Antitumor Potential of the Isoflavonoids (+)- and (−)-2,3,9-Trimethoxypterocarpan: Mechanism-of-Action Studies
Farias, Kaio; da Costa, Roner F.; Meira, Assuero S.; Diniz-Filho, Jairo; Bezerra, Eveline M.; Freire, Valder N.; Guest, Prue; Nikahd, Maryam; Ma, Xinghua; Gardiner, Michael G.; Banwell, Martin G.; de Oliveira, Maria da C. F.; de Moraes, Manoel O.; do Ó Pessoa, Claudia; ACS Medicinal Chemistry Letters  (2020) –; doi:10.1021/acsmedchemlett.0c00097

data_4517723
_publ_section_title
;
 Antitumor Potential of the Isoflavonoids (+)- and
 (&#x2212;)-2,3,9-Trimethoxypterocarpan: Mechanism-of-Action Studies
;
_journal_name_full               'ACS Medicinal Chemistry Letters'
_journal_paper_doi               10.1021/acsmedchemlett.0c00097
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H18 O5'
_chemical_formula_sum            'C18 H18 O5'
_chemical_formula_weight         314.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.099(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.76720(10)
_cell_length_b                   18.8707(4)
_cell_length_c                   16.6201(4)
_cell_measurement_reflns_used    8672
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.6470
_cell_measurement_theta_min      4.6580
_cell_volume                     1492.96(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -106.00  32.00   1.00    4.00    --  -37.08   0.00  60.00  138
  2  \w      8.00 108.00   1.00    4.00    --   37.08  19.00-180.00  100
  3  \w     20.00 104.00   1.00    4.00    --   37.08  57.00  60.00   84
  4  \w    -21.00  64.00   1.00    4.00    --   37.08 -77.00 120.00   85
  5  \w     20.00 104.00   1.00    4.00    --   37.08  57.00   0.00   84
  6  \w      8.00  36.00   1.00    4.00    --   37.08  82.00-110.18   28
  7  \w      6.00  76.00   1.00    4.00    --   37.08 -99.00 -60.00   70
  8  \w      4.00  30.00   1.00    4.00    --   37.08  89.00  85.35   26
  9  \w    -34.00  66.00   1.00    4.00    --   37.08 -19.00 150.00  100
 10  \w      6.00  76.00   1.00    4.00    --   37.08 -99.00  90.00   70
 11  \w      4.00  29.00   1.00    4.00    --   37.08  88.00 173.84   25
 12  \w    -16.00  56.00   1.00    4.00    --   37.08 -38.00   0.00   72
 13  \w     77.00 105.00   1.00    4.00    --   37.08  38.00 -30.00   28
 14  \w     86.00 118.00   1.00   17.50    --  111.00  25.00  30.00   32
 15  \w     63.00 146.00   1.00   17.50    --  111.00 178.00-150.00   83
 16  \w     90.00 129.00   1.00   17.50    --  111.00 -38.00  60.00   39
 17  \w     41.00 109.00   1.00   17.50    --  111.00-111.00 -90.00   68
 18  \w    130.00 159.00   1.00   17.50    --  111.00  38.00 -60.00   29
 19  \w     68.00 113.00   1.00   17.50    --  111.00 -25.00 -30.00   45
 20  \w     58.00  85.00   1.00   17.50    --  111.00 -64.00-180.00   27
 21  \w     66.00  98.00   1.00   17.50    --  111.00  12.00  90.00   32
 22  \w    115.00 143.00   1.00   17.50    --  111.00  12.00  90.00   28
 23  \w     93.00 123.00   1.00   17.50    --  111.00  38.00 -60.00   30
 24  \w     68.00  99.00   1.00   17.50    --  111.00 -64.00-150.00   31
 25  \w     93.00 120.00   1.00   17.50    --  111.00  38.00  30.00   27
 26  \w    152.00 178.00   1.00   17.50    --  111.00  64.00   0.00   26
 27  \w     49.00  76.00   1.00   17.50    --  111.00 -92.00  60.00   27
 28  \w     97.00 159.00   1.00   17.50    --  111.00  64.00  30.00   62
 29  \w     91.00 118.00   1.00   17.50    --  111.00  64.00   0.00   27
 30  \w     95.00 158.00   1.00   17.50    --  111.00  50.00-180.00   63
 31  \w    104.00 140.00   1.00   17.50    --  111.00  77.00 -60.00   36
 32  \w     93.00 140.00   1.00   17.50    --  111.00  64.00 -30.00   47
 33  \w    124.00 178.00   1.00   17.50    --  111.00  77.00 -90.00   54
 34  \w     98.00 154.00   1.00   17.50    --  111.00  50.00 120.00   56
 35  \w     99.00 133.00   1.00   17.50    --  111.00  38.00-150.00   34
 36  \w     69.00  96.00   1.00   17.50    --  111.00 -38.00-120.00   27
 37  \w    128.00 178.00   1.00   17.50    --  111.00  77.00 -30.00   50
 38  \w    116.00 143.00   1.00   17.50    --  111.00  77.00 150.00   27
 39  \w     93.00 157.00   1.00   17.50    --  111.00 -12.00 -60.00   64
 40  \w    101.00 144.00   1.00   17.50    --  111.00  50.00 150.00   43
 41  \w     46.00  94.00   1.00   17.50    --  111.00-111.00 -60.00   48
 42  \w     91.00 120.00   1.00   17.50    --  111.00 -50.00-180.00   29
 43  \w     42.00 135.00   1.00   17.50    --  111.00 -25.00 -90.00   93
 44  \w    104.00 130.00   1.00   17.50    --  111.00 -25.00  30.00   26
 45  \w     45.00 122.00   1.00   17.50    --  111.00 -25.00 150.00   77
 46  \w     93.00 125.00   1.00   17.50    --  111.00  38.00   0.00   32
 47  \w    106.00 133.00   1.00   17.50    --  111.00 111.00 -60.00   27
 48  \w     47.00  92.00   1.00   17.50    --  111.00 -92.00   0.00   45
 49  \w     92.00 119.00   1.00   17.50    --  111.00  38.00 -30.00   27
 50  \w     96.00 121.00   1.00   17.50    --  111.00 -64.00  30.00   25
 51  \w     59.00 130.00   1.00   17.50    --  111.00 -77.00 120.00   71
 52  \w     54.00  81.00   1.00   17.50    --  111.00 -15.00 135.45   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1706363000
_diffrn_orient_matrix_UB_12      0.0688945000
_diffrn_orient_matrix_UB_13      -0.0064262000
_diffrn_orient_matrix_UB_21      -0.0447006000
_diffrn_orient_matrix_UB_22      -0.0022381000
_diffrn_orient_matrix_UB_23      -0.0925138000
_diffrn_orient_matrix_UB_31      -0.2712695000
_diffrn_orient_matrix_UB_32      0.0436593000
_diffrn_orient_matrix_UB_33      0.0053263000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17369
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.115
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.332
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 2621 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         5951
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0390
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.1480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5716
_reflns_number_total             5951
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ml0c00097_si_002.cif
_cod_data_source_block           mn-(+)ptcscaled
_cod_database_code               4517723
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H18 O5'
_reflns_odcompleteness_completeness 98.47
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C27(H27), C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C13(H13), C16(H16), C17(H17), C21(H21), C26(H26), C31(H31),
 C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C23(H23A,H23B,H23C),
 C25(H25A,H25B,H25C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              11844
_shelx_hkl_checksum              10204
_ins_header
;
TITL MN-(+)PTCscaled in P2(1) 
REM P2(1) (#4 in standard setting)
CELL 1.54184   4.767174  18.870654  16.620141  90.0000  93.0993  90.0000
ZERR    4.00   0.000141   0.000420   0.000437   0.0000   0.0025   0.0000
LATT -1
SYMM -x, y+1/2,-z 
SFAC C H O
UNIT 72.00 72.00 20.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-02-01
_olex2_date_sample_submission    2019-12-18
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGen holder with oil'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.493
_oxdiff_exptl_absorpt_empirical_full_min 0.586