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. Author manuscript; available in PMC: 2015 Dec 1.
Published in final edited form as: Eur J Med Chem. 2015 Feb 28;94:123–131. doi: 10.1016/j.ejmech.2015.02.052

Table 3.

Aqueous solubility of compound 17 with various complexing acids (−R). The pKa of 17 is predicted around 6.0, which is similar to Ambien® (zolpidem).

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Acid (−R) Acid pKa Aqueous solubility (mg/mL)a
Free-basea / <0.080
Acetic acid 4.7 <0.080
HCl −7.0 <0.080
pTSA −2.8 ~0.25
Acetylsalicylic acid 3.5 <0.080
Stearic acid 4.7 <0.080
2-thiobarbituric acid 3.9 <0.080
L-ascorbic acid 4.1 <0.080
Salicylic acid 2.9 <0.080
Oxalic acid 1.2 ~0.50
Benzoic acid 4.2 <0.080
a

25 °C with 0.2 μM filtered, deionized water at pH 7.