- Naphthalimide/benzimide-based excited-state intramolecular proton transfer active luminogens: Aggregation-induced enhanced emission and potential for chemical modification
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Fluorescent organic particles are important in a number of areas, including medical imaging; hence, the development of organic materials that exhibit aggregation-induced emissions is an important objective. To that end, we report the synthesis of naphthalimide- and benzimide-based 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives (HNIBT and HPIBT, respectively) that exhibit aggregation-induced emission enhancement (AIEE), in contrast to most naphthalimide- or benzimide-based derivatives that are prone to aggregation-induced quenching. Experimental studies like single-crystal X-ray diffraction analysis and theoretical calculations demonstrate that the ability to undergo excited-state intramolecular proton transfer is pivotal for AIEE. Further studies revealed that a terminal alkynyl chain at the N-imide site of HPIBT has little impact on the emission behavior of the resultant compound (HPIBT-yl). HPIBT-Pe, an amphiphilic molecule obtained through the click reaction of HPIBT-yl and a tetraethylene-glycol-derived azide, self-assembled to form highly photostable particles that have long-term fluorescence imaging potential in cellular environments.
- Wang, Rong,Ding, Ju,Zhang, Yanrong
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- Synthesis and characterization of transparent polyimides derived from ester-containing dianhydrides with different electron affinities
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Two series of poly(ester imide)s derived from bis(trimellitic acid anhydride) phenyl ester (TAHQ) and bis[(3,4-dicarboxylic anhydride) phenyl] terephthalate (PAHP), as well as poly(ether imide)s based on hydroquinone diphthalic anhydride (HQDPA), were synthesized with aromatic diamines via solution polycondensation. These polyimide films were transparent with an ultraviolet-visible absorption cut-off wavelength below 375 nm, and with tensile strengths of 42.0-83.8 MPa, tensile moduli of 2.5-4.7 GPa and elongations at break of 2.1-5.4%. Compared with the poly(ether imide)s, the poly(ester imide)s showed higher glass transition temperatures (Tg), lower water absorption (WA) and lower temperature of 5% weight loss (Td5%). Moreover, the poly(ester imide)s derived from PAHP with a low electron affinity of 2.04 eV by theoretical calculation achieved better transparency, lower WA and slightly lower Tg than the corresponding TAHQ-based poly(ester imide)s.
- Zhou, Yu,Chen, Guofei,Wang, Wei,Wei, Lihong,Zhang, Qiuju,Song, Liping,Fang, Xingzhong
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- Preparation method of 4-hydroxyl phthalic anhydride
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The invention provides a preparation method of 4-hydroxyl phthalic anhydride. The preparation method comprises the following steps: carrying out diazotization and hydrolysis reaction by adopting sodium nitrite and sulfuric acid so as to prepare 4-hydroxyl phthalic acid from 4-amino phthalic acid in one step; finally, sublimating the 4-hydroxyl phthalic acid in vacuum to obtain the 4-hydroxyl phthalic anhydride, wherein the total yield of the reaction reaches 82 percent or more. The method provided by the invention has high 4-hydroxyl phthalic acid yield; a hydrolysis process is more stable anda few of byproducts are produced; the subsequent purification difficulty and cost are reduced. In a whole preparation flow, raw materials are easy to obtain; meanwhile, a reaction process is simple,and complicated reaction equipment and strict reaction conditions are not needed.
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Paragraph 0019; 0020; 0023
(2018/12/14)
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- A hydroxy benzoic anhydride preparation method
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The invention discloses a preparation method of hydroxy benzene anhydride. The preparation method comprises the following steps: mixing nitrophthalonitrile and an organic solvent, adding alkali and nitrite, performing heating and a reflux reaction, and performing aftertreatment so as to obtain hydroxyl phthalonitrile; mixing the hydroxyl phthalonitrile and a KOH aqueous solution, performing heating, reflux and filtration, collecting filtrate, after the filtrate is cooled, regulating the pH to be 1, performing multiple extraction, taking an extraction liquid, and performing aftertreatment so as to obtain hydroxyl phthalic acid; and finally performing vacuum sublimation on the hydroxyl phthalic acid so as to obtain the hydroxy benzene anhydride. The simple preparation method of the hydroxy benzene anhydride, provided by the invention, is mild in reaction conditions, simple and convenient to operate, easy to control, low in equipment requirements and very high in yield.
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Page/Page column 0041; 0044-0046
(2017/08/25)
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- Dental materials with improved hydrolysis stability based on phthalic acid monomers
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Dental material which contains a polymerizable phthalic acid derivative of the general Formula I: with R1=H, methyl or a C1-C5 alkyl residue; R2=H, a phenyl, benzyl or C1-C8 alkyl residue; Q1=is absent or is a C1-C15 alkylene residue, wherein the carbon chain can be interrupted by O or S; Q2=is absent or a (n+1)-valent aliphatic C1-C20 residue, wherein the carbon chain can be interrupted by O or S and wherein Q1 and Q2 cannot be absent simultaneously; X=is absent, is O, S or (—CO—NR4—)—, wherein R4 is H, CH3 or C2H5; Y=is absent, is O, S or (—CO—NR5—)—, wherein R5 is H, CH3 or C2H5; n, m=independently of one another in each case mean 1, 2 or 3; R3=H, CH3, C2H5, Cl, Br or OCH3, and wherein the two carboxyl groups of the benzene ring can together form an anhydride group.
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Page/Page column 9
(2016/08/17)
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- Synthesis of phthalimide derivatives as potential PPAR-γ ligands
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Paecilocin A, a phthalide derivative isolated from the jellyfish-derived fungus Paecilomyces variotii, activates PPAR-γ (Peroxisome proliferator-activated receptor gamma) in rat liver Ac2F cells. Based on a SAR (Structure-activity relationships) study and in silico analysis of paecilocin A-mimetic derivatives, additional N-substituted phthalimide derivatives were synthesized and evaluated for PPAR-γagonistic activity in both murine liver Ac2F cells and in human liver HepG2 cells by luciferase assay, and for adipogenic activity in 3T3-L1 cells. Docking simulation indicated PD6 was likely to bind most strongly to the ligand binding domain of PPAR-γ by establishing crucial H-bonds with key amino acid residues. However, in in vitro assays, PD1 and PD2 consistently displayed significant PPAR-activation in Ac2F and HepG2 cells, and adipogenic activity in 3T3-L1 preadipocytes.
- Eom, So Hyeon,Liu, Sen,Su, Mingzhi,Noh, Tae Hwan,Hong, Jongki,Kim, Nam Deuk,Chung, Hae Young,Yang, Min Hye,Jung, Jee H.
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- DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
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Compounds, pyridine N-oxides, and pharmaceutically acceptable salts of formula (I) are useful as inhibitors of the phosphodiesterase 4 (PDE4) enzyme and for preventing and/ or treating diseases of the respiratory tract characterized by airway obstruction, such as asthma or COPD.
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Paragraph 0607
(2013/05/08)
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- DERIVATIVES OF 1-PHENYL-2-PYRIDINYL ALKYL ALCOHOLS AS PHOSPHODIESTERASE INHIBITORS
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The invention relates to inhibitors of the phosphodiesterase 4 (PDE4) enzyme. More particularly, the invention relates to compounds that are derivatives of 1-phenyl-2-pyridinyl alkyl alcohols, methods of preparing such compounds, compositions containing them and therapeutic use thereof.
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Page/Page column 193
(2013/05/09)
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- Dental materials with improved hydrolysis stability based on phthalic acid monomers
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Dental material which contains a polymerizable phthalic acid derivative of the general Formula I: with R1═H, methyl or a C1-C5 alkyl residue; R2═H, a phenyl, benzyl or C1-C8 alkyl residue; Q1=is absent or is a C1-C15 alkylene residue, wherein the carbon chain can be interrupted by O or S; Q2=is absent or a (n+1)-valent aliphatic C1-C20 residue, wherein the carbon chain can be interrupted by O or S and wherein Q1 and Q2 cannot be absent simultaneously; X=is absent, is O, S or (—CO—NR4—)—, wherein R4 is H, CH3 or C2H5; Y=is absent, is O, S or (—CO—NR5—)—, wherein R5 is H, CH3 or C2H5; n, m=independently of one another in each case mean 1, 2 or 3; R3═H, CH3, C2H5, Cl, Br or OCH3, and wherein the two carboxyl groups of the benzene ring can together form an anhydride group.
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Paragraph 0075; 0076; 0077; 0078
(2013/04/13)
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- Design and synthesis of an orally active metabotropic glutamate receptor subtype-2 (mGluR2) positive allosteric modulator (PAM) that decreases cocaine self-administration in rats
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The modification of 3′-((2-cyclopentyl-6,7-dimethyl-1-oxo-2,3- dihydro-1H-inden-5-yloxy)methyl)biphenyl-4-carboxylic acid (BINA, 1) by incorporating heteroatoms into the structure and replacing the cyclopentyl moiety led to the development of new mGluR2 positive allosteric modulators (PAMs) with optimized potency and superior druglike properties. These analogues are more potent than 1 in vitro and are highly selective for mGluR2 vs other mGluR subtypes. They have significantly improved pharmacokinetic (PK) properties, with excellent oral bioavailability and brain penetration. The benzisothiazol-3-one derivative 14 decreased cocaine self-administration in rats, providing proof-of-concept for the use of mGluR2 PAMs for the treatment of cocaine dependence.
- Dhanya, Raveendra-Panickar,Sidique, Shyama,Sheffler, Douglas J.,Nickols, Hilary Highfield,Herath, Ananda,Yang, Li,Dahl, Russell,Ardecky, Robert,Semenova, Svetlana,Markou, Athina,Conn, P. Jeffrey,Cosford, Nicholas D. P.
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experimental part
p. 342 - 353
(2011/03/18)
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- Light effect on the stability of β-lapachone in solution: Pathways and kinetics of degradation
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Objectives The purpose of this work was to study the chemical stability of the new antitumoral β-lapachone (βLAP) to determine the degradation pathway/s of the molecule and the degradation kinetics in addition to identifying several degradation products. Method Samples of βLAP in solution were stored under conditions of darkness and illumination at 40°C at which the pseudo-first order rate constants for the βLAP degradation were determined. Furthermore, drug degraded solutions were concentrated and purified using Sephadex LH-20 and preparative thin-layer chromatography and degradation products were identified by nuclear magnetic resonance spectroscopy. Key findings The results revealed that βLAP shows two different degradation routes: hydrolysis in the dark and photolysis under the light. The βLAP exposure to light accelerated the drug degradation about 140 fold, compared with the samples stored in the absence of light. The hydrolysis produced hydroxylapachol as the main degradation product. The photolysis yielded phthalic acid, 6-hydroxy-3methylene-3H-isobenzofuran-1-one and a benzomacrolactone together with a complex mixture of other phthalate-derivatives such as 2-(2-carboxy-acetyl)-benzoic acid. Conclusions This study provides useful information for the development of βLAP dosage forms, their storage, manipulation and quality control.
- Cunha-Filho, Marcilio S.S.,Estevez-Braun, Ana,Perez-Sacau, Elisa,Echezarreta-Lopez, Ma Magdalena,Martinez-Pacheco, Ramon,Landin, Mariana
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experimental part
p. 1156 - 1160
(2012/03/10)
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- Development of tryptase inhibitors derived from thalidomide
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A novel series of tryptase inhibitors with a N-phenylphthalimide skeleton structurally derived from thalidomide (1) has been developed. Structure-activity relationship studies led to a potent and selective tryptase inhibitor, 2-(4-cyanophenyl)isoindole-1,3-dione-5-yl 3-(2-aminopyridin-5-yl)propanoate (7), with the IC50 value of 78 nM.
- Tetsuhashi, Masashi,Ishikawa, Minoru,Hashimoto, Mariko,Hashimoto, Yuichi,Aoyama, Hiroshi
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experimental part
p. 5323 - 5338
(2010/09/15)
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- Syntheses of aromatic substituted 6′-thiothalidomides
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A resurgence of interest in thalidomide has occurred as a consequence of its diverse immunomodulatory and anticancer actions, which has fuelled interest in synthetic analogues with higher potencies or less undesirable side effect profiles. Several novel aromatic substituted 6′-thiothalidomides were synthesized whose synthetic route and strategy were developed on the basis of an analysis of reaction mechanisms. The regioselectivity of mono-thionation of aromatic substituted thalidomides with Lawesson's reagent is described, and the chemoselectivity of hydrogenation between the nitro group and 6′-thiocarbonyl group is discussed. Full characterization of eight substituted 6′-thiothalidomides is reported. Georg Thieme Verlag Stuttgart.
- Luo, Weiming,Yu, Qian-Sheng,Tweedie, David,Deschamps, Jeffery,Parrish, Damon,Holloway, Harold W.,Li, Yazhou,Brossi, Arnold,Greig, Nigel H.
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experimental part
p. 3415 - 3422
(2009/05/26)
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- Acid groups containing hydrolytically stable monomers
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Monomer compound (I) is new. Monomer compound (I) of formula (R 1>-O-CO-C(=CHR)-Y 1>-O-Q(AH) n) is new. Either A : -CO 2->or SO 3->; or A+H +>AH; Q : 1-12C alkylene, 4-12C alkylene (interrupted by -O-,=N- or -S) or 6-15C arylene (optionally substituted by 1-4C alkyl, 1-4C alkoxy or halo), where arylene and aryl groups further carries acid groups A; Y 1>1-12C alkylene or 4-12C alkylene (interrupted by -O-, =N- or -S); R : CH 3or H; R 1>1-6C alkylene; and n : 1-3. Independent claims are also included for: (1) preparation of (I); (2) a composition comprising (I), a polymerizable monomer, optionally one/more initiator, and a filler, pigment and/or stabilizer; and (3) a dental material (II) comprising (I).
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Page/Page column 4-5
(2008/06/13)
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- Design and synthesis of phthalimide-type histone deacetylase inhibitors
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Several hydroxamic acid derivatives with a substituted phthalimide group as a linker and/or cap structure, prepared during structural development studies based on thalidomide, were found to have histone deacetylase (HDAC)-inhibitory activity. Structure-activity relationship studies indicated that nature of the substituent introduced at the phthalimide nitrogen atom, introduction of a hydroxamic acid structure, and distance between the N-hydroxyl group and the cap structure are important for HDAC-inhibitory activity.
- Shinji, Chihiro,Nakamura, Takanori,Maeda, Satoko,Yoshida, Minoru,Hashimoto, Yuichi,Miyachi, Hiroyuki
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p. 4427 - 4431
(2007/10/03)
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- (2-Amino-phenyl)-amides of ω-substituted alkanoic acids as new histone deacetylase inhibitors
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A variety of ω-substituted alkanoic acid (2-amino-phenyl)-amides were designed and synthesized. These compounds were shown to inhibit recombinant human histone deacetylases (HDACs) with IC50 values in the low micromolar range and induce hyperacetylation of histones in whole cells. They induced expression of p21WAF1/Cip1 and caused cell-cycle arrest in human cancer cells. Compounds in this class showed efficacy in human tumor xenograft models.
- Vaisburg, Arkadii,Bernstein, Naomy,Frechette, Sylvie,Allan, Martin,Abou-Khalil, Elie,Leit, Silvana,Moradei, Oscar,Bouchain, Giliane,Wang, James,Woo, Soon Hyung,Fournel, Marielle,Yan, Pu T.,Trachy-Bourget, Marie-Claude,Kalita, Ann,Beaulieu, Carole,Li, Zuomei,MacLeod, A. Robert,Besterman, Jeffrey M.,Delorme, Daniel
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p. 283 - 287
(2007/10/03)
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- Kinetics and mechanism of the formation of mono- and di-phthalate esters catalysed by titanium and tin alkoxides
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The kinetics and mechanism of the formation of phthalate mono-esters and phthalate di-esters from phthalic anhydride and a variety of mono- and di-hydric alcohols are reported and discussed. The kinetic work is extended to a mechanistic study of the same reactions using titanium tetra-n-butoxide and tri-n-butyltin ethoxide as catalysts. The results support a mechanism involving alkoxy ligand exchange at the metal as a crucial step in the catalysis.
- Hinde, Nicholas J.,Hall, C. Dennis
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p. 1249 - 1256
(2007/10/03)
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- Pyrophtalones VII. Synthese et activite anti-inflammatoire de (pyridinyl-4)-2 indanediones-1,3 substituees sur le noyau benzenique et/ou sur l'heterocycle
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Pyrophthalones VII.Synthesis and anti-inflammatory activity of 2-(4-pyridinyl)indane-1,3-diones diversely substituted on the benzene ring.Access routes to 2-(1,4-dihydro 4-pyridinylidene) indane-1,3-diones diversely substituted on the benzene ring are studied.The regiospecific attack of these β diketoenamines by alkyl iodides leads to N-substituted compounds.These derivatives may be obtained by any of three possible methods: (1) condensation of 4-methyl pyridine with ethyl phthalates in the absence of catalyst; (2) oxidative condensation of N-alkyl-pyridinium bromides with indane-1,3-diones; (3) aminolysis of 2-(4-4H-pyranylidene) indane-1,3-diones.Pharmacomodulation by the introduction of oxygen or sulfur containing functions (ether, thioether, alcohol, ketone, acid, ester, amide) on the nitrogen of the basic molecule is not very fruitful; only the acetic derivative 19 manifests marked antiinflammatory activity unaccompanied by anti-coagulant action.The presence of chloro, nitro or methoxyl groups on 5 after N-substitution by ethyl or piperidinylethyl groups appears to be more favorable.The most active compound 57 decreases prostaglandin production and leukocyte migration without affecting either cyclooxygenase or 5-lipoxygenase.Its interference, direct or indirect, with phospholipasic A2 activity may be envisaged in particular.Keywords - 2-(4-pyridinyl)indane-1,3-diones / heterocyclic β diketoenamines / partition coefficient / anti-inflammatory activity / mechanism of action
- Leblois, Danielle,Piessard, Sylvie,Baut, Guillaume Le,Kumar, Piyush,Brion, Jean-Daniel,et al.
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p. 229 - 238
(2007/10/02)
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