Structural simplification of bioactive natural products with multicomponent synthesis. 2. antiproliferative and antitubulin activities of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones.
Magedov, Igor V.; Manpadi, Madhuri; Ogasawara, Marcia A.; Dhawan, Adriana S.; Rogelj, Snezna; Van Slambrouck, Severine; Steelant, Wim F. A.; Evdokimov, Nikolai M.; Uglinskii, Pavel Y.; Elias, Eerik M.; Knee, Erica J.; Tongwa, Paul; Antipin, Mikhail Yu; Kornienko, Alexander; Journal of medicinal chemistry 51 (2008) 2561–2570; doi:10.1021/jm701499n

data_1504344
_publ_section_title
;
 Structural simplification of bioactive natural products with
 multicomponent synthesis. 2. antiproliferative and antitubulin activities
 of pyrano[3,2-c]pyridones and pyrano[3,2-c]quinolones.
;
_journal_issue                   8
_journal_name_full               'Journal of medicinal chemistry'
_journal_page_first              2561
_journal_page_last               2570
_journal_paper_doi               10.1021/jm701499n
_journal_volume                  51
_journal_year                    2008
_chemical_formula_moiety         'C17 H13 Cl2 N3 O2, C2 H6 O'
_chemical_formula_sum            'C19 H19 Cl2 N3 O3'
_chemical_formula_weight         408.27
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.757(8)
_cell_angle_beta                 74.660(9)
_cell_angle_gamma                80.836(9)
_cell_formula_units_Z            2
_cell_length_a                   9.120(6)
_cell_length_b                   10.251(6)
_cell_length_c                   11.299(7)
_cell_measurement_reflns_used    1677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.89
_cell_measurement_theta_min      2.33
_cell_volume                     964.1(10)
_computing_cell_refinement       'SAINT+ v. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINT+ v. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL v. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL v. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_sigmaI/netI    0.1265
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12392
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.362
_exptl_absorpt_correction_T_max  0.9312
_exptl_absorpt_correction_T_min  0.8993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1419
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0250P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2219
_reflns_number_total             4524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jm701499n-file004.cif
_cod_data_source_block           paul6a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               1504344