Design, synthesis, molecular docking and anti-proliferative activity of novel phenothiazine containing imidazo[1,2-a]pyridine derivatives against MARK4 protein
Bhakta, Avijit; Mukhtar, Sayeed; Anwar, Saleha; Haider, Shaista; Alahmdi, Mohammed Issa; Parveen, Humaira; Alsharif, Meshari A.; Wani, Mohmmad Younus; Chakrabarty, Anindita; Hassan, Md. Imtaiyaz; Ahmed, Naseem; RSC Medicinal Chemistry  (2024) –; doi:10.1039/D4MD00059E

data_7248496
_publ_section_title
;
 Design, synthesis, molecular docking and anti-proliferative activity of
 novel phenothiazine containing imidazo[1,2-a]pyridine derivatives against
 MARK4 protein
;
_journal_name_full               'RSC Medicinal Chemistry'
_journal_paper_doi               10.1039/D4MD00059E
_journal_year                    2024
_chemical_formula_moiety         'C26 H17 N3 O S, 0.333(H2 O)'
_chemical_formula_sum            'C26 H17.67 N3 O1.33 S'
_chemical_formula_weight         425.49
_chemical_melting_point          394.0(10)
_chemical_name_systematic
(10H-phenothiazin-2-yl)(2-phenylimidazo[1,2-a]pyridin-3-yl)methanone
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-17 deposited with the CCDC.	2024-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.0710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   12.1900(6)
_cell_length_b                   33.2340(16)
_cell_length_c                   16.1930(8)
_cell_measurement_reflns_used    9689
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      24.471
_cell_measurement_theta_min      2.228
_cell_volume                     6550.7(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-IV CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            373523
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.585
_diffrn_reflns_theta_min         1.673
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1163 before and 0.0621 after correction.
The Ratio of minimum to maximum transmission is 0.9661.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             2656
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM-Hexane mixture'
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     850
_refine_ls_number_reflns         16539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0481P)^2^+6.8177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1220
_refine_ls_wR_factor_ref         0.1343
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12152
_reflns_number_total             16539
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4md00059e2.cif
_cod_data_source_block           3a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '393-395' was changed to
'394.0(10)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7248496
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N00C(H00C), N00H(H00H), N00I(H00I), C00O(H00O), C00R(H00R), C00X(H00X),
 C00Y(H00Y), C015(H015), C016(H016), C01A(H01A), C01B(H01B), C01H(H01H),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01N(H01N), C01P(H01P),
 C01Q(H01Q), C01R(H01R), C01S(H01S), C01T(H01T), C01U(H01U), C01V(H01V),
 C01W(H01W), C01X(H01X), C01Y(H01Y), C01Z(H01Z), C020(H020), C021(H021),
 C022(H022), C023(H023), C024(H024), C025(H025), C026(H026), C027(H027),
 C028(H028), C029(H029), C02A(H02A), C02B(H02B), C02C(H02C), C02E(H02E),
 C02F(H02F), C02H(H02H), C02I(H02I), C02J(H02J), C02K(H02K), C02L(H02L),
 C02M(H02M), C02N(H02N), C02O(H02O)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'