Design, synthesis, biological evaluation and molecular docking studies of quinoline-anthranilic acid hybrids as potent anti-inflammatory drugs.
Siddique, Sidra; Hussain, Khalid; Shehzadi, Naureen; Arshad, Muhammad; Arshad, Muhammad Nadeem; Iftikhar, Sadaf; Saghir, Farhat; Shaukat, Ayisha; Sarfraz, Muhammad; Ahmed, Nisar; Organic & biomolecular chemistry 22 (2024) 3708–3724; doi:10.1039/d4ob00040d

data_7159911
_publ_section_title
;
 Design, synthesis, biological evaluation and molecular docking studies of
 quinoline-anthranilic acid hybrids as potent anti-inflammatory drugs.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3708
_journal_page_last               3724
_journal_paper_doi               10.1039/d4ob00040d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C18 H15 Cl N2 O2'
_chemical_formula_sum            'C18 H15 Cl N2 O2'
_chemical_formula_weight         326.77
_chemical_name_common
;
2-Amino-benzoic acid 2-chloro-6-methyl-quinolin-3-ylmethyl ester
;
_chemical_name_systematic
; 
2-Amino-benzoic acid 2-chloro-6-methyl-quinolin-3-ylmethyl ester
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2fgxwq
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2024-04-17 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.077(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5600(8)
_cell_length_b                   17.5287(18)
_cell_length_c                   9.6337(10)
_cell_measurement_reflns_used    948
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.9
_cell_measurement_theta_min      3.1
_cell_volume                     1589.5(3)
_computing_cell_refinement       'Bruker APEX3 (Bruker, 2014)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2014)'
_computing_data_reduction        'Bruker Apex3 SAINT (Bruker, 2014)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_unetI/netI     0.0534
_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       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.388
_diffrn_reflns_theta_min         2.164
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7056
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0727
_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^)+(0.0641P)^2^+3.2851P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2350
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1739
_reflns_number_total             3243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob00040d2.cif
_cod_data_source_block           nadeem_ma_sid_ccdc_DRARSHAD
_cod_depositor_comments          'Adding full bibliography for 7159911.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159911
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              73904