Highly Antiproliferative Latonduine and Indolo[2,3-<i>c</i>]quinoline Derivatives: Complex Formation with Copper(II) Markedly Changes the Kinase Inhibitory Profile.
Wittmann, Christopher; Bacher, Felix; Enyedy, Eva A.; Dömötör, Orsolya; Spengler, Gabriella; Madejski, Christian; Reynisson, Jóhannes; Arion, Vladimir B.; Journal of medicinal chemistry 65 (2022) 2238–2261; doi:10.1021/acs.jmedchem.1c01740

data_1566546
_publ_section_title
;
 Highly Antiproliferative Latonduine and Indolo[2,3-<i>c</i>]quinoline
 Derivatives: Complex Formation with Copper(II) Markedly Changes the
 Kinase Inhibitory Profile.
;
_journal_issue                   3
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              2238
_journal_page_last               2261
_journal_paper_doi               10.1021/acs.jmedchem.1c01740
_journal_volume                  65
_journal_year                    2022
_chemical_formula_moiety         'C26 H25 Cl2 Cu N6 O, 2(C3 H7 N O), Cl'
_chemical_formula_sum            'C32 H39 Cl3 Cu N8 O3'
_chemical_formula_weight         753.60
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                78.160(6)
_cell_angle_beta                 77.214(6)
_cell_angle_gamma                70.423(6)
_cell_formula_units_Z            1
_cell_length_a                   7.2313(10)
_cell_length_b                   9.2604(13)
_cell_length_c                   14.1201(19)
_cell_measurement_reflns_used    3656
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.68
_cell_measurement_theta_min      2.36
_cell_volume                     859.9(2)
_computing_cell_refinement       'Bruker SAINT V8.38A'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT V8.38A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1639
_diffrn_reflns_av_sigmaI/netI    0.0921
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            50235
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             391
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.890
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6261
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+5.1841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1779
_reflns_number_gt                4739
_reflns_number_total             6261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm1c01740_si_018.cif
_cod_data_source_block           feba603
_cod_database_code               1566546