- Novel chiral bis-dipolar 6,6'-disubstituted binaphthol derivatives for second-order nonlinear optics: Synthesis and linear and nonlinear optical properties
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A number of thermally and optically stable, bis-dipolar chiral molecules based on two geometries of the binaphthol (BN) system with different acceptors/substituents have been synthesized for the first time, and the synthetic routes are reported: optically
- Deussen,Hendrickx,Boutton,Krog,Clays,Bechgaard,Persoons,Bj?rnholm
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Read Online
- Synthesis and macroscopic second-order nonlinear optical properties of poly(ether imide)s containing a novel two-dimensional carbazole chromophore with nitro acceptors
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Taking advantage of the multifunctional characteristics of carbazole along with rational molecular design, a two-dimensional carbazole chromophore with strong nitro acceptors was synthesized by a facile synthetic route. A first molecular hyperpolarizability of 163 × 10-30 esu was acquired through solvatochromic methods. By doping of the chromophores into an organosoluble poly(ether imide), a series of guest-host NLO polymers were acquired. A high doping level up to 20 wt% was obtained without observing aggregation of NLO chromophores. The compatibility between chromophore and poly(ether imide) was also investigated by SEM and extraction experiments. In terms of compatibility, the molecular weight distribution of the polymer plays an important role. The second harmonic coefficients (d33) for the NLO-active poly(ether imide)s range from 7 to 23 pm V-1 depending on the doping level. The effect of two-dimensional structure on the NLO temporal stability was investigated by tracing the second harmonic coefficient as a function of time. Moreover, the relaxation behavior of the NLO systems was further examined by dielectric analysis. Large rotational cone volumes give the two-dimensional chromophore excellent orientational stability when the temperature approaches the glass transition temperature observed from DEA.
- Kuo, Wen-Jang,Hsiue, Ging-Ho,Jeng, Ru-Jong
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- From polynorbornene to the complementary polynorbornene by replication
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In undergoing a DNA-like replication process, the single-stranded polynorbornene acts as a template for norbornene monomer adhesion through ester linkages (see scheme). Polymerization of the adhered monomers affords the corresponding unsymmetric double-st
- Lin, Nai-Ti,Lin, Shu-Yi,Lee, Shern-Long,Chen, Chun-Hsien,Hsu, Chao-Hsiung,Hwang, Lian Pin,Xie, Zhen-Yu,Chen, Chung-Hsuan,Huang, Shou-Ling,Luh, Tien-Yau
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Read Online
- Selective esterification of phosphonic acids
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Here, we report straightforward and selective synthetic procedures for mono-and diesteri-fication of phosphonic acids. A series of alkoxy group donors were studied and triethyl orthoacetate was found to be the best reagent as well as a solvent for the performed transformations. An important temperature effect on the reaction course was discovered. Depending on the reaction temperature, mono-or diethyl esters of phosphonic acid were obtained exclusively with decent yields. The sub-strate scope of the proposed methodology was verified on aromatic as well as aliphatic phosphonic acids. The designed method can be successfully applied for small-and large-scale experiments without significant loss of selectivity or reaction yield. Several devoted experiments were performed to give insight into the reaction mechanism. At 30?C, monoesters are formed via an intermediate (1,1-diethoxyethyl ester of phosphonic acid). At higher temperatures, similar intermediate forms give diesters or stable and detectable pyrophosphonates which were also consumed to give diesters.31P NMR spectroscopy was used to assign the structure of pyrophosphonate as well as to monitor the reaction course. No need for additional reagents and good accessibility and straightforward purification are the important aspects of the developed protocols.
- Brodzka, Anna,Koszelewski, Dominik,Ostaszewski, Ryszard,Trzepizur, Damian
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- Visible-light-mediated phosphonylation reaction: formation of phosphonates from alkyl/arylhydrazines and trialkylphosphites using zinc phthalocyanine
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In this work, we developed a ligand- and base-free visible-light-mediated protocol for the photoredox syntheses of arylphosphonates and, for the first time, alkyl phosphonates. Zinc phthalocyanine-photocatalyzed Csp2-P and Csp3-P bond formations were efficiently achieved by reacting aryl/alkylhydrazines with trialkylphosphites in the presence of air serving as an abundant oxidant. The reaction conditions tolerated a wide variety of functional groups.
- Hosseini-Sarvari, Mona,Koohgard, Mehdi
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p. 5905 - 5911
(2021/07/12)
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- Discovery of 7H-pyrrolo[2,3-d]pyridine derivatives as potent FAK inhibitors: Design, synthesis, biological evaluation and molecular docking study
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Focal adhesion kinase (FAK) is an intracellular non-receptor tyrosine kinase responsible for development of various tumor types. Aiming to explore new potent inhibitors, two series of 2,4-disubstituted-7H-pyrrolo[2,3-d]pyrimidine derivatives were designed and synthesized on the base of structure-based design strategy. Biological evaluation indicated that most of these new compounds could potently inhibit FAK kinase, leading to the promising inhibitors against the proliferation of U-87MG, A-549, and MDA-MB-231 cancer cell lines. Among them, the optimized compound 18h potently inhibited the enzyme (IC50 = 19.1 nM) and displayed stronger potency than TAE-226 in U-87MG, A-549 and MDA-MB-231 cells, with IC50 values of 0.35, 0.24, and 0.34 μM, respectively. Compound 18h is a multi-target kinase inhibitor. Furthermore, compound 18h also exhibited relatively less cytotoxicity (IC50 = 3.72 μM) toward a normal human cell line, HK2. According to the flow cytometry and wound healing assay results, compound 18h effectively induced apoptosis and G0/G1 phase arrest of MDA-MB-231 cells and suppressed the migration of U-87MG, A-549 and MDA-MB-231 cells. The docking study of compound 18h was performed to elucidate its possible binding modes and to provide a structural basis for the further structural guidance design of FAK inhibitors. Collectively, these data support the further development of compound 18h as a lead compound for FAK-targeted anticancer drug discovery.
- Wang, Ruifeng,Zhao, Xiangxin,Yu, Sijia,Chen, Yixuan,Cui, Hengxian,Wu, Tianxiao,Hao, Chenzhou,Zhao, Dongmei,Cheng, Maosheng
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- Design, synthesis, biological evaluation and molecular docking study of novel thieno[3,2-d]pyrimidine derivatives as potent FAK inhibitors
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A series of 2,7-disubstituted-thieno[3,2-d]pyrimidine derivatives were designed, synthesized and evaluated as novel focal adhesion kinase (FAK) inhibitors. The novel 2,7-disubstituted-thieno[3,2-d]pyrimidine scaffold has been designed as a new kinase inhibitor platform that mimics the bioactive conformation of the well-known diaminopyrimidine motif. Most of the compounds potently suppressed the enzymatic activities of FAK and potently inhibited the proliferation of U-87MG, A-549 and MDA-MB-231 cancer cell lines. Among these derivatives, the optimized compound 26f potently inhibited the enzyme (IC50 = 28.2 nM) and displayed stronger potency than TAE-226 in U-87MG, A-549 and MDA-MB-231 cells, with IC50 values of 0.16, 0.27, and 0.19 μM, respectively. Compound 26f also exhibited relatively less cytotoxicity (IC50 = 3.32 μM) toward a normal human cell line, HK2. According to the flow cytometry results, compound 26f induced the apoptosis of MDA-MB-231 cells in a dose-dependent manner and effectively arrested MDA-MB-231 cells in G0/G1 phase. Further investigations revealed that compound 26f potently suppressed the migration of MDA-MB-231 cells. Collectively, these data support the further development of compound 26f as a lead compound for FAK-targeted anticancer drug discovery.
- Chen, Yixuan,Cheng, Maosheng,Hao, Chenzhou,Wang, Ruifeng,Wu, Tianxiao,Yang, Bowen,Yu, Sijia,Zhao, Dongmei,Zhao, Xiangxin
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- Novel compounds useful as fluorescent probes selectively binding to tau aggregates and preparation method thereof
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A compound having high selectivity for tau aggregates and a method for preparing the same. The present invention relates to a tau targeting fluorescent probe including the compound, a composition for detecting tau fiber protein comprising the fluorescent
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Paragraph 0365-0368
(2021/01/29)
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- ANTIMALARIAL COMPOUNDS
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Antimalarial compounds of the formula: in which n is 1 or 2; X is C or N; R1 is a moiety comprising a secondary amine and a tertiary amine joined by a C2 to C4 alkyl chain; and R2 is CF3, F, or H, or an analog, combination, derivative, prodrug, stereoisomer, or pharmaceutically acceptable salt thereof. Pharmaceutical compounds including the antimalarial compounds. Methods of treating or preventing malaria comprising administering an effective amount of the antimalarial compounds.
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Page/Page column 36-38
(2020/10/20)
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- Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines
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There is an urgent need to develop new efficacious antimalarials to address the emerging drug-resistant clinical cases. Our previous phenotypic screening identified styrylquinoline UCF501 as a promising antimalarial compound. To optimize UCF501, we herein report a detailed structure-activity relationship study of 2-arylvinylquinolines, leading to the discovery of potent, low nanomolar antiplasmodial compounds against a Plasmodium falciparum CQ-resistant Dd2 strain, with excellent selectivity profiles (resistance index 200). Several metabolically stable 2-arylvinylquinolines are identified as fast-acting agents that kill asexual blood-stage parasites at the trophozoite phase, and the most promising compound 24 also demonstrates transmission blocking potential. Additionally, the monophosphate salt of 24 exhibits excellent in vivo antimalarial efficacy in the murine model without noticeable toxicity. Thus, the 2-arylvinylquinolines represent a promising class of antimalarial drug leads.
- Huang, Guang,Murillo Solano, Claribel,Melendez, Joel,Shaw, Justin,Collins, Jennifer,Banks, Robert,Arshadi, Arash Keshavarzi,Boonhok, Rachasak,Min, Hui,Miao, Jun,Chakrabarti, Debopam,Yuan, Yu
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p. 11756 - 11785
(2020/11/26)
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- Tunable photophysical properties of thiophene based chromophores: A conjoined experimental and theoretical investigation
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In this paper we report the synthesis and photophysical properties of six novel thiophene derivatives (ThD) with D-π-A structure. The subject of this work is three nitrophenyls (1) BT-Th-NO2 and three benzonitriles (2) BT-Th-CN, substituted at
- Popczyk, Anna,Cheret, Yohan,Grabarz, Anna,Hanczyc, Piotr,Fita, Piotr,El-Ghayoury, Abdelkrim,Sznitko, Lech,Mysliwiec, Jaroslaw,Sahraoui, Bouchta
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supporting information
p. 6728 - 6736
(2019/05/04)
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- Second-generation aryl isonitrile compounds targeting multidrug-resistant Staphylococcus aureus
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Antibiotic resistance remains a major global public health threat that requires sustained discovery of novel antibacterial agents with unexploited scaffolds. Structure-activity relationship of the first-generation aryl isonitrile compounds we synthesized led to an initial lead molecule that informed the synthesis of a second-generation of aryl isonitriles. From this new series of 20 compounds, three analogues inhibited growth of methicillin-resistant Staphylococcus aureus (MRSA) (from 1 to 4 μM) and were safe to human keratinocytes. Compound 19, with an additional isonitrile group exhibited improved activity against MRSA compared to the first-generation lead compound. This compound emerged as a candidate worthy of further investigation and further reinforced the importance of the isonitrile functionality in the compounds’ anti-MRSA activity. In a murine skin wound model, 19 significantly reduced the burden of MRSA, similar to the antibiotic fusidic acid. In summary, 19 was identified as a new lead aryl isonitrile compound effective against MRSA.
- Kyei-Baffour, Kwaku,Mohammad, Haroon,Seleem, Mohamed N.,Dai, Mingji
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p. 1845 - 1854
(2019/03/28)
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- ZINC-BINDER BASED EBNA1-SPECIFIC COMPOUNDS
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The present disclosure relates to compounds useful in the treatment, imaging, and/or diagnosis of Epstein-Barr virus (EBV)-positive cells, such as cancer.
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Paragraph 00242-00243
(2019/08/08)
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- Light-Emitting Chiral Nematic Dimers with Anomalous Odd-Even Effect
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In this report, based on the results derived from the extensive study into the thermal and photophysical properties, an anomalous mesomorphic behavior of photoluminescent, chiral nematic (N*) liquid crystalline dimers, belonging to two different series ha
- Veerabhadraswamy,Bhat, Sachin A.,Hiremath, Uma S.,Yelamaggad, Channabasaveshwar V.
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p. 2836 - 2851
(2019/11/11)
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- Phosphamide-containing diphenylpyrimidine analogues (PA-DPPYs) as potent focal adhesion kinase (FAK) inhibitors with enhanced activity against pancreatic cancer cell lines
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A family of phosphamide-containing diphenylpyrimidine analogues (PA-DPPYs) were synthesized as potent focal adhesion kinase (FAK) inhibitors. The PA-DPPY derivatives could significantly inhibit the FAK enzymatic activity at concentrations lower than 10.69 nM. Among them, compounds 7a and 7e were two of the most active FAK inhibitors, possessing IC50 values of 4.25 nM and 4.65 nM, respectively. In particular, compound 7e also displayed strong activity against AsPC cell line, with an IC50 of 1.66 μM, but show low activity against the normal HPDE6-C7 cells (IC50 > 20 μM), indicating its low cell cytotoxicity. Additionally, flow cytometry analysis showed that after treatment with 7e (8 μM, 72 h), both AsPC and Panc cells growth were almost totally inhibited, with a cell viability rate of 16.8% and 18.1%, respectively. Overall, compound 7e may be served as a valuable FAK inhibitor for the treatment of pancreatic cancer.
- Liu, He,Wu, Bin,Ge, Yang,Huang, Jiaxin,Song, Shijie,Wang, Changyuan,Yao, Jihong,Liu, Kexin,Li, Yanxia,Li, Yongming,Ma, Xiaodong
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p. 6313 - 6321
(2017/11/16)
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- Design and synthesis of phosphoryl-substituted diphenylpyrimidines (Pho-DPPYs) as potent Bruton's tyrosine kinase (BTK) inhibitors: Targeted treatment of B lymphoblastic leukemia cell lines
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A family of phosphoryl-substituted diphenylpyrimidine derivatives (Pho-DPPYs) were synthesized and biologically evaluated as potent BTK inhibitors in this study. Compound 7b was found to markedly inhibit BTK activity at concentrations of 0.82?nmol/L, as well as to suppress the proliferations of B-cell leukemia cell lines (Ramos and Raji) expressing high levels of BTK at concentrations of 3.17?μM and 6.69?μM. Moreover, flow cytometry analysis results further indicated that 7b promoted cell apoptosis to a substantial degree. In a word, compound 7b is a promising BTK inhibitor for the treatment of B-cell lymphoblastic leukemia.
- Ge, Yang,Yang, Haijun,Wang, Changyuan,Meng, Qiang,Li, Lei,Sun, Huijun,Zhen, Yuhong,Liu, Kexin,Li, Yanxia,Ma, Xiaodong
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supporting information
p. 765 - 772
(2016/12/27)
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- Photoluminescent discotic liquid crystals derived from tris(N-salicylideneaniline) and stilbene conjugates: Structure-property correlations
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Luminescent discotic liquid crystals based on tris(N-salicylideneaniline)s [TSANs] bearing trans-stilbene fluorophores have been synthesized. Their mesomorphic and photophysical properties were studied. These TSANs existing in the form of C3h and Cs geometrical isomers of the keto-enamine tautomer self-assemble to form the columnar phase and exhibit fluorescence both in solution and mesophase states. These columnar mesophases also exhibit frozen (glassy) columnar phase, which ensures preserved fluorescence intensity, defect free alignment and simultaneous restriction on the motion of ionic impurities. These features make them promising candidates for the use in organic light emitting diodes, particularly as emissive layers. This study also led to an understanding about the dependence of their mesomorphism (mesophase type, stability and thermal range) and photophysical features on the number and pattern of their peripheral substitution, in comparison to the analogous columnar liquid crystalline TSANs reported earlier.
- Achalkumar, Ammathnadu S.,Veerabhadraswamy,Hiremath, Uma S.,Rao, Doddamane S. Shankar,Prasad, Subbarao Krishna,Yelamaggad, Channabasaveshwar V.
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p. 291 - 305
(2016/05/24)
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- Discovery of oral-available resveratrol-caffeic acid based hybrids inhibiting acetylated and phosphorylated STAT3 protein
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Constitutive activation of STAT3 has been found in a wide variety of cancers and demonstrated as a very attractive therapeutic target. Disrupting both acetylation and phosphorylation of STAT3 protein was hypothesized to greatly deactivate STAT3, therefore, treating cancers. To demonstrate the hypothesis, two series of novel resveratrol-caffeic acid hybrids were designed aiming to regulate both acetylation and phosphorylation of STAT3 protein, which is also the first report of the synthetic inhibitors simultaneously regulating two biological reactions of STAT3 to our knowledge. Most of these compounds were demonstrated with preferential antitumor activity with low IC50values against two cancer cell lines. Particularly, compound 7d was found as an excellent STAT3 inhibitor with over 50-fold better potency than resveratrol and caffeic acid. Meanwhile, the novel derivatives significantly inhibited the proliferation and induced the apoptosis of tumor cells. Molecular docking further disclosed the binding modes of STAT3 with the inhibitors. In addition, compound 7d orally and significantly suppressed breast cancer 4T1 xenograft tumor growth in vivo, indicating its great potential as an efficacious drug candidate for human cancer therapy.
- Li, Shanshan,Zhang, Wenda,Yang, Yanwei,Ma, Ting,Guo, Jianpeng,Wang, Shanshan,Yu, Wenying,Kong, Lingyi
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p. 1006 - 1018
(2016/11/09)
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- Influence of imidazolium ionic liquids on fluorescence of push-pull diphenylbutadienes
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A series of donor-acceptor substituted diphenylbutadienes have been synthesized and their fluorescence properties in organic solvents and imidazolium ionic liquid media were investigated. Substituted diphenylbutadienes show remarkable solvatochromic emiss
- Vasu, Anuji K.,Katla, Jagadish,Malek, Naved I.,Kanvah, Sriram
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- Arylmethyl phosphonate preparation method
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The invention provides an arylmethyl phosphonate preparation method. The method includes the following steps that arylmethyl ester, triethyl phosphate and a catalyst are sequentially added into a reactor and reacted for 5-8 h at the temperature of 100-200 DEG C after full stirring, and after excessive triethyl phosphate is distilled off through decompression, the mixture continues to be reacted for 3-7 h at the temperature of 100-200 DEG C; then, the mixture is cooled to the room temperature, a product is extracted through a mixed solvent, and arylmethyl phosphonate is obtained after the mixed solvent is removed. The catalyst is one or more of tetramethyl ammonium bromide, tetraethylammonium bromide, tetrabutyl ammonium bromide, benzyltrimethyl ammonium bromide, cetyl trimethyl ammonium bromide, cetyltrimethyl ammonium chloride, ammonium chloride, sodium iodide and potassium iodide. Arylmethyl phosphonate is synthesized through a one-step method, other solvents are not added, operation is easy, and the product yield is high and can be 85.3% at maximum.
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Paragraph 0040; 0041
(2017/01/02)
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- Design, synthesis, and biological evaluation of benzoselenazole-stilbene hybrids as multi-target-directed anti-cancer agents
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To identify novel multi-target-directed drug candidates for the treatment of cancer, a series of benzoselenazole-stilbene hybrids were synthesised by combining the pharmacophores of resveratrol and ebselen. The biological assay indicated that all of the h
- Yan, Jun,Guo, Yueyan,Wang, Yali,Mao, Fei,Huang, Ling,Li, Xingshu
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p. 220 - 229
(2015/03/31)
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- Crystal structures of the apo form and a complex of human LMW-PTP with a phosphonic acid provide new evidence of a secondary site potentially related to the anchorage of natural substrates
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Low molecular weight protein tyrosine phosphatases (LMW-PTP, EC 3.1.3.48) are a family of single-domain enzymes with molecular weight up to 18 kDa, expressed in different tissues and considered attractive pharmacological targets for cancer chemotherapy. Despite this, few LMW-PTP inhibitors have been described to date, and the structural information on LMW-PTP druggable binding sites is scarce. In this study, a small series of phosphonic acids were designed based on a new crystallographic structure of LMW-PTP complexed with benzylsulfonic acid, determined at 2.1 ?. In silico docking was used as a tool to interpret the structural and enzyme kinetics data, as well as to design new analogs. From the synthesized series, two compounds were found to act as competitive inhibitors, with inhibition constants of 0.124 and 0.047 mM. We also report the 2.4 ? structure of another complex in which LMW-PTP is bound to benzylphosphonic acid, and a structure of apo LMW-PTP determined at 2.3 ? resolution. Although no appreciable conformation changes were observed, in the latter structures, amino acid residues from an expression tag were found bound to a hydrophobic region at the protein surface. This regions is neighbored by positively charged residues, adjacent to the active site pocket, suggesting that this region might be not a mere artefact of crystal contacts but an indication of a possible anchoring region for the natural substrate - which is a phosphorylated protein.
- Fonseca, Emanuella M.B.,Trivella, Daniela B.B.,Scorsato, Valéria,Dias, Mariana P.,Bazzo, Natália L.,Mandapati, Kishore R.,De Oliveira, Fábio L.,Ferreira-Halder, Carmen V.,Pilli, Ronaldo A.,Miranda, Paulo C.M.L.,Aparicio, Ricardo
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p. 4462 - 4471
(2015/08/03)
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- Synthetic Strategy and Performances of a UV-Curable Poly Acryloyl Phosphinate Flame Retardant by Carbene Polymerization
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A route to synthesize poly ethyl (4-acrylamidebenzyl) phosphinate (PPAC) was discussed and the optimal route was determined. Diethyl benzylphosphonate was synthesized by Arbuzov reaction, then, a nitryl was introduced onto the aromatic ring by the nitration reaction of ethyl benzylphosphonate. Subsequently the carbene polymerization of the product was carried out. Finally, the nitryls were reduced and amidated to introduce the acryloyl group into the prepolymer to obtain the target product (PPAC). PPAC can rapidly photopolymerize under UV light irradiation. The addition of PPAC decreased the smoke production rate (SPR), CO2 production (CO2P), and CO production (COP) of the UV-cured resin.
- Yu, Jia,Li, Minglei,Yu, Yong,Gao, Yanjing,Liu, Jiancheng,Sun, Fang
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p. 1958 - 1970
(2015/12/12)
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- Discovery and characterization of aryl isonitriles as a new class of compounds versus methicillin- and vancomycin-resistant Staphylococcus aureus
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Methicillin- and vancomycin-resistant Staphylococcus aureus (MRSA and VRSA) have emerged as a global health concern. A new class of compounds featuring an aryl isonitrile moiety has been discovered that exhibits potent inhibitory activity against several clinically-relevant MRSA and VRSA isolates. Structure-activity relationship studies have been conducted to identify the aryl isonitrile group as the key functional group responsible for the observed antibacterial activity. The most potent antibacterial aryl isonitrile analogs (MIC 2 μM) did not show any toxicity against mammalian cells up to a concentration of 64 μM.
- Davis, Dexter C.,Mohammad, Haroon,Kyei-Baffour, Kwaku,Younis, Waleed,Creemer, Cassidy Noel,Seleem, Mohamed N.,Dai, Mingji
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p. 384 - 390
(2015/07/20)
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- Photoisomerization of Trans Ortho-, Meta-, Para-Nitro Diarylbutadienes: A Case of Regioselectivity
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A series of ortho-, meta- and para-substituted trans-nitro aryl (phenyl and pyridyl) butadienes have been synthesized and characterized. The effect of substitution and positional selectivity on their fluorescence and photoisomerization were systematically investigated. Among all dienes, meta- and para-nitro phenyl-substituted derivatives exhibit remarkable solvatochromic emission shifts due to intramolecular charge transfer. On the other hand, ortho derivatives undergo regioselective isomerization upon photoexcitation in contrast to inefficient isomerization of para and meta nitro-substituted dienes. Single crystal X-ray analysis revealed existence of intramolecular hydrogen bonding between the nitro group and the hydrogen of the proximal double bond. This restricts the rotation of the proximal double bond thereby allowing regioselective isomerization. The observations were also supported by NMR spectroscopic studies.
- Agnihotri, Harsha,Paramasivam, Mahalingavelar,Palakollu, Veerabhadraiah,Kanvah, Sriram
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p. 1324 - 1331
(2015/11/10)
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- Synthesis, crystal structure and computational studies of 4-nitrobenzylphosphonic acid
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4-Nitrobenzylphosphonic acid (1a) has been synthesized and structurally characterized by vibrational spectroscopy (IR and Raman) and single-crystal X-ray diffraction. Additionally, Hirshfeld surface analysis and computational methods have been used to com
- Wilk, Magdalena,Jarzembska, Katarzyna N.,Janczak, Jan,Hoffmann, Józef,Videnova-Adrabinska, Veneta
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p. 240 - 249
(2014/07/08)
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- Selective photoisomerization of methyl substituted nitro diphenylbutadienes
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A series of p-nitro substituted trans-diphenylbutadienes is synthesized and their photophysical and photochemical properties are investigated. All the dienes have a very low quantum yield of fluorescence but exhibit remarkable solvatochromic emission shifts attributed to twisted intramolecular charge transfer. Photochemical irradiation of simple p-nitro substituted diphenylbutadienes reveals inefficient or no detectable photoisomerization. However, substituting a methyl group on the butadiene chain of p-nitro substituted diphenylbutadiene or replacing the nitro group with cyano group yields the corresponding trans-cis isomers. In the case of simple nitrodienes, strong intramolecular charge transfer character in the excited state aids dissipation of absorbed energy through non-photochemical and non-radiative channels. The steric effect caused by the presence of methyl group lowers the isomerization barrier in methyl substituted dienes leading to a regioselective isomerization.
- Agnihotri, Harsha,Palakollu, Veerabhadra,Kanvah, Sriram
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- Design, synthesis, and evaluation of multitarget-directed resveratrol derivatives for the treatment of Alzheimer's disease
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A series of multitarget-directed resveratrol derivatives was designed and synthesized for the treatment of Alzheimer's disease (AD). In vitro studies indicated that most of the target compounds exhibit significant inhibition of self-induced β-amyloid (Aβ)
- Lu, Chuanjun,Guo, Yueyan,Yan, Jun,Luo, Zonghua,Luo, Hai-Bin,Yan, Ming,Huang, Ling,Li, Xingshu
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p. 5843 - 5859
(2013/08/23)
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- Designing anti-inflammatory drugs from parasitic worms: A synthetic small molecule analogue of the acanthocheilonema viteae product ES-62 prevents development of collagen-induced arthritis
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In spite of increasing evidence that parasitic worms may protect humans from developing allergic and autoimmune diseases and the continuing identification of defined helminth-derived immunomodulatory molecules, to date no new anti-inflammatory drugs have been developed from these organisms. We have approached this matter in a novel manner by synthesizing a library of drug-like small molecules based upon phosphorylcholine, the active moiety of the anti-inflammatory Acanthocheilonema viteae product, ES-62, which as an immunogenic protein is unsuitable for use as a drug. Following preliminary in vitro screening for inhibitory effects on relevant macrophage cytokine responses, a sulfone-containing phosphorylcholine analogue (11a) was selected for testing in an in vivo model of inflammation, collagen-induced arthritis (CIA). Testing revealed that 11a was as effective as ES-62 in protecting DBA/1 mice from developing CIA and mirrored its mechanism of action in downregulating the TLR/IL-1R transducer, MyD88. 11a is thus a novel prototype for anti-inflammatory drug development.
- Al-Riyami, Lamyaa,Pineda, Miguel A.,Rzepecka, Justyna,Huggan, Judith K.,Khalaf, Abedawn I.,Suckling, Colin J.,Scott, Fraser J.,Rodgers, David T.,Harnett, Margaret M.,Harnett, William
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p. 9982 - 10002
(2014/01/17)
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- Substituent effects on the 13C NMR chemical shifts of the imine carbon in N-(4-X-benzylidene)-4-(4-Y-styryl) anilines
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Long-range electronic substituent effects were targeted using the substituent dependence of δC(C=N), and specific cross-interactions were explored extendedly. A wide set of N-(4-X-benzylidene)- 4-(4-Y-styryl) anilines, p-X-C6H4
- Fang, Zhengjun,Cao, Chenzhong,Chen, Guanfan
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p. 1343 - 1350
(2013/08/24)
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- Light emitting, star-shaped tris(N-salicylideneaniline) discotic liquid crystals bearing trans-stilbene fluorophores: Synthesis and characterization
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Star-shaped tris(N-salicylideneaniline) discotics possessing trans-stilbene fluorophores have been synthesized by condensing 1,3,5-triformylphloroglucinol with 4-(alkoxystyryl)benzen-amines, and characterized. 1H and 2D 1H-1/su
- Achalkumar,Yelamaggad
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p. 7108 - 7112
(2013/01/15)
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- Synthesis and evaluation of 18F-labeled styryltriazole and resveratrol derivatives for β-amyloid plaque imaging
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In the present study, a styryltriazole and four resveratrol derivatives were synthesized as candidates for β-amyloid (Aβ) plaque imaging. On the basis of their binding affinities to Aβ(1-42) aggregates, the styryltriazole (1, Ki = 12.8 nM) and one resveratrol derivative (5, Ki = 0.49 nM) were labeled with 18F. In normal mice, tissue distribution of [18F]5 showed good initial brain uptake (3.26% ID/g at 2 min) but slow wash-out from brains (2-to-60 min uptake ratio: 2.9). Furthermore, it underwent in vivo metabolic defluorination (1.88% ID/g at 2 min and 9.73% ID/g at 60 min). In contrast, [18F]1 displayed high initial brain uptake (5.38% ID/g at 2 min) with rapid wash-out from brains (0.52% ID/g at 60 min; 2-to-60 min uptake ratio: 10.3). These results indicate that [ 18F]1 has in vivo kinetics comparable to PET radiopharmaceuticals currently under commercial development, demonstrating that [18F]1 is a desirable PET radioligand for Aβ plaque imaging.
- Lee, Iljung,Choe, Yearn Seong,Choi, Joon Young,Lee, Kyung-Han,Kim, Byung-Tae
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experimental part
p. 883 - 892
(2012/04/04)
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- Synthesis of α-arylphosphonates using copper-catalyzed α-arylation and deacylative α-arylation of β-ketophosphonates
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Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts have been developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data. Copyright
- Rout, Laxmidhar,Regati, Sridhar,Zhao, Cong-Gui
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experimental part
p. 3340 - 3346
(2012/01/17)
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- Polyethylene glycol-promoted dialkyl, aryl/heteroaryl phosphonates
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A new, straightforward polyethylene glycol-promoted method for Michaelis-Arbuzov rearrangement has been described.
- Naidu, K. Reddi Mohan,Dadapeer, Naidu E.,Reddy, C. Bhupendra,Rao, A. Janardhan,Reddy, C. Suresh,Raju, C. Naga
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experimental part
p. 3462 - 3468
(2011/09/16)
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- Direct conversion of benzylic and allylic alcohols to phosphonates
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Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth- Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI2.
- Barney, Rocky J.,Richardson, Rebekah M.,Wiemer, David F.
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supporting information; experimental part
p. 2875 - 2879
(2011/05/19)
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- Thermoreversible covalent self-assembly of oligo(p-phenylenevinylene) bridged gold nanoparticles
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Organic-inorganic hybrids have been fabricated through mild Diels-Alder cross-linking between maleimide bearing oligo(p-phenylenevinylene) (OPV) and furan functionalized gold nanoparticles with, diameter smaller than 2 nm. The OPV ligands afford strong reaction, ability toward furan group due to their maleimide moieties. These small gold nanoparticles form close-packed homogeneous hybrids with well-defined interfaces by incorporating OPV ligands in solutions. Covalent assembly and disassembly of gold nanoparticles can be achieved by repeated thermal stimuli on as-obtained hybrids, which can be monitored by fluorescence changes of OPVs and surface plasmon resonance absorption. Moreover, the dramatic photophysical properties and assembly behavior of these hybrids allow this procedure to be performed as a smart assay for monitoring the process of the Diels-Alder reaction.
- Liu, Xiaofeng,Liu, Huibiao,Zhou, Weidong,Zheng, Haiyan,Yin, Xiaodong,Li, Yuliang,Guo, Yanbing,Zhu, Mei,Ouyang, Canbin,Zhu, Daoben,Xia, Andong
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experimental part
p. 3179 - 3185
(2010/12/18)
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- COMPOUNDS AND METHODS FOR INHIBITING NHE-MEDIATED ANTIPORT IN THE TREATMENT OF DISORDERS ASSOCIATED WITH FLUID RETENTION OR SALT OVERLOAD AND GASTROINTESTINAL TRACT DISORDERS
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The present disclosure is directed to corn- pounds and methods for the treatment of disorders associated with fluid retention or salt overload, such as heart failure (in particular, congestive heart failure), chronic kidney disease, end-stage renal disease, liver disease, and peroxisome proliferator-activated receptor (PPAR) gamma agonist-induced fluid retention. The present disclosure is also directed to compounds and methods for the treatment of hypertension. The present disclosure is also directed to compounds and methods for the treatment of gastrointestinal tract disorders, including the treatment or reduction of pain associated with gastrointestinal tract disorders. The methods generally comprise administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that is designed to be substantially active in the gastrointestinal (GI) tract to inhibit NHE-mediated antiport of sodium ions and hydrogen ions therein. More particularly, the method comprises administering to a mammal in need thereof a pharmaceutically effective amount of a compound, or a pharmaceutical composition comprising such a compound, that inhibits NHE-3, -2 and/ or -8 mediated antiport of sodium and/or hydrogen ions in the GI tract and is designed to be substantially impermeable to the layer of epithelial cells, or more specifically the epithelium of the GI tract. As a result of the compound being substantially impermeable, it is not absorbed and is thus essentially systemically non-bioavailable, so as to limit the exposure of other internal organs (e.g., liver, heart, brain, etc.) thereto. The present disclosure is still further directed to a method wherein a mammal is administered such a compound with a fluid-absorbing polymer, such that the combination acts as described above and further provides the ability to sequester fluid and/or salt present in the GI tract
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Page/Page column 152
(2010/08/04)
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- A novel competitive class of α-glucosidase inhibitors: (E)-1-phenyl-3-(4-styrylphenyl)urea derivatives
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Competitive glycosidase inhibitors are generally sugar mimics that are costly and tedious to obtain because they require challenging and elongated chemical synthesis, which must be stereo-and regiocontrolled. Here, we show that readily accessible achiral
- Kim, Jun Young,Lee, Ji Won,Kim, Young Soo,Lee, Yuno,Ryu, Young Bae,Kim, Songmi,Ryu, Hyung Won,Curtis-Long, Marcus J.,Lee, Keun Woo,Lee, Woo Song,Park, Ki Hun
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body text
p. 2125 - 2131
(2011/12/05)
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- NOVEL MINOR GROOVE BINDERS
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There is provided compounds of formula (I), wherein R1, R11, R12, Qa, X, Qb, Qc, A and D have meanings given in the description, or a pharmaceutically acceptable salt or solvate thereof, which compound, salt or solvate binds to the minor groove of DNA.
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Page/Page column 53
(2008/06/13)
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- Phosphonated Fluoroquinolones, Antibacterial Analogs Thereof, and Methods for the Prevention and Treatment of Bone and Joint Infections
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The present invention relates to phosphonated fluoroquinolones, antibacterial analogs thereof, and methods of using such compounds. These compounds are useful as antibiotics for prevention and/or the treatment of bone and joint infections, especially for the prevention and/or treatment of osteomyelitis.
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Page/Page column 75-76
(2008/12/09)
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- Antimicrobial lexitropsins containing amide, amidine, and alkene linking groups
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The synthesis and properties of 80 short minor groove binders related to distamycin and the thiazotropsins are described. The design of the compounds was principally predicated upon increased affinity arising from hydrophobic interactions between minor groove binders and DNA. The introduction of hydrophobic aromatic head groups, including quinolyl and benzoyl derivatives, and of alkenes as linkers led to several strongly active antibacterial compounds with MIC for Staphylococcus aureus, both methicillin-sensitive and -resistant strains, in the range of 0.1-5 μg mL-1, which is comparable to many established antibacterial agents. Antifungal activity was also found in the range of 20-50 μg mL-1 MIC against Aspergillus niger and Candida albicans, again comparable with established antifungal drugs. A quinoline derivative was found to protect mice against S. aureus infection for a period of up to six days after a single intraperitoneal dose of 40 mg kg-1.
- Anthony, Nahoum G.,Breen, David,Clarke, Joanna,Donoghue, Gavin,Drummond, Allan J.,Ellis, Elizabeth M.,Gemmell, Curtis G.,Helesbeux, Jean-Jacques,Hunter, Iain S.,Khalaf, Abedawn I.,Mackay, Simon P.,Parkinson, John A.,Suckling, Colin J.,Waigh, Roger D.
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p. 6116 - 6125
(2008/09/16)
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- Dielectric and Fluorescent Probes To Investigate Glass Transition, Melt, and Crystallization in Polyolefins
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Investigation of glass transition dynamics in polyolefins by broadband dielectric spectroscopy (DRS) is facilitated by the addition of a novel dielectric probe, (4,4′-N,N-dibutylamino)-(E)-nitrostilbene (DBANS), which introduces dipoles and made the polym
- Van Den Berg, Otto,Sengers, Wilco G.F.,Jager, Wolter F.,Picken, Stephen J.,Wuebbenhorst, Michael
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p. 2460 - 2470
(2007/10/03)
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- Spectroscopic Correlations between Supermolecules and Molecules. Anatomy of the Ion-Modulated Electronic Properties of the Nitrogen Donor in Monoazacrown-Derived Intrinsic Fluoroionophores
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The synthesis, absorption and emission spectra, fluorescence quantum yields, and fluorescence lifetimes of three compound series of trans-4,4′-disubstituted aminostilbenes (1-3) are reported. The chromo-/fluoroionophoric behavior of the monoaza-15-crown-5
- Yang, Jye-Shane,Hwang, Chung-Yu,Hsieh, Chia-Chun,Chiou, Shih-Yi
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p. 719 - 726
(2007/10/03)
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- N-acylamino benzyl ether derivatives
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This invention relates to N-acylamino aryl derivatives of the formula 1where R1, R21, R22, R23, R3, R4, R5 R6, R7, R8, R, and n are as defined herein and where X is —CHRO, —OCHR—, —CH2S—, —SCH2—, —CH2CH2—, —CH=CH— or —C≡C—. The compounds of the invention are selective monoamine oxidase B inhibitors, and they are therefore useful in the treatment of diseases mediated by monoamine oxidase B, for example, for the treatment of Alzheimer's disease or senile dementia.
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- N-ACYLAMINOBENZENE DERVATIVES AS SELECTIVE MONOAMINE OXIDASE B INHIBITORS
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This invention relates to N-acylamino aryl derivatives of the general formula (I), wherein R1 is halogen, halogen-(C1-C6)-alkyl, cyano, C1-C6-alkoxy or halogen-(C1-C6)-alkoxy; R
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- Photoinduced electron transfer in a mesogenic donor-acceptor-donor system
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A novel donor-acceptor-donor molecule consisting of two oligo(p-phenylene vinylene) (OPV4) units attached to a central perylene bisimide (PERY) core is described. This OPV4-PERY-OPV4 is the first mesogenic molecule that incorporates both p- and n-type sem
- Peeters, Emiel,Van Hal, Paul A.,Meskers, Stefan C. J.,Janssen, Rene A. J.,Meijer
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p. 4470 - 4474
(2007/10/03)
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- A fluorescence emission study of nitro- and nitromethyl-substituted 1,4- diarylbutadienes in solid state
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1-(4-Nitrophenyl)-4-phenylbuta-1E,3E-diene 1, 1,4-di (4-nitrophenyl)buta-1E,3E-diene 2, 1-phenyl-2-methyl-4-(4-nitrophenyl) buta-1E,3E-diene 3, and 1-4-di (4-nitrophenyl)-2-methylbuta-1E,3E-diene 4 have been synthesized and their fluorescence emissions in
- Singh,Kanvah
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p. 965 - 973
(2007/10/03)
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- Synthesis and electronic spectra of substituted oligo(phenylenevinylene)s
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A series of substituted oligo(p-phenylenevinylene)s (OPVs) with five benzene rings was prepared via PO-activated olefinations and Knoevenagel condensations. The central ring is substituted with two octyloxy groups to ensure good solubility of the OPVs and the lateral styrene units carry further substituents, with either electron-accepting or donating character and also combinations thereof. The spectral features of these OPVs are dominated by the basic chromophore; further auxochrome groups on the lateral rings (meta and para positions) shift the absorption and emission spectra only slightly to longer wavelengths. Significant bathochromic shifts (absorption ca 20 nm, emission ca 40 nm) are observed for OPVs with cyano groups on the terminal vinylene segments. The absorption spectra are independent from the concentration and solvatochromism is very small. The OPVs are photochemically stable to near-UV irradiation (366 nm) in neutral solution, whereas mid-UV irradiation (254 nm) causes decomposition of the chromophore. The presence of traces of acids or amines leads to different photochemical pathways. Copyright
- Detert, Heiner,Sugiono, Erli
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p. 587 - 590
(2007/10/03)
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- Simple synthetic route to soluble polyimides via nitro-displacement reaction and their second-order nonlinear optical properties
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Nonlinear optical (NLO) functionalized polyimides were directly synthesized using the nitro-displacement reaction between an alkanediol monomer and a diimide monomer without a thermal curing step. The polyimides were soluble in aprotic polar solvents such
- Lee Yeong-Beom,Woo, Han Young,Yoon, Chong-Bok,Shim, Hong-Ku
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p. 2345 - 2350
(2007/10/03)
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- Synthesis of aryl(difluoromethylenephosphonates) via electrophilic fluorination of α-carbanions of benzylic phosphonates with N- fluorobenzenesulfonimide.
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The electrophilic fluorination of a wide variety of benzylic phosphonates with N-fluorobenzenesulfonimide has been examined. The fluorination reaction proceeds well in the presence of an array of functional groups such as nitro, bromo, ketone, ester, phenyl and ether groups. Phenyl and biphenyl derivatives containing two α,α-difluoromethylenephosphonate groups can also be prepared. This procedure is compatible with methyl or ethyl phosphonate esters but not with t-butyl esters or with benzylic phosphonates containing an additional benzylic moiety at the para-position.
- Taylor, Scott D.,Kotoris, Christopher C.,Dinaut, A. Nicole,Chen, Mei-Jin
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p. 1691 - 1714
(2007/10/03)
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- A Reinvestigation of the Preparation, Properties, and Applications of Aminomethyl and 4-Methylbenzhydrylamin
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Mild, efficient conditions have been developed for the preparation of 4-methylbenzhydrylamine polystyrene (MBHA) and aminomethyl polystyrene (AMPS) resins by a two-step procedure with synthons 1a and 1c. The products possess excellent swelling characteristics and acylate readily with linkers yielding useful derivatives, which retain good swelling and reactivity. Comparative studies with these resins, and their poly(ethylene glycol) (PEG) derivatives, yield insights into the role of spacer arm and environment effects in synthesis facilitation.
- Howard Adams,Cook, Ronald M.,Hudson, Derek,Jammalamadaka, Vasu,Lyttle, Matthew H.,Songster, Michael F.
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p. 3706 - 3716
(2007/10/03)
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