- 2, 3-dihydronaphthalo [2, 3-b] furan-4, 9-diketone compound as well as preparation method and application thereof
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The invention provides a 2, 3-dihydronaphthalo [2, 3-b] furan-4, 9-diketone compound as well as a preparation method and application thereof, and belongs to the technical field of medicines. The invention particularly provides the 2, 3-dihydronaphthalo [2, 3-b] furan-4, 9-diketone compounds shown as general formulas I-A and I-B, a pharmaceutical composition containing the compounds, and a preparation method of the compounds. The compound has STAT3 inhibitory activity and can be used for preparing drugs for treating and/or preventing diseases related to STAT3 activity, and the diseases comprisevarious cancers such as breast cancer, lung cancer, oral cancer, kidney cancer, esophageal cancer, liver cancer, stomach cancer, intestinal cancer, cervical cancer and ovarian cancer.
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Paragraph 0215-0217
(2020/11/05)
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- SMALL MOLECULE INHIBITORS OF A PROTEIN COMPLEX
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Compositions and methods for treating thrombosis, inflammation, and atherosclerosis by administration of a compound that binds to KRIT1 to inhibit binding with HEG1.
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Paragraph 00178
(2020/12/29)
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- Highly Efficient Microwave-assisted One-Pot Synthesis of Aromatic Nitriles from Aromatic Aldehydes
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A highly efficient and environmentally benign protocol is described for the microwave-assisted one-pot synthesis of aromatic nitriles from aromatic aldehydes by the reaction with hydroxylamine hydrochloride in DMSO, which involves the intermediate formation of aldoximes and subsequent dehydration. The developed synthetic methodology can be readily accomplished with various aldehydes containing both electron-donor and electron-acceptor groups, providing excellent yields of the target products in shorter reaction times (1–2 min) compared to previously reported methodologies.
- Pujari,Thorat,Mahipal,Bhondwe
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p. 702 - 706
(2019/07/17)
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- Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl) methane
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Difluoro(phenylsulfanyl)methane (PhSCF 2 H) was found to undergo a reaction with aromatic compounds mediated by SnCl 4, through a thionium intermediate characterized by NMR and TD-DFT analyses, leading to the formation of a mixture of S, S ′-diphenyl dithioacetal and aromatic aldehyde which, after oxidative hydrolysis, provides the aromatic aldehyde in good to excellent yields. The salient feature of the present work is the reaction of activated aromatic compounds containing a deactivating ester functional group, leading to the formylated products in good yields.
- Betterley, Nolan M.,Kongsriprapan, Sopanat,Chaturonrutsamee, Suppisak,Deelertpaiboon, Pramchai,Surawatanawong, Panida,Pohmakotr, Manat,Soorukram, Darunee,Reutrakul, Vichai,Kuhakarn, Chutima
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p. 2033 - 2040
(2018/03/21)
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- Synthesis of pharmacologically important naphthoquinones and anticancer activity of 2-benzyllawsone through DNA topoisomerase-II inhibition
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Naphthoquinones are naturally occurring biologically active entities. Practical de novo syntheses of three naphthoquinones i.e. lawsone (1), lapachol (2), and β-lapachone (3b) have been achieved from commercially available starting materials. The conversion of lapachol (2) to β-lapachone (3b) was achieved through p-TSA/Iodine/BF3-etherate mediated regioselective cyclisation. Further, 2-alkyl and 2-benzyllawsone derivatives have been prepared as possible anticancer agents. Four derivatives exhibited significant anticancer activity and the best analogue i.e. compound 21a exhibited potential anticancer activity (IC50?=?5.2?μM) against FaDu cell line. Compound 21a induced apoptosis through activation of caspase pathway and exerted cell cycle arrest at S phase in FaDU cells. It also exhibited significant topoisomerase-II inhibition activity. Compound 21a was found to be safe in Swiss albino mice up to 1000?mg/kg oral dose.
- Kumar, Balagani Sathish,Ravi, Kusumoori,Verma, Amit Kumar,Fatima, Kaneez,Hasanain, Mohammad,Singh, Arjun,Sarkar, Jayanta,Luqman, Suaib,Chanda, Debabrata,Negi, Arvind S.
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p. 1364 - 1373
(2017/02/18)
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- Naphthyl, (substituted) aryl, piperazine base trunk apperception composition
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The invention discloses (substituted) naphthyl, (substituted) aryl, piperazinyl amidine compound with new structures and salt of medical acid, a preparation method and a purification method of the compound and the salt of the medical acid, and a medicine composition containing the compound, wherein the compound has double inhibition activities of 5-hydroxytryptamine (5-HT) reuptake and noradrenalin (NE) reuptake, and shows strong depression resistance in animal experiments. The compound can be used for treating tristimania, and can also be used for treating other nervous system diseases related to the 5-HT and the NE.
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Paragraph 0357; 0358
(2016/10/08)
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- Remarkable Ability of the Benzylidene Ligand To Control Initiation of Hoveyda–Grubbs Metathesis Catalysts
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The structure of the chelating benzylidene ligand offers the unique ability to control the initiation of Hoveyda–Grubbs metathesis catalysts. Apart from steric and electronic effects acting on the step involving opening of the chelate ring, changes related to the following ligand-exchange process may also play a critical role. Our mechanistic model reveals that ligands substituted at the 6-position of the benzylidene ring enter the metathesis cycle in a nonoptimal chelating conformation, and thus the coordination number of the ruthenium center transiently increases to six (associative mechanism). In effect, the synthesis and initiation of the catalysts becomes difficult, and the energy barrier of the ligand-exchange process is controlled by the structure of the coordinating OR group. Moreover, we explain how isomeric naphthalene ligands affect the catalytic performance by an indivisible combination of steric and π-electron delocalization effects.
- Basak, Tymoteusz,Grudzień, Krzysztof,Barbasiewicz, Micha?
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supporting information
p. 3513 - 3523
(2016/07/29)
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- Evaluation of synthetic naphthalene derivatives as novel chemical chaperones that mimic 4-phenylbutyric acid
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The chemical chaperone 4-phenylbutyric acid (4-PBA) has potential as an agent for the treatment of neurodegenerative diseases. However, the requirement of high concentrations warrants chemical optimization for clinical use. In this study, novel naphthalene derivatives with a greater chemical chaperone activity than 4-PBA were synthesized with analogy to the benzene ring. All novel compounds showed chemical chaperone activity, and 2 and 5 possessed high activity. In subsequent experiments, the protective effects of the compounds were examined in Parkinson's disease model cells, and low toxicity of 9 and 11 was related to amphiphilic substitution with naphthalene.
- Mimori, Seisuke,Koshikawa, Yukari,Mashima, Yu,Mitsunaga, Katsuyoshi,Kawada, Koichi,Kaneko, Masayuki,Okuma, Yasunobu,Nomura, Yasuyuki,Murakami, Yasuoki,Kanzaki, Tetsuto,Hamana, Hiroshi
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p. 811 - 814
(2015/02/19)
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- Time resolved spectroscopic studies on a novel synthesized photo-switchable organic dyad and its nanocomposite form in order to develop light energy conversion devices
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UV-vis absorption, steady state and time resolved spectroscopic investigations in pico and nanosecond time domain were made in the different environments on a novel synthesized dyad, 3-(2-methoxynaphthalen-1-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (MNTMA) in its pristine form and when combined with gold (Au) nanoparticles i.e., in its nanocomposite structure. Both steady state and time resolved measurements coupled with the DFT calculations performed by using Gaussian 03 suit of software operated in the linux operating system show that though the dyad exhibits mainly the folded conformation in the ground state but on photoexcitation the nanocomposite form of dyad prefers to be in elongated structure in the excited state indicating its photoswitchable nature. Due to the predominancy of elongated isomeric form of the dyad in the excited state in presence of Au Nps, it appears that the dyad MNTMA may behave as a good light energy converter specially in its nanocomposite form. As larger charge separation rate (kCS ～ 4 × 10 s-1) is found relative to the rate associated with the energy wasting charge recombination processes (kCR ～ 3 × 10s-1) in the nanocomposite form of the dyad, it demonstrates the suitability of constructing the efficient light energy conversion devices with Au-dyad hybrid nanomaterials.
- Dutta, Gopa,Paul, Abhijit,Yadav, Somnath,Bardhan, Munmun,De, Asish,Chowdhury, Joydeep,Jana, Aindrila,Ganguly, Tapan
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p. 5775 - 5784
(2015/01/30)
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- Palladium-catalyzed amination of chloromethylnaphthalene and chloromethylanthracene derivatives with various amines
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Palladium-catalyzed amination of chloromethylnaphthalene and chloromethylanthracene derivatives to produce naphthylamines and anthrylamines in satisfactory to good yields has been developed. The unprecedented amination reactions proceeded smoothly under mild conditions in the presence of Pd(PPh3)4 as a catalyst.
- Zhang, Sheng,Wang, Yi,Feng, Xiujuan,Bao, Ming
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supporting information; experimental part
p. 5492 - 5495
(2012/05/20)
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- Arylalkylamine vanadium (V) salts for the treatment and/or prevention of Diabetes mellitus
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This invention provides compounds of formula (IIA) and pharmaceutical compositions thereof, where M, a, b, and R1-R5 are as defined herein, for treating human type 1 and type 2 diabetes, particularly insulin-resistant diabetes. Pharmaceutical compositions comprising the compounds of formula (IIA) are also disclosed.
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Page/Page column 18
(2010/11/26)
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- ARYLALKYLAMINE VANADIUM (V) SALTS FOR THE TREATMENT AND/OR PREVENTION OF DIABETES MELLITUS
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This invention provides compounds and pharmaceutical compositions thereof for treating human type 1 and type 2 diabetes, particularly insulin-resistant diabetes.
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Page/Page column 45
(2010/02/15)
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- COMPOSITION OF SSAO SUBSTRATES AND METAL COMPOUNDS OF THE VLA AND VLB GROUPS OF THE PERIODIC TABLE
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This invention relates to (pharmaceutical) compositions comprising a combination of SSAO substrates and pharmaceutically acceptable compounds of the Vla and Vlb group of the periodic table, i.e. selenium (VI)-, molybdenum (VI)- and tungsten (V)/(VI) compounds, etc. and to their use as insulin mimetic, i.e., to treat illness Diabetes mellitus, Obesity, or their symptoms. A here discovered synergism between the compounds of the Vla and Vlb groups of the periodic table, i.e. selenium (VI)-, molybdenum (VI)- and tungsten (V)/(VI) com-pounds, etc. and the SSAO substrates makes the effective concentration of the compounds of the Via and Vlb groups of the periodic table in the (pharmaceutical) composition one order of magnitude lower than the corresponding compound of the Vla and Vlb groups alone. Consequently the inventive (pharmaceutical) composition has much lower toxicity than the known compounds or compositions in the art alone, what is a crucial advantage of the former for its use in the treatment and/or prevention of Diabetes mellitus, particularly of Diabetes type 2, or Obesity.
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Page/Page column 26
(2010/11/08)
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- A facile and efficient ZrCl4 catalyzed conversion of aldehydes to geminal-diacetates and dipivalates and their cleavage
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A novel, mild and efficient method has been developed for the preparation of geminal-diacetates and dipivalates in high yields through a reaction of aldehydes with acetic anhydride or pivalic anhydride using Zirconium (IV) chloride as a catalyst under solvent free conditions. Regeneration of aldehydes from the acylals was also achieved using the same catalyst in CH3OH.
- Smitha,Reddy, Ch. Sanjeeva
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p. 9571 - 9576
(2007/10/03)
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- A new fluorous/organic amphiphilic ether solvent, F-626: Execution of fluorous and high temperature classical reactions with convenient biphase workup to separate product from high boiling solvent
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A new fluorous/organic amphiphilic ether solvent, 1H,1H,2H,2H-perfluorooctyl 1,3-dimethylbutyl ether (F-626), is introduced. The basic properties of F-626, especially the partition coefficients with organic solvents/FC-72 (perfluorohexane), were investigated. F-626 was easy to remove by fluorous biphase treatment. Using F-626 as a solvent, LAH reduction, catalytic hydrogenation, and fluorous reductive radical reactions were successful. Classical high temperature reactions up to 200°C, such as the Vilsmeier formylation, the Wolff-Kishner reduction, and the Diels-Alder reaction, were also examined in F-626. The yields of the products in F-626 were almost comparable with those conducted in common organic solvents, which prove that F-626 has the potential to be an easily recyclable high boiling solvent.
- Matsubara, Hiroshi,Yasuda, Shinji,Sugiyama, Hiroyuki,Ryu, Ilhyong,Fujii, Yasuyuki,Kita, Katsumi
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p. 4071 - 4076
(2007/10/03)
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- Vilsmeier Formylation and Glyoxylation Reactions of Nucleophilic Aromatic Compounds Using Pyrophosphoryl Chloride
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Reactions of N,N-dimethylformamide and N-methylformanilide with pyrophosphoryl chloride lead to the formation of reagents that undergo reactions with a wide range of nucleophilic aromatic substrates, including indoles, pyrroles, thiophenes, furans, and methoxy-substituted carbocyclic arenes to afford, after hydrolysis of the initial products, good to excellent yields of the expected aldehydes; reactions with methyl oxamates allow the preparation of methyl arylglyoxylates. Key words: pyrophosphoryl chloride, N,N-dimethylformamide, methoxyarene, heterocyle, formylation
- Downie, Ian M.,Earle, Martyn J.,Heaney, Harry,Shuhaibar, Khamis F.
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p. 4015 - 4034
(2007/10/02)
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- 4,4'-Binaphthylidene-1,1'-diones - Colour and Structure
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Synthesis and properties of various 4,4'-binaphthylidene-1,1'-diones are described.The UV spectra of the deep red to purple diones may be calculated on the base of substituent increments.The experimental values of the analyzed substituents can be reproduced using PPP calculations with satisfying accuracy, which makes it possible to predict also absorption maxima of hitherto unknown 4,4'-binaphthylidene-1,1'-diones.Keywords: 4,4'-Binaphthylidene-1,1'-diones, Phenol Oxidation
- Kral, Andreas,Laatsch, Hartmut
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p. 1401 - 1407
(2007/10/02)
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- Manganese(III)-Mediated Formylation of Aromatic Compounds in the Presence of Malonic Acid
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The reaction of naphthlenes with malonic acid in the presence of manganese(III) acetate gives naphthalenecarbaldehydes and naphthalenecarboxylic acids.Similar reactions of anthracene, pyrene, and methoxybenzenes also yield formylated and carboxylated products.It was found that the formyl group introduced to the aromatic ring was not derived from carboxymethyl radical generated directly by the thermolysis of manganese(III) acetate, but from a dicarboxymethyl radical formed by the interaction of malonic acid and manganese(III) acetate.In addition, it was also found that the dicarboxymethyl radicals attacked the position of the highest electron density on the aromatic ring and that this formylation was effective when the ionization potential of the aromatic copound was lower than 7.8 eV.
- Nishino, Hiroshi,Tsunoda, Katsunori,Kurosawa, Kazu
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p. 545 - 550
(2007/10/02)
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- Process for nucleophilic fluoroalkylation of aldehydes
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Aryl difluoromethyl sulfone adds to alkehydes under phase transfer conditions to give novel substituted alcohols of the general formula wherein R is an aryl, cycloaliphatic, sec- or tert-aliphatic, or heterocyclic group and Ar is an aryl group. The substituted alcohols of formula I are of particular utility as intermediates in the synthesis of a variety of useful end products. For example, the products of formula I may be utilized in desulfonylation reactions, oxidation reactions and fluorination reactions.
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- Study of Reactions Leading to Sulfine Formation. 3. Competition of Reaction Pathways in the Reaction of Methoxide Ion with Methyl 1-Naphthylmethanesulfinates
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In CD3O1-/CD3OD methyl 1-naphthylmethanesulfinates, NpCH2S(O)OCH3 (2), undergo both exchange of CH3O by CD3O by substitution at the sulfinyl group and elimination to form the sulfine, NpCH=S=O.With use of methyl (2-methoxy-1-naphthyl)methanesulfinate (2a) it has been shown that formation of the sulfine takes place by an (E1cB)irrev mechanism.The rates of substitution (ks) and elimination (ke) of a series of 2 have been determined in CD3O1-/CD3OD by 1H NMR spectroscopy, and the effect of several reaction variables on the competition between substitution and elimination has been examined.Salient results are as follows: (1) the rate of elimination is markedly increased by the presence of electron-withdrawing substituents on the aromatic ring, but the rate of substitution is increased only modestly by the same substituents; (2) substituents at the 2-position of the naphthyl group cause a large decrease in ks (steric hindrance to substitution at S=O) but have little effect on ke (elimination rate not sensitive to steric requirements of ortho substituents); (3) the activation energy for elimination is almost 9 kcal/mol greater than the activation energy for substitution.This large difference in activation energy contrasts with the 1-2 kcal/mol difference for elimination vs substitution found14 with alkyl halides.
- Kice, John L.,Lotey, Harvinder
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p. 3596 - 3602
(2007/10/02)
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- THE 1,4-ADDITION OF SINGLET OXYGEN TO 2,6-DIMETHOXY-1-(2-METHOXYETHENYL)-BENZENE AND 2-METHOXY-1-(2-METHOXYETHENYL)NAPHTHALENE. THE 1,4-ENDO-PEROXIDES AS EQUIVALENTS OF 6-OXO-2,4-CYCLOHEXADIENYLIDENACETATES.
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The sensitized photooxygenation of vinylarenes 1 and 2 gave the corresponding 1,4-endoperoxides which were decomposed under mild conditions into quinone methides bearing ester function at the exocyclic carbon.
- Matsumoto, Masakatsu,Kuroda, Keiko,Suzuki, Yoshito
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p. 3253 - 3256
(2007/10/02)
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- SYNTHESIS OF AROMATIC ALDEHYDES VIA 2-ARYL-N,N'-DIACYL-4-IMIDAZOLINES
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Diacylimidazolium ions yield adducts with aromatic compounds.Thus the N,N'-diacetylimidazolium ion and indole gives 1,3-diacetyl-2-(3-indolyl)-4-imidazoline.Less reactive substrates such as thiophene, anisole and 1,3-dimethylbenzene fail to react with this reagent but do form adducts (e.g. 1,3-bis-(trifluoroacetyl)-2-(2-thienyl)-4-imidazoline) with an imidazole/trifluoroacetic anhydride reagent.All of the adducts could be converted to the corresponding aldehyde under mild conditions.The synthetic scope of the new synthesis is similar to that of the Vilsmeier-Haack reaction.
- Bergman, Jan,Renstroem, Lars,Sjoeberg, Birger
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p. 2505 - 2512
(2007/10/02)
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