10075-63-5Relevant academic research and scientific papers
An efficient reduction of nitro and bromine naphthalene derivatives
Dong,Zhang,Huang,Meng,Li
, p. 837 - 841 (2017)
Reduction of 1,5-dimethoxy-4-nitronaphthalene by hydrazine hydrate was optimized in the course of current study. Influence of metals, temperature and solvents upon the process was tested. Yield of the reaction was the highest in the presence of Zn powder in DMF. Moderate heating made the process slightly more efficient than that at room temperature, whereas high temperature led to a decreased yield. The current approach made it possible to exclude high pressure and diminish experimental costs.
Structure-property relationship of D-A type copolymers based on phenanthrene and naphthalene units for organic electronics
Kim, Yeong-A,Kang, Minji,Jeon, Ye-Jin,Hwang, Kyeongil,Kim, Yeon-Ju,Jang, Soo-Young,Kim, In-Bok,Kwon, Gucheol,Kim, Dong-Yu
, p. 10332 - 10342 (2017)
Four donor-acceptor (D-A) type conjugated polymers (PA1, PA2, PA3 and PA4) based on phenanthrene and naphthalene as the donating units with or without dimethoxy substitution were synthesized for organic field effect transistors (OFETs) and bulk-heterojunction organic photovoltaics (OPVs). Dimethoxy substituents have significant effects on the optical, electrochemical, charge transport and photovoltaic properties depending on the donor-polyaromatic (PA) compounds. The optical band gaps of these PA-based copolymers from the smallest to the largest are as follows: 1.52 eV (1,5-dimethoxy substituted naphthalene (PA4)), 1.59 eV (unsubstituted naphthalene (PA3)), and 1.63 eV (unsubstituted phenanthrene (PA1), and substituted 9,10-dimethoxy phenanthrene (PA2)). While the values vary depending on the compounds, both PA2 and PA4 are found to have higher highest occupied molecular orbital (HOMO) energy levels than those of PA1 and PA3 due to the electron donating nature of dimethoxy substituents. The PA based copolymers without dimethoxy substituents showed highly balanced ambipolar behavior with ～1 cm2 V-1 s-1, whereas the electron mobility of dimethoxy modified PA (MeOPA) based copolymers was suppressed. The inverted bulk heterojunction OPVs based on PA1 and PA3 exhibited power conversion efficiency (PCE) as high as 5.3% and 5.8%, respectively. The PCEs of PA copolymer-based OPV devices were mainly affected by an increase in the open circuit voltage rather than by the photocurrent or fill factor.
Crystal structures, DFT calculations and Hirshfeld surface analysis of two (E)-3-(aryl)-1-(naphthalen-1-yl)prop-2-en-1-one chalcone derivatives, potential Mycobacterium tuberculosis Enoyl ACP reductase (InhA) inhibitors and optical materials: conformational differences within the prop-2-en-1-one unit
Albuquerque, Magaly Gir?o,Gon?alves, Raoni Schroeder B.,Lima, Camilo Henrique da Silva,Machado, Sérgio de Paula,Maia, Fernanda Lima de Azevedo,Oliveira, Laudicéa do Nascimento,Wardell, James L.,Wardell, Solange M. S. V.,da Silva, Talis Uelisson
, (2021)
A combined structural and computational study has been conducted on two chalcone compounds, namely (E)-3-(4-bromophenyl)-1-(4,8-dimethoxynaphthalen-1-yl)prop-2-en-1-one (1), and (E)-3-(3,4-dichlorophenyl)-1-(4,8-dimethoxynaphthalen-1-yl)prop-2-en-1-one (2). These compounds are members of a series of compounds identified from a molecular modelling study as potentially active Mycobacterium tuberculosis Enoyl ACP reductase (InhA) inhibitors. In addition, the computational study indicated that the compounds have potential as optical materials. The combined study revealed that both molecules in the solid state displayed similar overall molecular conformations between a ‘‘T’’ and a ‘‘Y’’ shape, but with different arrangements in the bridging prop-2-en-1-one unit: an anti-periplanar in 1 and a syn-periplanar in 2. The experimental and calculated bond lengths and angles for anti-periplanar 1 and syn-periplanar 2 were generally in good agreement.Theoretical calculations at the B3LYP/DGTZVP level in the gas phase, DMSO and water media indicated that for both compounds, the syn-periplanar form was the energy local minimum while the anti-periplanar form was the energy global minimum. However, the energy differences are very small, with slight variations when using the different basis sets (0.80 and 0.84 kcal/mol using the B3LYP/DGTVP theory level in gas phase, 0.28 and 0.32 in DMSO and 0.27 and 0.31 kcal/mol in water). The differences in the solid state arrangements within the bridging prop-2-en-1-one unit in 1 and 2 arise from variations in the intermolecular interactions, with halogen bonds being considered to be an important factor in stabilizing a syn-periplanar arrangement in compound 2. PLATON and Hirshfeld surface analyses confirmed the important intermolecular interactions in 1 and 2. Calculations were also carried out on the electronic and vibrational spectra, dipole moments and charge distributions of 1 and 2. The HOMO was located in the dimethoxynaphthalenyl region of the molecule with mild donor character, while the LUMO was located in the propenyl and phenyl regions of each molecule. The energy gaps between these orbitals are 3.35 eV for 1 3.25 eV for 2. The delocalization present in compounds 1 and 2 facilitates the HOMO-LUMO charge transfer process. The total electronic molecular dipolar moments (μTotal) were calculated to be 4.1511 and 5.9316 D for 1 and 2, respectively. The values of μTotal found for 1 and 2 are both larger than reported values for similar compounds, indicating that the compounds studied here should exhibit a good non-linear optical response.
Prekinamycin and an isosteric-isoelectronic analogue exhibit comparable cytotoxicity towards K562 human leukemia cells
Abbott, Glenn L.,Wu, Xing,Zhao, Zhufeng,Guo, Lei,Birman, Vladimir B.,Hasinoff, Brian B.,Dmitrienko, Gary I.
, p. 1364 - 1370 (2014)
The synthesis of N-cyanobenzo[b]carbazoloquinone 4, an isosteric- isoelectronic analogue of prekinamycin, is described. Cytotoxicity studies with K562 human leukemia cells reveal that the cyanamide analogue has a bioactivity profile similar to that of pre
An efficient synthesis of 2-formyM,4,5,8-tetramethoxynaphthalene
Wang, Rubing,Zheng, Xiaogang,Zhou, Wen,Peng, Ying,Zhu, Mengyuan,Li, Shaoshun
, p. 520 - 521 (2010)
An improved synthetic method of 2-formyl-1,4,5,8-tetramethoxynaphthalene in 73% overall yield is described. This method has several advantages compared with the reported synthesis: first, the reactant is cheaper and the yield is higher; second, the reaction condition is milder and the reagent used is more friendly to environment; third, the work-up of each step is simpler; fourth, the protocol reported is more suitable for large-scale preparation.
Discovery of heterocycle-containing α-naphthoflavone derivatives as water-soluble, highly potent and selective CYP1B1 inhibitors
Dong, Jinyun,Huang, Guang,Cui, Qing,Meng, Qingqing,Li, Shaoshun,Cui, Jiahua
, (2021)
Cytochrome P450 1B1 (CYP1B1) has been well validated as an attractive target for cancer prevention and drug resistance reversal. In continuation of our interest in this area, herein, a set of forty-six 6,7,10-trimethoxy-α-naphthoflavone derivatives varying in B ring was synthesized and screened against CYP1 enzymes, leading to the identification of fluorine-containing compound 15i as the most potent and selective CYP1B1 inhibitor (IC50 value of 0.07 nM), being 84-fold more potent than that of the template molecule ANF. Alternatively, the amino-substituted derivative 13h not only possessed a potent inhibitory effect on CYP1B1 (IC50 value of 0.98 nM), but also had a substantially increased water solubility as compared with the lead ANF (311 μg/mL for 13h and 5 μg/mL for ANF). The current study expanded the structural diversity of CYP1B1 inhibitors, and compound 13h could be considered as a promising starting point with great potential for further studies.
Regioselective Monomethylation of Unsymmetrical Naphthalenediols with Methanolic HCl
Bell, Kevin H.,McCaffery, Leslie F.
, p. 731 - 737 (1993)
Treatment of naphthalene-1,3-diol and naphthalene-1,7-diol with methanol containing dry hydrogen chloride at room temperature gives exclusively 3-methoxy-1-naphthol and 7-methoxy-1-naphthol, respectively.Of the other two unsymmetrical naphthalenediols, the 1,2-isomer was unreactive and the 1,6-isomer gave a mixture of regioisomers under the same conditions.Two symmetrical diols (the 1,5- and 2,7-isomers) examined by the same procedure gave the monomethyl ethers in 60-70percent yields.
Total Synthesis of Shikalkin
Terada, Akira,Tanoue, Yasuhiro,Hatada, Akira,Sakamoto, Hiroshi
, p. 987 - 988 (1983)
The first total syntheses of dihydroshikalkin and shikalkin were accomplished.
Selective bromination of 1-bromonaphthalene: Efficient synthesis of bromonaphthalene derivatives
Cakmak, Osman,Demirtas, Ibrahim,Balaydin, Halis T
, p. 5603 - 5609 (2002)
Selective and specific preparation methods are described for 1,4-dibromonaphthalene, 1,5-dibromonaphthalene and 1,3,5-tribromonaphthalene. The reaction of 1-bromonaphthalene and naphthalene with stoichometric quantities of bromine by using a minimum amount of solvent (methylene chloride) at -30 and -50°C smoothly affords 1,4-dibromonaphthalene in 90% yield. Photobromination of 1-bromonaphthalene in CCl4 at -30°C gives 1,2,3,4,5-pentabromo-1,2,3,4-tetrahydronaphthalenes, whereas 1,5-dibromonaphthalene is obtained at reflux (77°C) in 80% yield under the same conditions. Dehydrobromination of the pentabromide by t-BuOK affords 1,3,5-tribromonaphthalene as a sole product (91%). 1,5-Dibromo- and 1,3,5-tribromonaphthalenes were efficiently converted to the corresponding methoxy naphthalene derivatives.
Oxidative dimerization of 4-methoxynaphthylamines in the presence of semiconductors
Takeya, Tetsuya,Takahashi, Yosuke,Okamoto, Iwao,Tamura, Osamu
, p. 1479 - 1488 (2010)
Three types of 4-methoxynaphthylamines 4a-c were oxidized by treatment with metal oxides under molecular oxygen (O2). 4-Methoxy-1-naphthylamine 4a and 4,6-dimethoxy-1-naphthylamine 4b, on treatment with TiO2 under O2, gave mainly 2-amino-1,4-naphthoquinone derivatives 5a and 5b, respectively whereas 4,8-dimethoxy-1-naphthylamine 4c afforded an unique carbazole 6c as the major product.
