18979-55-0Relevant academic research and scientific papers
Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors
Alavi, Seyed Jamal,Seyedi, Seyed Mohammad,Saberi, Satar,Safdari, Hadi,Eshghi, Hossein,Sadeghian, Hamid
, p. 259 - 266 (2020/10/12)
In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).
Unprecedented Regioregular Poly(1,4-arylene)s Prepared by Nickel(II)-Catalyzed Cross-Coupling Polymerization of 2,5-Disubstituted Bromo(chloro)arylene
Shibuya, Yushin,Nakagawa, Naoki,Miyagawa, Naoki,Suzuki, Toyoko,Okano, Kentaro,Mori, Atsunori
, p. 9547 - 9550 (2019/06/24)
The unprecedented synthesis of regioregular head-to-tail-type poly(1,4-arylene)s bearing different substituents at the 2- and 5-positions is described. They were prepared by the polymerization of 2,5-disubstituted bromo(chloro)arylenes by selective halogen–metal exchange with a Grignard reagent and subsequent cross-coupling polymerization with a nickel catalyst [NiCl2(dppp)]. Formation of the regioregular poly(1,4-arylene)s were confirmed by NMR spectroscopy, and showed remarkable differences to those polymers having uncontrolled regioregularity. Polymerization of bromo(chloro)arylenes with a chiral alkoxy substituent also led to the regioregular head-to-tail-type polyarylene, which demonstrated circular dichroism, thus suggesting formation of a structure with higher-order regularity.
Chemoselective deoxygenation of ether-substituted alcohols and carbonyl compounds by B(C6F5)3-catalyzed reduction with (HMe2SiCH2)2
Yang, Wenyu,Gao, Lu,Lu, Ji,Song, Zhenlei
supporting information, p. 4834 - 4837 (2018/05/23)
B(C6F5)3-catalyzed deoxygenation of ether-substituted alcohols and carbonyl compounds has been developed using (HMe2SiCH2)2 as the reductant. This unique reagent shows distinct superiority over traditional one silicon-centered hydrosilanes, giving the corresponding alkanes in high yields with good tolerance of ethers, aryl halides and alkenes. The control experiments suggest that (HMe2SiCH2)2 might facilitate the approach in an intramolecular Si/O activation manner.
New phosphorescent platinum(ii) complexes with tetradentate C*N^N*C ligands: liquid crystallinity and polarized emission
Zhang, Shilin,Luo, Kaijun,Geng, Hao,Ni, Hailiang,Wang, Haifeng,Li, Quan
, p. 899 - 906 (2017/01/29)
New phosphorescent, liquid crystalline cyclometalated tetradentate platinum complexes (Pt-L16, Pt-L12 and Pt-L6) based on the tetradentate C*N^N*C ligands (C*N^N*C = 6,6′-bis(4-(alkoxy)-phenoxy)-2,2′-bipyridine) are designed and synthesized. Their crystal structure, and photophysical, electrochemical and liquid crystal characteristics were investigated. The X-ray structure of Pt-L12 shows a severe distortion of this complex towards a tetrahedral geometry. All complexes are emissive both in degassed solution and in the solid state at room temperature with emission maxima in the red region of the spectrum. Pt-L16 and Pt-L12 show monotropic smectic liquid crystal characteristics. Moreover, these liquid crystal complexes can be aligned on a rubbed nylon-6 glass substrate and produce polarized emission with a dichroic ratio of 5.1.
B(C6F5)3-Catalyzed Chemoselective Defunctionalization of Ether-Containing Primary Alkyl Tosylates with Hydrosilanes
Chatterjee, Indranil,Porwal, Digvijay,Oestreich, Martin
supporting information, p. 3389 - 3391 (2017/03/17)
Catalytic C(sp3)?O bond cleavage promoted by B(C6F5)3 /Et3SiH proceeds preferentially with primary tosylates in the presence of primary and secondary silyl ethers and aryl ethers. This reactivity difference enables the chemoselective defunctionalization of several 1,n-diols, and the efficiency of the new procedure is highlighted by the selective deoxygenation of the hydroxymethyl group of an orthogonally protected carbohydrate. Tosylates with an adjacent phenyl group are cleaved with anchimeric assistance.
Nonplanar Ladder-Type Polycyclic Conjugated Molecules: Structures and Solid-State Properties
Liu, Kuojin,Qiu, Feng,Yang, Chongqing,Tang, Ruizhi,Fu, Yubin,Han, Sheng,Zhuang, Xiaodong,Mai, Yiyong,Zhang, Fan,Feng, Xinliang
, p. 3332 - 3338 (2015/07/08)
Using an efficient intramolecular carbon-carbon cross-coupling reaction, a series of new ladder-type conjugated molecules have been prepared successfully in high yields. Such a pyran-fused polycylic structure possesses an extended π-conjugated backbone with flexible conformation, which gives these molecules interesting properties, including high solubility in common organic solvents, excellent thin film-forming abilities, blue fluorescent emission with good quantum yields, and aggregate formation in a binary solvent. The self-assembly behaviors of these molecules as well as various nanostructures can be finely tailored by varying the substituted group on the molecular periphery. The powder and single-crystal X-ray diffraction analyses revealed that the synergetic effect of π-π stacking and van der Waals interactions play a key role in controlling the morphologies of these aggregates. More importantly, self-assembled molecules exhibit good fluorescent performance, due to their twist backbone conformation. (Figure Presented).
Intramolecular charge transfer interactions and molecular order of rod like mesogens
Reddy, M. Guruprasad,Lobo, Nitin P.,Varathan,Easwaramoorthi,Narasimhaswamy
, p. 105066 - 105078 (2015/12/30)
A mesogenic 4-((4-(alkoxy)phenoxy)carbonyl)phenyl-4-(dimethylamino)benzoate series with terminal chains varying from C2 to C12 carbons (even number carbons only) are synthesised and their mesophase transitions are examined by hot-stage optical polarising microscopy as well as differential scanning calorimetry. Accordingly, enantiotropic nematic mesophase for all the homologs and an additional smectic A phase for the C12 homolog is observed. Powder X-ray diffraction studies confirm the interdigitated bilayer organization in the smectic A phase for the C12 homolog. It is remarkable that the mesogens under investigation only differ in the linking unit i.e. ester versus imine in contrast to recently reported mesogens, yet show a large difference in certain properties. Accordingly, the crystal structure of the C4 homolog reveals a triclinic lattice with P1 space group in which the molecules are packed in a slipped co-facial configuration. Additionally, a detailed investigation of the C12 mesogen by UV-visible and fluorescence spectroscopy as well as computational methods unveils interesting features. The fluorescence spectrum of the C12 mesogen is observed at 366 nm with a shoulder at 433 nm and a large solvent polarity induced red-shift is noticed in contrast to a structurally similar homolog examined recently. Further, the C12 mesogen in solvents such as ethyl acetate, dichloromethane, chloroform, tetrahydrofuran, acetonitrile and dimethyl sulfoxide exhibited dual emission. Therefore, density functional theory and time dependent density functional theory calculations are utilized to obtain insight. Besides variation in the dihedral angle between rings B and C for the C12 mesogen, it is found that the highest occupied molecular orbital (HOMO) is localized on the N,N-dimethylaminobenzene moiety while the lowest unoccupied molecular orbital (LUMO) is mostly concentrated on the phenyl benzoate unit. Time dependent-density functional theory (TD-DFT) calculations disclose the orbitals involved in the dominant excited state electronic transitions and their corresponding energies together with oscillator strength. The high resolution 1D and 2D separated local field (SLF) solid state 13C NMR investigation of the C12 mesogen lead to the orientational order parameters of the phenyl rings of the core in the SmAd phase. The temperature versus alignment induced chemical shifts reveals an increase in chemical shifts with a decrease in temperature in the smectic Ad phase in concurrence with order parameter values. Thus, understanding the photophysical properties of mesogens with dimethylamino moieties would facilitate better design of molecules for application in organic light emitting diodes for polarized emission.
AMINE COMPOUNDS HAVING ANTI-INFLAMMATORY, ANTIFUNGAL, ANTIPARASITIC AND ANTICANCER ACTIVITY
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, (2014/08/19)
Amine compounds having activity against inflammation, fungi, unicellular parasitic microorganisms, and cancer are described. The compounds contain a monocyclic, bicyclic, or tricyclic aromatic ring having one, two, or three ring nitrogen atoms.
Synthesis and liquid crystal property of new fluoro coumarin carboxylates
Mahadevan, Kittappa M.,Harishkumar, Hosanagara N.,Masagalli, Jagadeesh N.,Srinivasa, Hosapalya T.
, p. 20 - 35 (2013/08/24)
New liquid crystalline 4-alkoxyphenyl-coumarin-3-carboxylates 6a-e, 7a-g, 8a-e, and 9a-e were prepared by reacting various coumarin-3-carboxylic acids 5a-d with 4-(alkoxy) phenols 4a-g in the presence of 1(3-dimethylaminopropyl-3- ethylcarbodiimide/dimethyl amino pyridine (EDCI/DMAP) as a coupling agent. The structures of the new coumarin derivatives were confirmed by spectral analysis and the liquid crystalline property was established by polarizing optical microscope and by differential scanning calorimetric techniques. The diethyl amine and morpholine were taken as electron-donating and -CF3 as electron-withdrawing groups at the seventh position of the coumarin-3-carboxylic acids to check the mesomorphic property in all new 4-alkoxyphenyl-coumarin-3- carboxylates. Among them, only 4-alkoxyphenyl-7-triflouromethyl-coumarin-3- carboxylates 7a-g exhibited liquid crystalline SmA phase.
Heterogeneous palladium-catalyzed synthesis of aromatic ethers by solvent-free dehydrogenative aromatization: Mechanism, scope, and limitations under aerobic and non-aerobic conditions
Sutter, Marc,Lafon, Romain,Raoul, Yann,Metay, Estelle,Lemaire, Marc
supporting information, p. 5902 - 5916 (2013/09/23)
Starting from cyclohexanone derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. The process was also used with tetralone derivatives and polyols. Several reactions were performed to propose a mechanism for this transformation. The formation of an enol ether followed by a dehydrogenation reaction seem to be the key steps of this reaction. Aryl ethers were prepared in good yields and with good selectivities in a solvent-free and heterogeneous catalytic dehydrogenative alkylation of cyclohexanones with various alcohols. Three different complementary routes were used, and for the first time, non-aerobic, safe conditions could be used. Moreover, the catalyst could be recycled several times with no decrease in the yield of the aryl ether. Copyright
