Investigation of the anticancer activity of modified 4-hydroxyquinolone analogues: in vitro and in silico studies
Bouone, Yousra Ouafa; Bouzina, Abdeslem; Djemel, Abdelhak; Bardaweel, Sanaa K.; Ibrahim-Ouali, Malika; Bakchiche, Boulanouar; Benaceur, Farouk; Aouf, Nour-Eddine; RSC Advances 15 (2025) 3704–3720; doi:10.1039/D5RA00252D

data_7249916
_publ_section_title
;
 Investigation of the anticancer activity of modified 4-hydroxyquinolone
 analogues: in vitro and in silico studies
;
_journal_issue                   5
_journal_name_full               'RSC Advances'
_journal_page_first              3704
_journal_page_last               3720
_journal_paper_doi               10.1039/D5RA00252D
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         '2(C17 H17 N O3)'
_chemical_formula_sum            'C34 H34 N2 O6'
_chemical_formula_weight         566.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2fvmdb
_audit_creation_date             2023-04-26
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-08 deposited with the CCDC.	2025-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.296(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3460(7)
_cell_length_b                   16.9005(8)
_cell_length_c                   15.8105(10)
_cell_measurement_reflns_used    10946
_cell_measurement_temperature    296
_cell_measurement_theta_max      75.9980
_cell_measurement_theta_min      3.8700
_cell_volume                     2909.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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    -11.00  14.00   1.00    2.00    --  -40.54  19.00  43.00   25
  2  \w   -120.00   0.00   1.00    2.00    --  -40.54 -19.00-123.00  120
  3  \w     -3.00  22.00   1.00    2.00    --   40.54 -19.00-123.00   25
  4  \w     17.00 120.00   1.00    2.00    --   40.54  19.00  43.00  103
  5  \w     51.00  80.00   1.00   20.00    --  112.00 -19.00-123.00   29
  6  \w    124.00 169.00   1.00   20.00    --  112.00  19.00  43.00   45
  7  \w    -25.00   1.00   1.00    2.00    --   40.54 -38.00 120.00   26
  8  \w     14.00  47.00   1.00    2.00    --   40.54 -38.00 120.00   33
  9  \w     23.00  95.00   1.00    2.00    --   40.54-125.00-120.00   72
 10  \w     41.00  75.00   1.00    2.00    --   40.54-125.00 -30.00   34
 11  \w     84.00 119.00   1.00   20.00    --  112.00  61.00 -30.00   35
 12  \w     85.00 153.00   1.00   20.00    --  112.00  30.00 -60.00   68
 13  \w     76.00 112.00   1.00   20.00    --  112.00-111.00-180.00   36
 14  \w     38.00  64.00   1.00   20.00    --  112.00 -94.00 120.00   26
 15  \w     36.00 102.00   1.00   20.00    --  112.00 -94.00   0.00   66
 16  \w     74.00 105.00   1.00   20.00    --  112.00 -94.00 120.00   31
 17  \w     41.00 108.00   1.00   20.00    --  112.00 -61.00   0.00   67
 18  \w    125.00 152.00   1.00   20.00    --  112.00  61.00 -30.00   27
 19  \w     43.00  69.00   1.00   20.00    --  112.00 -94.00-180.00   26
 20  \w     85.00 110.00   1.00   20.00    --  112.00 -94.00-180.00   25
 21  \w     83.00 111.00   1.00   20.00    --  112.00-111.00 -60.00   28
 22  \w     31.00  64.00   1.00   20.00    --  112.00 -94.00-120.00   33
 23  \w     40.00 100.00   1.00   20.00    --  112.00-111.00 -90.00   60
 24  \w    121.00 146.00   1.00   20.00    --  112.00  61.00 -60.00   25
 25  \w     82.00 109.00   1.00   20.00    --  112.00-111.00  60.00   27
 26  \w     87.00 116.00   1.00   20.00    --  112.00  61.00 -90.00   29
 27  \w    136.00 176.00   1.00   20.00    --  112.00  61.00 -90.00   40
 28  \w     84.00 118.00   1.00   20.00    --  112.00  61.00-150.00   34
 29  \w     62.00  91.00   1.00   20.00    --  112.00 -30.00 -30.00   29
 30  \w     51.00 106.00   1.00   20.00    --  112.00 -94.00 -60.00   55
 31  \w     46.00  94.00   1.00   20.00    --  112.00 -77.00 -60.00   48
 32  \w     84.00 149.00   1.00   20.00    --  112.00  30.00  60.00   65
 33  \w    101.00 144.00   1.00   20.00    --  112.00  77.00-120.00   43
 34  \w    104.00 132.00   1.00   20.00    --  112.00  45.00   0.00   28
 35  \w     37.00  86.00   1.00   20.00    --  112.00 -94.00-150.00   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1323574000
_diffrn_orient_matrix_UB_12      0.0172744000
_diffrn_orient_matrix_UB_13      -0.0555193000
_diffrn_orient_matrix_UB_21      0.0376026000
_diffrn_orient_matrix_UB_22      -0.0144739000
_diffrn_orient_matrix_UB_23      -0.0850909000
_diffrn_orient_matrix_UB_31      -0.0319543000
_diffrn_orient_matrix_UB_32      -0.0883706000
_diffrn_orient_matrix_UB_33      0.0030500000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25203
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.348
_diffrn_reflns_theta_min         3.915
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.00213(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     386
_refine_ls_number_reflns         6077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0548P)^2^+0.3999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1121
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5235
_reflns_number_total             6077
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ra00252d2.cif
_cod_data_source_block           yd1
_cod_database_code               7249916
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'c17 h17 n o3'
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.857
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C12(H12A,H12B), C14(H14A,H14B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C25(H25), C5(H5), C4(H4), C8(H8), C2(H2A), C22(H22), C6(H6), C19(H19), C3(H3),
  C20(H20), C23(H23), C21(H21)
2.c Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C33(H33A,H33B,
 H33C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5A)
;
_shelx_res_checksum              89890
_shelx_hkl_checksum              10699
_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 1.096
_oxdiff_exptl_absorpt_empirical_full_min 0.897