Citation: Ying-Ying Yu, Wei Sun, Lei Dong, Hai-Dong Liu, Dan Jiang, Jun-Hai Xiao, Xiao-Hong Yang, Song Li. Design, synthesis, and screen of cathepsin K inhibitors[J]. Chinese Chemical Letters, ;2013, 24(8): 715-718. shu

Design, synthesis, and screen of cathepsin K inhibitors

Ying-Ying Yu ^a,b ,
Wei Sun ^a,b ,
Lei Dong ^a,c ,
Hai-Dong Liu ^b ,
Dan Jiang ^b ,
Jun-Hai Xiao ^b,, ,
Xiao-Hong Yang ^a,, ,
Song Li ^b

1.
a School of Pharmaceutical Sciences, Jilin University, Changchun 130021, China;
2.
b Laboratory of Computer-Aided Drug Design and Discovery, Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China;
3.
c First Affiliated Hospital of Jilin University, Changchun 130021, China

Corresponding author: Jun-Hai Xiao, Xiao-Hong Yang,
Received Date: 6 March 2013
Available Online: 23 April 2013

We synthesized a series of epoxysuccinic acid derivatives and evaluated their in vitro cathepsin K inhibitory activity The screening results show that the potency of compounds 9e, 9d, 9p, 9j and 9k (IC₅₀≤0.005 μmol/L) were equal to or greater than that of the lead compound 9a. Less hydrophobic compounds showed weaker potency, which can be explained by the hydrophobic nature of the cathepsin K binding pockets.
- Epoxysuccinic acid derivatives,
- Synthesis,
- Inhibitors,
- Cathepsin K
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  [22] Analytic data for compounds. 3:[α]_D²⁰+ 107.1 (c 1.00, EtOH). 9a: Mp: 126-127℃;[α]_D²⁰+ 51.7 (c 1.00, EtOH); ¹H NMR (400 MHz, CDC_l3): δ 6.80 (d, 1H, J = 8.0 Hz), 6.16 (s, 1H), 4.35 (m, 1H), 4.27 (s, 2H), 3.69 (s, 1H), 3.48 (s, 1H), 3.11-3.41 (m, 2H), 1.47-1.76 (m, 4H), 1.41 (q, 2H, J = 7.0 Hz), 1.32 (t, 3H, J = 7.0 Hz), 0.85-1.04 (m, 12H); ¹³CNMR(100 MHz, CDC_l3): δ 170.9, 166.5, 166.2, 62.3, 53.8, 52.9, 50.4, 41.3, 41.2, 24.6, 23.2, 22.8, 22.7, 22.2, 13.9, 12.3, 11.3; MS (FAB) m/z 343.2 (M⁺). Anal. Calcd. for C₁₇H₃0N₂O₅: C 59.63, H 8.83, N 8.18; Found: C 59.78, H 8.60, N 7.95. IR (KBr, cm^-1): 3290, 2960, 1755, 1642, 1555, 900. 9b: Mp: 138-139℃; ¹H NMR (400 MHz, CDC_l3): δ 8.57 (d, 1H, J = 8.4 Hz), 6.04 (s, 1H), 4.10-4.40 (m, 3H), 3.71 (s, 1H), 3.58 (s, 1H), 2.90-3.10 (m, 2H), 0.80-1.70 (m, 17H); ¹³C NMR (100 MHz, CDC_l3): δ 170.9, 166.5, 166.0, 62.4, 53.8, 52.9, 51.4, 41.3, 41.2, 24.8, 22.8, 22.7, 22.2, 14.0, 11.3; MS (FAB) m/z 315.2 (M⁺). 9c: Mp: 154-156 ℃;. ¹HNMR(400 MHz, CDC_l3): δ 6.90 (d, 1H, J = 8.6 Hz), 7.95 (d, 1H, J = 7.6 Hz), 4.25-4.41 (m, 3H), 4.03-4.04 (m, 1H), 3.70 (s, 1H), 3.49 (s, 1H), 0.91-1.57 (m, 18H); ¹³C NMR (100 MHz, CDC_l3): δ170.1, 166.6, 165.9, 62.3, 53.8, 52.7, 51.4, 41.6, 41.5, 24.8, 22.8, 22.5, 22.4, 22.2, 13.99; MS (FAB) m/z 315.2 (M⁺). 9d: Mp: 139-141 ℃; ¹H NMR (400 MHz, CDC_l3): δ 8.56 (d, 1H, J = 8.6 Hz), 8.03 (d, 1H, J = 7.4 Hz), 4.29-4.31 (m, 1H), 4.17-4.19 (m, 2H), 3.71 (s, 1H), 3.57 (s, 1H), 2.90-3.10 (m, 2H), 1.10-1.60 (m, 12H), 0.85-1.04 (m, 9H); ¹³C NMR (100 MHz, CDC_l3): δ 170.9, 166.5, 166.0, 62.4, 53.8, 52.9, 51.4, 41.3, 41.2, 24.8, 23.2, 22.8, 22.7, 22.2, 14.0, 11.3; MS (FAB) m/ z 329.2 (M⁺). 9e: Mp: 133-135 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.54 (d, 1H, J = 8.4 Hz), 5.91 (s, 1H), 4.25-4.29 (m, 3H), 3.68 (s, 1H), 3.46 (s, 1H), 3.22-3.26 (m, 2H), 1.30-1.54 (m, 12H), 0.90-0.93 (m, 9H); ¹³C NMR (100 MHz, CDC_l3): δ 170.7, 166.5, 166.0, 62.4, 53.8, 53.0, 51.3, 41.2, 39.7, 29.1, 28.9, 24.8, 22.8, 22.3, 22.1, 14.0; MS (FAB) m/z 343.2 (M⁺). 9f: Mp: 175-177 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.89 (d, 1H, J = 8.6 Hz), 6.14 (t, 1H, J = 3.2 Hz), 4.22-4.27 (m, 3H), 3.71 (d, 1H, J = 1.6 Hz), 3.54 (d, 1H, J = 1.6 Hz), 3.15-3.28 (m, 2H), 0.92-1.85 (m, 17H); ¹³C NMR (100 MHz, CDC_l3): δ 170.2, 166.6, 165.9, 62.3, 57.6, 53.8, 52.9, 52.7, 41.3, 37.3, 25.0, 22.7, 15.2, 14.0, 11.3, 11.1; MS (FAB) m/z 315.2 (M⁺). 9g: Mp: 211-212 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.87 (d, 1H, J = 8.0 Hz), 5.84 (s, 1H), 4.15-4.29 (m, 4H), 3.70 (s, 1H), 3.55 (s, 1H), 0.90-1.81 (m, 18H); ¹³C NMR (100 MHz, CDC_l3): δ 169.1, 166.6, 165.9, 62.3, 57.3, 53.8, 52.9, 52.7, 41.7, 37.5, 25.0, 22.8, 22.7, 22.5, 15.2, 14.0, 11.2; MS (FAB) m/z 315.2 (M⁺). 9h: Mp: 187-188 ℃; ¹HNMR (400 MHz, CDC_l3): δ 6.88 (d, 1H, J = 12.0 Hz), 6.10 (s, 1H), 4.21-4.29 (m, 3H), 3.70 (s, 1H), 3.49 (s, 1H), 3.21-3.33 (m, 2H), 0.90-1.85 (m, 19H); ¹³C NMR (100 MHz, CDC_l3): δ 170.0, 166.6, 166.0, 62.3, 57.4, 53.9, 53.8, 52.9, 39.3, 37.3, 31.4, 25.0, 20.0, 15.3, 14.0, 13.7, 11.1; MS (FAB) m/z 329.2 (M⁺). 9i: Mp: 189-190 ℃; ¹H NMR (400 MHz, CDC_l3): δ 7.12 (m, 1H), 6.43 (s, 1H), 4.25-4.29 (m, 1H), 3.73-3.81 (m, 3H), 3.18-3.53 (m, 3H), 0.90-1.84 (m, 20H); ¹³C NMR (100 MHz, CDC_l3): δ 170.2, 167.2, 165.9, 57.5, 53.8, 52.6, 38.2, 37.9, 37.4, 25.8, 25.0, 22.4, 22.3, 15.3, 11.1; MS (FAB) m/z 343.2 (M⁺). 9j: Mp: 158-159 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.75 (d, 1H, J = 8.2 Hz), 5.86 (s, 1H), 4.16-4.29 (m, 3H), 3.69 (s, 1H), 3.47 (s, 1H), 3.21-3.32 (m, 2H), 0.89-1.85 (m, 21H); ¹³C NMR (100 MHz, CDC_l3): δ 169.9, 166.5,[(Fig._2)TD$FIG] Fig. 2. Molecular model of compound 9a, which binds with cathepsin K. Compound 9a is shown as a stick model and colored according to its atom color. Cathepsin K is shown as a cartoon model and colored according to its secondary structure. The S2 and S3 subsites of cathepsin K are labeled accordingly. This figure was generated with an automated molecular docking and database screening program DOCK 4.0[26]. Y.-Y. Yu et al. / Chinese Chemical Letters 24 (2013) 715-718 717 166.0, 62.4, 57.4, 57.3, 53.9, 53.0, 39.6, 37.3, 29.1, 29.0, 25.0, 22.3, 15.4, 14.0, 11.1; MS (FAB) m/z 343.2 (M⁺). 9k: Mp: 175-176 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.65 (d, 1H, J = 0.6 Hz), 5.70 (s, 1H), 4.14-4.26 (m, 3H), 3.69 (s, 1H), 3.53 (s, 1H), 3.18-3.33 (m, 2H), 0.87-1.83 (m, 23H); ¹³C NMR (100 MHz, CDC_l3): δ 170.0, 166.5, 165.9, 62.3, 57.5, 53.8, 52.8, 39.6, 37.3, 31.4, 29.4, 26.5, 25.0, 22.5, 15.4, 14.0, 11.2; MS (FAB) m/z 357.2 (M⁺). 9l: Mp: 95-96 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.97-7.32 (m, 5H), 5.07-5.11 (m, 1H), 4.24-4.27 (m, 2H), 3.35-3.64 (m, 8H), 2.90-3.00 (m, 4H), 1.30-1.33 (m, 3H); ¹³C NMR (100 MHz, CDC_l3): δ 169.0, 166.5, 165.3, 135.4, 129.5, 128.7, 127.5, 66.4, 66.0, 62.3, 53.8, 53.7, 52.7, 48.9, 48.8, 46.0, 42.3, 39.7, 14.0; MS (FAB) m/z 377.2 (M⁺). 9m: Mp: 183-185 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.82 (d, 1H, J = 0.4 Hz), 4.93 (s, 1H), 4.27-4.28 (m, 2H), 2.50-3.80 (m, 9H), 1.50-1.70 (m, 3H), 1.39-1.48 (m, 1H), 0.85-1.00 (m, 6H); ¹³C NMR (100 MHz, CDC_l3): δ 169.1, 166.5, 164.9, 135.4, 129.6, 128.7, 127.4, 66.4, 66.0, 62.2, 53.8, 53.7, 52.5, 48.9, 48.8, 46.0, 42.2, 39.7, 14.1 MS (FAB) m/z 359.2 (M⁺). 9n: Mp: 178-179 ℃; ¹H NMR (400 MHz, CDC_l3): δ 6.89 (d, 1H, J = 0.8 Hz), 4.79 (s, 1H), 4.24-4.26 (m, 2H), 3.67 (s, 2H), 1.80-3.56 (m, 8H), 1.50-1.62 (m, 2H), 1.40-1.50 (m, 1H), 1.29-1.33 (m, 3H), 0.91-1.00 (m, 6H); ¹³C NMR (100 MHz, CDC_l3): δ 169.0, 166.5, 165.3, 135.4, 129.5, 128.7, 127.5, 66.4, 65.9, 62.2, 53.8, 53.8, 52.5, 48.5, 48.3, 46.0, 42.3, 38.9, 14.0MS (FAB) m/z 327.2 (M⁺). 9p: Mp: 139-141 ℃; ¹H NMR (400 MHz, CDC_l3): δ 8.54 (d, 1H, J = 8.0 Hz), 8.0 (s, 1H), 4.26-4.30 (m, 1H), 3.66 (s, 1H), 3.44 (s, 1H), 3.11-3.47 (m, 2H), 1.47-1.76 (m, 4H), 1.41 (m, 2H), 0.85-1.04 (m, 12H); ¹³C NMR (100 MHz, CDC_l3): δ 170.8, 166.6, 166.2, 53.8, 52.9, 50.0, 41.2, 41.2, 24.5, 23.0, 22.8, 22.7, 22.1, 13.9, 11.3; MS (FAB) m/z 315.2 (M⁺).
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