The Scientific World Journal / 2013 / Article / Tab 1

Research Article

Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates

Table 1

Structure of the target compounds 19a23d and comparison of calculated lipophilicities (log  ) with determined log  values; calculated values of solubility (log  ), molar volume (MV [cm3]), surface tension (ST [dyne/cm]), and determined p values, and in vitro antimycobacterial activity (MIC [ mol/L]) of compounds compared to ciprofloxacin (CPX), isoniazid (INH), pyrazinamide (PZA), and rifampicin (RIF) standards.

274570.table.001
CompoundR1R2Log  Log  Log  p MVa [cm3]STa [dyne/cm]MIC [ mol/L]
MAPMI

19aCH32-OCH30.38702.52−3.078.82331.9250.65275550
19bC2H52-OCH30.39762.71−3.398.90348.4349.73128533
19cC3H72-OCH30.40893.15−3.708.67364.9348.9164259
19dC4H92-OCH30.42283.44−4.008.73381.4448.1662201
20aCH34-OCH30.38812.95−3.128.25331.9250.65550550
20bC2H54-OCH30.39993.40−3.448.23348.4349.73533533
20cC3H74-OCH30.41083.70−3.757.99364.9348.91259259
20dC4H94-OCH30.42414.09−4.058.18381.4448.1662121
21aCH32,6-OCH30.38652.33−3.039.14355.9249.10516516
21bC2H52,6-OCH30.39562.54−3.348.88372.4348.32501501
21cC3H72,6-OCH30.40522.84−3.658.90388.9447.62117487
21dC4H92,6-OCH30.41773.13−3.948.58405.4446.9959114
22aCH32-F0.39043.00−3.517.98316.2851.45564564
22bC2H52-F0.40113.13−3.847.99341.4250.42547547
22cC3H72-F0.42063.54−4.157.97348.5449.51265265
22dC4H92-F0.43413.88−4.467.96364.6648.69124124
23aCH34-F0.39152.63−3.528.04316.2851.45564564
23bC2H54-F0.40323.21−3.828.09341.4250.42547547
23cC3H74-F0.42283.66−4.118.16348.5449.5166265
23dC4H94-F0.43654.16−4.398.08364.6648.6964258
CPX181181
INH>1823>729
PZA>2031>812
RIF>109

Calculated for the uncharged molecule; MAP: Mycobacterium avium subsp. paratuberculosis CIT03; MI: Mycobacterium intracellulare.

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