Citation: Shou-Xin Wang, Zhen Fang, Zhi-Jin Fan, Dun Wang, Yue-Dong Li, Xiao-Tian Ji, Xue-Wen Hua, Yun Huang, Tatiana A. Kalinina, Vasiliy A. Bakulev, Yury Yu. Morzherin. Synthesis of tetrazole containing 1,2,3-thiadiazole derivatives via U-4CR and their anti-TMV activity[J]. Chinese Chemical Letters, ;2013, 24(10): 889-892. shu

Synthesis of tetrazole containing 1,2,3-thiadiazole derivatives via U-4CR and their anti-TMV activity

1.
a School of Basic Sciences, Jining Medical University, Jining 272067, China;
2.
b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China;
3.
c Department of Plant Pathology, Sichuan Agricultural University, Chengdu 611130, China;
d The Ural Federal University Named after the First President of Russia B.
d The Ural Federal University Named after the First President of Russia B.N. Yeltsin, Yeltsin UrFU, 620002 Ekaterinburg, Russia

Corresponding author: Zhi-Jin Fan, Yun Huang,
Received Date: 7 April 2013
Available Online: 7 May 2013
Fund Project: This study was funded in part by the NSF of Tianjin (No. 10JCZDJC17500) (No. 10JCZDJC17500) the National Key Project for Basic Research (No. 2010CB126105) (No. 2010CB126105)the Foundation of Achievements Transformation and Application of Tianjin Agricultural Science and Technology (No. 201002250) (No. 2011BAE06B02)

A series of novel tetrazole containing 1,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Their structures were confirmed by melting points, IR, ¹H NMR, and HRMS (ESI). Preliminary bioassay indicated that most target compounds exhibited very good direct anti-TMV activity at 100 μg/mL, which was equal to or higher than that of ribavirin. Among them, compounds 4b, 4c and 4i also showed equivalent protection effect to ribavirin in vivo at 100 μg/mL.
- 1,2,3-Thiadiazole,
- Tetrazole,
- Anti-TMV activity,
- Ugi reaction
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  [26] Selected characteristic data for the target compounds. 4a: White solid; yield 59%; mp 75-76 ℃; ¹H NMR (400 MHz, CDCl₃): δ 0.93 (t, 3H, J = 7.6 Hz, propyl-CH₃), 1.26-2.07 (m, 13H, propyl-CH₂, 10cyclohexyl-H, NH), 2.45-2.62 (m, 2H, propyl-CH₂), 2.65 (s, 3H, thiadiazole-CH₃), 4.58-4.66 (m, ¹H, cyclobutyl-CH), 5.76 (s, ¹H, CH). HRMS: Calcd. for C₁₄H₂₃N₇S (M+Na)⁺: 344.1628, Found: 344.1630; IR (KBr pellet press, cm 1): v3325, 2951, 2863, 1495, 1450, 1229, 1106, 1009, 809, 759. 4b: White solid; yield 47%; mp 96-97 ℃; ¹H NMR (400 MHz, CDCl₃):d 1.13 (t, 6H, J = 6.0 Hz, 2 isopropyl-CH₃), 1.26-2.07 (m, 11H, 10 cyclohexyl-H, NH), 2.63 (s, 3H, thiadiazole-CH₃), 2.64-2.71 (m, ¹H, isopropyl-CH), 4.54-4.62 (m, ¹H, cyclobutyl-CH), 5.83 (s, ¹H, CH). HRMS: Calcd. for C₁₄H₂₃N₇S (M+Na)⁺: 344.1628, Found: 344.1626; IR (KBr pellet press, cm 1): v 3276, 2934, 2857, 1501, 1451, 1241, 1126, 1009, 832. 4c: White solid; yield 51%; mp 96-97 ℃; ¹H NMR (400 (M+H)⁺z, CDCl₃): (0.43-0.54 (m, 4H, cyclopropyl-H), 1.33-2.05 (m, 11H, cyclohexyl-H, NH), 2.58 (s, ¹H, cyclopropyl-CH), 2.66 (s, 3H, thiadiazole-CH₃), 4.27-4.35 (m, ¹H, cyclohexyl-CH), 5.58 (s, ¹H, CH). HRMS: Calcd. for C₁₄H₂₁N₇S (M+H)+: 320.1652, Found: 320.1657; IR (KBr pellet press, cm-1): n 3268, 2938, 2856, 1501, 1446, 1239, 1162, 1022, 801, 680. 4d: White solid; yield 53%; mp 88-89 ℃; ¹H NMR (400 (M+H)⁺z, CDCl₃): δ 1.31-2.17 (m, 17H, 5 cyclopropyl-H, 10 cyclohexyl-H, CH₂), 2.63 (s, 3H, thiadiazole-CH₃), 3.13 (s, ¹H, NH), 4.53-4.60 (m, ¹H, cyclohexyl-H), 5.72 (s, ¹H, CH). HRMS: Calcd. for C₁₅H₂₃N₇S (M+Na)⁺: 356.1628, Found: 356.1623; IR (KBr pellet press, cm 1): v3265, 2941, 2856, 1501, 1466, 1241, 1151, 1009, 810. 4e: White solid; yield 57%; mp 119-120 ℃; ¹H NMR (400 (M+H)⁺z, CDCl₃): δ 1.10 (s, 9H, 3t-butyl-CH₃), 1.26-2.07 (m, 11H, 10 cyclohexyl-H, NH), 2.57 (s, 3H, thiadiazole-CH₃), 4.37-4.45 (m, ¹H, cyclohexyl-CH), 5.84 (s, ¹H, CH). HRMS: Calcd. for C₁₅H25N7S (M+Na)⁺: 358.1784, Found: 358.1787; IR (KBr pellet press, cm-1): v3327, 2938, 2865, 1453, 1231, 1103, 1076, 861, 741. 4f: White solid; yield 60%; mp 87-88 ℃; ¹H NMR (400 MHz, CDCl₃):d 1.26-2.17 (m, 17H, 6 cyclobutyl-H, 10 cyclohexyl-H, NH), 2.63 (s, 3H, thiadiazole-CH₃), 3.11-3.14 (m, ¹H, cyclobutyl-CH), 4.49-4.56 (m, ¹H, cyclohexyl-CH), 5.70 (s, ¹H, CH). HRMS: Calcd. for C₁₅H₂₃N₇S (M+Na)⁺: 356.1628, Found: 356.1629; IR (KBr pellet press, cm 1): v3264, 2941, 2856, 1501, 1451, 1241, 1150, 1105, 1009, 809, 759. 4g: White solid; yield 58%; mp 122-123 ℃; ¹H NMR (400 MHz, CDCl₃):d 1.32-2.00 (m, 19H, 8 cyclopentyl-H, 10 cyclohexyl-H, NH), 2.63 (s, 3H, thiadiazole-CH₃), 2.89-2.95 (m, ¹H, cyclopentyl-CH), 4.53-4.60 (m, ¹H, cyclohexyl-CH), 5.72 (s, ¹H, CH). HRMS: Calcd. for C16H25N7S (M H) : 346.1819, Found: 346.1814; IR (KBr pellet press, cm 1): v3271, 2938, 2857, 1499, 1449, 1236, 1087, 1005, 844, 732. 4h: White solid; yield 47%; mp 98-99 ℃; ¹H NMR (400 (M+H)⁺z, CDCl₃):d 1.11-2.05 (m, 21H, 20 cyclohexyl-H, NH), 2.30-2.32 (m, ¹H, cyclohexyl-CH), 2.62 (s, 3H, thiadiazole-CH₃), 4.56-4.64 (m, ¹H, cyclohexyl-H), 5.90 (s, ¹H, CH). HRMS: Calcd. for C17H27N7S (M H) : 360.1976, Found: 360.1973; IR (KBr pellet press, cm 1): v3286, 2927, 2850, 1451, 1236, 1106, 1012, 824, 686. 4i: White solid; yield 55%; mp 96-97 ℃; ¹H NMR(400 (M+H)⁺z, CDCl₃):d 1.26-1.99 (m, 10H, cyclohexyl-H), 2.65 (s, 3H, thiadiazole-CH₃), 4.35-4.41 (m, ¹H, cyclohexyl-H), 4.72 (d, ¹H, J = 8.0 Hz, NH), 6.32 (d, ¹H, J = 8.0 Hz, CH), 6.66-7.09 (m, 4H, Ph-H). HRMS: Calcd. for C17H20FN7S (M+H)+: 374.1558, Found: 374.1555; IR (KBr pellet press, cm 1): v3401, 2936, 2860, 1620, 1527, 1453, 1251, 1191, 1057, 738. 4j: Pale yellow solid; yield 50%; mp 115-116 ℃; ¹H NMR (400 (M+H)⁺z, CDCl₃):d 1.26-1.99 (m, 10H, 10 cyclohexyl-H), 2.66 (s, 3H, thiadiazole-CH₃), 4.27-4.33 (m, ¹H, cyclohexyl-CH), 5.09 (d, ¹H, J = 6.0 Hz, NH), 6.23 (d, ¹H, J = 7.6 Hz, CH), 6.56 (d, ¹H, J = 8.4 Hz, Ph-H), 6.70 (s, ¹H, Ph-H), 6.85 (d, ¹H, J = 8.4 Hz, Ph-H), 7.12 (t, ¹H, J = 8.0 Hz, Ph-H). HRMS: Calcd. for C17H20ClN7S (M H) : 388.1117, Found: 388.1112; IR (KBr pellet press, cm 1): v3410, 2937, 2861, 1598, 1484, 1446, 1272, 1158, 1012, 845, 759. 4k: Pale yellow solid; yield 46%; mp 152-153 ℃; ¹H NMR (400 MHz, CDCl₃):d 1.26-2.01 (m, 10H, 10 cyclohexyl-H), 2.66 (s, 3H, thiadiazole-CH₃), 4.25-4.32 (m, ¹H, cyclohexyl-CH), 4.80 (d, ¹H, J = 7.2 Hz, NH), 6.20 (d, ¹H, J = 7.2 Hz, CH), 6.63 (d, 2H, J = 8.8 Hz, Ph-H), 7.18 (d, 2H, J = 8.4 Hz, Ph-H). HRMS: Calcd. for C17H20ClN7S (M H) : 388.1117, Found: 388.1119; IR (KBr pellet press, cm 1): v3285, 2944, 2856, 1598, 1497, 1442, 1296, 1245, 1103, 1011, 837. 4l: White solid; yield 45%; mp 149-150 (oC; ¹H NMR (400 MHz, CDCl₃):d 1.17 (t, 3H, J = 7.6 Hz, ethyl-CH₃), 1.24-2.00 (m, 10H, 10 cyclohexyl-H), 2.50 (q, 2H, J = 15.2 Hz, ethyl-CH₂), 2.63 (s, 3H, thiadiazole-CH₃), 4.27-4.34 (m, ¹H, cyclohexyl-CH), 4.41 (d, ¹H, J = 5.2 Hz, NH), 6.18 (d, ¹H, J = 8.0 Hz, CH), 6.63 (d, 2H, J = 8.4 Hz, Ph-H), 7.05 (d, 2H,, J = 8.4 Hz, Ph-H). HRMS: Calcd. for C19H25N7S (M+Na)⁺: 406.1784, Found: 406.1783; IR (KBr pellet press, cm 1): v3419, 2935, 2862, 1616, 1523, 1446, 1281, 1102, 818, 756. 4m: White solid; yield 48%; mp 143-144 (C; ¹H NMR (400 (M+H)⁺z, CDCl₃): δ 1.27-2.00 (m, 10H, cyclohexyl-H), 2.15 (s, 3H, Ph-CH₃), 2.65 (s, 3H, thiadiazole-CH₃), 4.29-4.34 (m, ¹H, cyclohexyl-CH), 4.75 (d, ¹H, J = 7.6 Hz, NH), 6.19 (d, ¹H, J = 7.6 Hz, CH), 6.36-6.41 (m, 2H, PhH), 7.00 (t, ¹H, J = 8.4 Hz, PhH). HRMS: Calcd. for C₁₈H₂₂FN₇S (M-H)^-: 386.1569, Found: 386.1571; IR (KBr pellet press, cm^-1): v3285, 2927, 2849, 1496, 1450, 1236, 1133, 1012, 824, 686.
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