that the process route is complex, a great amount of byproducts can be generated and are hard to purify, the reaction condition is rigorous, the environment pollution is severe and the like in a conventional method for synthesizing o-phenylenediamine derivatives. The method disclosed by the invention comprises the following steps: by taking azobenzene and a derivative of the azobenzene as raw materials, synthesizing the o-nitro azobenzene and the derivative of the o-nitro azobenzene under the coactions of a catalyst, an oxidant and a nitrating agent, and further reducing by using a reducing agent, thereby obtaining the o-phenylenediamine and the derivative of the o-phenylenediamine. The method provided by the invention has the advantages that the raw materials are cheap and easy to obtain, the operation is simple, convenient and safe, the synthesis steps are short, the purification is simple, no great waste acid pollution is caused, and the like.
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Paragraph 0048-0050
(2017/07/20)
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- Trisazo compd. dye, ink composition, recording method and colored material
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A coloring matter for black ink which is highly soluble in water-based media, and ink compositions containing the same. The ink compositions can produce black recorded images which exhibit excellent light fastness and ozone gas fastness. The coloring matter consists of at least one trisazo compound represented by general formula (1), tautomers thereof, and salts of both. In general formula (1), R1 is unsubstituted C1-4 alkyl or the like; R2 is cyano or the like; R3 is a chlorine atom or the like; R5 to R7 are a hydrogen atom, unsubstituted C1-4 alkyl, sulfo-substituted C1-4 alkoxy, or the like; R8 to R10 are a hydrogen atom, unsubstituted C1-4 alkyl, sulfo-substituted C1-4 alkylthio, or the like; A is sulfo-substituted 2-naphthothiazolyl or the like; and a to d represent the positions at which the ring is substituted with R3 and sulfo.
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Paragraph 0222; 0234; 0235
(2016/12/26)
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- Property modulation of benzodithiophene-based polymers via the incorporation of a covalently bonded novel 2,1,3-benzothiadiazole-1,2,4-oxadiazole derivative in their main chain for polymer solar cells
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Two new electron accepting monomers (BBOB and BOB) containing two serially connected different electron deficient units, such as 2,1,3-benzothiadiazole and 1,2,4-oxadiazole, were prepared and copolymerized with electron-rich benzodithiophene (BDT) derivative to afford polymers P(BDT-BBOB) and P(BDT-BOB), respectively. The optical band gaps of P(BDT-BBOB) and P(BDT-BOB) are calculated to be 2.32 eV and 1.99 eV, respectively, and their highest occupied molecular energy levels are determined to be -5.31 eV and -5.27 eV, respectively. Each of the newly synthesized polymers, i.e.P(BDT-BBOB) and P(BDT-BOB), is used as an electron donor, along with PC61BM as an electron acceptor, in the preparation of polymer solar cells (PSCs). The PSCs made with the configuration of ITO/PEDOT:PSS/P(BDT-BBOB) or P(BDT-BOB):PC61BM (1 : 2 wt%)/LiF/Al gave a maximum power conversion efficiency (PCE) of 1.76% and 2.46%, respectively, and the device performance was further improved to 3.31% and 4.21%, respectively, by simply treating the photoactive layer of PSCs with isopropyl alcohol. Overall, the opto-electrical and photovoltaic properties of the two polymers are found to be quite dependent on the configuration of the covalently bonded 2,1,3-benzothiadiazole and 1,2,4-oxadiazole units incorporated in the polymer main chain.
- Agneeswari, Rajalingam,Tamilavan, Vellaiappillai,Song, Myungkwan,Hyun, Myung Ho
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p. 8515 - 8524
(2015/02/19)
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- Synthesis and electronic and photophysical properties of [2.2]- and [3.3]paracyclophane-based donor-donor′-acceptor triads
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Three types of the donor(D)-donor′(D′)-acceptor(A) triads 1-6 with different D-A combinations, carbazole (Cz, D)-[n.n]PCP(D′)-1,8-naphthalimide (NI, A) (1-3), 10H-phenothiazine (PTZ, D)-[n.n]PCP(D′)-NI(A) (4, 5), and 10-methyl-10H-phenothiazine (Me-PTZ, D)-[2.2]PCP-2,1,3-benzothiadiazole (BTD, A) 6, were synthesized for the elucidation of their photophysical properties. The absorption spectra and electrochemical properties indicated that the chromophores (D, D′, and A) do not interact with each other in the ground state. Cz-(CH2)3-[2.2]PCP-(CH2)3-NI 1 and Cz-(CH2)3-[3.3]PCP-(CH2)3-NI 2 show an exciplex emission between the PCP and NI moieties in cyclohexane and the intensity of the band is much higher in 2 than in 1, whereas Cz-(CH2)2-[2.2]PCP-(CH2)2-NI 3 does not show any exciplex emission in cyclohexane. These results indicated that the combination of [3.3]PCP and a trimethylene chain is preferable for the exciplex formation. PTZ-(CH2)3-[2.2]PCP-(CH2)3-NI 4 shows a broad band at 519 nm in cyclohexane, which is associated with the formation of the exterplex band among the NI, [2.2]PCP, and PTZ moieties, while PTZ-(CH2)3-[3.3]PCP-(CH2)3-NI 5 does not show the band. Me-PTZ-(CH2)2-[2.2]PCP-(CH2)2-BTD 6 shows a broad fluorescence band due to both the BTD and PTZ moieties in cyclohexane. In CH3CN, the fluorescence spectra of 1-6 suggest the presence of a photoinduced charge separation process. The study of the photoinduced charge separation process will be soon reported elsewhere.
- Miyazaki, Takaaki,Shibahara, Masahiko,Fujishige, Jun-Ichi,Watanabe, Motonori,Goto, Kenta,Shinmyozu, Teruo
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p. 11440 - 11453
(2015/01/16)
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- AZO COMPOUND, INK COMPOSITION, RECORDING METHOD AND COLORED MATERIAL
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Provided are: a dye which exhibits extremely excellent (ozone) gas resistance, extremely high print density, low color rendering properties, low color saturation, and high-quality black hue when is recorded on a paper only for inkjet printing purposes, i.e., an azo compound represented by formula (1), a tautomer of the azo compound, or a salt of the azo compound or the tautomer; and an ink composition containing the dye, particularly a black ink composition for inkjet recording applications. In the formula, R1 represents a (C1-C4) alkyl group, or the like; R2 represents a cyano group, or the like; R3 and R4 independently represent a hydrogen atom, a sulfo group, a (C1-C4) alkoxy group, or the like; R5 and R7 independently represent a (C1-C4) alkylthio group, or the like; R6 and R8 independently represent a (C1-C4) alkylcarbonylamino group; R9 and R10 independently represent a (C1-C4) alkoxy group, or the like; and R11 to R13 independently represent a hydrogen atom, a sulfo group, or the like.
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Paragraph 0179
(2013/11/05)
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- INDAZOLE DERIVATIVES AS ADENOSINE MONOPHOSPHATE DEAMINASE (AMPD) INHIBITORS FOR USE IN DIABETES AND RELATED DISEASES OF METABOLIC SYNDROME
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Herein, we describe a method for treatment of diabetes and other disorders classified as Metabolic Syndrome. The invention provides novel AMP Deaminase (AMPD) inhibitors comprising novel indazole and benzotriazole derivatives including a phosphorous containing derivative, a carboxylic acid, or an amino acid ester prodrug. The invention also provides support for a novel mechanism of action for the existing drug metformin: direct inhibition of the enzyme AMPD. The inhibition of AMPD in turn activates AMP Kinase, known to be linked to the action of metformin. The invention also makes novel use of a double inhibitor assay allowing identification of selective AMPD inhibitors over ADA inhibitors. The new inhibitors, structurally distinct from metformin, offer selectivity that may obviate side effects known for metformin itself, providing new benefits for diabetes and Metabolic Syndrome.
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(2012/06/01)
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- Process for the production of the toluene diisocyanate
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The invention relates to a process for the production of toluene diisocyanate, in which the crude toluenediamine obtained from the hydrogenation is purified and then phosgenated. The purification step reduces the total amount of cyclic ketones to less than 0.1 % by weight, based on 100% by weight of the toluenediamine.
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(2008/06/13)
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- Efficient method for the synthesis of benzimidazoquinazoline derivatives with three-point diversity
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An efficient strategy for the preparation of a novel heterocyclic ring system of benzimidazoquinazolines with three-point diversity has been described. The compounds were obtained by treating o-phenylene diamines with o-nitrobenzaldehyde to give benzimidazoles, followed by reduction of the nitro group to give an amine. Derivatization of the resulting amine with isothiocyanates followed by in situ cyclodesulfurization at rt furnished the title compounds in high yields and purities. Copyright Taylor & Francis Group, LLC.
- Saha, Biswajit,Sharma, Sunil,Kundu, Bijoy
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p. 3455 - 3470
(2008/02/13)
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- Benzimidazole compound
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An object of the present invention is to provide a novel chemical compound useful as a therapeutic or prophylactic agent for acid-related diseases, having an excellent inhibitory effect against gastric acid secretion, an excellent effect of maintaining the inhibitory effect against gastric acid secretion, thereby maintaining intragastric pH high for a long time, and having more safety and appropriate physicochemical stability. Provided is a compound represented by where R1 and R3 may be the same or different and each represent a hydrogen atom or a C1-C6 alkyl group; R2 represents (5,5-dimethyl-1,3-dioxan-2-yl)methoxy group, 5,7-dioxaspiro[2.5]oct-6-ylmethoxy group, 1,5,9-trioxaspiro[5.5]undec-3-ylmethoxy group, or (2,2-dimethyl-1,3-dioxan-5-yl)methoxy group; R4, R5, R6 and R7 represent a hydrogen atom, halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C1-C6 alkoxy group or C1-C6 haloalkoxy group; and W1 represents a single bond, methylene or ethylene group, a salt thereof or a solvate of these.
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Page/Page column 77
(2008/06/13)
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- Stepwise unidirectional synthesis of oligo phenylene vinylenes with a series of monomers. Use in plastic solar cells
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Four new monomers for directional stepwise synthesis of oligophenylenevinylenes (OPVs) (4-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5- dipropoxyphenyl]vinyl}benzyl)phosphonic acid diethyl ester, (5-{2-[4-(5,5- dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]vinyl}thiophene-2-ylmethyl) phosphonic acid diethyl ester, (5-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5- dipropoxyphenyl]vinyl}thiophene-2-ylmethyl)phosphonic acid diethyl ester, and (7-{2-[4-(5,5-dimethyl[1,3]dioxan-2-yl)-2,5-dipropylphenyl]-vinyl}benzo[1,2,5] thiadiazol-4-ylmethyl)phosphonic acid diethyl ester have been prepared. Trimeric OPVs were then synthesized and tested as active materials in photovoltaic cells. Conversion efficiencies in the range of 0.5-1% were obtained in blends with the soluble C60 derivative PCBM. A terpyridine end-functionalized trimer and a heterotrimer with a mixed composition of monomers were also prepared.
- Jorgensen, Mikkel,Krebs, Frederik C.
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p. 6004 - 6017
(2007/10/03)
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- IMIDAZO(1,2-a)PYRIDINE DERIVATIVE
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A compound reprsented by the following formula (I), its salts or nsolvates thereof capable of specifically or selectively expressig an antifungal activity in a broad spectrum based on the novel mechanism thereof of 1,6-β-glucan synthesis inhibition, and an antifungal agent containing any of them.
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- The nitration of 8-methylquinoxalines in mixed acid
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8-Methylquinoxalines are nitrated surprisingly efficiently at C-5 following a simple nitration protocol with mixed acid at 40-50°C. The implications of halogen functionalisation at C-6 and modification of the mixed acid conditions on the relative rates of conversion and process safety are discussed. Competing side reactions for 6-halo-8-methylquinoxalines involve hydrolysis at C-6 and halogenation at C-7 or C-5.
- Marterer, Wolfgang,Prikoszovich, Walter,Wiss, Jacques,Prashad, Mahavir
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p. 318 - 323
(2013/09/06)
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- Process for separating mixtures of materials having different boiling points
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A mixture of materials having different boiling points is separated into fractions having different boiling points. The separated fraction containing the desired product is stripped using the vapors of a lower boiling fraction. The process of the present invention is particularly useful for recovering a desired isomer or isomer mixture from a technical mixture obtained during production of an aromatic amine such as toluenediamine. Little or no unwanted isomer or by-product is present in the isomer or isomer mixture product of this process.
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Page column 7
(2008/06/13)
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- A practical method for the reduction of 2,1,3-benzothiadiazoles to 1,2-benzenediamines with magnesium and methanol
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A new and practical method for the reduction of 2,1,3-benzothiadiazoles to 1,2-benzenediamines with magnesium and methanol is described. Sensitive functional groups such as bromo, chloro, cyano, and ester are well tolerated under these new conditions.
- Prashad, Mahavir,Liu, Yugang,Repi?, Oljan
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p. 2277 - 2279
(2007/10/03)
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- An original way for synthesis of new nitro-benzothiadiazole derivatives
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The C-alkylation reaction of 4-chloromethyl-7-nitro-2,1,3-benzothiadiazole with 2-nitropropane anion which is shown to proceed by an SRN1 mechanism is an original way for the synthesis of new 2,1,3-benzothiadiazoles.
- Vanelle, Patrice,Liegeois, Celine Tremblais,Meuche, Jacobine,Maldonado, Jose,Crozet, Michel P.
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p. 955 - 962
(2007/10/03)
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- Synthesis of Novel 1-, 1,4- and 1,7-Substituted 2-Mercapto- and 2-Methylmercapto- Benzimidazoles: Acyclic Analogues of the HIV-1 RT Inhibitor, TIBO
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Synthetic approaches towards acyclic analogues of the HIV-1 RT inhibitor TIBO ring system, lacking either the diazepine C7 methylene, C5-N6 bond or the N1-N6 two-carbon bridge, are reported, utilizing ring opening reactions of 2-methylaziridines.A number of isomeric 2-methylmercaptobenzimidazole analogues have also been prepared, and the regiochemistry of 2-methylmercaptobenzimidazole alkylations is discussed, as a convenient route to 1,2,7-trifunctionalized benzimidazoles.
- Gardiner, John M.,Loyns, Colin R.
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p. 11515 - 11530
(2007/10/02)
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- Heterocyclic amines having central nervous system activity
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Tricyclic nitrogen containing compounds, having central nervous system activity of the following structural formula: STR1 and pharmaceutically acceptable salts thereof wherein R1, R2, and R3 are independently hydrogen, C1-6 alkyl, alkenyl, or alkynyl, C3-10 cycloalkyl, or R1 and R2 are joined to form a C3-7 cyclic amine which can contain additional heteroatoms; X is hydrogen, C1-6 alkyl halogen, hydroxy, alkoxy, cyano, carboxamide, carboxyl, or carboalkoxyl; A is SO2, N, CH, CH2, CHCH3, C=O, C=S, C-SCH3, C=NH, C-NH2, C-NHCH3, C--NHCOOCH3, or C--NHCN. B is CH2, CH, C=O, N, NH or N--CH3 ; n is 0 or 1; and D is CH, CH2, C=O, O, N, NH or N--CH3. These new compounds are suitable for treating schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure in animal or human hosts.
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- Process for the preparation of aromatic bis dialkyl ureas
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Aromatic bis (dialkyl) ureas such as the bis (dimethyl) urea of 2,4-toluenediamine are prepared by reacting an aromatic diamine with isocyanic acid (HNCO) to convert the amino groups of the diamine to urea groups (--NHCONH2) to give an aromatic bis urea which is then reacted with a dialkyl amine having from 1 to 8 carbon atoms to produce the desired aromatic bis (dialkyl) urea.
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- Imidazole compounds and their use as transglutaminase inhibitors
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Imidazole compounds including imidazoles and imidazolium salts, and their use as transglutaminase inhibitors are disclosed.
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- An integrated process for the preparation of aromatic mono- and polyisocyanates from aromatic amines
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A multi-step process for the preparation of aromatic mono- and polyisocyanates in which an aromatic mono- or polyamine and isocyanic acid are reacted to form an aromatic urea which is then reacted with a dialkyl amine to give an aromatic dialkyl urea product. The aromatic dialkyl urea is thermally treated in an inert organic solvent in the presence of a reaction promoter to produce the isocyanate.
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- Tertiary butyl derivatives of toluenediamine and mixtures as antioxidant for organic materials
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This invention relates to the use of tertiary butyl derivatives of toluenediamine and specifically 5-tert-butyl-2,4-toluenediamine as an antioxidant material for preventing oxidation of organic materials.
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- 2-(4-pyridylaminomethyl)-benzimidazole derivatives having antiviral activity
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Provided herein is an antiviral 2-(4-pyridylaminomethyl)-benzimidazole of the formula: STR1 wherein R is a radical selected from the groups consisting of hydrogen, short-chain alkyl, short-chain alkoxy, benzoyl, halogenomethyl, halogen, nitro and amino groups; the preparation of these compounds and antiviral composition containing such compounds.
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- Mono-tertiary-alkylated toluenediiso-cyanates and derivatives
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This invention relates to a class of tertiary-alkyltoluene--diisocyanates having alkyl groups orthoto an isocyanate group. More particularly the aromatic isocyanates are represented by the formulas: wherein R1, R2 and R3 are C1-3alkyl groups or R2 and R3 are combined to form a C5-6membered ring. The above described alkylated aromatic diisocyanates have been found to be well suited for use as an isocyanate reactant in forming polyurethane and polyurea elastomer systems.
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- Process for the manufacture of benzimidazolones-(2)
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Process for the manufacture of benzimidazolones-(2) wherein an o-phenylenediamine is reacted with optionally alkylated urea in the ratio of 1 to 1.3 moles per mole o-phenylenediamine in an organic solvent which has a solubility in water of not more than 5 g/l and has a boiling point above 100° C, at a temperature between 100° and 200° C.
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