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_4517722
_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_formula_moiety         'C22 H24 O6'
_chemical_formula_sum            'C22 H24 O6'
_chemical_formula_weight         384.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 104.836(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0596(19)
_cell_length_b                   4.9375(7)
_cell_length_c                   24.003(3)
_cell_measurement_reflns_used    490
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      58.7910
_cell_measurement_theta_min      5.9810
_cell_volume                     1839.8(4)
_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      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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    -87.00  -6.00   1.00  130.00    --  -36.84 125.00-150.00   81
  2  \w   -103.00 -56.00   1.00  130.00    --  -36.84 -38.00  60.00   47
  3  \w    -53.00 -18.00   1.00  130.00    --  -36.84 -38.00  60.00   35
  4  \w     28.00 111.00   1.00  180.00    --   84.62-125.00 -30.00   83
  5  \w     64.00 154.00   1.00  180.00    --   84.62  30.00  90.00   90
  6  \w     50.00 102.00   1.00  180.00    --   84.62 -61.00 -60.00   52
  7  \w     28.00 111.00   1.00  180.00    --   84.62-125.00-180.00   83
  8  \w     70.00 140.00   1.00  180.00    --   84.62  15.00  30.00   70
;
_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      -0.0209595000
_diffrn_orient_matrix_UB_12      -0.2846536000
_diffrn_orient_matrix_UB_13      0.0190518000
_diffrn_orient_matrix_UB_21      0.0680652000
_diffrn_orient_matrix_UB_22      -0.1232807000
_diffrn_orient_matrix_UB_23      -0.0274771000
_diffrn_orient_matrix_UB_31      0.0689539000
_diffrn_orient_matrix_UB_32      0.0352731000
_diffrn_orient_matrix_UB_33      0.0574059000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.1482
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4792
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        61.069
_diffrn_reflns_theta_max         61.069
_diffrn_reflns_theta_min         3.810
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35960
_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    1.388
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2751
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0762
_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^)+(0.0360P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1392
_reflns_number_total             2751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ml0c00097_si_003.cif
_cod_data_source_block           mn-fc-178scaled
_cod_database_code               4517722
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 H24 O6 '
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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:
 C2(H2), C3(H3), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C17(H17), C22(H22)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              10063
_shelx_hkl_checksum              35193
_ins_header
;
TITL MN-FC-178scaled in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184  16.059572   4.937543  24.002774  90.0000 104.8364  90.0000
ZERR    4.00   0.001872   0.000726   0.003341   0.0000   0.0115   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H O
UNIT 88.00 96.00 24.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2020-01-28
_olex2_date_sample_submission    2019-12-10
_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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.640