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_1566547
_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         'C54 H49 Br2 N12 Ni O2, 2(C3 H7 N O), Cl'
_chemical_formula_sum            'C60 H63 Br2 Cl N14 Ni O4'
_chemical_formula_weight         1298.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                87.172(3)
_cell_angle_beta                 75.925(5)
_cell_angle_gamma                85.319(4)
_cell_formula_units_Z            2
_cell_length_a                   9.7632(13)
_cell_length_b                   15.6735(15)
_cell_length_c                   19.622(2)
_cell_measurement_reflns_used    9460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.714
_cell_measurement_theta_min      2.161
_cell_volume                     2901.4(6)
_computing_cell_refinement       'Bruker SAINT v8.40b'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT v8.40b'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Photon III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            58171
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.720
_diffrn_reflns_theta_min         2.141
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  0.6025
_exptl_absorpt_correction_T_min  0.5452
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_description       plate
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         1.074
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     745
_refine_ls_number_reflns         11045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0331
_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^)+(0.0348P)^2^+3.1505P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0833
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9289
_reflns_number_total             11045
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jm1c01740_si_021.cif
_cod_data_source_block           chwi850
_cod_database_code               1566547
_shelx_estimated_absorpt_t_min   0.811
_shelx_estimated_absorpt_t_max   0.982
_shelxl_version_number           2014-3
_shelx_res_checksum              40117
_shelx_hkl_checksum              58473