Abstract
C19H14F4O2, monoclinic, P21/c (no. 14), a = 11.8614(10) Å, b = 7.9148(6) Å, c = 16.7999(16) Å, β = 99.150(9)°, V = 1557.1(2) Å3, Z = 4, R gt (F) = 0.0446, wR ref (F 2) = 0.1150, T = 100 K.
Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.
Data collection and handling.
| Crystal: | Colourless block |
| Size: | 0.13 × 0.12 × 0.11 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.13 mm-1 |
| Diffractometer, scan mode: | SuperNova |
| θ max, completeness: | 25.5°, >99% |
| N(hkl)measured, N(hkl)unique, R int: | 6570, 2891, 0.033 |
| Criterion for I obs, N(hkl)gt: | I obs > 2σ(I obs), 2362 |
| N(param)refined: | 227 |
| Programs: | CRYSALISPRO [1], SHELX [2, 3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | U iso*/U eq |
|---|---|---|---|---|
| C1 | 0.28309 (15) | 0.5351 (2) | 0.78121 (11) | 0.0242 (4) |
| C2 | 0.27811 (15) | 0.5544 (2) | 0.86916 (11) | 0.0236 (4) |
| C3 | 0.36931 (15) | 0.6621 (2) | 0.91647 (11) | 0.0284 (4) |
| H3A | 0.367680 | 0.648498 | 0.973661 | 0.034* |
| H3B | 0.354869 | 0.779988 | 0.902764 | 0.034* |
| C4 | 0.48686 (16) | 0.6116 (3) | 0.89791 (11) | 0.0327 (5) |
| H4A | 0.543716 | 0.689546 | 0.924611 | 0.039* |
| H4B | 0.505830 | 0.499491 | 0.919318 | 0.039* |
| C5 | 0.59270 (16) | 0.6416 (2) | 0.77932 (12) | 0.0323 (5) |
| H5 | 0.658930 | 0.662887 | 0.815598 | 0.039* |
| C6 | 0.59774 (17) | 0.6400 (2) | 0.69787 (12) | 0.0322 (5) |
| H6 | 0.666504 | 0.657909 | 0.679216 | 0.039* |
| C7 | 0.49842 (17) | 0.6113 (2) | 0.64475 (11) | 0.0287 (4) |
| C8 | 0.39622 (16) | 0.5805 (2) | 0.67011 (11) | 0.0269 (4) |
| H8 | 0.330568 | 0.560696 | 0.633021 | 0.032* |
| C9 | 0.39252 (15) | 0.5795 (2) | 0.75310 (11) | 0.0236 (4) |
| C10 | 0.49092 (15) | 0.6120 (2) | 0.80877 (11) | 0.0262 (4) |
| C11 | 0.19726 (15) | 0.4668 (2) | 0.89900 (11) | 0.0255 (4) |
| H11 | 0.151055 | 0.397381 | 0.862845 | 0.031* |
| C12 | 0.17339 (14) | 0.4679 (2) | 0.98250 (11) | 0.0237 (4) |
| C13 | 0.14704 (14) | 0.3193 (2) | 1.02263 (11) | 0.0222 (4) |
| C14 | 0.12003 (14) | 0.3241 (2) | 1.09972 (11) | 0.0236 (4) |
| H14 | 0.103418 | 0.224366 | 1.124732 | 0.028* |
| C15 | 0.11756 (14) | 0.4778 (2) | 1.14019 (11) | 0.0239 (4) |
| C16 | 0.14380 (15) | 0.6255 (2) | 1.10272 (11) | 0.0256 (4) |
| H16 | 0.143609 | 0.728480 | 1.129337 | 0.031* |
| C17 | 0.17037 (15) | 0.6187 (2) | 1.02523 (11) | 0.0268 (4) |
| H17 | 0.186882 | 0.719063 | 1.000702 | 0.032* |
| C18 | 0.0905 (2) | 0.6203 (2) | 1.26099 (12) | 0.0370 (5) |
| H18A | 0.166907 | 0.663892 | 1.271356 | 0.056* |
| H18B | 0.064546 | 0.597491 | 1.311225 | 0.056* |
| H18C | 0.041027 | 0.701959 | 1.231018 | 0.056* |
| C19 | 0.15198 (15) | 0.1506 (2) | 0.98292 (11) | 0.0268 (4) |
| F1 | 0.50222 (10) | 0.61374 (15) | 0.56421 (7) | 0.0421 (3) |
| F2 | 0.25497 (9) | 0.11891 (13) | 0.96276 (8) | 0.0411 (3) |
| F3 | 0.07742 (10) | 0.13620 (13) | 0.91407 (7) | 0.0377 (3) |
| F4 | 0.12968 (10) | 0.02243 (12) | 1.02984 (7) | 0.0356 (3) |
| O1 | 0.20172 (11) | 0.48343 (16) | 0.73312 (8) | 0.0323 (3) |
| O2 | 0.08882 (11) | 0.46776 (15) | 1.21546 (8) | 0.0307 (3) |
Source of material
5 mL of sodium hydroxide aqueous solution (25%) was added dropwise to the mixture of 7-fluoro-3,4-dihydronaphthalen-1(2H)-one (700 mg, 4.26 mmol) and 4-methoxy-2-(trifluoromethyl)benzaldehyde (870 mg, 4.26 mmol) in 10 mL methanol and stirred at room temperature for 4 h. The in process-control was monitored by silica gel thin layer chromatography (TLC, 254 nm). When the reaction was finished, the precipitate was suction filtered out, and a 50% methanol aqueous solution was added dropwise to wash, and the filter cake was vacuum dried at 65 °C to obtain a light yellow solid. Suitable crystals of the title compound were obtained by recrystallization in dichloromethane and methanol (1:1, v/v) system and dried under vacuum at 65 °C for 5 h.
Experimental details
The H atoms were placed in idealized positions and treated as riding on their parent atoms, with d(C–H) = 0.96 Å (methyl), U iso(H) = 1.5 U eq(C), and d(C–H) = 0.97 Å (methylene), U iso(H) = 1.2U eq(C), and d(C–H) = 0.93 Å (aromatic), U iso(H) = 1.2U eq(C). Displacement ellipsoids are drawn at the 40% probability level.
Comment
Studies have shown that the development of an anti-inflammatory and low toxic NF-/KB inhibitor is of great significance for the treatment of inflammatory neurodegenerative CNS diseases [4], [5], [6].
Existing studies have used 3,4-dihydronaphthalen-1(2H)-one (DHN) derivatives with anti-tumor and anti-inflammatory activities as novel allergic and inflammatory responses modifiers [7] and as potential retinoic acid (RA)-metabolizing enzymes inhibitors to treat skin diseases and cancer. However, there are few studies on DHN derivatives as anti-neuroinflammatory drugs. Therefore, it is of great significance to study the synthesis and crystal structure of novel benzylidene-substituted DHN derivatives with anti-neuroinflammatory activity. Our group also synthesized some of these compounds in the early stage, and studied their anti-neuroinflammatory activity. The results showed that the fluorine-substituted compounds had better activity [8], [9], [10]. In this study, a new benzylidene-substituted DHN derivative was designed and synthesized through Claisen–Schmidt condensation reactions (see the Figure).
Single-crystal structure analysis revealed that the title compound crystallized in the monoclinic space group P21/c. The ORTEP diagram is presented in the Figure. Bond lengths and angles are all in the expected ranges [11–13]. There is only one molecule in the asymmetric unit. The molecule adopts the E stereochemistry [14]. The 3,4-dihydronaphthalen-1(2H)-one, the 7-fluorophenyl and 4-methoxy-2-(trifluoromethyl) phenyl groups are not coplanar. This twisted configuration may increase likelihood of interactions with bioactive molecules, for the purposes of creating more potent biological activity [15].
Funding source: Science and Technology Innovation Development Plan of Yantai
Award Identifier / Grant number: 2020XDRH105
Funding source: National Natural Science Foundation of China 10.13039/501100001809
Award Identifier / Grant number: 81473104
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Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Research funding: This work was supported by Science and Technology Innovation Development Plan of Yantai (No. 2020XDRH105) and the National Natural Science Foundation of China (No. 81473104).
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Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
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© 2021 Qing-Guo Meng et al., published by De Gruyter, Berlin/Boston
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