Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone derivatives as new anti-cancer agents
Gusakov, Evgeniy A.; Topchu, Iuliia A.; Mazitova, Aleksandra M.; Dorogan, Igor V.; Bulatov, Emil R.; Serebriiskii, Ilya G.; Abramova, Zinaida I.; Tupaeva, Inna O.; Demidov, Oleg P.; Toan, Duong Ngoc; Lam, Tran Dai; Bang, Duong Nghia; Boumber, Yanis A.; Sayapin, Yurii A.; Minkin, Vladimir I.; RSC Advances 11 (2021) 4555–4571; doi:10.1039/D0RA10610K

data_7242164
_publ_section_title
;
 Design, synthesis and biological evaluation of 2-quinolyl-1,3-tropolone
 derivatives as new anti-cancer agents
;
_journal_issue                   8
_journal_name_full               'RSC Advances'
_journal_page_first              4555
_journal_page_last               4571
_journal_paper_doi               10.1039/D0RA10610K
_journal_volume                  11
_journal_year                    2021
_chemical_compound_source        'Rostov-on-Don, Russia'
_chemical_formula_moiety         'C25 H26 Cl2 N2 O4'
_chemical_formula_sum            'C25 H26 Cl2 N2 O4'
_chemical_formula_weight         489.38
_chemical_melting_point          509
_chemical_name_common
5,7-di(tert-butyl)-2-(4,7-dichloro-8-methyl-2-quinolyl)-4-nitro-1,3-tropolone
_chemical_name_systematic
5,7-di(tert-butyl)-2-(4,7-dichloro-8-methyl-2-quinolyl)-4-nitro-1,3-tropolone
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-10-26 deposited with the CCDC.	2021-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                88.165(3)
_cell_angle_beta                 87.926(3)
_cell_angle_gamma                73.153(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6690(2)
_cell_length_b                   9.8456(4)
_cell_length_c                   15.9190(6)
_cell_measurement_reflns_used    16515
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6340
_cell_measurement_theta_min      4.6460
_cell_volume                     1149.35(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -74.00  35.00   1.00    1.00    --  -41.35  77.00-180.00  109
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00  60.00   99
  3  \w    -66.00  33.00   1.00    1.00    --  -41.35  38.00-120.00   99
  4  \w    -74.00  35.00   1.00    1.00    --  -41.35  77.00 -30.00  109
  5  \w      1.00  82.00   1.00    1.00    --   41.35 -99.00   0.00   81
  6  \w     35.00 137.00   1.00    1.00    --  107.59 -61.00  30.00  102
  7  \w     34.00 122.00   1.00    1.00    --  107.59-125.00-180.00   88
  8  \w     31.00 140.00   1.00    1.00    --  107.59 -77.00 150.00  109
  9  \w     34.00 122.00   1.00    1.00    --  107.59-125.00   0.00   88
 10  \w     82.00 178.00   1.00    1.00    --  107.59  45.00-180.00   96
 11  \w     31.00 136.00   1.00    1.00    --  107.59 -30.00 150.00  105
 12  \w     25.00 109.00   1.00    1.00    --  107.59 -94.00   0.00   84
 13  \w     35.00 133.00   1.00    1.00    --  107.59 -45.00 -60.00   98
 14  \w     82.00 178.00   1.00    1.00    --  107.59  45.00 120.00   96
 15  \w     55.00 178.00   1.00    1.00    --  107.59  15.00 120.00  123
 16  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00-180.00  100
 17  \w   -113.00 -65.00   1.00    1.00    --  -41.35-138.00 -41.00   48
 18  \w   -113.00 -13.00   1.00    1.00    --  -41.35 -57.00 -90.00  100
 19  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00  30.00  108
 20  \w     75.00 178.00   1.00    1.00    --  107.59  77.00  60.00  103
 21  \w     82.00 178.00   1.00    1.00    --  107.59  45.00-120.00   96
 22  \w     78.00 178.00   1.00    1.00    --  107.59  61.00   0.00  100
 23  \w     75.00 178.00   1.00    1.00    --  107.59  77.00-180.00  103
 24  \w     55.00 178.00   1.00    1.00    --  107.59  15.00 -30.00  123
 25  \w     78.00 178.00   1.00    1.00    --  107.59  61.00  30.00  100
 26  \w     82.00 178.00   1.00    1.00    --  107.59  45.00 150.00   96
 27  \w     75.00 178.00   1.00    1.00    --  107.59  77.00 -60.00  103
 28  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00 120.00  108
 29  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00-150.00  108
 30  \w   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00 -30.00   99
 31  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00 -60.00  108
 32  \w     78.00 117.00   1.00    1.00    --  107.59  61.00 -90.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0046500000
_diffrn_orient_matrix_UB_12      -0.0345779000
_diffrn_orient_matrix_UB_13      0.0951084000
_diffrn_orient_matrix_UB_21      0.0806549000
_diffrn_orient_matrix_UB_22      -0.1590487000
_diffrn_orient_matrix_UB_23      -0.0182021000
_diffrn_orient_matrix_UB_31      0.1938096000
_diffrn_orient_matrix_UB_32      0.0158176000
_diffrn_orient_matrix_UB_33      0.0023413000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21532
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.028
_diffrn_reflns_theta_min         4.694
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.838
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate'
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.197
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4600
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0325
_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^)+(0.0484P)^2^+0.5465P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0855
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4477
_reflns_number_total             4600
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra10610k2.cif
_cod_data_source_block           jo_161_100
_cod_database_code               7242164
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C25 H26 Cl2 N2 O4'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C51(H51), C35(H35), C27(H27), C10(H10)
2.b Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C6(H6A,H6B,H6C), C12(H12A,H12B,
 H12C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C)
;
_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 1.586
_oxdiff_exptl_absorpt_empirical_full_min 0.659
_shelx_res_checksum              76525