Microwave-assisted synthesis and in vitro and in silico studies of pyrano[3,2-c]quinoline-3-carboxylates as dual acting anti-cancer and anti-microbial agents and potential topoisomerase II and DNA-gyrase inhibitors
Aly, Ashraf A.; Abd El-Naby, Hisham A.; Ahmed, Essam Kh.; Gedamy, Sageda A.; Rissanen, Kari; Nieger, Martin; Brown, Alan B.; Shehat, Michael G.; Shaaban, Marwa M.; Atta, Amal; RSC Advances 15 (2025) 1941–1956; doi:10.1039/D4RA06201A

data_7249817
_publ_section_title
;
 Microwave-assisted synthesis and in vitro and in silico studies of
 pyrano[3,2-c]quinoline-3-carboxylates as dual acting anti-cancer and
 anti-microbial agents and potential topoisomerase II and DNA-gyrase
 inhibitors
;
_journal_issue                   3
_journal_name_full               'RSC Advances'
_journal_page_first              1941
_journal_page_last               1956
_journal_paper_doi               10.1039/D4RA06201A
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C19 H16 N2 O5'
_chemical_formula_sum            'C19 H16 N2 O5'
_chemical_formula_weight         352.34
_chemical_name_systematic
'ethyl 2-amino-4-(furan-2-yl)-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylate'
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-12-07 deposited with the CCDC.	2024-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                106.141(3)
_cell_angle_beta                 103.673(2)
_cell_angle_gamma                100.320(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2266(2)
_cell_length_b                   8.5847(3)
_cell_length_c                   12.5866(3)
_cell_measurement_reflns_used    10226
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      78.3
_cell_measurement_theta_min      3.8
_cell_volume                     800.60(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'omega scans, 0.5 deg.'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17010
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.251
_diffrn_reflns_theta_min         3.836
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       blocks
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0651P)^2^+0.2659P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3087
_reflns_number_total             3430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra06201a2.cif
_cod_data_source_block           sb1526_hy_compound_3a
_cod_database_code               7249817
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              172
_shelx_hkl_checksum              85562