Startseite Crystal structure of benzo[d][1,3]dioxol-5-yl-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18O5
Artikel Open Access

Crystal structure of benzo[d][1,3]dioxol-5-yl-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18O5

  • Wei Sun ORCID logo , Yan Wang , Xiao-ping Zhou , Mu-xin Zhang , Jin-zhu Yang und Di Liang ORCID logo EMAIL logo
Veröffentlicht/Copyright: 26. April 2021

Abstract

C21H18O5, monoclinic, P21 (no. 4), a = 9.1511(4) Å, b = 5.6679(3) Å, c = 16.7731(9) Å, β = 93.435(2)°, V = 868.42(8) Å3, Z = 2, Rgt(F) = 0.0410, wRref(F2) = 0.1204, T = 296(2) K.

CCDC no.: 2071609

The molecular structure is shown in 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:Colourless block
Size:0.16 × 0.15 × 0.12 mm
Wavelength:Cu Kα radiation (1.54178 Å)
μ:0.79 mm−1
Diffractometer, scan mode:Bruker D8 VENTURE, φ and ω
θmax, completeness:68.5°, >99%
N(hkl)measured, N(hkl)unique, Rint:14,578, 3182, 0.041
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 2705
N(param)refined:237
Programs:Bruker [1], Olex2 [2], SHELX [3], [4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.8702 (2)0.4082 (4)−0.13037 (14)0.0781 (6)
C10.9623 (4)0.2064 (6)−0.1357 (2)0.0857 (10)
H1A1.0045120.204937−0.1866930.128*
H1B0.9054300.065835−0.1298130.128*
H1C1.0389080.212750−0.0940390.128*
O20.7303 (4)0.6910 (9)0.35086 (17)0.174 (2)
C20.8013 (3)0.4413 (5)−0.06060 (17)0.0618 (7)
O40.8150 (3)0.7959 (5)0.66137 (15)0.0911 (7)
C40.6420 (3)0.6997 (5)0.00671 (19)0.0641 (7)
H40.5856270.8361800.0069780.077*
O30.6102 (2)0.4312 (4)0.41733 (14)0.0752 (6)
C30.7125 (3)0.6448 (6)−0.05937 (19)0.0678 (7)
H30.7024750.741461−0.1041770.081*
O50.9948 (2)0.5118 (5)0.67856 (13)0.0858 (7)
C50.6520 (2)0.5546 (5)0.07557 (16)0.0565 (6)
C60.7398 (3)0.3488 (4)0.07346 (17)0.0571 (6)
C70.8140 (3)0.2954 (5)0.00438 (18)0.0629 (7)
H70.8717190.1605640.0030160.075*
C90.6749 (3)0.2599 (5)0.20812 (18)0.0664 (7)
H90.6819490.1604170.2522670.080*
C80.7475 (3)0.2032 (5)0.14261 (18)0.0662 (7)
H80.8035820.0663100.1429330.079*
C100.5885 (3)0.4673 (5)0.21099 (18)0.0619 (7)
C110.5785 (3)0.6087 (5)0.14506 (18)0.0593 (7)
H110.5216810.7446610.1458590.071*
C120.5137 (3)0.5211 (6)0.2873 (2)0.0702 (8)
H120.4575990.3812530.3011810.084*
C130.6302 (3)0.5624 (7)0.35340 (19)0.0775 (9)
C140.4106 (4)0.7289 (8)0.2831 (3)0.0950 (11)
H14A0.4631380.8684190.2694440.142*
H14B0.3698520.7505890.3339890.142*
H14C0.3331300.7001260.2430960.142*
C150.7131 (3)0.4501 (6)0.48289 (18)0.0654 (7)
C160.7019 (3)0.6350 (6)0.53592 (19)0.0689 (7)
H160.6298820.7501970.5289610.083*
C170.8034 (3)0.6380 (5)0.59936 (18)0.0648 (7)
C180.9095 (3)0.4664 (6)0.61018 (18)0.0648 (7)
C190.9197 (3)0.2837(6)0.55801(19)0.0710(8)
H190.9917550.1687510.5654550.085*
C200.8176 (3)0.2765 (6)0.4931 (2)0.0696 (7)
H200.8201410.1537060.4563700.084*
C210.9468 (4)0.7325 (8)0.7062 (2)0.0866 (10)
H21A1.0214090.8512970.6994210.104*
H21B0.9290560.7225910.7625360.104*

Source of material

Naproxen acylchloride was synthesized according to the literature method [5]. Naproxen (0.01 mol, 2.30 g) was dissolved in dichloromethane (10 mL), and then oxalyl chloride (0.012 mol, 1.1 mL) and two drops of N,N-dimethylformamide were dropwise added at 0 °C. The solution was stirred for 2 h at room temperature. After the solvent and excess oxalyl chloride was removed by vacuum distillation, a yellow solid was obtained.

3,4-(Methylenedioxy)phenol (sesamol, 0.01 mol, 1.38 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 reaction mixture was filtrated 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 finally dried with anhydrous Na2SO4. The solution was filtrated, and concentrated under vacuum to obtain the crude product. The crude product was purified by recrystallization in ethyl acetate. The single crystals were obtained from tetrahydrofuran.

Experimental details

A suitable crystal was selected and tested on a Bruker D8 VENTURE diffractometer. Using OLEX2 [2], the structure was solved with the SHELXT [3] structure solution program using Intrinsic Phasing and refined with the SHELX [4] refinement package.

Comment

Naproxen is a well-known nonsteroidal anti-inflammatory drug. It is usually used for treating rheumatic, rheumatoid arthritis and osteoarthritis. However, it often brings gastrointestinal side effects such as ulcers, gastric perforation and bleeding in long-term administration because of its carboxylic acid group. In order to overcome the side effects, many researchers have transformed naproxen into a prodrug. Studies also found that many prodrugs can improve the liposolubility, especially suitable for transdermal delivery mode. Because sesamol has anti-inflammatory and antioxidant effects [6], [7], we synthesized a naproxen-sesamol eater as a prodrug based on the combination principles. We expect to reduce the side effects of naproxen and improve its bioavailability.

The title molecule consists of two moieties: the naphthalene moiety and the 1,2-methylenedioxybenxene group (see the figure). The naphthalene ring and 1,2-methylenedioxybenxene ring are not coplanar with a dihedral angle of 53.5°. One carbon–oxygen double bond exists in the compound, the C–O double bond distance (C13–O2) is 1.173(4) Å. The bond lengths of C1–O1 and C13–O3 are 1.427(4) and 1.327(4) Å, respectively. The other C–O bond lengths range from 1.372(4) to 1.429(4) Å. The C–C bond lengths from 1.352(5) to 1.518(4) Å. The torsion angles of C14–C12–C13–O2 and O3–C15–C16–C17 are −75.5(6)° and 178.3(2)°, respectively. All the bond lengths and angles are in the expected ranges [8].


Corresponding author: Di Liang, School of Pharmaceutical Sciences, Jilin University, Changchun130021, P. R. China, E-mail:

Funding source: Jilin Province Science and Technology Development Project

Award Identifier / Grant number: 2020010111YY

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

  2. Research funding: This work was supported by the research funds of Jilin Province Science and Technology Development Project (2020010111YY).

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

References

1. BRUKER. SAINT, APEX2 and SADABS; Bruker AXS Inc.: Madison, Wisconsin, USA, 2009.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. Sheldrick, G. M. A short history of SHELX. Acta Crystallogr. 2008, A64, 112–122; https://doi.org/10.1107/s0108767307043930.Suche in Google Scholar

5. Huang, Z. J., Carlos, A. V., Khaled, R. A. A., Morshed, A. C., Julie, A. R., Jenna, F. D., King, S. B., Edward, E. K. 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, 77, 1356–1364; https://doi.org/10.1021/jm101403g.Suche in Google Scholar

6. Yashaswini, P. S., Appu Rao, A. G., Singh, S. A. Inhibition of lipoxygenase by sesamol corroborate. Int. J. Biol. Macromol. 2017, 77, 781–787; https://doi.org/10.1016/j.ijbiomac.2016.06.048.Suche in Google Scholar

7. Hayesa, J. E., Allena, P., Bruntona, N., O’Gradyb, M. N., Kerry, J. P. Phenolic composition and in vitro antioxidant capacity of four commercial phytochemical products: olive leaf extract (Olea europaea L.), lutein, sesamol and ellagic acid. Food Chem. 2011, 77, 948–955; https://doi.org/10.1016/j.foodchem.2010.11.092.Suche in Google Scholar

8. Lei, D., Xiaohong, Y., Di, L., Wei, S. Crystal structure of 2-acetyl-5-methoxyphenyl 2-(6-methoxynaphthalen-2-yl) propanoate, C23H22O5. Z. Kristallogr. NCS 2013, 228, 317–318; https://doi.org/10.1524/ncrs.2013.0150.Suche in Google Scholar

Received: 2021-03-30
Accepted: 2021-04-12
Published Online: 2021-04-26
Published in Print: 2021-07-27

© 2021 Wei Sun et al., 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. Crystal structure of poly[(μ2-aqua-tetraaqua-(μ3-glutarato-κ4O,O′:O′:O′′)-(μ5-glutarato-κ6O:O,O′:O′:O′′:O′′′)distrontium(II)], C10H22O13Sr2
  4. The crystal structure of acetato-κ1O-{(2-(2-(2-aminophenoxy)ethoxy)phenyl)(4-oxo-4-phenylbut-2-en-2-yl)amido-κ2N,N′,O}copper(II), C26H26CuN2O5
  5. Crystal structure of dimethanolato-k2O:O-bis(1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κN)-bis(thiocyanato-κN)dicopper(II), C34H32Cu2N12O2S2
  6. Crystal structure of poly[diaqua-bis(μ2-3-(pyrimidin-5-yl)benzoato-κ2N:O)cobalt(II)] dihydrate, [Co(C11H11O2N2)2(H2O)2]
  7. Crystal structure of bis(3,3-dimethyl-1-phenylbut-1-en-2-yl)(trimethylsilyl)amido-k1N)zinc(II), Zn(C15H24NSi)2
  8. Crystal structure of catena-poly[(μ2-methanolato-κ2O:O)-(μ2-1-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)-(thiocyanato-κ1N)copper(II)] 0.25 hydrate, C17H16CuN6OS ⋅ 0.5H2O
  9. The crystal structure of 2-amino-5-nitroanilinium iodide monohydrate, C6H8IN3O2
  10. The crystal structure of 3-amino-5-carboxypyridin-1-ium perchlorate monohydrate, C6H9ClN2O7
  11. Crystal structure of 7-hydroxy-2,4-dimethoxy-9,10-dihydrophenanthrene from Arundina graminifolia, C16H16O3
  12. Crystal structure of 6,6′-((1E, 1′E)-(((1R, 2R)-1,2-diphenylethane-1,2-diyl) bis(azanylylidene))bis(methanylylidene))bis(2-ethylphenol), C32H32N2O2
  13. The crystal structure of 2-amino-5-carboxypyridin-1-ium iodide monohydrate, C6H9IN2O3
  14. The crystal structure of 2-(3,5-difluorophenyl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C16H11BF2N2
  15. Crystal structure of bis{(2-pyridinyl)-1-phenyl-1-isopropylmethanolato-κ2N,O}nickel, C30H32N2NiO2
  16. Crystal structure of poly[(m3-3-carboxyadamantane-1-carboxylato-κ3O:O′:O″)-(phenanthroline-κ2N,N′)sodium(II)], C24H23N2NaO4
  17. Crystal structure of 2-phenylethynyl-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C22H20B2F4N4
  18. Crystal structure of 4-tert-butyl-2-N-(2-pyridylmethyl)aminophenol, C16H20N2O
  19. The crystal structure of (3Z,3′Z)-4,4′-((1,4-phenylenebis(methylene))bis(azanediyl))bis(pent-3-en-2-one), C18H24N2O2
  20. Crystal structure of (morpholine-1-carbodithioato-κ2-S,S′)bis(triphenylphosphine-κ-P)gold(I), C41H38AuNOP2S2
  21. Crystal structure of 1,4-bis(4-bromobenzyl)-4-(4-chlorophenyl)-1,4-dihydropyridine-3-carbonitrile, C26H19Br2ClN2
  22. The crystal structure of fac-tricarbonyl (N′-benzoyl-N,N-diphenylcarbamimidothioato-κ2S,O)-(pyrazole-κN)rhenium(I) — methanol (1/1) C26H23O4N4SRe
  23. The crystal structure of Ba2Mn(SeO3)2Cl2 containing 1[Mn(SeO3)2Cl2]4− chains
  24. Crystal structure of 3,3′,3″-((1E,1′E,1″E)-((nitrilotris(ethane-2,1-diyl))tris(azaneylylidene)) tris(methaneylylidene))tris(4-hydroxy-1-naphthaldehyde) monohydrate, C42H36N4O6·H2O
  25. The crystal structure of 4-(6-acetyl-5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl)benzonitrile, C14H12N6O
  26. Crystal structure of benzo[d][1,3]dioxol-5-yl-2-(6-methoxynaphthalen-2-yl)propanoate, C21H18O5
  27. The crystal structure of ethyl 5-methyl-7-(4-(phenylthio)phenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, C20H19N5O2S
  28. Crystal structure of N′,N‴-((propane-2,2-diylbis(1H-pyrrole-5,2-diyl))bis(methaneylylidene))-di(isonicotinohydrazide)– water – dimethylformamide (1/4/2), C25H24N8O2·4H2O·2C3H7NO
  29. Synthesis and crystal structure of 4-(2,4-dinitrophenoxy)benzaldehyde, C13H8N2O6
  30. The crystal structure of 1-dodecylpyridin-1-ium bromide monohydrate, C17H32BrNO
  31. Crystal structure of (E)-amino(2-(4-(dimethylamino)benzylidene)hydrazineyl)methaniminium nitrate, C10H16N6O3
  32. Crystal structure of (E)-(2-((1H-pyrrol-2-yl)methylene)hydrazineyl)(amino)methaniminium nitrate monohydrate, C6H12N6O4
  33. The crystal structure of hexakis(1-propylimidazole-κ1N)copper(II) dichloride, C36H60Cl2CuN12
  34. The crystal structure of bis{(μ2-3,3-dimethyl-1-phenylbut-1-en-2-yl)((dimethylamino)dimethylsilyl)amido-κ3N,N′:N′}dilithium, C32H54Li2N4Si2
  35. The crystal structure of methyl 4-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)benzoate, C18H15BN2O2
  36. Crystal structure of (E)-N-(1-((2-chlorothiazol-5-yl)methyl)pyridin-2(1H)-ylidene)-2,2,2-trifluoroacetamide, C11H7ClF3N3OS
  37. Crystal structure of N′, N‴-((propane-2,2-diylbis(1H-pyrrole-5,2-diyl))bis (methaneylylidene))di(picolinohydrazide) – water – methanol (1/1/1), C25H24N8O2·H2O·CH3OH
  38. Crystal structure of 3-(2-chloro-benzyl)-7-[4-(2-chloro-benzyl)-piperazin-1-yl]-5,6,8-trifluoro-3H-quinazolin-4-one, C26H21Cl2F3N4O
  39. Crystal structure of N1,N2-bis(2-fluorobenzyl)benzene-1,2-diamine,C20H18F2N2
  40. The crystal structure of 2-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine, C17H13BN2O2
  41. The crystal structure of 6,6′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene)) bis(2-bromo-4-nitrophenol) — dimethylsulfoxide (1/2), C14H8Br2N4O6⋅2(C2H6OS)
  42. Selective biocatalytic synthesis and crystal structure of (2R,6R)-hydroxyketaminium chloride, C13H17Cl2NO2
  43. Crystal structure of bis{tetraaqua-[μ3-1-(4-carboxylatophenyl)-5-methyl-1H-pyrazole-3-carboxylate-κ4N,O,O′,O″] [μ2-1-methyl-1H-pyrazole-3,5-dicarboxylate-κ3N,O:O]dicobalt(II)} dihydrate, C36H44Co4N8O26
  44. Crystal structure of diethyl-2,2′-naphthalene-2,3-diylbis(oxy)diacetate, C18H20O6
  45. Synthesis and crystal structure of poly[(μ3-2-(2-carboxylatophenyl)-1H-benzo[d]imidazole-5-carboxylato-κO,O′:O′;:O″, O″′)-(μ2-1-(4-(1Himidazol-1-yl)phenyl)-1H-imidazole-κ2N:N′)cadmium(II)], C27H18CdN6O4
  46. The crystal structure of catena-poly[diaqua-bis(μ2-2-((2-(2-phenylacetyl)hydrazineylidene)methyl)benzoato-κ2O:O')zinc(II)], C32H30N4O8Zn
  47. The crystal structure of 2-(3,4-dimethoxyphenyl)-2,3-dihydro-1H-naphtho [1,8-de][1,3,2]diazaborinine, C18H17BN2O2
  48. The crystal structure of hexakis(1-ethylimidazole-κ1N)nickel(II) dichloride – 1-ethylimidazole (1/2), C40H64Cl2NiN16
  49. Crystal structure of diaqua-bis(2,4-dinitrophenolato-κ2O,O′)copper(II) 1.5 hydrate, C12H13CuN4O13.5
  50. Crystal structure of N′,N‴-((1E,1′E)-((decane-1,10-diylbis(oxy))bis(2,1-phenylene)) bis(methaneylylidene))di(isonicotinohydrazide), C36H40N6O4
  51. The crystal structure of 2-[(R)-1-(naphthalen-1-yl)ethyl]-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-one, C19H20NO2
  52. Synthesis and crystal structure of (1E,2E)-3-(anthracen-9-yl)-1-(4-methoxyphenyl)prop-2-en-1-one oxime, C24H19NO2
  53. Synthesis and crystal structure of (2E,2′E)-3,3′-(1,3-phenylene)bis(1-(3-bromophenyl)prop-2-en-1-one), C24H16Br2O2
  54. The crystal structure of catena-poly[bis(µ2-1,2-bis((1H-imidazol-1-yl)methyl)benzene- κ2N:N′)-bis(nitrato-κO)copper(II)], C28H28N10O6Cu
  55. Synthesis and crystal structure of the novel chiral acetyl-3-thiophene-5-(9-anthryl)-2-pyrazoline, C23H18N2OS
  56. Crystal structure of (E)-3-(dimethylamino)-1-(thiophen-3-yl)prop-2-en-1-one, C9H11NOS
  57. Crystal structure of catena-poly[aqua-(4-iodopyridine-2,6-dicarboxylato-κ3N,O,O′)-(μ2-4-amino-4H-1,2,4-triazole-κ2N:N′) copper(II)], C9H8N5O5CuI
  58. Crystal structure of cyclopropane-1,2,3-triyltris(phenylmethanone), C24H18O3
  59. Crystal structure of bis(amino(thioureido)methaniminium) terephthalate, C12H18N8O4S2
  60. A three-dimensional Eu(III) framework in the crystal structure of dimethylaminium poly[dimethylformamide-κ1N)bis(μ4-terephthalato-κ4O:O′:O′′:O′′′)europium(III)] monohydrate, C21H25EuN2O10
  61. Crystal structure of 2-methoxyphenyl 2-(6-methoxynaphthalen-2-yl)propanoate, C21H20O4
  62. The crystal structure of Hexakis(diethylamido)dimolybdenum, Mo2(NEt2)6
Heruntergeladen am 23.9.2025 von https://www.degruyterbrill.com/document/doi/10.1515/ncrs-2021-0116/html
Button zum nach oben scrollen