Home Physical Sciences Crystal structure of 1-(2-(1H-indol-3-yl)ethyl)-4-benzyl-3-hydroxy-3,6-diphenylpiperazine-2,5-dione, C33H29N3O3
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Crystal structure of 1-(2-(1H-indol-3-yl)ethyl)-4-benzyl-3-hydroxy-3,6-diphenylpiperazine-2,5-dione, C33H29N3O3

  • Ying Fen Li , Xian Wei , Song Bai and Meng Lan Lv ORCID logo EMAIL logo
Published/Copyright: July 14, 2020

Abstract

C33H29N3O3, triclinic, P1̅ (no. 2), a = 7.1229(8) Å, b = 12.8851(13) Å, c = 15.0472(15) Å, α = 92.354(2)°, β = 103.338(2)°, γ = 91.502(2)°, V = 1341.7(2) Å3, Z = 2, Rgt(F) = 0.0364, wRref(F2) = 0.1074, T = 296(2) K.

CCDC no.: 2009028

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:0.30 × 0.28 × 0.27 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:0.08 mm−1
Diffractometer, scan mode:Bruker Apex-II, φ and ω
θmax, completeness:25.0°, 99%
N(hkl)measured, N(hkl)unique, Rint:6862, 4688, 0.018
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 3871
N(param)refined:354
Programs:Bruker [1], SHELX [2]
Table 2:

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

AtomxyzUiso*/Ueq
O11.05577(14)0.31690(7)0.19289(7)0.0420(3)
O21.12495(12)0.22906(8)0.36611(6)0.0360(2)
H21.21890.22810.34330.054*
O30.50126(13)0.21694(8)0.36264(7)0.0430(3)
N10.81535(19)0.69119(9)−0.02533(8)0.0431(3)
H10.85340.7118−0.07210.052*
N20.76650(16)0.35307(8)0.22118(7)0.0312(3)
N30.80410(14)0.19376(8)0.34729(7)0.0276(2)
C10.5113(2)0.79071(11)−0.03781(9)0.0413(4)
H1A0.51840.8246−0.09040.050*
C20.3618(2)0.80656(12)0.00410(11)0.0470(4)
H2A0.26490.8509−0.02120.056*
C30.3525(2)0.75725(12)0.08416(11)0.0488(4)
H30.25070.77040.11170.059*
C40.4913(2)0.68950(11)0.12308(10)0.0412(3)
H40.48340.65700.17620.049*
C50.64436(19)0.67045(10)0.08126(9)0.0320(3)
C60.6524(2)0.72210(10)0.00096(9)0.0330(3)
C70.9074(2)0.62201(11)0.03528(11)0.0429(4)
H71.02080.58980.03140.051*
C80.8100(2)0.60677(10)0.10202(9)0.0360(3)
C90.8562(2)0.53299(11)0.17795(10)0.0441(4)
H9A0.82980.56480.23320.053*
H9B0.99210.51780.19030.053*
C100.7342(2)0.43218(10)0.15125(9)0.0369(3)
H10A0.59890.44900.13790.044*
H10B0.76100.40210.09550.044*
C110.61472(18)0.33756(10)0.27115(9)0.0300(3)
H110.49270.32650.22530.036*
C120.63777(17)0.24360(10)0.32988(8)0.0289(3)
C130.95630(17)0.20753(9)0.29776(8)0.0262(3)
C140.92629(18)0.29877(10)0.23300(8)0.0290(3)
C150.59419(19)0.43426(10)0.32943(9)0.0338(3)
C160.7512(2)0.47782(13)0.39306(11)0.0516(4)
H160.87100.44800.40060.062*
C170.7309(3)0.56593(14)0.44580(12)0.0643(5)
H170.83700.59480.48860.077*
C180.5551(3)0.61054(14)0.43504(13)0.0651(5)
H180.54180.66950.47050.078*
C190.3999(3)0.56832(14)0.37238(15)0.0658(5)
H190.28070.59880.36510.079*
C200.4180(2)0.47988(12)0.31911(12)0.0497(4)
H200.31110.45150.27650.060*
C210.8224(2)0.10543(10)0.40939(9)0.0350(3)
H21A0.92860.06370.40060.042*
H21B0.70530.06190.39240.042*
C220.8565(2)0.13885(11)0.50956(10)0.0432(4)
C231.0352(3)0.17620(15)0.55799(12)0.0684(5)
H231.13580.18220.52840.082*
C241.0677(4)0.20509(18)0.65068(14)0.0925(8)
H241.18930.23070.68210.111*
C250.9255(6)0.19635(18)0.69508(15)0.0953(9)
H250.94850.21600.75690.114*
C260.7470(5)0.1586(2)0.64936(17)0.0974(9)
H260.64880.15200.68040.117*
C270.7108(3)0.12975(17)0.55583(13)0.0729(6)
H270.58870.10450.52500.087*
C280.96301(18)0.11024(9)0.23576(8)0.0294(3)
C291.1305(2)0.08695(12)0.20803(11)0.0438(4)
H291.24410.12570.23250.053*
C301.1293(3)0.00591(13)0.14382(12)0.0551(4)
H301.2415−0.00830.12470.066*
C310.9640(3)−0.05317(12)0.10855(11)0.0529(4)
H310.9640−0.10700.06540.063*
C320.7979(2)−0.03254(12)0.13726(10)0.0486(4)
H320.6864−0.07350.11460.058*
C330.7969(2)0.04945(11)0.20009(9)0.0380(3)
H330.68380.06370.21840.046*

Source of material

Benzaldehyde (2.0 mmol), 2-(1H-indol-3-yl)ethan-1-amine (2.0 mmol), 2-oxo-2-phenylacetic acid (2.0 mmol) and (isocyanomethyl)benzene (2.0 mmol) were mixed and stirred overnight in CH3OH (2.5 mL) at room temperature. The reaction mixture was monitored by TLC. When the reaction was completed, the solvent was removed under reduced pressure. Then the crude residue was subjected to diisopropylamine (2.0 equiv.) and CH3CN (3.0 mL) solution under microwave irradiation condition at 140 °C for 10 min. After the microwave vial was cooled to room temperature, the residue was purified by silica gel column chromatography using a gradient of ethyl acetate/hexane (0–100%) to afford the title product.

Experimental details

A suitable crystal was selected and collected on a Bruker APEX-II CCD. All hydrogen atoms were added using a riding model using the default parameters of the SHELX program (Table 2).

Comment

Piperazine-2,5-diones are widely employed in drug discovery and typically exhibit a wide range of important biological activities [3]. The Ugi four-component reaction (U-4CR), followed by various post-condensation transformations, is well known as a versatile and highly efficient synthetic strategy for the preparation of cyclic compounds [4], [5]. We previously reported the use of this strategy to achieve the construction of various pyrazine compounds.

The asymmetric unit of the title compound contains one molecule. The bond lengths and angles in both crystallographically independent molecules are in the normal ranges [6]. In conclusion, we have developed a facile process for the synthesis of 1-(2-(1H-indol-3-yl)ethyl)-4-benzyl-3-hydroxy-3,6-diphenylpiperazine-2,5-dione using a Ugi four-component reaction. This facile procedure can be readily used to synthesize a diverse range of compounds for high throughput screening in medicinal chemistry.

Acknowledgements

This work was financially supported by the Natural Science Foundation of China (Grant No. 51973042), Excellent young scientific and technological talents of Guizhou, China (Grant No. QKHPTRC [2019]5652).

References

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

2. Sheldrick, G. M.: Crystal Structure Refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Search in Google Scholar PubMed PubMed Central

3. Welz, A.; Koba, M.: Piperazine derivatives as dangerous abused compounds. Acta Pharm. 70 (2020) 423–441.10.2478/acph-2020-0035Search in Google Scholar PubMed

4. Li, Y.; Meng, J. P.; Lei, J.; Chen, Z. Z.; Tang, D. Y.; Zhu, J.; Zhang, J.; Xu, Z. G.: Efficient synthesis of fused oxazepino-isoquinoline scaffolds via an Ugi, followed by an intramolecular cyclization. ACS Comb. Sci. 19 (2017) 324–330.10.1021/acscombsci.7b00002Search in Google Scholar PubMed

5. Song, G. T.; Meng, J. P.; Zhu, J.: Crystal structure of 2-(8-bromo-2-phenylimidazo[1,2-α]pyridin-3-yl)-6,7-dimethyl-3-phenylquinoxaline, C29H21BrN4. Z. Kristallogr. NCS 233 (2018) 575–577.10.1515/ncrs-2017-0335Search in Google Scholar

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Received: 2020-05-24
Accepted: 2020-06-10
Published Online: 2020-07-14
Published in Print: 2020-10-27

©2020 Ying Fen Li et al., published by De Gruyter, Berlin/Boston

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

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  66. Crystal structure of 4-[(3,5-dichlorophenyl)carbamoyl]butanoic acid, C11H11Cl2NO3
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  71. Crystal structure of 2-(pyridin-2-ylamino)pyridinium chloride dibenzyldichlorostannane, [C10H10N3]Cl, C14H14Cl2Sn
  72. Crystal structure of 4-[(3-methoxyphenyl)carbamoyl]butanoic acid, C12H15NO4
  73. Crystal structure of dichlorido-bis(tri-4-tolylphosphane oxide-κO)-di(4-chlorophenyl-κC)tin(IV), C54H50Cl4O2P2Sn
  74. Crystal structure of dichloridodimethylbis(tri-4-tolylphosphane oxide-κO)-tin(IV), C44H48Cl2O2P2Sn
  75. Crystal structure of chlorido(2-methylquinolin-8-olato-κ2N,O)-bis(4-tolyl-κC)tin(IV), C24H22ClNOSn
  76. Crystal structure of (E)-dichloro(1-chloro-3-methoxyprop-1-en-2-yl)(4-methoxyphenyl)-λ4-tellane, C11H13Cl3O2Te
  77. Crystal structure of bis{N-methyl-N′-[3-(4-methoxyphenyl)-1-methylpropane-1-ylidene]carbamohydrazonothioato}zinc(II), C26H36N6O2S2Zn
  78. Crystal structure of (2-carboxy-4-(3-carboxy-5-carboxylatophenoxy)benzoato-κ2O,O′)bis(1,10-phenantroline-κ2N,N′)cobalt(II), C40H24N4O9Co
  79. The crystal structure of (3S,8R,10R,14R)-17-((2S,5S)-5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4,4,8,10,14-pentamethyl-12-oxohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate, C32H52O5
  80. Crystal structure of (μ2-1,1′-bis(diphenylphosphino)ferrocene-κ2P,P′)-bis[(Z)N-(3-fluorophenyl)-O-methylthiocarbamato-S]digold(I) chloroform solvate, C50H42Au2F2FeN2O2P2S2, CHCl3
  81. Crystal structure of poly[bis(μ2-1,4-di(1H-imidazol-1-yl)benzene-κ2N:N′)-(μ2-tetraoxidomolybdato(VI)-κ2O:O′)cobalt(II)], C24H20N8O4MoCo
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