Home Crystal structure of 1-(4-((benzo[d][1,3]dioxol-5-yloxy)methyl)phenethyl)-4-(3-chlorophenyl) piperazin-1-ium chloride, C26H28Cl2N2O3
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Crystal structure of 1-(4-((benzo[d][1,3]dioxol-5-yloxy)methyl)phenethyl)-4-(3-chlorophenyl) piperazin-1-ium chloride, C26H28Cl2N2O3

  • Hong Chen EMAIL logo , Hui-Xia Jia and Qi-Tai Xu
Published/Copyright: December 9, 2017

Abstract

C26H28Cl2N2O3, monoclinic, P21/c (no. 14), a = 13.422(3) Å, b = 7.0011(14) Å, c = 26.249(5) Å, β = 101.06(3)°, V = 2420.8(9) Å3, Z = 4, Rgt(F) = 0.0516, wRref(F2) = 0.1370, T = 296 K.

CCDC no.: 1402519

The crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal:Block, colorless
Size:0.30 × 0.10 × 0.10 mm
Wavelength:Mo radiation (0.71073 Å)
μ:9.5 mm−1
Diffractometer, scan mode:Bruker P4, ω-scans
2θmax, completeness:68.2°, >98%
N(hkl)measured, N(hkl)unique, Rint:39188, 4439, 0.089
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3123
N(param)refined:299
Programs:Bruker programs [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
Cl10.74454(6)0.60009(15)0.80257(3)0.0877(3)
Cl20.36791(6)0.23715(10)0.52937(3)0.0672(2)
O10.10602(19)0.8289(4)0.22125(8)0.0908(8)
O2−0.0435(2)0.6095(4)0.05155(8)0.0959(8)
O3−0.09168(18)0.9128(4)0.02059(8)0.0864(7)
N10.42623(15)0.6717(3)0.65995(7)0.0493(5)
N20.34226(14)0.6588(3)0.55024(7)0.0452(5)
H20.35040.52160.54490.054*
C10.6136(2)0.6255(4)0.78260(10)0.0577(7)
C20.5547(2)0.6326(4)0.81984(10)0.0603(7)
H2A0.58330.62980.85500.072*
C30.4514(2)0.6440(4)0.80275(10)0.0638(8)
H30.40920.64570.82700.077*
C40.4087(2)0.6530(4)0.75071(10)0.0574(7)
H40.33860.66130.74050.069*
C50.4695(2)0.6498(4)0.71292(9)0.0473(6)
C60.5737(2)0.6333(4)0.73020(9)0.0551(7)
H60.61660.62740.70630.066*
C70.49202(19)0.6530(4)0.62203(9)0.0525(6)
H7A0.50530.51870.61710.063*
H7B0.55640.71510.63530.063*
C80.44482(18)0.7409(4)0.57028(9)0.0493(6)
H8A0.43910.87790.57430.059*
H8B0.48840.71750.54540.059*
C90.27692(19)0.6832(4)0.58989(9)0.0535(6)
H9A0.21130.62450.57750.064*
H9B0.26620.81820.59520.064*
C100.3261(2)0.5928(4)0.64064(9)0.0564(7)
H10A0.28350.61340.66610.068*
H10B0.33180.45610.63580.068*
C110.2909(2)0.7439(4)0.49953(9)0.0502(6)
H11A0.28240.88010.50410.060*
H11B0.22390.68800.48940.060*
C120.3498(2)0.7121(5)0.45654(10)0.0683(8)
H12A0.41350.78140.46430.082*
H12B0.36510.57730.45440.082*
C130.2891(2)0.7794(5)0.40509(10)0.0593(7)
C140.2689(2)0.9716(5)0.39575(10)0.0680(8)
H140.29231.06060.42160.082*
C150.2143(2)1.0324(5)0.34838(11)0.0691(8)
H150.20121.16200.34280.083*
C160.1789(2)0.9027(5)0.30907(10)0.0623(7)
C170.1981(2)0.7126(5)0.31815(11)0.0678(8)
H170.17480.62400.29220.081*
C180.2524(2)0.6507(5)0.36587(10)0.0650(8)
H180.26420.52080.37150.078*
C190.1216(3)0.9784(5)0.25782(11)0.0778(9)
H19A0.05671.03000.26230.093*
H19B0.16011.08020.24560.093*
C200.0572(2)0.8698(5)0.17149(10)0.0678(8)
C210.0305(2)1.0506(5)0.15351(11)0.0749(9)
H210.04621.15510.17550.090*
C22−0.0204(3)1.0779(5)0.10207(12)0.0793(10)
H22−0.03961.19920.08950.095*
C23−0.0407(2)0.9218(5)0.07151(11)0.0660(8)
C24−0.0132(2)0.7428(5)0.08970(11)0.0675(8)
C250.0361(2)0.7112(5)0.13948(11)0.0761(9)
H250.05480.58880.15140.091*
C26−0.0928(3)0.7162(6)0.00771(13)0.0915(12)
H26A−0.05820.6967−0.02110.110*
H26B−0.16230.6728−0.00280.110*

Source of material

The title compound was synthesized from 2-(4-((benzo[d][1,3]dioxol-5-yloxy)methyl)phenyl)ethyl 4-methylbenzenesulfonate (65% yield) in form of colorless crystals. To a solution of 2-(4-((benzo[d][1,3]dioxol-5-yl-oxy)methyl)phenyl)ethyl 4-methylbenzenesulfonate (100 mg, 0.23 mmol) in acetonitrile (CH3CN, 10 mL) was added 1-(3-chlorophenyl)piperazine (1.2 equiv) and potassium carbonate (6.0 equiv). The reaction mixture was stirred at reflux for 16 h. After cooling to ambient temperature, the reaction mixture was filtered through a Büchner funnel. After filtration the filtrate was concentrated in vacuo and the residue was purified by silica gel column chromatography using ethyl acetate/petroleum ether (1/5, v/v) as eluent to afford the product, and the title compound was recrystallized from trichloromethane and n-hexane [3].

Experimental details

The hydrogen atoms were assigned with isotropic displacement factors Uiso(H) = 1.2Ueq (N and imidazol C), or Uiso(H) = 1.5Ueq (methyl C) and included in the final refinements by using geometrical restraints, with C—H = 0.93 Å (imidazol) or C–H = 0.96 Å (methyl), and N—H = 0.86 Å.

Discussion

Compounds with arylpiperazine moieties have a wide range of activities including antiarrhythmic [4], diuretic [5], antiallergic [6], antidepressant [7], anxiolytic [8], antipsychotic [9], antimalarial [10], antiplasmodial [11] and anti-proliferative [12], [13], [14] properties. In addition, these compounds also display receptor-blocking properties [15], [16], [17], [18], [19]. Moreover, arylpiperazine derivatives have been reported as anticancer drugs for site-directed chemotherapy of prostate cancer in our previous work [20, 21] , and some derivatives showed significant cytotoxic activity against the tested prostate cancer cell lines.

The molecule of the title compound shows an aryl, a piperazine and the benzo[d][1,3]dioxole dihydrosulfide moieties. The 2-chloro-phenyl moiety is connected to the 1,4-piperazine moiety via a C—N bond, then the above fragment further is connected by a C6H4 unit via an ethylene group. The termial fragment of molecule is the benzo[d][1,3]dioxole dihydrosulfide unit. The central aryl ring and benzo[d][1,3]dioxole dihydrosulfide ring are almost into the same plane. In the molecule, the N(1)—C(5), N(1)—C(7), N(1)—C(10), N(2)—C(11), N(2)—C(9), N(2)—N(8) bond lengths are found to be 1.452(3) Å, 1.456(3) Å, 458(3) Å, 1.500(3) Å, 1.494(3) Å and 1.491(3) Å, respectively, which are nearly equal to other typical single bonds. The bond lengths of C(24)—O(2) and C(26)—O(2) are found to be 1.372(4) and 1.424(4) Å, respectively. The bond angles C5—N1—C10, C5—N1—C7, C10—N1—C7, C9—N2—C11, C8—N2—C11 and C8—N2—C9 are 118.8(2)°, 118.4(2)°, 111.7(19)°, 109.97(18)°, 113.34(19)° and 109.64(18)°, respectively. N2—C11—C12 and C11—C12—C13 are 112.7(2)°, 110.5(3)°. Bond lengths and all other geometic parameters of the title molecule are in the expected ranges [22].

Acknowledgements

This work was supported by the Natural Science Foundation of China (no. 81401462), Henan Province Science and Technology Attack Plan Foundation (no. 162102310477), the Key Scientific Research Project of Higher Education of Henan Province (nos. 16A350008, 17A150039 and 17B350001) and National Scientific Research Foundation of Luoyang Normal University (no. 2015-PYJJ-005).

References

Bruker: APEX2, SAINT and SADABS. Brucker AXS Inc., Madison, WI, USA (2009).Search in Google Scholar

Sheldrick, G. M.: SHELXT-Integrated space-group and crystal-structure determination. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053273314026370Search in Google Scholar

Chen, H.; Liang, X.; Xu, F.; Xu, B.-B.; He, X.-L.; Huang, B.-Y.; Yuan, M.: Synthesis and cytotoxic activity evaluation of novel arylpiperazine derivatives on human prostate cancer cell lines. Molecules 9 (2014) 12048–12064.10.3390/molecules190812048Search in Google Scholar

Szkaradek, N.; Rapacz, A.; Pytka, K.; Filipek, B.; Siwek, A.; Cegla, M.; Marona, H.: Synthesis and preliminary evaluation of pharmacological properties of some piperazine derivatives of xanthone. Bioorg. Med. Chem. 9 (2013) 514–522.10.1016/j.bmc.2012.11.014Search in Google Scholar

Cecchetti, V.; Fravolini, A.; Schiaffella, F.; Tabarrini, O.; Bruni, G.; Segret, G.: o-Chlorobenzenesulfonamidic derivatives of (aryloxy)propanolamines as beta-blocking/diuretic agents. J. Med. Chem. 9 (1993) 157–161.10.1021/jm00053a020Search in Google Scholar

Walsh, D. A.; Chen, Y. H.; Green, J. B.; Nolan, J. C.; Yannit, J. M.: The synthesis and antiallergy activity of 1-(aryloxy)-4-(4-arylpiperazinyl)-2-butanol derivatives. J. Med. Chem. 9 (1990) 1823–1827.10.1021/jm00168a044Search in Google Scholar

Seo, H. J.; Park, E. J.; Kim, M. J.; Kang, S. Y.; Lee, S. H.; Kim, H. J.; Lee, K. N.; Jung, M. E.; Lee, M.; Kim, M. S.; Son, E. J.; Park, W. K.; Kim, J.; Lee, J.: Design and synthesis of novel arylpiperazine derivatives containing the imidazole core targeting 5-HT(2A) receptor and 5-HT transporter. J. Med. Chem. 9 (2011) 6305–6318.10.1021/jm200682bSearch in Google Scholar

Kikumoto, R.; Tobe, A.; Fukami, H.; Egawa, M.: Synthesis and antianxiety activity of (omega-piperazinylalkoxy)indan derivatives. J. Med. Chem. 9 (1983) 246–250.10.1021/jm00356a024Search in Google Scholar

Jaen, J. C.; Wise, L. D.; Heffner, T. G.; Pugsley, T. A.; Meltzed, L. T.: Dopamine autoreceptor agonists as potential antipsychotics 1 (Aminoalkoxy)anilines. J. Med. Chem. 9 (1988) 1621–1625.10.1021/jm00403a022Search in Google Scholar

Cross, R. M.; Namelikonda, N. K.; Mutka, T. S.; Luong, L.; Kyle, D. E.; Manetsch, R.: Synthesis, antimalarial activity, and structure-activity relationship of 7-(2-phenoxyethoxy)-4(1H)-quinolones. J. Med. Chem. 9 (2011) 8321–8327.10.1021/jm200718mSearch in Google Scholar

Clarkson, C.; Musonda, C. C.; Chibale, K.; Campbella, W. E.; Smitha, P.: Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity. Bioorg. Med. Chem. 9 (2003) 4417–4422.10.1016/S0968-0896(03)00491-7Search in Google Scholar

Berardi, F.; Abate, C.; Ferorelli, S.; De Robertis, A. F.; Leopoldo, M.; Colabufo, N. A.; Niso, M.; Perrone, R.: Novel 4-(4-aryl)cyclohexyl-1-(2-pyridyl)piperazines as Delta(8)-Delta(7) sterol isomerase (emopamil binding protein) selective ligands with antiproliferative activity. J. Med. Chem. 9 (2008) 7523–7531.10.1021/jm800965bSearch in Google Scholar PubMed

Abate, C.; Niso, M.; Contino, M.; Colabufo, N. A.; Ferorelli, S.; Perrone, R.; Berardi, F.: 1-Cyclohexyl-4-(4-arylcyclohexyl)piperazines: Mixed and human (8)–(7) sterol isomerase ligands with antiproliferative and P-glycoprotein inhibitory activity. ChemMedChem 9 (2011) 73–80.10.1002/cmdc.201000371Search in Google Scholar PubMed

Liu, W.-H.; Chang, J.-X.; Liu, Y.; Luo, J.-W.; Zhang, J.-W.: Design, synthesis and activities of novel benzothiazole derivatives containing arylpiperazine. Acta Pharm. Sin. B9 (2013) 1259–1265.Search in Google Scholar

Leopoldo, M.; Lacivita, E.; Passafiume, E.; Contino, M.; Colabufo, N. A.; Berardi, F.; Perrone, R.: 4-[omega-[4-arylpiperazin-1-yl]alkoxy]phenyl)imidazo[1,2-a]pyridine derivatives: fluorescent high-affinity dopamine D3 receptor ligands as potential probes for receptor visualization. J. Med. Chem. 9 (2007) 5043–5047.10.1021/jm070721+Search in Google Scholar PubMed

Chen, X.; Sassano, M. F.; Zheng, L. Y.; Setola, V.; Chen, M.; Bai, X.; Frye, S. V.; Wetsel, W. C.; Roth, B. L.; Jin, J.: Structure-functional selectivity relationship studies of α-arrestin-biased dopamine D2 receptor agonists. J. Med. Chem. 9 (2012) 7141–7153.10.1021/jm300603ySearch in Google Scholar PubMed PubMed Central

Romeiro, L. A.; Da Silva Ferreira, M.; Da Silva, L. L.; Castro, H. C.; Miranda, A. L.; Silva, C. L.; Noël, F.; Nascimento, J. B.; Araújo, C. V.; Tibiri cá, E.; Barreiro, E. J.; Fraga, C. A.: Discovery of LASSBio-772, a 1,3-benzodioxole N-phenylpiperazine derivative with potent alpha 1A/D-adrenergic receptor blocking properties. Eur. J. Med. Chem. 9 (2011) 3000–3012.10.1016/j.ejmech.2011.04.032Search in Google Scholar PubMed

Baran, M.; Kepczynska, E.; Zylewski, M.; Siwek, A.; Bednarski, M.; Cegla, M. T.: Studies on novel pyridine and 2-pyridone derivatives of N-arylpiperazine as α-adrenoceptor ligands. Med. Chem. 9 (2014) 144–153.10.2174/0929867320999131122114922Search in Google Scholar PubMed

Ananthan, S.; Saini, S. K.; Zhou, G.; Hobrath, J. V.; Padmalayam, I.; Zhai, L.; Bostwick, J. R.; Antonio, T.; Reith, M. E.; McDowell, S.; Cho, E.; McAleer, L.; Taylor, M.; Luedtke, R. R.: Design, synthesis, and structure-activity relationship studies of a series of [4-(4-carboxamidobutyl)]-1-arylpiperazines: insights into structural features contributing to dopamine D3 versus D2 receptor subtype selectivity. J. Med. Chem. 9 (2014) 7042–7060.10.1021/jm500801rSearch in Google Scholar PubMed PubMed Central

Chen, H.; Xu, F.; Liang, X.; Xu, B.-B.; Yang, Z.-L.; He, X.-L.; Huang, B.-Y.; Yuan, M.: Design, synthesis and biological evaluation of novel arylpiperazine derivatives on human prostate cancer cell lines. Bioorg. Med. Chem. Lett. 9 (2015) 285–287.10.1016/j.bmcl.2014.11.049Search in Google Scholar PubMed

Chen, H.; Xu, F.; Xu, B.-B.; Xu, J.-Y.; Shao, B.-H.; Huang, B.-Y.; Yuan, M.: Design, synthesis and biological evaluation of novel arylpiperazine derivatives on human prostate cancer cell lines. Chinese Chem. Lett. 9 (2016) 277–282.10.1016/j.cclet.2015.09.016Search in Google Scholar

Al-Wahaibi, L. H.; Hassan, H. M.; Abo-Kamar, A. M.; Ghabbourand, H. A.; El-Emam, A. A.: Crystal structure of 4-bromobenzyl (Z)-N′-(adamantan-1-yl)-4-phenylpiperazine-1-carbothioimidate, C28H34BrN3S. Z. Kristallogr. NCS 232 (2017) 189–191.10.1515/ncrs-2016-0184Search in Google Scholar

Received: 2017-8-19
Accepted: 2017-11-24
Published Online: 2017-12-9
Published in Print: 2018-1-26

©2018 Hong Chen et al., published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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  44. The crystal structure of trans-tetraaqua-bis(p-tolylsulfinato-κO)calcium(II)), C14H22O8S2Ca
  45. The crystal structure of (E)-N′-(pyridin-2-ylmethylene)pyrazine-2-carbohydrazide, C11H9N5O
  46. Crystal structure of (E)-3-(pyren-1-yl)-1-(pyridin-4-yl)prop-2-en-1-one, C24H15NO
  47. Crystal structure of catena-poly[diaqua-(μ2-tartrato-κ4O,O′:O′′,O′′′)cobalt(II)], C4H8CoO8
  48. Crystal structure of 4-chloro-2-methyl-6-(4-(trifluoromethoxy)phenyl)pyrimidine, C12H8ClF3N2O
  49. Crystal structure of 1-(4-fluorophenyl)-N-(5-((triphenylstannyl)thio)thiophen-2-yl)methanimine, C27H20FN3S2Sn
  50. Crystal structure of methyl (Z)-2-(5-fluoro-2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, C10H8FN3OS2
  51. Crystal structure of tert-butyl (Z)-4-(2-(5-methoxy-3-(2-((methylthio)carbonothioyl)hydrazono)-2-oxoindolin-1-yl)ethyl)piperazine-1-carboxylate, C22H31N5O4S2
  52. The crystal structure of (E)-2-((2-(o-tolylcarbamothioyl)hydrazono)methyl)benzoic acid, C16H15N3O2S
  53. Crystal structure of 2-chloro-1,3-di-tert-pentyl-4,4-diphenyl-1,3,2λ3,4-diazaphosphasiletidine, C22H32ClN2PSi
  54. Crystal structure of tetramethyl 5,5′-(buta-1,3-diyne-1,4-diyl)diisophthalate, C24H18O8
  55. Crystal structural of 2-amino-4-(4-methoxyphenyl)-3-cyano-7,7-dimethyl-5-oxo-4H-5,6,7,8-tetrahydrobenzo[b]pyran, C19H20N2O3
  56. Crystal structure of 1,3,5-tris((trimethylsilyl)methyl)-1,3,5-triazinane-2,4,6-trione, C15H33N3O3Si3
  57. The crystal structure of bis(2-benzoyl-5-hydroxylphenolato-κ2O,O′)copper(II), C26H18CuO6
  58. Crystal structure of 2,6-bis(3-(pyrazin-2-yl)-1H-1,2,4-triazol-5-yl)pyridine – 1-ethyl-3-methyl-1H-imidazol-3-ium bromide (1/1), C23H22N13Br
  59. The crystal structure of (E)-N-benzyl-N′-benzylidene-4-methylbenzenesulfonohydrazide, C21H20N2O2S
  60. Crystal structure of ethyl (E)-5-((2-(3-hydroxybenzoyl)hydrazono)methyl)-3,4-dimethyl-1H-pyrrole-2-carboxylate – water – ethanol (1/1/1), C19H27N3O6
  61. The crystal structure of (E)-4-(3-ethoxy-2-hydroxybenzylideneamino)benzoic acid, C16H15NO4
  62. Crystal structure of (μ2-N,N′-bis((pyridin-4-yl)methyl)ethanediamide-κ2N:N′)-tetrakis(diethylcarbamodithioato-κ2S,S′)dizinc(II), C34H54N8O2S8Zn2
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