Home Physical Sciences Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
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Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7

  • Zhuyun Liu ORCID logo EMAIL logo , Pengfei Ding , Shanshan Yang , Donghua Zhai , Yunying Sha , Ruifang Zhang and Lizhong Wang
Published/Copyright: December 23, 2024
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 240 Issue 1

Abstract

C31H37NO7, monoclinic, P21 (no. 4), a = 8.1269(1) Å, b = 11.0527(1) Å, c = 16.3586(2) Å, β = 97.973(1)°, V = 1455.19(3) Å3, Z = 2, Rgt (F) = 0.0467, wRref (F 2) = 0.1308, T = 293(2) K.

CCDC no.: 2362487

A part of 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: Colourless block
Size: 0.16 × 0.12 × 0.10 mm
Wavelength:

μ:		 Cu Kα radiation (1.54184 Å)

0.70 mm−1
Diffractometer, scan mode:

θ max, completeness:		 XtaLAB Synergy, ω

66.6°, >99 %
N(hkl)measured, N(hkl)unique, R int: 42561, 5127, 0.068
Criterion for I obs, N(hkl)gt: I obs >  2σ(I obs), 4702
N(param)refined: 356
Programs: CrysAlisPRO, 1 Olex2 2 , 3
Table 2:

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

Atom x y z U iso*/U eq
C1 0.6012 (3) 0.6137 (3) 0.89752 (17) 0.0566 (6)
C2 0.4303 (3) 0.6300 (3) 0.89772 (17) 0.0621 (7)
C3 0.3182 (4) 0.5324 (4) 0.8733 (2) 0.0755 (10)
C4 0.3714 (5) 0.7408 (4) 0.9217 (2) 0.0832 (11)
H4 0.257709 0.752352 0.920608 0.100*
C5 0.4775 (6) 0.8316 (4) 0.9467 (3) 0.0928 (12)
H5 0.437260 0.904698 0.963945 0.111*
C6 0.6459 (5) 0.8160 (4) 0.9465 (2) 0.0853 (10)
H6 0.718186 0.879327 0.963013 0.102*
C7 0.7083 (4) 0.7088 (3) 0.9224 (2) 0.0683 (8)
H7 0.822131 0.699648 0.922591 0.082*
C8 0.8221 (3) 0.4772 (3) 0.87548 (16) 0.0522 (6)
H8 0.875186 0.536187 0.842791 0.063*
C9 0.9123 (3) 0.4671 (3) 0.96346 (18) 0.0625 (7)
H9A 1.018735 0.508065 0.968148 0.075*
H9B 0.846627 0.503853 1.001997 0.075*
C10 0.8967 (4) 0.2732 (3) 0.91209 (19) 0.0675 (8)
C11 0.8328 (3) 0.3522 (3) 0.84333 (16) 0.0533 (6)
C12 0.7903 (3) 0.3135 (3) 0.76617 (17) 0.0564 (6)
H12 0.806448 0.231882 0.755841 0.068*
C13 0.7192 (3) 0.3899 (3) 0.69534 (16) 0.0545 (6)
H13A 0.766487 0.470460 0.702390 0.065*
H13B 0.600252 0.396931 0.695378 0.065*
C14 0.7518 (3) 0.3395 (2) 0.61170 (15) 0.0489 (5)
H14 0.706400 0.257255 0.608419 0.059*
C15 0.9337 (4) 0.3270 (3) 0.6039 (2) 0.0700 (8)
C16 1.0561 (4) 0.3723 (6) 0.6556 (3) 0.1031 (15)
H16A 1.165233 0.362582 0.645623 0.124*
H16B 1.033673 0.414072 0.702103 0.124*
C17 0.9629 (5) 0.2591 (5) 0.5282 (3) 0.0938 (12)
H17A 0.922709 0.176775 0.531332 0.113*
H17B 1.081111 0.255776 0.525136 0.113*
C18 0.8740 (5) 0.3200 (5) 0.4513 (2) 0.0912 (12)
H18A 0.887251 0.271298 0.403346 0.109*
H18B 0.924052 0.398382 0.444631 0.109*
C19 0.6885 (4) 0.3365 (3) 0.45646 (17) 0.0604 (7)
H19 0.648566 0.254713 0.465943 0.073*
C20 0.6591 (3) 0.4089 (2) 0.53565 (15) 0.0496 (6)
C21 0.7232 (5) 0.5393 (3) 0.5383 (2) 0.0721 (9)
H21A 0.715062 0.573790 0.591434 0.108*
H21B 0.657610 0.586031 0.496281 0.108*
H21C 0.837171 0.539849 0.528795 0.108*
C22 0.4726 (3) 0.4088 (3) 0.54030 (17) 0.0601 (7)
H22A 0.438915 0.327352 0.552659 0.072*
H22B 0.451118 0.460638 0.585455 0.072*
C23 0.3670 (5) 0.4516 (4) 0.4613 (2) 0.0801 (9)
H23A 0.250278 0.444616 0.467297 0.096*
H23B 0.390591 0.536030 0.451829 0.096*
C24 0.4025 (5) 0.3771 (3) 0.38809 (18) 0.0728 (9)
H24 0.368931 0.293360 0.396649 0.087*
C25 0.5846 (5) 0.3765 (3) 0.37335 (18) 0.0742 (9)
C26 0.1788 (5) 0.3555 (4) 0.2761 (2) 0.0871 (11)
C27 0.0722 (7) 0.4237 (5) 0.2103 (3) 0.1130 (16)
H27A 0.017421 0.488508 0.234838 0.170*
H27B −0.009424 0.370210 0.181794 0.170*
H27C 0.139911 0.456294 0.172017 0.170*
C28 0.6036 (7) 0.2826 (4) 0.3056 (2) 0.1012 (14)
H28A 0.709845 0.292585 0.287136 0.152*
H28B 0.517116 0.294233 0.260023 0.152*
H28C 0.595653 0.202588 0.327536 0.152*
C29 0.6409 (8) 0.5033 (4) 0.3477 (2) 0.1088 (17)
H29A 0.581730 0.565017 0.374074 0.131*
H29B 0.758712 0.513203 0.366311 0.131*
C30 0.5844 (6) 0.6319 (4) 0.2364 (2) 0.0859 (10)
C31 0.5579 (9) 0.6481 (5) 0.1454 (3) 0.126 (2)
H31A 0.656627 0.624804 0.123287 0.189*
H31B 0.533224 0.731385 0.132445 0.189*
H31C 0.466675 0.598399 0.121665 0.189*
N1 0.2240 (4) 0.4560 (5) 0.8564 (3) 0.1049 (12)
O1 0.6463 (2) 0.50224 (18) 0.87444 (13) 0.0593 (5)
O2 0.9359 (3) 0.3401 (2) 0.98130 (12) 0.0692 (6)
O3 0.9139 (5) 0.1656 (3) 0.91437 (17) 0.1045 (10)
O4 0.2956 (4) 0.4253 (2) 0.31613 (16) 0.0983 (9)
O5 0.1614 (5) 0.2510 (3) 0.2906 (2) 0.1191 (12)
O6 0.6096 (5) 0.5189 (3) 0.25982 (14) 0.1034 (10)
O7 0.5770 (6) 0.7125 (4) 0.2845 (2) 0.1312 (14)

1 Source of materials

To the solution of andrographolide (9.95 g, 28.4 mmol) and 2,2-dimethoxypropane (24 mL, 195.3 mmol) in 20 mL of anhydrous dichloromethane, PPTS (0.71 g, 2.8 mmol) was added and the reaction mixture was heated at 40 °C. The reaction was monitored by TLC and then treated with ethyl acetate and sat. NaHCO3 after the reaction was completed. The organic phase was washed with brine, dried over anhydrous Na2SO4, and then filtered organic solution was evaporated to dryness. The residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 1:1) to produce 3,19-acetonylidene andrographolide (10.01 g, 24.7 mmol) as a white solid 4 . Under N2 atmosphere, compound 3,19-acetonylidene andrographolide (3.94 g, 10.1 mmol), PPh3 (3.97 g, 15.1 mmol) and 2-hydroxybenzonitrile (1.80 g, 15.1 mmol) were dissolved in 30 mL of anhydrous THF. The solution was cooled to 0 °C and then treated with DIAD (3 mL, 15.1 mmol) in 5 mL of anhydrous THF. The reaction was stirred overnight at room temperature after being stirred at 0 °C for 1 h. After distilling of the volatile solvents, the residue was dissolved in ethyl acetate and washed with brine about 5 times and dried over anhydrous Na2SO4. The filtered organic solution was evaporated to dryness and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 5:1) to give 14-(R)-(2′-cyano-phenoxy)-3,19-isopropylidene andrographolide (3.05 g, 6.2 mmol) as a white solid 4 . Compound 14-(R)-(2′-cyano-phenoxy)-3,19-isopropylidene andrographolide (2.45 g, 5.0 mmol) was added in 15 mL of methanol and then treated with p-toluenesulphonic acid monohydrate (0.10 g, 0.5 mmol) at 20 °C for 30 min. Diluted by ethyl acetate and washed with sat. NaHCO3, brine, the organic phase was dried over anhydrous Na2SO4, filtered, evaporated by a rotavap to dryness. Compound 14-(R)-(2′-cyano-phenoxy)-andrographolide (2.03 g, 4.5 mmol) was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 10:7) 4 . Compound 14-(R)-(2′-cyano-phenoxy)-andrographolide (1.81 g, 4.0 mmol) was added in 10 mL of acetic anhydride and then treated with zinc chloride (0.05 g, 0.4 mmol) at 60 °C for 1 h. The solution was cooled to room temperature and then diluted by ethyl acetate and washed with sat. NaHCO3, brine, the organic phase was dried over anhydrous Na2SO4, The filtered organic solution was evaporated to dryness and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 4:1) to give 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl-isopropylidene andrographolide (1.50 g, 2.8 mmol) as a white solid. Crystals of the title compound were obtained by recrystallization from a 1:1 system of ethyl acetate: petroleum ether.

2 Experimental details

X-ray reflections on compound cocrystal were collected on a XtaLAB Synergy HyPix diffractometer. All H atoms attached to carbon were included using a riding-model using Olex2, 2 with C–H = 0.93–0.98 Å, and their Uiso values were set to 1.2 U eq. The structure was solved with the OLEX2 3 structure solution program.

3 Comment

The title compound, 14-R-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide is an important derivative of natural active substances. To the best of our knowledge, there is no example of an title compound that has been reported so far. The asymmetric unit of the title structure contains one 14-R-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide molecule. The bond lengths and angles within the structure of 14-R-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide are unexceptional and lie within the expected ranges. In details, the C–O distances within 4-isobutoxybenzaldehyde oxime have values between 1.191(6)–1.463(4) Å. The C26–O5 distance is 1.191(6) Å and the C30–O7 distance is 1.195(5) Å, which suggest an O=C double bond. So esterification is as expected. Andrographolide is a diterpenoid lactone bioactive agent used in traditional medicine in China. 5 It is derived from the plant leaves of Andrographis paniculata. Andrographolide has many pharmacological actions, such as antiviral, antiinflammatory, anticancer, 6 , 7 and antimalarial. 8 Despite being safe at high doses of 17 g/kg per day in humans, the efficacy of andrographolide is limited by poor bioavailability of 2.67 % (reported in rats). 9 This is partly owing to its poor aqueous solubility (46 mg/L). 10 A significant drop in the bioavailability of andrographolide is due to transformation to four metabolites. The main metabolite of andrographolide was identified as 14-deoxy-12-R-sulfoandrographolide. 11 The title compound is obtained by linking 2′-cyano-phenoxy to andrographolide so that andrographolide will not take this reaction. Then andrographolide can have better bioavailability.

Corresponding author: Zhuyun Liu, Taizhou Polytechnic College, School of Intelligent Pharmaceutical Manufacturing and New Chemical Engineering Materials, No. 8 Tianxing Road, Taizhou Medical High Tech Zone, Taizhou, Jiangsu 225300, P.R. China, E-mail:

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

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

  3. Research funding: The work was supported by General Project for Natural Science Research in Jiangsu Province Universities (23KJD350004), 2023 Jiangsu Vocational College Student Innovation and Entrepreneurship Cultivation Plan Project (G-2023–1731), and 2023 Jiangsu Province University “Blue Project” Excellent Teaching Team.

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Received: 2024-09-16
Accepted: 2024-11-29
Published Online: 2024-12-23
Published in Print: 2025-02-25

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

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

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https://doi.org/10.1515/ncrs-2024-0374
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  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
  4. Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
  5. Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
  6. Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
  7. Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
  8. Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
  9. The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
  10. The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
  11. The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
  12. The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
  13. Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
  14. The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
  15. The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
  16. Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
  17. The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
  18. Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
  19. The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
  20. The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
  21. Crystal structure of (−)-flavesine H, C15H22N2O2
  22. Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
  23. Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
  24. The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
  25. The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
  26. Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
  27. The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
  28. The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
  29. The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
  30. Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
  31. Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
  32. Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
  33. Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
  34. Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
  35. Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
  36. The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
  37. The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
  38. Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
  39. The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
  40. Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
  41. Crystal structure of CaPtZn
  42. Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
  43. The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
  44. Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
  45. The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
  46. Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
  47. The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
  48. Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
  49. Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
  50. Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
  51. Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
  52. Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
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