Startseite Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
Artikel Open Access

Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5

  • Dong-li Jiang ORCID logo , Yang Liu , Ying Cui und Rui Li ORCID logo EMAIL logo
Veröffentlicht/Copyright: 29. April 2024

Abstract

C23H24O5, monoclinic, C2 (no. 4), a = 23.958(2) Å, b = 5.8145(5) Å, c = 17.839(3) Å, β = 129.974(3)°, V = 1904.3(4) Å3, Z = 4, Rgt (F) = 0.0435, wRref (F 2) = 0.1140, T = 153(2) K.

CCDC no.: 2348593

The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.12 × 0.11 × 0.10 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.09 mm−1
Diffractometer, scan mode: Bruker Apex-II, φ and ω
θ max, completeness: 27.7°, >99 %
N(hkl)measured, N(hkl)unique, R int: 31,278, 4413, 0.050
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3832
N(param)refined: 257
Programs: Bruker, 1 Olex2, 2 SHELX 3
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x y z U iso*/U eq
C1 0.07244 (16) 0.5877 (7) 0.1310 (2) 0.0317 (7)
H1A 0.081880 0.607079 0.085405 0.048*
H1B 0.091135 0.721498 0.174424 0.048*
H1C 0.019871 0.574017 0.094022 0.048*
C2 0.20363 (19) −0.0922 (6) 0.3999 (2) 0.0306 (7)
H2A 0.165465 −0.186716 0.389851 0.046*
H2B 0.228384 −0.002727 0.460205 0.046*
H2C 0.238968 −0.191867 0.405081 0.046*
C3 0.21729 (15) 0.2173 (5) 0.3252 (2) 0.0195 (5)
C4 0.18294 (14) 0.3930 (5) 0.2544 (2) 0.0197 (5)
C5 0.22381 (15) 0.5614 (5) 0.2548 (2) 0.0205 (5)
H5 0.200278 0.680105 0.207064 0.025*
C6 0.30001 (15) 0.5571 (5) 0.3256 (2) 0.0197 (5)
H6 0.328005 0.673829 0.326085 0.024*
C7 0.33467 (15) 0.3827 (5) 0.39490 (19) 0.0188 (5)
C8 0.29290 (16) 0.2123 (5) 0.3943 (2) 0.0201 (5)
H8 0.316504 0.092390 0.441453 0.024*
C9 0.41623 (15) 0.3701 (5) 0.4659 (2) 0.0211 (6)
H9A 0.431344 0.209254 0.469386 0.025*
H9B 0.435575 0.466233 0.441327 0.025*
C10 0.45513 (15) 0.6765 (5) 0.5790 (2) 0.0212 (6)
C11 0.44945 (17) 0.9385 (6) 0.6850 (2) 0.0288 (7)
H11A 0.474945 0.985807 0.752683 0.043*
H11B 0.400012 0.888322 0.655004 0.043*
H11C 0.446967 1.068587 0.647976 0.043*
C12 0.49109 (15) 0.7380 (5) 0.6837 (2) 0.0213 (6)
H12 0.488409 0.601270 0.715261 0.026*
C13 0.57095 (15) 0.7961 (5) 0.7396 (2) 0.0192 (6)
C14 0.59138 (16) 1.0053 (5) 0.7215 (2) 0.0205 (6)
H14 0.554732 1.105465 0.671227 0.025*
C15 0.66343 (15) 1.0639 (5) 0.7757 (2) 0.0196 (5)
H15 0.675846 1.204884 0.762727 0.023*
C16 0.71979 (15) 0.9174 (5) 0.8510 (2) 0.0178 (5)
C17 0.69964 (15) 0.7055 (5) 0.86724 (19) 0.0168 (5)
C18 0.62481 (15) 0.6494 (5) 0.8104 (2) 0.0179 (5)
H18 0.611596 0.507254 0.821487 0.021*
C19 0.75529 (15) 0.5588 (5) 0.9428 (2) 0.0185 (5)
H19 0.742719 0.414228 0.953087 0.022*
C20 0.82703 (16) 0.6235 (5) 1.0012 (2) 0.0206 (6)
H20 0.863704 0.525299 1.052455 0.025*
C21 0.84656 (15) 0.8364 (5) 0.9851 (2) 0.0196 (6)
C22 0.79457 (15) 0.9802 (5) 0.9108 (2) 0.0195 (6)
H22 0.808403 1.120303 0.899336 0.023*
C23 0.94448 (17) 1.0936 (6) 1.0419 (3) 0.0323 (7)
H23A 0.930856 1.106687 0.977169 0.048*
H23B 0.997548 1.104313 1.092471 0.048*
H23C 0.921618 1.218253 1.050656 0.048*
O1 0.10803 (10) 0.3847 (4) 0.18783 (14) 0.0250 (5)
O2 0.17161 (11) 0.0610 (4) 0.31876 (16) 0.0265 (5)
O3 0.44821 (11) 0.4473 (3) 0.56452 (14) 0.0217 (4)
O4 0.43538 (13) 0.8145 (4) 0.51544 (16) 0.0309 (5)
O5 0.92049 (11) 0.8785 (4) 1.04958 (15) 0.0249 (5)

1 Source of materials

Naproxen acylchloride was synthesized according to the literature method. 4 3,4-Dimethoxybenzyl alcohol (0.01 mol, 1.69 g) and 4-(dimethylamino)-pyridin (DMAP, 0.0015 mol, 0.18 g) were dissolved in dry tetrahydrofuran (20 mL) and triethylamine (0.015 mol, 2 mL). The solution of naproxen acylchloride in dry tetrahydrofuran was dropwise added at 0 °C. The reaction mixture was stirred for 2 h at room temperature. The mixture was filtrated to remove the solid and the filtrate was concentrated under vacuum to remove the solvent. The residue was dissolved in dichloromethane, successively washed with 5 % NaOH solution and water to pH = 7, and dried with anhydrous Na2SO4. The solution was filtrated, and concentrated under vacuum to obtain crude product. The crude product was purified by recrystallization in ethanol. The crystals were obtained from tetrahydrofuran solution.

2 Experimental details

Coordinates of hydrogen atoms were refined with constraints. The U iso values were set to be 1.5U eq of the carrier atom for methyl H atoms and 1.2U eq for the remaining H atoms.

3 Comment

Naproxen is one of the strongest non-steroidal anti-inflammatory drugs (NSAIDs), inhibits the cyclooxygenase (COX) enzymes both COX-1 and COX-2. Inhibits both COX-1 and COX-2 which are the enzymes of cyclooxygenase (COX). Naproxen displays analgesic, anti-inflammatory, and antipyretic activity. In addition, the researchers reported anticancer l activities of naproxen derivatives. 5 In cure of advancing prostate cancer, naproxen was discovered to be reliable and effective with early repetitive disease in a phase II clinical trial. 6 By inducing apoptosis and cell cycle arrest toward bladder cancer cells, naproxen displayed anticancer influences. Naproxen inhibited protein kinase B (AKT) phosphorylation and induced apoptosis in rat urinary bladder cancers. 7 In order to achieve high efficiency, low toxicity and cost anti-tumor drugs, we chose naproxen as a core compound and modify its structures.

There is one title molecule in the asymmetric unit. The title compound contained one pyridine ring and one naphthyl moiety. The bond distances of C–O are 1.467(3) Å (C9–O3), 1.347(3) Å (C10–O3), 1.377(3) Å (C4–O1), 1.428(4) Å (C1–O1), 1.379(3) Å (C21–O5), 1.419(4) Å (C23–O5), 1.370(3) Å (C3–O2), 1.431(4) (C2–O2), and 1.210(4) Å (C10–O4), respectively. The bond distance of C10–O4 is shorter than those of C9–O3, C10–O3, C4–O1, C4–O1, C1–O1, C21–O5, C23–O5, C3–O2 and C2–O2, indicating C10–O4 is double bond. The dihedral angles of ring 1 (C3–C4–C5–C6–C7–C8) and ring 2 (C13–C14–C15–C16–C17–C18), ring 1 (C3–C4–C5–C6–C7–C8) and ring 3 (C16–C17–C19–C20–C21–C22), ring 2 (C13–C14–C15–C16–C17–C18) and ring 3 (C16–C17–C19–C20–C21–C22) are 7.062°, 7.511°, 3.201°, respectively. The other bond distances and angles are in their normal ranges according to the previously reported compounds. 8 10


Corresponding author: Rui Li, China–Japan Union Hospital of Jilin University, Changchun 130021, China, E-mail:

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1. Bruker. SAINT and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2000.Suche in Google Scholar

2. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. OLEX2: A Complete Structure Solution, Refinement and Analysis Program. J. Appl. Crystallogr. 2009, 42, 339–341; https://doi.org/10.1107/s0021889808042726.Suche in Google Scholar

3. Sheldrick, G. M. Crystal Structure Refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar

4. Huang, Z.; Velázquez, C. A.; Abdellatif, K. R. A.; Chowdhury, M. A.; Reisz, J. A.; DuMond, J. F.; King, S. B.; Knaus, E. E. Ethanesulfohydroxamic Acid Ester Prodrugs of Nonsteroidal Anti-inflammatory Drugs (NSAIDs): Synthesis, Nitric Oxide and Nitroxyl Release, Cyclooxygenase Inhibition, Anti-inflammatory, and Ulcerogenicity Index Studies. J. Med. Chem. 2011, 54, 1356–1364; https://doi.org/10.1021/jm101403g.Suche in Google Scholar PubMed

5. Han, M. I.; Kucukguzel, S. G. Anticancer and Antimicrobial Activities of Naproxen and Naproxen Derivatives. Mini Rev. Med. Chem. 2020, 20, 1300–1310; https://doi.org/10.2174/1389557520666200505124922.Suche in Google Scholar PubMed

6. Srinivas, S.; Feldman, D. A Phase II Trial of Calcitriol and Naproxen in Recurrent Porstate Cancer. Anticancer Res. 2009, 29, 3605–3610.Suche in Google Scholar

7. Kim, M. S.; Kim, J. E.; Lim, D. Y.; Huang, Z.; Chen, H.; Langfald, A.; Lubet, R. A.; Grubbs, C. J.; Dong, Z.; Bode, A. M. Naproxen Induces Cell Cycle Arrest and Apoptosis in Human Urinary Bladder Cancer Cell Lines and Chemically Induced Cancers by Targeting P13–K. Canc. Prev. Res. 2014, 7, 236–245; https://doi.org/10.1158/1940-6207.capr-13-0288.Suche in Google Scholar PubMed PubMed Central

8. Wang, L. L.; Xue, D. D. Crystal Structure of 3-phenylpropyl 2-(6-methoxynaphthalen-2-yl)propanpate, C23H24O3. Z. Kristallogr. N. Cryst. Struct. 2022, 237, 517–519; https://doi.org/10.1515/ncrs-2022-0114.Suche in Google Scholar

9. Liang, D.; Yang, X. H.; Sun, W.; Wang, W. N.; Yang, J. Z.; Liu, Y. Y.; Wang, G. S. Synthesis, Crystal Structure and Biological Activities of Naproxen-Eugenol Ester Progrug. Chem. Res. Chinese Univ. 2013, 29, 245–248; https://doi.org/10.1007/s40242-013-2266-9.Suche in Google Scholar

10. Kanazawa, H.; Inada, A. Crystal Structure of β-Benzyl DL-Aspartate N-Carboxyanhydride. Acta Crystallogr. 2017, E73, 445–447; https://doi.org/10.1107/s2056989017003024.Suche in Google Scholar

Received: 2024-03-08
Accepted: 2024-04-16
Published Online: 2024-04-29
Published in Print: 2024-08-27

© 2024 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

Artikel in diesem Heft

  1. Frontmatter
  2. New Crystal Structures
  3. The crystal structure of hexaquazinc(II) poly[hexakis(μ2-4-methylbenzenesulfinato-κ2O:O′) dizinc(II)]
  4. The crystal structure of poly[((2-(4,5-dihydro-1H-pyrazol-4-yl)-1,3-dioxoisoindoline-5-carbonyl)oxy)(1-(dimethylamino)ethoxy)zinc[II]], C16H14ZnN4O5
  5. Crystal structure of bis[(triaqua-4-iodopyridine-2,6-dicarboxylato-κ 3 N,O,O )cobalt(II)] trihydrate, C14H22N2O17I2Co2
  6. Crystal structure of bis(methanol-κO)-bis(nitrato-kO)-bis(1-((2-(2-chloro-4-(4-chlorophenoxy)phenyl)-4-methyl-1,3-dioxolan-2-yl)methyl)-1H-1,2,4-triazole-κN)cadmium(II), C40H42O14N8Cl4Cd
  7. Crystal structure of poly[μ2-dichlorido-(μ2-1-[(2,4-dimethyl-1H-triazole-1-yl)methyl]-1H-benzotriazole-κ2N:N′)cadmium(II)], C11H12CdN6Cl2
  8. The crystal structure of (3aS, 4R, 7S, 7aR)-hexahydro-4, 7-methano-1H-isoindole-1, 3-(2H)-dione, C9H11NO2
  9. The crystal structure of N-(acridin-9-yl)-4-chloro-N-(4-chloro-butanoyl) butanamide, C21H20Cl2N2O2
  10. Crystal structure of 3,3′-dimethoxy-4,4′-oxy-di-benzaldehyde, C16H14O5
  11. The crystal structure of tetrakis(μ 2-2-amino-3,5-dibromobenzoate-κ 2 O:O′)-octakis(n-butyl-κ 1 C)-bis(μ 3-oxo)tetratin(II), C60H92Br8N4O10Sn4
  12. Crystal structure of methyl-1-(naphthalen-1-yl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b] indole-3-carboxylate, C23H20N2O2
  13. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  14. Crystal structure of 6,6′-((1E,1′E)-((2-phenylpyrimidine-4,6-diyl)bis(hydrazin-2-yl-1-ylidene))bis(methaneylylidene))bis(2-methoxyphenol)monohydrate, C26H26N6O5
  15. Crystal structure of bis(N,N,N-trimethylbutanaminium) tetrathiotungstate(VI), (BuMe3N)2[WS4]
  16. The crystal structure of 2,3,9-triphenyl-9-(2-phenylbenzofuran-3-yl)-9H-9λ 5-benzo[4,5][1,2]oxaphospholo[2,3-b][1,2,5]oxadiphosphole 2-oxide, C40H28O4P2
  17. Crystal structure of 1–methyl-3-propyl-4-nitro-1H-pyrazole-5-carboxylic acid, C8H11N3O4
  18. Crystal structure of N-(benzo[d]thiazol-2-yl)-2-chloroacetamide, C9H7ClN2OS
  19. The crystal structure of N-benzyl-2-chloro-N-(p-tolyl) acetamide, C16H16ClNO
  20. Crystal structure of 3,4-dimethoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C23H24O5
  21. Crystal structure of 2,5-bis(2,5-dimethoxybenzyl)-3,6-dimethyl-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione, C26H28N2O6
  22. Crystal structure of poly[(μ3-5-bromoisophthalato-κ4 O,O′ :O″,O‴)-(μ2-1,2-bis(1,2,4-triazole-1-ylmethyl)benzene-κ2 N:N′)cobalt(II)], C20H15BrCoN6O4
  23. The crystal structure of bis(2-(piperidin-1-ium-4-yl)-1Hbenzo[d]imidazol-3-ium) dihydrogen decavanadate, C24H36N6O28V10
  24. Crystal structure of diaqua-bis(1-(3-carboxyphenyl)-5-methyl-4-oxo-1,4-dihydropyridazine3-carboxylato-O,O′)-cobalt(ii)dihydrate, C26H36N4O14Co
  25. Crystal structure of poly[(μ2-5-bromoisophthalato-κ4 O,O :O ,O )-(μ2-1,4-bis(2-methylimidazol-1-ylmethyl)benzene-N:N)cadmium(II)], C24H21BrCdN4O4
  26. The crystal structure of dimethyl 8-(3-methoxy-2-(methoxycarbonyl)-3-oxoprop-1-en-1-yl)-4-methyl-1-(p-tolyl)-1,3a,4,8b-tetrahydro-3H-furo[3,4-b]indole-3,3-dicarboxylate. C28H29NO9
  27. Crystal structure of (3R)-1-(3,5-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate chloride, C21H23ClN2O4
  28. Synthesis and crystal structure of 3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-(methylsulfonyl)benzoic acid, C12H13NO5S
  29. The crystal structure of hexaaquamagnesium(II) bis-3-(1,2,3,4-tetrahydrobenzo[4,5]imidazo[1,2-α]pyridin-1-yl)benzoate, C36H42N4O10Mg
  30. Crystal structure of 4-formyl-2-methoxyphenyl 2-acetoxybenzoate, C17H14O6
  31. Crystal structure of poly[octakis(μ-oxido)-tris(μ-1,1′-[[1,1′-biphenyl]-4,4′-diylbis(methylene)]bis(1H-imidazole))-tetrakis(oxido)-tetra-vanadium-dimanganese(II)dihydrate], C30H29MnN6O7V2
  32. Crystal structure of 4,8a-bis(4-chlorophenyl)-1,5,6-tris(4-fluorobenzyl)-1,4,4a,4b,5,6,8a,8b-octahydrocyclobuta[1,2-b:3,4-c′]dipyridine-3,8-dicarbonitrile, C45H33Cl2F3N4
  33. Crystal structure of benzo[d][1,3]dioxol-5-ylmethyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H20O5
  34. Crystal structure of N-benzoyl-N-phenylhydroxylaminato-dicarbonylrhodium(I), [Rh(BNA)CO2]
  35. The crystal structure of N-(2-((2-methoxynaphthalen-1-yl)ethynyl)phenyl)-4-methylbenzenesulfonamide, C26H21NO3S
  36. The crystal structure of methyl ((4-aminobenzyl)sulfonyl)-d-prolinate, C13H18N2O4S
  37. The crystal structure of dichlorido-(N-isopropyl-N-(pyridin-2-ylmethyl)propan-2-amine-κ 2 N, N′)palladium(II), C12H20N2PdCl2
  38. Crystal structure of poly[(μ 2-5-hydroxyisophthalato-κ4 O,O′:O″,O‴)-(μ 2-1,4-bis(2-methylimidazolyl)-1-butene-N:N′)nickel(II)], C20H20NiN4O5
  39. The crystal structure of {hexakis(1-methyl-1H-imidazole-κ 1 N)cobalt(II)}(μ 2-oxido)-hexaoxido-dimolybdenum(VI)— 1-methyl-1H-imidazole (1/2), C32H48CoMo2N16O7
  40. Synthesis, crystal structure and nonlinear optical property of 1-((propan-2-ylideneamino)oxy)propan-2-yl-4-methylbenzenesulfonate, C13H19O4NS
  41. The crystal structure of N,N-(ethane-1,1-diyl)dibenzamide, C16H16N2O2
  42. Crystal structure of 1-(4-bromophenyl)-3-(diphenylphosphoryl)-3-hydroxypropan-1-one, C21H18BrO3P
  43. The crystal structure of fac-tricarbonyl(bis(3,5-dimethyl-4H-pyrazole)-κ1 N)-((nitrato)-κ1 O)-rhenium(I)— 3,5-dimethyl-4H-pyrazole(1/1), C18H23N7O6Re
  44. The crystal structure of 4′-chloro-griseofulvin: (2S,6′R)-4′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-3′-ene-2′,3-dione, C16H14Cl2O5
  45. Crystal structure of tetraethylammonium bicarbonate–1-(diaminomethylene)thiourea(1/1)
  46. Crystal structure of 1-cyclohexyl-4-p-tolyl-1,4-dihydropyridine-3,5-dicarboxylic acid dimethyl ester, C22H27NO4
  47. The crystal structure of catena-poly(μ2-1,4-bis-(1H-imidazol-1-yl)benzene-copper(I)) dichloridocopper(I), {[CuC12H10N4]+[CuCl2]} n
  48. The crystal structure of propane-1-aminium-2-carbamate, C4H10N2O2
  49. Crystal structure of 5,6,3′,4′,5′-pentamethoxy-flavone dihydrate, C20H24O9
  50. Crystal structure of (E)-N-(2-bromophenyl)-4-(4-(3,5-dimethoxystyryl)phenoxy)pyrimidin-2-amine, C26H22BrN3O3
  51. Crystal structure of methyl (3R)-1-(2-bromo-4-fluorophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride hydrate, C19H19BrClFN2O3
  52. The crystal structure of 1-(2-chlorophenyl)-3-(p-tolyl)urea, C14H13ClN2O
  53. The crystal structure of 1-cyclohexyl-3-(p-tolyl)urea, C14H20N2O
  54. Crystal structure of ((benzyl(hydroxy)-amino)(4-chlorophenyl)methyl)-diphenylphosphine oxide, C26H23ClNO2P
  55. The crystal structure of ethyl 3-(1-methyl-1H-indole-2-carbonyl)-2-phenylquinoline-4-carboxylate, C28H22N2O3
  56. The crystal structure of 1,4-bis(1H-imidazol-3-ium-1-yl)benzene dinitrate, C12H12N4 2+·2(NO3 )
  57. Crystal structure of tris(hexafluoroacetylacetonato-κ2O,O′) bis(triphenylphosphine oxide-κ1O)samarium(III), C51H33F18O8P2Sm
  58. Crystal structure of 1-(4-(dimethylamino)phenyl)-2,3-bis(diphenylphosphoryl)propan-1-one, C35H33NO3P2
  59. Crystal structure of diaqua[bis(μ 2-pyridine 2,6-dicarboxylato) bismuth(III) potassium(I)], C14H10BiKN2O10
  60. Crystal structure of (R)-N, N -dimethyl-[1, 1′-binaphthalene]-2, 2′-diamine, C22H20N2
  61. Crystal structure of 1-phenyl-4-(2-furoyl)-3-furyl-1H-pyrazol-5-ol, C18H12N2O4
  62. Crystal structure of bis(14,34-dimethyl[11,21:23,31-terphenyl]-22-yl)diselane, C40H34Se2
Heruntergeladen am 29.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2024-0118/html
Button zum nach oben scrollen