Startseite Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO
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Crystal structure of 3β-methoxy-20α-dimethylamino-pregn-5-ene, C24H41NO

  • Shao-Jie Huo , Ji-Chun Wu , Xi-Chen He , Qi-Yun Wu und Jiang Du EMAIL logo
Veröffentlicht/Copyright: 31. August 2018

Abstract

C24H41NO, orthorhombic, P212121 (no. 19), a = 6.3752(16) Å, b = 12.607(3) Å, c = 26.943(7) Å, V = 2165.4(10) Å3, Z = 4, Rgt(F) = 0.0573, wRref(F2) = 0.1232, T = 173 K.

CCDC no.: 1861145

The crystal structure of the title compound (systematic name: 1-((3S,9S,10R,13S,14S)-3-methoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N,N-dimethylethan-1-amine) 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:

Crystal collection and handling.

Crystal:Block, colorless
Size:0.28 × 0.15 × 0.12 mm
Wavelength:Mo Kα radiation (λ = 0.71073 Å)
μ:0.065 mm−1
Diffractometer, scan mode:Bruker APEX-II, Φ and ω-scans
θmax, completeness:27.1°, >99%
N(hkl)measured, N(hkl)unique, Rint:12457, 4735, 0.0721
Criterion for Iobs, N(hkl)gt:Iobs > 2σ(Iobs), 3072
N(param)refined:242
Programs:Bruker programs [1], OLEX2 [2], SHELX [3, 4]
Table 2:

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

AtomxyzUiso*/Ueq
O10.0452(4)0.77064(18)0.28539(9)0.0418(7)
N10.7851(4)−0.0559(2)0.47607(10)0.0337(7)
C10.1107(5)0.4805(2)0.31164(12)0.0298(8)
H1A0.05940.41810.29290.036
H1B0.04470.47870.34490.036
C20.0382(5)0.5811(2)0.28480(12)0.0319(8)
H2A0.09060.58050.25020.038
H2B−0.11700.58310.28380.038
C30.1198(5)0.6787(3)0.31136(12)0.0323(8)
H30.06280.67960.34590.039
C40.3575(5)0.6743(2)0.31374(12)0.0330(8)
H4A0.41520.67690.27960.040
H4B0.41020.73710.33200.040
C50.4329(5)0.5747(2)0.33921(11)0.0275(8)
C60.5569(6)0.5800(3)0.37860(12)0.0318(8)
H60.59590.64860.38990.038
C70.6405(6)0.4869(2)0.40664(12)0.0324(8)
H7A0.56600.48130.43880.039
H7B0.79110.49860.41380.039
C80.6154(5)0.3824(2)0.37817(11)0.0246(7)
H80.72370.37890.35140.030
C90.3953(5)0.3769(2)0.35448(11)0.0232(7)
H90.29280.38500.38230.028
C100.3517(5)0.4702(2)0.31808(11)0.0257(7)
C110.3554(5)0.2666(2)0.33200(12)0.0280(8)
H11A0.20810.26310.32050.034
H11B0.44670.25780.30260.034
C120.3956(5)0.1740(2)0.36785(12)0.0277(8)
H12A0.29240.17680.39530.033
H12B0.37570.10600.35000.033
C130.6177(5)0.1780(2)0.38937(11)0.0217(7)
C140.6440(5)0.2883(2)0.41290(11)0.0237(7)
H140.52870.29430.43790.028
C150.8459(6)0.2803(3)0.44299(12)0.0346(8)
H15A0.84600.33180.47070.042
H15B0.97020.29330.42180.042
C160.8438(6)0.1654(3)0.46253(13)0.0358(9)
H16A0.82060.16460.49890.043
H16B0.97920.13010.45540.043
C170.6628(5)0.1075(2)0.43561(11)0.0246(7)
H170.53680.11200.45760.029
C180.7811(5)0.1557(3)0.34859(12)0.0309(8)
H18A0.77300.21120.32320.046
H18B0.75250.08660.33340.046
H18C0.92180.15530.36320.046
C190.4556(5)0.4500(3)0.26713(11)0.0324(8)
H19A0.60260.42980.27200.049
H19B0.44870.51470.24710.049
H19C0.38130.39260.25000.049
C200.7118(5)−0.0103(3)0.42859(12)0.0298(8)
H200.8328−0.01440.40500.036
C210.5321(6)−0.0718(3)0.40469(15)0.0493(11)
H21A0.5636−0.14790.40550.074
H21B0.5152−0.04890.37020.074
H21C0.4021−0.05820.42300.074
C220.6242(6)−0.0649(3)0.51411(14)0.0523(11)
H22A0.55750.00430.51910.079
H22B0.6883−0.08850.54530.079
H22C0.5184−0.11660.50360.079
C230.8974(6)−0.1556(3)0.47009(16)0.0506(11)
H23A0.8001−0.21050.45860.076
H23B0.9581−0.17680.50200.076
H23C1.0098−0.14650.44560.076
C240.0485(8)0.8629(3)0.31472(15)0.0541(12)
H24A−0.00870.92250.29560.081
H24B0.19320.87880.32440.081
H24C−0.03690.85180.34450.081

Source of material

The stems and roots of Sarcococca hookeriana (14.5 kg) were extracted three times using MeOH with ultrasonic treatment. The extract was concentrated and partitioned between EtOAc and 1% aq. H2SO4. The acid-soluble fraction was alkalinized with aq. Na2CO3 to pH 9 and followed by exhaustive extraction with CH2Cl2 to afford crude alkaloids. The crude alkaloids were roughly separated by CC (SiO2; CH2Cl2/MeOH/Et2NH, 100:0:0–10:1:0–5:1:1) to give five fractions: Frs. A—E. The title compound Pachyaximine A was obtained from Fr. A by silica gel column chromatography using petroleum ether/ethylacetate/diethylamine (50:1:1) as the eluent and recrystallization with dichloromethane.

Experimental details

All hydrogen atoms were positioned geometrically, with the d(C—H) = 0.95–1.00 Å. The Uiso(H) were set to 1.2 times Ueq(C) for the methylene groups as well as methyl groups, at 1.5 times Ueq(C) for the methyl groups.

Discussion

Previous studies have shown that S. hookeriana contains pregnane-type steroidal alkaloids [5]. These compounds have cholinesterase inhibition [6], antileishmanial [7], antibacterial [8] and estrogen biosynthesis-promoting [9] activities.

The title compound crystallizes with one molecule in the asymmetric unit of the space group P212121 (cf. the figure). Geometric parameters of the title structure are in the usual ranges. The compound contains one methoxy, one double bond and one dimethylamino group. The double bond were confirmed by the distance of 1.325(4) Å (C5—C6). The dimethylamino group was confirmed by the distance of 1.455(4) Å, 1.454(4) Å (C22—N1 and C23—N1), respectively. The compound contains three six membered rings and one five membered ring. The intermolecular connection was achieved by van der Waals interactions only.

Funding source: National Natural Science Foundation of China

Award Identifier / Grant number: 30960529

Funding statement: The authors gratefully acknowledge support from The National Natural Science Foundation of China [No. 30960529] and the Science and Technology Project of Guizhou Province [No. 2016–1015].

References

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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. 42 (2009) 339–341.10.1107/S0021889808042726Suche in Google Scholar

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Sheldrick, G. M.: Crystal structure refinement with SHELXL. Acta Crystallogr. C71 (2015) 3–8.10.1107/S2053229614024218Suche in Google Scholar PubMed PubMed Central

Kumar, A.; Sati, S. C.; Sati, M. D.; Kumar, S.; Singh, D.; Bhatt, U.; Kaur, G.: Chemical and potential biological perspectives of genus Sarcococca (Buxaceae). Nat. Prod. J. 5 (2015) 28–49.10.2174/2210315505666150219233014Suche in Google Scholar

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Devkota, K. P.; Wansi, J. D.; Lenta, B. N.; Khan, S.; Choudhary, M. I.; Sewald, N.: Bioactive steroidal alkaloids from Sarcococca hookeriana. Planta Med. 76 (2010) 1022–1025.10.1055/s-0029-1240896Suche in Google Scholar PubMed

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Received: 2018-05-31
Accepted: 2018-08-09
Published Online: 2018-08-31
Published in Print: 2018-11-27

©2018 Shao-Jie Huo et al., published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  1. Cover and Frontmatter
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  3. Crystal structure of diaqua-bis(2-bromo-4-chloro-6-formylphenolato-κ2O,O′)cobalt(II), C16H16Cl2CrN3O7
  4. Crystal structure of catena-poly[(μ2-1-(4-(1H-pyrazol-1-yl)phenyl)ethan-1-one-κ2N:O)-bis(1,1,1-trifluoro-4-oxo-4-(thiophen-2-yl)but-2-en-2-olato-κ2O,O′)copper(II)], C27H18CuF6N2O5S2
  5. Crystal structure of ethyl 2-amino-4-(3,5-difluorophenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C18H15F2NO5
  6. Crystal structure of 5,5′-dimethoxy-2,2′-[1,1′-(ethylenedioxydinitrilo)diethylidyne]diphenol, C20H24N2O6
  7. Crystal structure of (E)-1-(4-(((E)-3,5-dichloro-2-hydroxybenzylidene)amino)phenyl)ethan-1-one O-methyl oxime, C16H14Cl2N2O2
  8. Crystal structure of 2,3,9,10,16,17,23,24-octakis(2,6-dimethylphenoxy)phthalocyanine - trichloromethane (1/2), C98H84Cl6N8O8
  9. Crystal structure of methyl 2-((1-(2-(methoxycarbonyl)benzyl)-1H-1,2,3-triazol-4-yl)methoxy)-1-naphthoate, C24H21N3O5
  10. Crystal structure of catena-poly[(μ2-3,3′-thiodipropionato-κ2O:O′)-(bipyridine-κ2N,N′)copper(II)] C16H16CuN2O4S
  11. Crystal structure of [4-chloro-2-(((2-((3-ethoxy-2-oxidobenzylidene)amino)phenyl)imino)(phenyl)methyl)phenolato-κ4N,N′,O,O′}nickel(II) - ethyl acetate (1/1), C32H29ClN2NiO5
  12. Crystal structure of (4-(4-chlorophenyl)-5-ethyl-1,3-dioxane-5-carboxylato-κ2O,O′)-(5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-κ4N,N′,N′′,N′′′)nickel(II) perchlorate monohydrate, C29H52Cl2N4NiO9
  13. Crystal structure of ethyl 2-amino-4-(3,4-dimethylphenyl)-7-methyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carboxylate, C20H21NO5
  14. Structure and photochromism of 1,2-bis[2-methyl-5-(3-quinolyl)-3-thienyl]-3,3,4,4,5,5-hexafluorocyclopent-1-ene, C33H20F6N2S2
  15. Crystal structure of catena-poly[diaqua-bis(μ2-3,5-di(1H-1,2,4-triazol-1-yl)benzoate-κ2N:N′)cobalt(II))] 2.5 hydrate, C22H23CoN12O8.50
  16. The crystal structure of dichlorido(1,3-dimesityl-1H-3λ4-imidazol-2-yl)(morpholine-κN)palladium(IV), C25H33Cl2N3OPd
  17. Crystal structure of catena-poly[bis(4,4′-dipyridylaminium-kN)-(μ2-germanowolframato-κ2O:O′)-(2,2′-bipyridine-κ2N,N′)copper(II)] with a Keggin-type heteropolyoxoanion, [Cu(C10H8N2)(C10H10N3)2][GeW12O40] ⋅ H2O
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  19. The crystal structure of 2-hydroxy-4-((2-hydroxy-4-methoxy-3,6-dimethylbenzoyl)oxy)-3,6-dimethylbenzoic acid–methanol (1/1), C20H24O8
  20. Crystal structure of guanidinium tetrapropylammonium bis(hydrogencarbonate) dihydrate, C15H40N4O8
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  22. Crystal structure of 2-(4-(4H-1,2,4-triazol-4-yl)phenyl)acetic acid, C10H9N3O4
  23. Crystal structure of 4,4′-(1,4-phenylene)bis(1H-imidazol-3-ium)bis(2-carboxybenzoate), C30H26N4O8
  24. Crystal structure of 4,4′-(4,10-diphenyl-4,10-dihydropyreno[4,5-d:9,10-d′]diimidazole-5,11-diyl)bis(N,N-diphenylaniline), C66H44N6
  25. Crystal structure of catena-poly[diaqua-bis(μ2-5-(3-(1H-imidazol-5-yl)phenyl)tetrazol-2-ido-κ2N:N′)cobalt(II)], C20H18CoN12O2
  26. Crystal structure of 1,3-dimethyl-2-(p-tolyl)-1H-perimidin-3-ium iodide 1.5 hydrate, C20H22IN2O1.5
  27. Crystal structure of 2-(4-methoxyphenyl)chromane, C16H16O2
  28. Crystal structure of poly[(μ2-2-carboxy-5-nitroisophthalato-κ2O:O′)-(μ2-4-((1H-imidazol-1-yl)methyl)pyridine-κ2N:N′)zinc(II)], C18H12N4O8Zn
  29. Crystal structure of bis(1-((2-ethyl-4-methyl-1H-imidazol-1-yl)methyl)-1H-benzo[d][1,2,3]triazole-κ2N:N′)tetraiodidodicadmium(II), [Cd2(C13H15N5)2I4]
  30. Crystal structure of tetramethylammonium bis(acetato-κ1O)-tetrakis(μ3-3-((hydroxyimino)methyl)-5-methoxy-2-oxidobenzoate-κ5O,O′:O′,N:O′′)tetrazinc(II) — N,N′-dimethylformamide — water (1/2/2), C62H96Zn4N10O28
  31. Crystal structure of poly[(μ4-5-tert-butylisophthalato-κ4O:O′:O′′:O′′′)-(1,3-dimethyl-2-imidazolidinone-κO)zinc(II)] C17H22N2O5Zn
  32. Crystal structure of [tris(2-benzimidazolylmethyl)amine-κ4N,N′,N′′,N′′′]-[(pyridine-2,6-dicarboxylato-κ2O,N)]cadmium(II)–methanol (1:3) C34H36CdN8O7
  33. The crystal structure of bis(1H-benzo[d]imidazol-2-amine-κN)-diiodidocadmium(II), C14H14CdI2N6
  34. Crystal structure of tetrakis(1H-benzimidazol-2-amine)-κN)-bis(μ2-sulfonato-κ2O:O′)dizinc(II) - methanol (1/1), C30H36N12O10S2Zn2
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  38. Crystal structure of 4-((E)-((E)-5-(2-fluorobenzylidene)-1-((4-fluorophenyl)sulfonyl)-4-oxopiperidin-3-ylidene)methyl)benzonitrile, C26H18F2N2O3S
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  40. The crystal structure of 9-butoxy-2-(hydroxymethyl)-2H-imidazo[1,5-a]quinolin-10-ium bromide, C17H21O2N2Br
  41. Crystal stucture of 2-(tert-butyl)-6-(hydroxymethyl)-4-methylphenol, C12H18O2
  42. Crystal structure of catena-poly[(2-(5-chloroquinolin-8-yloxy)-1-(pyrrolidin-1-yl)ethan-1-one-κ3N,O,O′)-(dinitrato-κ2O,O′)mercury(II)], C15H15N4O8ClHg
  43. Crystal structure of dimethyl (3aS,6R,6aS,7S)-1H,3H,6H,7H-3a,6:7,9a-diepoxybenzo[de]isochromene-3a1,6a-dicarboxylate, C16H16O7
  44. The crystal structure of 2-(dimethoxymethyl)-4-(4-methylphenyl)-1H-imidazole—petroleum ether-chloroform (3/1), C27H33Cl3N4O4
  45. Crystal structure of 8-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carbaldehyde, C9H5F3N2O
  46. The crystal structure of N,N-diethyl-4,6-bis(naphthalen-2-yloxy)-1,3,5-triazin-2-amine, C27H24N4O2
  47. Crystal structure of 5-bromo-7-chloro-3,3a-dihydrocyclopenta[b]chromen-1(2H)-one, C12H8BrClO2
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