Synthesis of 6,8-diaminopurines via acid-induced cascade cyclization of 5-aminoimidazole precursors and preliminary anticancer evaluation
Senhorães, Nádia R.; Silva, Bruna F.; Sousa, Raquel; Leite, Bruna P.; Gonçalves, Jorge M.; Almeida Paz, Filipe A.; Pereira-Wilson, Cristina; Dias, Alice M.; Organic & Biomolecular Chemistry 22 (2024) 1500–1513; doi:10.1039/D3OB01985C

data_7159788
_publ_section_title
;
 Synthesis of 6,8-diaminopurines via acid-induced cascade cyclization of
 5-aminoimidazole precursors and preliminary anticancer evaluation
;
_journal_issue                   7
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_page_first              1500
_journal_page_last               1513
_journal_paper_doi               10.1039/D3OB01985C
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         '2(C19 H19 N6), 2(C2 F3 O2), C2 H6 O S, H2 O'
_chemical_formula_sum            'C44 H46 F6 N12 O6 S'
_chemical_formula_weight         984.99
_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   mixed
_audit_creation_date             '4 October 2023'
_audit_creation_method           'SHELXL-2019/3, manual editing plus enCIFer'
_audit_update_record
;
2023-10-04 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                100.594(4)
_cell_angle_beta                 108.280(4)
_cell_angle_gamma                94.426(4)
_cell_formula_units_Z            2
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_cell_length_b                   13.5757(17)
_cell_length_c                   14.5009(19)
_cell_measurement_reflns_used    9872
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.39
_cell_volume                     2322.0(5)
_computing_cell_refinement       'SAINT V8.37a'
_computing_data_collection       'APEX3 2016.9-0'
_computing_data_reduction        'SAINT V8.37a'
_computing_molecular_graphics    DIAMOND
_computing_publication_material  SHELXL-2019/2
_computing_structure_refinement  SHELXL-2018/3
_computing_structure_solution    'SHELXT 2014/5'
_diffrn_ambient_temperature      180(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker D8 QUEST '
_diffrn_measurement_method       '\w / \f scans'
_diffrn_radiation_monochromator  'Multi-layer X-ray mirror'
_diffrn_radiation_source         'Sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            59622
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.521
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9969
_exptl_absorpt_correction_T_min  0.9548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
  SADABS-2016/2
  Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
  J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.224
_refine_diff_density_min         -0.703
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         8466
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1334
_refine_ls_R_factor_gt           0.0857
_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^)+(0.1203P)^2^+5.4933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2240
_refine_ls_wR_factor_ref         0.2585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5411
_reflns_number_total             8466
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01985c2.cif
_cod_data_source_block           3c_TFA
_cod_depositor_comments          'Adding full bibliography for 7159788.cif.'
_cod_database_code               7159788
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.997
_exptl_absorpt_special_details
;
?
;
_shelx_res_checksum              67469