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_7249818
_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         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_chemical_name_systematic
'ethyl 2-amino-4-(furan-2-yl)-6-methyl-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                91.662(2)
_cell_angle_beta                 90.972(2)
_cell_angle_gamma                115.979(2)
_cell_formula_units_Z            4
_cell_length_a                   7.9731(2)
_cell_length_b                   8.1795(2)
_cell_length_c                   28.7599(7)
_cell_measurement_reflns_used    13893
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      78.7
_cell_measurement_theta_min      6.0
_cell_volume                     1684.46(8)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_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_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9888
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.169
_diffrn_reflns_theta_min         3.076
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       blocks
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.031
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         9888
_refine_ls_number_restraints     34
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0743P)^2^+0.6918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1419
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8552
_reflns_number_total             9888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra06201a2.cif
_cod_data_source_block           sb1525_hy_compound_3b
_cod_original_cell_volume        1684.45(8)
_cod_database_code               7249818
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.973
_shelx_res_checksum              47388
_shelx_hkl_checksum              42053