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Citation: Jian Yang, Ju-Rong Li, Jing-Xiang Yang, Long-Long Li, Wen-Jie Ouyang, Shu-Wen Wu, Fang Zhang. Synthesis and anti-HIV-1 activity of the conjugates of gossypol with oligopeptides and D-glucosamine[J]. Chinese Chemical Letters, ;2014, 25(7): 1052-1056. doi: 10.1016/j.cclet.2014.05.030 shu

Synthesis and anti-HIV-1 activity of the conjugates of gossypol with oligopeptides and D-glucosamine

  • 1.

    a Department of Pharmacy, Renmin Hospital of Wuhan University, Wuhan 430060, China;

  • 2.

    b The College of Life Sciences, State Key Laboratory of Virology, Modern Virology Research Center, Wuhan University, Wuhan 430072, China;

  • 3.

    c Wuhan University School of Pharmaceutical Sciences, Wuhan 430071, China

  • Corresponding author: Jian Yang, 
  • Received Date: 20 February 2014
    Available Online: 13 May 2014

    Fund Project: We gratefully acknowledge the National Natural Science Foundation of China (No. 30770228) for financial support. (No. 30770228)

  • A series of novel gossypol derivatives were synthesized and screened for their in vitro anti-HIV-1 activity. The results showed that replacing the aldehyde groups of gossypol with certain oligopeptides and Dglucosamine not only reduced the cytotoxicity of gossypol derivatives but also enhanced their antiviral activity against HIV-1. Interestingly, D-glucosamine derivative of gossypol that lacked the COONa group also exhibited the same potent anti-HIV-1 activity as oligopeptide derivatives with the COONa group. These compounds blocked the entry of HIV-1IIIB into target cell, which was similar to T20. Furthermore, the molecular docking analysis rationalized their anti-HIV-1 activity. The results also implied that certain oligopeptides and D-glucosaminewere important moities to prepare gossypol derivatives as HIV-1 entry inhibitors besides certain amino acids.
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      [12] Analytical data for compounds: 1: Yellow crystal; 92.9% yield, mp 213-214℃(decomposition); IR (KBr, cm-1): vmax 3483, 3361, 2962, 2928, 1616, 1504, 1369, 1311, 1247, 1092, 1038; 1H NMR (400 MHz, DMSO-δ6): δ 13.1896 (broad, 2H, 2×=CH-NH), 9.7048 (broad, 2H, ×=CH-NH), 8.4878 (s, 2H, 2×6-OH), 7.7589 (s, 2H, 2×Glu-OH), 7.4442 (s, 2H, 2×4-H), 5.3526 (s, 2H, 2×Glu-OH), 5.2442 (s, 2H, 2×Glu-OH), 5.2017 (d, 2H, J=7.8 Hz, 2×Glu-C17HN), 5.0785 (s, 2H, 2×Glu-OH), 3.6644-3.3482 (m, 12H, 2 × 4×Glu-CH, 2×Glu-CH2), 3.1835 (sept, 2H, 2×CH(CH3)2), 1.9323 (s, 6H, 2×Ar-CH3), 1.4344 (d, 12H, J=6.3 Hz, 2×CH(CH3)2); 13C NMR (100 MHz, DMSO-δ6): δ 171.9593, 162.3969, 149.5768, 146.3828, 131.0172, 126.8700, 126.2059, 120.0529, 116.4998, 116.0120, 103.1450, 90.6044, 72.3004, 71.5499, 70.3252, 60.7674, 55.7574, 26.4723, 20.3102, 20.3102, 20.1543; MS (ESI+): m/z 841.8 [M+H]+. 2: Yellow crystal; 92.6% yield, mp 177-178℃; IR (KBr, cm-1):vmax 3485, 2961, 1756, 1610, 1542, 1490, 1418, 1369, 1321, 1216, 1077, 1038; 1H NMR (300 MHz, CDCl3):δ 13.505 (s, 2H, ×=CH-NH), 9.581 (d, 2H, J=9.3 Hz, ×=CH-NH), 7.755 (s, 2H, 2×-OH), 7.599 (s, 2H, 2×4-H), 5.854 (d, 2H, J=7.8 Hz, 2×Glu-C17HN), 5.609 (s, 2H, 2×1-OH), 5.428-3.702(m, 12H, 2×4×Glu-CH, 2×Glu-CH2), 3.592 (sept, 2H, 2×CH(CH3)2), 2.073(s, 24H, 2 × 4×COCH3), 1.958 (s, 6H, 2×Ar-CH3), 1.515 (d, 12H, J=6.3 Hz, 2×CH(CH3)2); 13C NMR(75 MHz, CDCl3):δ 173.64, 170.57, 169.88, 169.63, 168.71, 162.49, 149.16, 146.80, 132.36, 129.49, 128.40, 118.53, 115.98, 114.22, 104.15, 92.07, 72.68, 72.33, 67.71, 63.99, 61.48, 27.43, 20.79, 20.65, 20.59, 20.46, 20.24, 20.19, 19.96; MS (ESI+): m/z 1176.1 [M-H]-. 3: Yellow crystal; 88.2% yield, mp 210℃(decomposition); IR (KBr, cm-1):vmax 3483, 3377, 2963, 2871, 1616, 1520, 1494, 1401, 1308, 1246, 1168, 1021; 1HNMR(400 MHz, DMSOd6):δ13.2702 (s, 2H, 2×=CH-NH), 9.6983 (s, 2H, ×=CH-NH), 8.3898 (s, 2H, 2×-OH), 8.1827 (m, 2H, 2×N19-H), 7.3605 (s, 2H, 2×4-H), 4.4452 (m, 4H, 2×20-H), 3.6750 (m, 2H, 2×C17HN), 3.5397 (sept, 2H, 2×CH(CH3)2), 1.9473 (d, 6H, J=5.5 Hz, 2×17-CH3), 1.8841 (s, 6H, 2×Ar-CH3), 1.4247 (d, 12H, J=6.3 Hz, 2×CH(CH3)2); 13C NMR (100 MHz, DMSO-δ6):δ177.8820, 177.4359, 175.0255, 157.9823, 151.4497, 145.2643, 132.0330, 128.6840, 127.1184, 121.3668, 117.6309, 116.2757, 103.4103, 61.2516, 48.2834, 26.8479, 25.5420, 25.5420, 25.2018, 23.7551; MS (ESI+): m/z 773.8 [[M-2Na+H]-2Na+H]-. 4: Yellow crystal; 85.3% yield, mp 237℃(decomposition); IR (KBr, cm-1):vmax 3483, 3371, 2973, 2932, 2871, 1614, 1520, 1453, 1407, 1365, 1309, 1244, 1168, 1056; 1H NMR (400 MHz, DMSO-δ6):δ13.2743 (s, 2H,5CH-NH), 10.0064 (s, 2H, ×=CH-NH), 8.2501 (s, 2H, 2×=5OH), 8.1609 (d, 2H, J=6.5 Hz, 2×N19-H), 7.3257 (s, 2H, 2×4-H), 4.4312 (m, 2H, 2×20-H), 3.9447 (m, 2H, 2×C17HN), 3.6738 (sept, 2H, 2×CH(CH3)2), 1.9384 (d, 6H, J=5.5 Hz, 2×20-CH3), 1.8869 (s, 6H, 2×Ar-CH3), 1.4259 (d, 12H, J=6.2 Hz, 2×CH(CH3)2), 1.1897 (d, 6H, J=5.5 Hz, 2×17-CH3); 13C NMR (100 MHz, DMSOd6):δ174.9651, 172.5518, 169.2470, 160.3944, 150.9108, 146.1267, 131.1563, 126.7315, 126.5257, 121.0936, 116.4858, 116.0166, 103.7602, 55.9979, 49.4534, 26.4918, 20.3004, 20.3004, 20.0538, 18.6808, 18.5059; MS (ESI+): m/z 801.9[M-2Na+H]-. 5: Yellow crystal; 90.8% yield, mp 255℃(decomposition); IR (KBr, cm-1):vmax 3483, 3356, 2968, 2871, 1609, 1520, 1453, 1405, 1364, 1313, 1242. 1H NMR (400 MHz, DMSO-δ6):δ13.2983 (s, 2H, ×=CH-NH), 9.8831 (s, 2H, ×=CH-NH), 8.5003 (s, 2H, 2×-OH), 8.3374 (d, 2H, J=7.5 Hz, 2×N19-H), 7.3494 (s, 2H, 2×4-H), 4.4792 (m, 2H, 2×20-H), 3.9668 (m, 2H, 2×C17HN), 3.6590 (sept, 2H, CH(CH3)2), 2.6711 (s, 2H, 2×23a-H), 2.6079 (s, 2H, 2×23b-H), 1.9081 (s, 6H, 2×Ar-CH3), 1.4091 (d, 12H, J=6.3 Hz, 2×CH(CH3)2), 3)2), 1.1654 (d, 6H, J=6.8 Hz, 2 × 20-CH3); MS (ESI+): m/z 886.8 [M-4Na]-. 6: Yellow crystal; 86.6% yield, mp 200℃(decomposition); IR (KBr, cm-1):vmax 3488, 3378, 2960, 1665, 1613, 1519, 1496, 1452, 1396, 1309, 1244, 1173, 1027; 1H NMR (400 MHz, DMSO-d6):δ 13.1768 (s, 2H, ×=CH-NH), 9.8977 (s, 2H, ×=CH-NH), 8.4118 (s, 2H, 2×-OH), 8.1870 (d, 2H, J=7.6 Hz, 2×N19-H), 7.4019 (s, 2H, 2×4-H), 7.0479 (m, 4H, 2×25-H, 2×27-H), 6.9959 (m, 4H, 2×24-H, 2×28-H), 6.9116 (m, 2H, 2×26-H), 4.3655 (m, 2H, 2×20-H), 4.1789 (m, 2H, 2×C17HN), 3.6901 (sept, 2H, 2×CH(CH3)2), 3.0095 (s, 2H, 2×22a-H), 2.7714 (s, 2H, 2×22b-H), 1.9433 (s, 6H, 2×Ar-CH3), 1.4417 (d, 12H, J=6.2 Hz, 2×CH(CH3)2), 1.3624(d, 6H, J=6.5 Hz, 2×17-CH3); 13C NMR (100 MHz, DMSO-d6):δ175.2311, 173.4149, 169.3054, 160.3966, 150.1252, 146.1848, 138.4853, 129.3677, 129.3677, 129.2596, 129.2596, 127.7315, 131.1251, 126.6372, 125.6573, 122.1602, 118.6773, 116.5517, 103.6638, 57.3238, 55.1120, 37.2806, 26.4901, 20.2914, 20.2914, 19.6090, 19.5816; MS (ESI+):m/z 954.0 [M-2Na+H]-. 7: Brown crystal; 88.7% yield, mp 201℃(decomposition); IR (KBr, cm-1):vmax 3483, 3317, 2964, 1617, 1538, 1399, 1312, 1245, 1168, 1028; 1H NMR (400 MHz, DMSO-δ6):δ12.9935 (s, 2H, ×=CH-NH), 9.9501 (s, 2H, ×=CH-NH), 8.8190 (m, 2H, 2×N19-H), 8.4218 (s, 2H, 2×-OH), 7.6883 (m, 2H, 2×N22-H), 7.3458 (s, 2H, 2×4-H), 4.3017 (m, 4H, 2×20-H), 3.7871 (m, 4H, 2×23-H), 3.7077 (m, 4H, 2×C17H2N), 3.6791 (sept, 2H, 2×CH(CH3)2), 1.9421 (s, 6H, 2×Ar-CH3), 1.4308 (d, 12H, J=7.0 Hz, 2×CH(CH3)2); MS (ESI+): m/z 859.8 [[M-2Na+H]-2Na+H] . 8: Brown crystal; 87.4% yield, mp 233℃(decomposition); IR (KBr, cm-1):vmax 3483, 3364, 2977, 1613, 1521, 1453, 1406, 1364, 1309, 1244, 1168, 1104, 1057, 1025; 1HNMR (400 MHz, DMSO-d6):δ13.2814 (s, 2H, ×=CH-NH), 9.9811 (s, 2H, ×=CH-NH), 8.7155 (d, 2H, J=7.6 Hz, 2×N19H), 8.4064 (s, 2H, 2×-OH), 7.7190 (d, 2H, J=6.8 Hz, 2×N22H), 7.3609 (s, 2H, 2×4-H), 4.3606 (m, 2H, 2×20-H), 4.2436 (m, 2H, 2×23-H), 3.8355 (m, 2H, 2×C17HN), 3.6803 (sept, 2H, 2×CH(CH3)2), 1.9385 (s, 6H, 2×Ar-CH3), 1.4989 (d, 6H, J=6.3 Hz, 2×20-CH3), 1.4301 (d, 12H, J=6.3 Hz, 2×CH(CH3)2), 1.2282 (d, 6H, J=6.2 Hz, 2×23-CH3), 1.1751 (d, 6H, J=6.3 Hz, 2×17-CH3); 13CNMR (100 MHz, DMSO-d6):δ174.9121, 170.6384, 172.2762, 170.1312, 160.4444, 149.2146, 146.0314, 131.1066, 126.8046, 126.4187, 121.9770, 117.0177, 116.0765, 103.8738, 55.9931, 49.0865, 48.5153, 26.4920, 20.2776, 20.2776, 20.0402, 18.6090, 18.5126, 17.9255; MS (ESI+): m/z 944.0 [[M-2Na+H]-2Na+H]-.

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