Citation: Shuai Mua, Xiao-Shuai Xie, Duan Niu, Da-Shuai Zhang, Deng-Ke Liu, Chang-Xiao Liu. Synthesis and biological evaluation of novel derivatives of desloratadine[J]. Chinese Chemical Letters, ;2013, 24(6): 531-534. shu

Synthesis and biological evaluation of novel derivatives of desloratadine

1.
a School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China;
2.
b State Key Laboratory of Drug Delivery Technology and Pharmacokinetics, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China;
3.
c Graduate School of Tianjin Medical University, Tianjin 300070, China;
4.
d Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China

Corresponding author: Chang-Xiao Liu,
Received Date: 2 February 2013
Available Online: 11 March 2013

Series of novel derivatives of desloratadine designed as arginine vasopressin receptor antagonists were synthesized and structurally characterized by melting points, ¹H NMR and HRMS. Their in vivo diuretic activities were evaluated on rats, and several target compounds showed promising diuretic results, especially compounds 8, 18, 27 and 31. Further in vitro bonding assay and cAMP assay showed that these compounds had a higher affinity to vasopressin V2 receptor than V1a receptor. Our studies indicated that desloratadine may be an active substructure for novel arginine vasopressin receptor antagonist development.
- Derivatives of desloratadine,
- Arginine vasopressin receptor antagonists,
- Diuretic activity
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  [7] 3: ¹H NMR (400 MHz, CDC_l3): δ 2.08 (s, 3H), 2.29-2.53 (m, 4H), 2.76-2.88 (m, 2H), 3.12-3.40 (m, 4H), 3.61-3.67 (m, 1H), 3.99-4.07 (m, 1H), 7.07-7.16 (m, 4H), 7.42 (d, 1H, J = 7.6 Hz), 8.38 (d, 1H, J = 3.2 Hz). 4: ¹H NMR (400 MHz, CDC_l3): δ 1.14 (t, 3H, J = 7.4 Hz), 2.34-2.72 (m, 6H), 2.76-2.89 (m, 2H), 3.12-3.43 (m, 4H), 3.64-3.70 (m, 1H), 4.03-4.11 (m, 1H), 7.08-7.17 (m, 4H), 7.43-7.45 (d, 1H, J = 7.6 Hz), 8.40 (d, 1H, J = 3.6 Hz). 5: ¹H NMR (400 MHz, CDC_l3): δ 1.13 (dd, 6H, J₁ = 9.28.0 Hz, J₂ = 9.216.0 Hz), 2.32-2.58 (m, 4H), 2.76-2.89 (m, 3H), 3.10-3.43 (m, 4H), 3.71-3.77 (m, 1H), 4.05-4.12 (m, 1H), 7.08-7.17 (m, 4H), 7.44 (d, 1H, J = 7.2 Hz), 8.40 (d, 1H, J = 3.6 Hz). 6: ¹H NMR (400 MHz, CDC_l3): δ 0.96 (t, 3H, J = 9.2 Hz), 1.63-1.78 (m, 2H), 2.33-2.40 (m, 5H), 2.45-2.56 (m, 1H), 2.57-2.89 (m, 2H), 3.10-3.43 (m, 4H), 3.64-3.72 (m, 1H), 7.08-7.17 (m, 4H), 7.43 (d, 1H, J = 7.6 Hz), 8.39-8.41 (t, 1H, J = 2.2 Hz). 7: ¹H NMR (400 MHz, CDC_l3): δ 1.62-1.75 (m, 3H), 2.39-2.48 (m, 3H), 2.49-2.66 (m, 1H), 2.68-2.88 (m, 2H), 2.99-3.29 (m, 1H), 3.31-3.49 (m, 3H), 3.65-4.23 (m, 2H), 4.54-4.62 (m, 1H), 7.08-7.17 (m, 4H), 7.43 (d, 1H, J = 7.6 Hz), 8.40 (d, 1H, J = 3.6 Hz). 8: ¹H NMR (400 MHz, CDC_l3): δ 2.09-2.19 (m, 2H), 2.30-2.43 (m, 3H), 2.46-2.59 (m, 3H), 2.76-2.89 (m, 2H), 3.08-3.42 (m, 4H), 3.62-4.10 (m, 4H), 7.08-7.17 (m, 4H), 7.44 (d, 1H, J = 7.6 Hz), 8.40 (d, 1H, J = 4.8 Hz). 9: ¹H NMR (400 MHz, CDC_l3): δ 1.37 (t, 3H, J = 14.2 Hz), 2.37-2.45 (m, 2H), 2.47-2.51 (m, 1H), 2.52-2.65 (m, 1H), 2.76-2.90 (m, 2H), 2.96 (q, 2H, J = 7.5 Hz), 3.13-3.20 (m, 2H), 3.30-3.42 (m, 2H), 3.47-3.66 (m, 2H), 7.09-7.18 (m, 4H), 7.44 (dd, 1H, J₁ = 9.21.2 Hz, J₂ = 9.28.8 Hz), 8.40 (dd, 1H, J₁ = 9.21.2 Hz, J₂ = 9.25.6 Hz). 10: ¹H NMR (400 MHz, CDC_l3): δ 2.49-2.54 (m, 3H), 2.60-2.66 (m, 1H), 2.75-2.89 (m, 2H), 3.00-3.06 (m, 2H), 3.28-3.47 (m, 4H), 6.01 (d, 1H, J = 10.0 Hz), 6.22 (d, 1H, J = 16.4 Hz), 6.43 (dd, 1H, J₁ = 9.26.0 Hz, J₂ = 9.216.8 Hz), 7.07-7.17 (m, 4H), 7.43 (d, 1H, J = 8.8 Hz), 8.39 (d, 1H, J = 6.0 Hz). 11: ¹H NMR (400 MHz, CDC_l3): δ 2.31-2.58 (m, 4H), 2.76-2.89 (m, 2H), 3.22-3.43 (m, 4H), 3.62 (br s, 1H), 4.14 (br s, 1H), 7.11-7.46 (m, 10H), 8.38 (br s, 1H). 12: ¹H NMR (400 MHz, CDC_l3): δ 2.28-2.64 (m, 6H), 2.75-2.95 (m, 2H), 3.078 (br s, 1H), 3.29-3.44 (m, 4H), 4.26 (br s, 1H), 7.04-7.46 (m, 9H), 8.33 (d, 0.5H, J = 3.6 Hz), 8.43 (d, 0.5H, J = 3.6 Hz). 13: ¹H NMR (400 MHz, CDC_l3): δ 2.35-2.50 (m, 7H), 2.77-2.89 (m, 2H), 3.27-3.42 (m, 4H), 3.66 (br s, 1H), 4.16 (br s, 1H), 7.12-7.44 (m, 9H), 8.38 (br s, 1H). 14: ¹H NMR (400 MHz, CDC_l3): δ 2.33-2.48 (m, 7H), Table 2 The substituents, melting points, HRMS, purity and diuretic activity of compounds 11-31. Compound X R2 Melting point (8C) ESI-HRMS [M⁺H]+ Purity (HPLC, %) Total volume of urine (0-20 h, mL) 11 CO H 91.3-92.6 415.1572 98.3 6.6 3.7 12 CO 2-CH3 80.5-81.3 429.1726 99.1 5.8 3.2 13 CO 4-CH3 165.2-165.8 429.1724 98.2 9.6 2.1 14 CO 3-CH3 93.6-94.8 429.1732 98.3 8.0 4.4 15 CO 2-Cl 109.5-110.8 449.1190 99.9 5.8 3.1 16 CO 3-Cl 96.0-96.8 449.1185 96.8 5.9 4.5 17 CO 2-F 129.8-131.5 433.1481 97.2 6.0 2.4 18 CO 2,5-DiF 159.5-161.0 451.1385 97.4 21.1 5.6 19 CO 2-OCH3 105.2-107.9 445.1676 99.3 16.8 4.8 20 CO 3-OCH3 71.2-72.8 445.1676 99.9 11.5 1.9 21 CO 3-NO2 193.8-194.6 460.1427 99.9 9.6 4.1 22 CO 4-NO2 188.2-189.0 460.1427 98.9 9.5 0.7 23 SO2 2-CH3 92.8-94.9 465.1395 99.6 14.9 4.0 24 SO2 4-CH3 209.2-209.7 465.1395 99.9 5.4 2.4 25 SO2 2-Cl 169.8-170.4 485.0857 96.6 10.3 4.8 26 SO2 2-NO2 176.9-177.6 496.1097 98.3 9.4 3.6 27 SO2 3-NO2 221.7-222.8 496.1088 98.5 26.5 4.3 28 SO2 4-NO2 >230 496.1087 98.9 17.7 5.5 29 SO2 2,5-DiCl 95.8-96.0 519.0463 98.5 13.0 3.0 30 SO2 2,5-DiOCH3 182.9-184.3 511.1452 99.9 21.4 5.5 31 SO2 2-CH3-5-NO2 178.1-179.2 510.1241 99.5 24.0 5.1 Table 3 In vitro binding and cAMP assay data. Compound Radioligand binding assay cAMP assay (V2, IC₅₀, nmol/L) V2 (IC₅₀, nmol/L) V1a (IC₅₀, nmol/L) V1a/V2 5 20 440 22 130 8 11 160 15 260 11 35 930 27 93 12 9 540 60 30 15 13 820 63 69 18 16 490 31 180 23 8 380 48 45 27 9 91 10 37 S. Mu et al. / Chinese Chemical Letters 24 (2013) 531-534 533 2.75-2.88 (m, 2H), 3.22-3.42 (m, 4H), 3.62 (br s, 1H), 4.16 (br s, 1H), 7.10-7.24 (m, 8H), 7.43 (d, 1H, J = 7.2 Hz), 8.36 (br s, 1H). 15: ¹H NMR (400 MHz, CDC_l3):d 2.17-2.66 (m, 4H), 2.75-2.88 (m, 2H), 3.01-3.67 (m, 1H), 3.28-3.44 (m, 4H), 4.14-4.28 (m, 1H), 7.02-7.44 (m, 9H), 8.29-8.41 (m, 1H). 16: ¹H NMR (400 MHz, CDC_l3): δ 2.28-2.68 (m, 4H), 2.77-2.89 (m, 2H), 3.22-3.42 (m, 4H), 3.59 (br s, 1H), 4.11 (br s, 1H), 7.12-7.26 (m, 4H), 7.27-7.39 (m, 3H), 7.41-7.46 (m, 2H), 8.38 (br s, 1H). 17: ¹H NMR (400 MHz, CDC_l3): δ 2.24-2.27 (m, 4H), 2.75-2.96 (m, 2H), 3.19 (br s, 1H), 3.31-3.55 (m, 4H), 4.13-4.40 (m, 1H), 7.02-7.24 (m, 6H), 7.32-7.38 (m, 2H), 7.45-7.51 (m, 1H), 8.34-8.48 (m, 1H). 18: ¹H NMR (400 MHz, CDC_l3): δ 2.28-2.64 (m, 4H), 2.74-2.89 (m, 2H), 3.17-3.28 (m, 1H), 3.30-3.51 (m, 4H), 4.11-4.21 (m, 1H), 7.02-7.17 (m, 7H), 7.42 (dd, 1H, J₁ = 9.28.0 Hz, J₂ = 9.211.2 Hz), 8.38 (dd, 1H, J₁ = 9.24.0 Hz, J₂ = 9.230.8 Hz). 19: ¹H NMR (400 MHz, CDC_l3): δ 2.20-2.49 (m, 4H), 2.52-2.88 (m, 2H), 3.00-3.12 (m, 1H), 3.23-3.46 (m, 4H), 3.756-3.84 (m, 3H), 4.19-4.31 (m, 1H), 6.83-6.98 (m, 2H), 7.03-7.16 (m, 5H), 7.27-7.44 (m, 2H), 8.32-8.42 (m, 1H). 20: ¹H NMR (400 MHz, CDC_l3): δ 2.02-2.68 (m, 4H), 2.75-2.89 (m, 2H), 3.22-3.43 (m, 4H), 3.60-3.86 (m, 4H), 4.07-4.37 (m, 1H), 6.89-6.94 (m, 3H), 7.12-7.15 (m, 4H), 7.26-7.59 (m, 2H), 8.39 (br s, 1H). 21: ¹H NMR (400 MHz, CDC_l3): δ 2.18-2.45 (m, 4H), 2.81-2.82 (m, 2H), 3.42-3.44 (m, 5H), 3.96 (br s, 1H), 7.11-7.30 (m, 4H), 7.56-7.87 (m, 3H), 8.21-8.36 (m, 3H). 22: ¹H NMR (400 MHz, DMSO-d6): δ 2.18-2.32 (m, 2H), 2.41 (br s, 1H), 2.79-2.84 (m, 2H), 3.17-3.36 (m, 6H), 3.97 (br s, 1H), 7.05-7.32 (m, 4H), 7.54-7.57 (m, 1H), 7.68 (d, 2H, J = 8.4 Hz), 8.25-8.36 (m, 3H). 23: ¹H NMR (400 MHz, CDC_l3): δ 2.33-2.44 (m, 3H), 2.54-2.60 (m, 4H), 2.63-2.83 (m, 2H), 3.01-3.07 (m, 2H), 3.29-3.48 (m, 4H), 7.05-7.14 (m, 4H), 7.26-7.30 (m, 2H), 7.41-7.45 (m, 2H), 7.86 (t, 1H, J = 4.0 Hz), 8.39 (d, 1H, J = 3.2 Hz). 24: ¹H NMR (400 MHz, CDC_l3): δ 2.36-2.37 (m, 2H), 2.44-2.63 (m, 5H), 2.70-2.83 (m, 2H), 2.93-3.00 (m, 2H), 3.17-3.32 (m, 4H), 6.99-7.13 (m, 4H), 7.31 (d, 2H, J = 8.0 Hz), 7.38-7.41 (m, 1H), 7.63 (d, 2H, J = 9.6 Hz), 8.35-8.36 (dd, 1H, J₁ = 9.21.6 Hz, J₂ = 9.24.8 Hz). 25: ¹H NMR (400 MHZ, DMSO-d6): δ 2.21-2.43 (m, 4H), 2.75-2.81 (m, 2H), 3.07-3.12 (m, 2H), 3.22-3.44 (m, 4H), 7.06 (d, 1H, J = 8.4 Hz), 7.16-7.19 (m, 2H), 7.28 (s, 1H), 7.53 (t, 2H, J = 6.4 Hz), 7.67 (q, 2H, J = 8.1 Hz), 7.96 (d, 1H, J = 7.6 Hz), 8.31 (d, 1H, J = 4.0 Hz). 26: ¹H NMR (400 MHz, CDC_l3): δ 2.39-2.43 (m, 2H), 2.46-2.64 (m, 2H), 2.73-2.87 (m, 2H), 3.16-3.39 (m, 4H), 3.50-3.59 (m, 2H), 7.05-7.16 (m, 4H), 7.42 (dd, 1H, J₁ = 9.21.6 Hz, J₂ = 9.27.6 Hz), 7.59-7.72 (m, 3H), 7.96-7.98 (m, 1H), 8.37 (t, 1H, J = 2.4 Hz). 27: ¹H NMR (400 MHz, CDC_l3): δ 2.40-2.41 (m, 2H), 2.50-2.57 (m, 1H), 2.62-2.68 (m, 1H), 2.71-2.86 (m, 2H), 3.09-3.15 (m, 2H), 3.22-3.36 (m, 4H), 7.01 (d, 2H, J = 8.0 Hz), 7.11-7.15 (m, 3H), 7.45 (d, 1H, J = 7.6 Hz), 7.76 (t, 1H, J = 8.0 Hz), 8.07-8.10 (m, 1H), 8.37 (d, 1H, J = 6.4 Hz), 8.44-8.59 (m, 1H), 8.59 (d, 1H, J = 2.0 Hz). 28: ¹H NMR (400 MHz, CDC_l3): δ 2.34-2.39 (m, 2H), 2.46-2.49 (m, 1H), 2.60-2.62 (m, 1H), 2.72-2.81 (m, 2H), 2.99-3.03 (m, 2H), 3.20-3.33 (m, 4H), 6.98 (d, 1H, J = 8.4 Hz), 7.05-7.13 (m, 3H), 7.39 (d, 1H, J = 7.6 Hz), 7.91-7.94 (m, 2H), 8.33-8.37 (m, 3H). 29: ¹H NMR (400 MHz, CDC_l3): δ 2.33-2.49 (m, 3H), 2.54-2.60 (m, 1H), 2.72-2.86 (m, 2H), 3.14-3.38 (m, 4H), 3.49-3.57 (m, 2H), 7.03-7.15 (m, 4H), 7.40-7.43 (m, 3H), 8.01 (t, 1H, J = 0.6 Hz), 8.36 (d, 1H, J = 4.8 Hz). 30: ¹H NMR (400 MHz, CDC_l3): δ 2.29-2.57 (m, 4H), 2.71-2.84 (m, 2H), 3.04-3.13 (m, 2H), 3.24-3.37 (m, 2H), 3.44-3.77 (m, 2H), 3.77 (s, 3H), 3.83 (s, 3H), 6.92-7.13 (m, 6H), 7.39-7.41 (m, 2H), 8.36 (dd, 1H, J₁ = 9.21.6 Hz, J₂ = 9.24.8 Hz). 31: ¹H NMR (400 MHz, CDC_l3): δ 2.38-2.62 (m, 4H), 2.73-2.88 (m, 5H), 3.12-3.52 (m, 6H), 7.03-7.15 (m, 4H), 7.43-7.51 (m, 2H), 8.25-8.37(m, 2H), 8.70 (d, 1H, J = 2.4 Hz).
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