33626-98-1Relevant articles and documents
Trinaphthylamines as robust organic materials for two-photon-induced fluorescence
Bordeau, Guillaume,Lartia, Rémy,Metge, Germain,Fiorini-Debuisschert, Céline,Charra, Fabrice,Teulade-Fichou, Marie-Paule
, p. 16836 - 16837 (2008)
The synthesis of a novel π-conjugated trinaphthylamines series is described. These original push?pull octupolar systems exhibit large two-photon action cross section (σφ up to 510 GM) increased by a factor of 2?3 as compared to their triphenylamines analogues. This substantial improvement of the two-photon absorption properties is attributed to the stronger donor character of the trinaphthyl core. Copyright
Photoactuators based on the dynamic molecular crystals of naphthalene acrylic acids driven by stereospecific [2+2] cycloaddition reactions
Liu, Jiaxi,Ye, Kaiqi,Shen, Yanbing,Peng, Jiang,Sun, Jingbo,Lu, Ran
supporting information, p. 3165 - 3175 (2020/03/19)
The photomechanical effects of the dynamic molecular crystals of halogen-substituted naphthalene acrylic acids (1FNaAA, 1ClNaAA, 1BrNaAA, 1INaAA and 6BrNaAA) have been investigated. Upon UV irradiation, the needle-like crystal of 1FNaAA curls away from the light source, while the slice-like crystal of 6BrNaAA bends towards the light source. Moreover, the light-induced bending, flipping and bursting are observed for the elongated needle-like crystals of 1FNaAA, and the slice-like crystals of 1ClNaAA and 1BrNaAA show bending, cracking, coiling, rotating and twisting triggered by 365 nm light. It is found that stereospecific [2+2] cycloaddition reactions take place in the crystals to afford one stereoisomer of β-type cyclobutanes, since 1FNaAA, 1ClNaAA, 1BrNaAA and 6BrNaAA pack in a head-to-head mode, which satisfies the Schmidt's topo-photochemical criteria. The strain can be generated and accumulated during the photodimerization, and the release of the strain leads to the photomechanical effects. This provides new clues for the development of photomechanical molecular crystals based on acrylic acids bearing halogen-substituted aromatic units.
Method for synthesizing adapalene intermediate 6-bromo-2-naphthoate
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Paragraph 0029-0034; 0047-0054, (2019/03/30)
The invention provides a method for synthesizing adapalene intermediate 6-bromo-2-naphthoate. The method comprises the following steps: 1), mixing 2-naphthalic acid and an organic solvent uniformly, adding a catalyst, performing stirring, introducing protective gas, controlling pressure at 4-7 atmospheres, controlling the temperature at 130-155 DEG C, maintaining the conditions for 50-70 minutes,then adding dropwise a mixed aqueous solution containing bromide salt and benzenesulfonic acid, adding dropwise an aqueous solution containing only hypobromite, controlling the total dropwise additiontime within 90-150 minutes, heating the system to 165-180 DEG C after dropwise addition, raising pressure to 11-17 atmospheres to continue the reaction for 5-7 hours and ending the reaction; 2) removing solid by filtering while the mixed solution is hot, adding the solid to ice water with weight 3-5 times that of the filtrate, and performing extraction, drying, evaporative concentration for removing a solvent to obtain a product. The method has high yield, and no harmful substances are discharged.
Enantioselective α-Benzylation of Acyclic Esters Using π-Extended Electrophiles
Schwarz, Kevin J.,Yang, Chao,Fyfe, James W. B.,Snaddon, Thomas N.
supporting information, p. 12102 - 12105 (2018/09/11)
The first asymmetric cooperative Lewis base/palladium catalyzed benzylic alkylation of acyclic esters is reported. This reaction proceeds via stereodefined C1-ammonium enolate nucleophiles. Critical to its success was the identification of benzylic phosphate electrophiles, which were uniquely reactive. Alkylated products were obtained with very high levels of enantioselectivity, and this method has been applied toward the synthesis of the thrombin inhibitor DX-9065a.
N - heterocyclic compound, intermediate, preparation method, pharmaceutical composition and application (by machine translation)
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Paragraph 0153; 0154; 0155; 0156; 0157, (2017/10/31)
The invention discloses a N - heterocyclic compound, intermediate, preparation method, pharmaceutical composition and application. The invention of SHP2 N - heterocyclic compound to have high selectivity, can effectively inhibit the cell in the SHP2 downstream signal path ERK phosphorylation level, to tumor cells has very good inhibition activity, it has broad drug development prospects; its preparation method is simple, mild reaction conditions, high yield and purity, after treatment is simple, environmental protection, and is favorable for industrial production. (by machine translation)
Liquid crystal compound, a liquid crystal display element and a liquid crystal composition (by machine translation)
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Paragraph 0172; 0173, (2016/10/07)
PROBLEM TO BE SOLVED: high stability to light, high point, a lower limit temperature of the crystal phase, low viscosity, appropriate optical anisotropy, large dielectric constant anisotropy, large dielectric constant of the short axis direction, a suitable elastic constant, physical properties such as compatibility with at least one of a liquid crystalline compound satisfiability 1, a liquid crystal composition, the composition of the liquid crystal display element. SOLUTION: compound represented by eq. (1). (R 1 the C1-15 alkyl; ring A 1-ring A 4 is 1,4 - 1,4-phenylene; Z 1-Z 5 cyclometallized ethylxylene or to at least one of the 1-CF 2 O-; X 1 or fluorine-OCF 3; W 1 and W 2 are independent of the specific position, H, F, or chlorine substituted 1,4-phenylene group or naphthalene -2,6-diyl group; each a-d, 0 or 1) selected drawing: no (by machine translation)
Discovery and crystallography of bicyclic arylaminoazines as potent inhibitors of HIV-1 reverse transcriptase
Lee, Won-Gil,Frey, Kathleen M.,Gallardo-Macias, Ricardo,Spasov, Krasimir A.,Chan, Albert H.,Anderson, Karen S.,Jorgensen, William L.
, p. 4824 - 4827 (2015/10/28)
Non-nucleoside inhibitors of HIV-1 reverse transcriptase (HIV-RT) are reported that incorporate a 7-indolizinylamino or 2-naphthylamino substituent on a pyrimidine or 1,3,5-triazine core. The most potent compounds show below 10 nanomolar activity towards wild-type HIV-1 and variants bearing Tyr181Cys and Lys103Asn/Tyr181Cys resistance mutations. The compounds also feature good aqueous solubility. Crystal structures for two complexes enhance the analysis of the structure-activity data.
Design and synthesis of 2-phenylnaphthalenoids and 2-phenylbenzofuranoids as DNA topoisomerase inhibitors and antitumor agents
Hao, Huilin,Chen, Wang,Zhu, Jing,Lu, Chunhua,Shen, Yuemao
, p. 277 - 287 (2015/09/01)
Abstract Eight 2-phenylnaphthalenoids (2PNs) (3a-h) and twenty four 2-phenylbenzofuranoids (2PBFs) (4a - 4j, 5a-5j, 6a, 6f-6h) were successfully designed, synthesized and their antiproliferative and in vitro DNA topoisomerase inhibitory activities were evaluated. Nine compounds (four 2PNs and five 2PBFs) showed either TopoI or TopoIIα inhibitory activities. Six compounds (four 2PNs and two 2PBFs) exhibited potent cytotoxicity with IC50 values for 72 h exposure ranging from 0.3 to above 20 μM against MDA-MB-231, MDA-MB-435, HepG2 and PC3 cell lines. The two 2PBFs displayed comparable and even better antiproliferative as well as TopoIIα inhibitory activities than 2PNs. Interestingly, the active 2PBFs displayed different mechanisms of TopoIIα inhibition from that of 2PNs, suggesting that the chromophore scaffold replacement may result in a change of the binding site of inhibitors to TopoIIα. Furthermore, the mechanisms of antiproliferation on MDA-MB-231 cells indicate that compounds 5a and 5f are promising for further development of anticancer agents. The results of this study reveal that the evolutionary strategy of medicinal chemistry through scaffold hopping is a promising strategy for structure optimization of TopoIIα inhibitors.
Synthesis of mono- and bibrachial naphthalene-based macrocycles with pyrene or ferrocene units for anion detection
Granzhan, Anton,Teulade-Fichou, Marie-Paule
experimental part, p. 1349 - 1360 (2009/04/18)
Three bibrachial cyclobisintercaland-type macrocycles with a 2,6-naphthylene scaffold and pyrene, ferrocene, or primary amino groups in side chains were synthesized by a [2+2]-cyclocondensation of functionalized diethylenetriamine derivatives with naphthalene-2,6-dialdehyde, whereas their monobrachial counterparts were prepared by a [1+1]-cyclocondensation of polyamines with a corresponding dialdehyde building block. The pyrene-functionalized macrocycles are able to bind orthophthalate and terephthalate anions in aqueous medium, as monitored by the changes in their fluorescence (excimer or monomer) properties.
Structural modifications of 6-naphthalene-2-carboxylate retinoids
Yu, Kuo-Long,Ostrowski, Jacek,Chen, Simon,Tramposch, Kenneth M.,Reczek, Peter R.,Mansuri, Muzammil M.,Starrett Jr., John E.
, p. 2865 - 2870 (2007/10/03)
The keto linker of 2-naphthoate retinoid 1 has been found nonessential for RAR transactivation activity and can be replaced with heteroatoms such as S, O, N without significant reduction of the activity. On the other hand, substitutions on the aromatic rings of retinoids 1 and 2 resulted in analogs with reduced potentcy and RAR selectivity.
