Supporting Information. Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4-
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- Μαριάμ Γιάνναρης
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1 Supporting Information Synthesis and in vitro pharmacological evaluation of N-[(1-benzyl-1,2,3-triazol-4- yl)methyl]-carboxamides on D-secoestrone scaffolds Johanna Szabó a, Ildikó Bacsa a, János Wölfling a, Gyula Schneider a, István Zupkó b, Mónika Varga c, Bianka E. Herman d, László Kalmár e, Mihály Szécsi d, Erzsébet Mernyák a, * a Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary b Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H Szeged, Hungary c Cereal Research Non-Profit Ltd., P.O.Box 391, H-6701 Szeged, Hungary d 1st Department of Medicine, University of Szeged, Korányi fasor 8 10, H-6720 Szeged, Hungary e Department of Obstetrics and Gynecology, University of Szeged, Semmelweis u. 1, H-6725 Szeged, Hungary Fax: bobe@chem.u-szeged.hu
2 Figure: The numbering used in the NMR-assignments of the triazolyl products Benzyloxy-14β-(prop-2-en-yl)-N-(prop-2-yn-1-yl)-des-D-estra-1,3,5(10)-trien-13αcarboxamide (6) From compound 2 (390 mg, 1.00 mmol). Yield: 329 mg (77%), oil, Rf = 0.59 (dichloromethane). 1 H NMR (500 MHz, DMSO-d6): δ [ppm] = 1.05(s, 3H, 18-H3); 2.75(m, 2H, 6-H2); 3.01(s, 1H, C CH); 3.84(m, 2H, HN-CH2); 4.92(m, 2H, 16a-H2); 5.05(s, 2H, OCH2); 5.81(m, 1H, 16-H); 6.69(d, 1H, J=2.2Hz, 4-H); 6.75(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.16(d, 1H, J=8.6Hz, 1-H); 7.31(t, 1H, J=7.6Hz, 4'-H); 7.38(t, 2H, J=7.6Hz, 3'-H, 5'-H); 7.42(d, 2H, J=7.6Hz, 2'-H, 6'-H); 8.01(t, 1H, J=5.2Hz, NH). 13 C NMR δ [ppm] = 15.1(C-18); 25.7; 26.8; 28.2; 29.6; 34.6; 36.7; 40.6; 42.5; 45.2; 46.7; 68.8(OCH2); 72.1(C CH); 81.7(C CH); 112.3(C-2); 114.1(C-4); 114.5(C-16a); 126.2(C-1); 127.4(2C: C-2, C-6 ); 127.6(C-4 ); 128.2(2C: C-3, C-5 ); 132.0(C-10); and 137.3(C-5 and C-1 ); 139.5(C- 16); 156.1(C-3); 177.0(C-17). MS m/z (%): 352 (100). Anal. Calcd. for C29H33NO2: C, 81.46; H, Found: C, 81.35; H, 7.89%. 3-Methyloxy-14β-(prop-2-en-yl)-N-(prop-2-yn-1-yl)-des-D-estra-1,3,5(10)-trien-13βcarboxamide (7)
3 From compound 3 (314 mg, 1.00 mmol). Yield: 284 mg (81%), oil, Rf = 0.54 (dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.30(s, 3H, 18-H3); 2.20(s, 1H, C CH); 2.84(m, 2H, 6-H2); 3.77(s. 3H, OCH3); 3.98(m, 2H, NH-CH2); 5.01(m, 2H, 16a-H2); 5.76(s, 1H, NH); 5.87(m, 1H, 16-H); 6.60(d, 1H, J=2.2Hz, 4-H); 6.67(dd, 1H, J=2.2Hz, J=8.6Hz, 2-H); 7.15(d, 1H,J=8.6Hz, 1-H). 13 C NMR δ [ppm] = 27.2(C-18); 27.4; 27.8; 29.1; 30.4; 35.1; 39.7; 42.3; 43.6; 46.6; 51.7; 55.2(OCH3); 71.5(C CH); 82.6(C CH); 111.5(C-2); 113.3(C-4); 113.9(C-16a); 126.2(C-1); 132.4(C-10); 138.1(C-5); 140.9(C-16); 157.4(C-3); 175.7(C-17). MS m/z (%): 352 (100). Anal. Calcd. for C23H29NO2: C, 78.59; H, Found: C, 78.67; H, 8.25%. 3-Benzyloxy-14β-(prop-2-en-yl)-N-(prop-2-yn-1-yl)-des-D-estra-1,3,5(10)-trien-13βcarboxamide (8) From compound 4 (390 mg, 1.00 mmol). Yield: 354 mg (83%), oil, Rf = 0.68 (dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.31(s, 3H, 18-H3); 2.83(m, 2H, 6-H2); 2.98(s, 1H, C CH); 3.81(m, 2H, HN-CH2); 5.01(m, 2H, 16a-H2); 5.02(s, 2H, OCH2); 5.70(m, 1H, NH); 5.86(m, 1H, 16-H); 6.69(d, 1H, J=2.2Hz, 4-H); 6.75(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.12(d, 1H, J=8.6Hz, 1-H); 7.31(t, 1H, J=7.5Hz, 4 -H); 7.38(t, 1H, J=7.5Hz, 3 -H 5 -H); 7.42(t, 1H, J=7.5Hz, 2 -H, 6 -H); 7.87(t, 1H, J=5.6Hz, 1H, NH). 13 C NMR δ [ppm] = 27.1(C-18); 27.4; 27.8; 29.1; 30.4; 35.1; 39.7; 42.3; 43.6; 51.7; 46.5; 69.9(OCH2); 71.5(C CH); 79.8(C CH) 112.3(C-2); 114.4(C-4); 113.9(C-16a); 126.3(C-1); 127.4(2C: C- 2, C-6 ); 127.8(C-4 ); 128.4(2C: C-3, C-5 ); 132.7(C-10); 137.3(C-1 ); 138.1(C-5); 140.9(C-16); 156.7(C-3); 175.7(C-17). MS m/z (%): 428 (100), 429 (36). Anal. Calcd. for C29H33NO2: C, 81.46; H, Found: C, 81.55; H, 7.92%.
4 3-Methyloxy-N-{[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des-Destra-1,3,5(10)-trien-13α-carboxamide (10b) From compound 5 (351 mg, 1.00 mmol). Yield: 513 mg (97%), mp C, Rf = 0.29 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.15(s, 3H, 18- H3); 2.82(m, 2H, 6-H2); 3.77(s, 3H, OCH3); 4.51(m, 2H, HN-CH2); 4.82(m, 2H, 16a-H2); 5.61(m, 2H, N-CH2); 5.71(m, 1H, 16-H); 6.62(d, 1H, J=2.2Hz, 4-H); 6.70(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.17(d, 1H,J=8.6Hz, 1-H); 7.39(d, 2H, J=8.5Hz, 2 -H, 6 -H); 7.61(s, 1H, C=CH); 8.21(d, 2H, J=8.2Hz, 3 -H,5 -H). 13 C NMR δ [ppm] = 15.2(C-18); 25.9; 27.2; 29.6; 34.9; 35.2; 37.9; 40.9; 42.9; 45.6; 47.4; 53.2; 55.2(OCH3); 111.6(C-2); 113.4(C-4); 114.3(C- 16a); 124.3(3C: C=CH, C-2, C-6 ); 126.3(C-1); 128.6(2C: C-3, C-5 ); 132.0(C-10); 137.8(C-5); 138.6(C-16); 139.6(C-1 ); 141.3(C-4 ); 145.2(C=CH); 157.5(C-3); 178.6(C-17). MS m/z (%): 159 (100), 59 (50), 552 (38), 530 (31). Anal. Calcd. for C30H35N5O4: C, 68.03; H, Found: C, 67.92; H, 6.51%. 3-Methyloxy-N-{[1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des- D-estra-1,3,5(10)-trien-13α-carboxamide (10c) From compound 5 (351 mg, 1.00 mmol). Yield: 473 mg (95%), mp C, Rf = 0.40 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.14(s, 3H, 18- H3); 2.34(s, 3H, 4 -CH3); 2.81(m, 2H, 6-H2); 3.77(s, 3H, OCH3); 4.47(m, 2H, HN-CH2); 4.80(m, 2H, 16a-H2); 5.44(m, 2H, N-CH2); 5.71(m, 1H, 16-H); 6.62(m, 1H, J=2.2Hz, 4-H); 6.65(m, 1H, NH); 6.70(dd, 1H, J=2.2Hz, 2-H); 7.15(overlapping multiplets, 5H: 1-H and 2 - H, 3 -H, 5 -H, 6 -H); 7.46(s, 1H, C=CH). 13 C NMR δ [ppm] = 15.2(C-18); 24.1(4 -CH3); 25.9; 27.2; 30.2; 35.0; 35.2; 37.8; 40.9; 42.9; 45.5; 47.3; 54.0(N-CH2); 55.2(OCH3); 111.6(C- 2); 113.4(C-4); 114.6(C-16a); 122.2(C=CH); 126.3(C-1); and 129.7(2x2C: C-2,C-3,
5 C-5, C-6 ); 131.3(C-1 ); 132.0(C-10); 137.8(C-5); 138.7(C-4 ); 139.0(C-16); 145.2(C=CH); 157.5(C-3); 178.4(C-17). MS m/z (%): 499 (100), 500 (38). Anal. Calcd. for C31H38N4O2: C, 74.67; H, Found: C, 74.81; H, 7.47%. 3-Benzyloxy-N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-14β-(prop-2-en-yl)-des-D-estra- 1,3,5(10)-trien-13α-carboxamide (11a) From compound 6 (427 mg, 1.00 mmol). Yield: 543 mg (97%), mp C, Rf = 0.38 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.15(s, 3H, 18- H3); 2.82(s, 2H, 6-H2); 4.50(m, 2H, HN-CH2); 4.80(m, 2H, 16a-H2); 5.02(s, 2H, OCH2); 5.50(s, 2H, N-CH2); 5.70(m, 1H, 16-H); 6.70(d, 1H, J=2.2Hz, 4-H); 6.74(m, 1H, NH); 6.77(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.16(d, 1H, J=8.6Hz, 1-H); 7.27(m, 2H) and 7.31(m, 1H) and 7.37(m, 5H) and 7.42(m, 2H): benzylic aromatic protons; 7.52(s, 1H, C=CH). 13 C NMR δ [ppm] = 15.3(C-18); 25.9; 27.2; 30.2; 34.9; 35,2; 37.8; 41.0; 42.9; 45.5; 47.3; 54.3; 69.9(OCH2); 112.4(C-2); 114.0(C-4), 114.2(C-16a); 122.6(C=CH); 126.3(C-1); 127.4(2C) and and 128.1(2C) and 128.5(2C) and and 129.1(2C): benzylic aromatic protons; 132.5(C-10); 134.2(C-1 ); 137.2(C-1 ); 137.9(C-5); 138.8(C-16); 145.4(C=CH); 156.8(C-3); 178.4(C-17). MS m/z (%): 561 (100), 562 (44). Anal. Calcd. for C36H40N4O2: C, 77.11; H, Found: C, 76.98; H, 7.27%. 3-Benzyloxy-N-{[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des-Destra-1,3,5(10)-trien-13α-carboxamide (11b) From compound 6 (427 mg, 1.00 mmol). Yield: 581 mg (96%), mp C, Rf = 0.22 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.15(s, 3H, 18-
6 H3); 2.82(m, 2H, 6-H2); 4.51(m, 2H, HN-CH2); 4.82(m, 2H, 16a-H2); 5.02(s, 2H, OCH2); 5.60(s, 2H, N-CH2); 5.71(m, 1H, 16-H); 6.55(s, 1H, NH); 6.70(d, 1H, J=2.2Hz, 4-H); 6.77(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.10(d, 1H, J=8.6Hz, 1-H); 7.31(m, 1H, 4'-H); (overlapping multiplets, 6H, 2'-H, 3'-H, 5'-H, 6'-H, 2 -H, 6 -H); 7.60(s, 1H, C=CH); 8.21(m, 2H, 3 -H, 5 -H). 13 C NMR δ [ppm] = 15.2(C-18); 25.9; 27.2; 30.1; 35.1; 35.2; 37.9; 40.9; 42.9; 45.6; 47.4; 53.1; 69.9(OCH2); 112.5(C-2); 114.5(C-4); 114.7(C-16a); 124.3(C=CH); and 127.4(2C) and and 128.5(4C) and 128.6(2C): C-1, C-2, C-3, C-4, C-5, C-6 C-2, C-3, C5, C-6 ; 132.4(C-10); 136.8(C-1 ); 137.8(C-5); 139.0(C-16); 139.6(C-1 ); 141.4(C-4 ); 145.8(C=CH); 156.8(C-3); 178.6(C-17). MS m/z (%): 606 (100), 236 and 607 (40), 620 (36). Anal. Calcd. for C36H39N5O4: C, 71.38; H, Found: C, 71.45; H, 6.33%. 3-Benzyloxy-N-{[1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des- D-estra-1,3,5(10)-trien-13α-carboxamide (11c) From compound 6 (427 mg, 1.00 mmol). Yield: 557 mg (97%), oil, Rf = 0.44 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.15(s, 3H, 18-H3); 2.35(s, 3H, 4 -CH3); 2.81(m, 2H, 6-H2); 4.48(m, 2H, HN-CH2); 4.80(m, 2H, 16a-H2); 5.03(s, 2H, OCH2); 5.44(s, 2H, N-CH2); 5.71(m, 1H, 16-H); 6.65(m, 1H, NH); 6.70(d, 1H, J=2.2Hz, 4-H); 6.77(dd, 1H, J=2.2Hz, J=8.6Hz, 2-H); 7.17(overlapping multiplets, 5H, 1-H, 2 -H, 3 - H, 5 -H, 6 -H); 7.31(t, 1H, J=7.3Hz, 4 -H); 7.37(t, 2H, J=7.3Hz, 3 -H, 5 -H); 7,42(d, 2H, J=7.3Hz, 2 -H, 6 -H); 7.49(s, 1H, C=CH). 13 C NMR δ [ppm] = 15.2(C-18); 21.2(4 -CH3); 25.9; 27.2; 30.2; 35.0; 35.2; 37.9; 40.9; 42.9; 45.5; 47.3; 54.1; 69.9(OCH2); 112.4(C-2); 114.5(C-4); 114.6(C-16a); 122.3(C=CH); 126.3(C-1); 127.4(2C: C-2, C-6 ); 127.8(C-4 ); 128.2(2C, C-3, C-5 ); 128.5(2C) and 129.8(2C): C-2, C-3, C-5, C-6 ; 131.2(C-1 );
7 132.5(C-10); 137.2(C-1 ); 137.9(C-5); 138.8(C-16); 145.2(C-4 ); 145.6(C=CH); 156.8(C-3); 178.4(C-17). MS m/z (%): 575 (100), 576 (42), 597 (34). Anal. Calcd. for C37H42N4O2: C, 77.32; H, Found: C, 77.45; H, 7.28%. 3-Benzyloxy-N-({1-[4-(propan-2-yl)benzyl]-1H-1,2,3-triazol-4-yl}methyl)-14β-(prop-2-enyl)-des-D-estra-1,3,5(10)-trien-13α-carboxamide (11d) From compound 6 (427 mg, 1.00 mmol). Yield: 590 mg (98%), mp C, Rf = 0.51 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.14(s, 3H, 18- H3); 1.24(d, 6H, J=7.0Hz, CH(CH3)2); 2.80(m, 2H, 6-H2); 2.91(m, 1H, CH(CH3)2); 4.41(m, 2H, HN-CH2); 4.80(m, 2H, 16a-H2); 5.02(s, 2H, OCH2); 5.44(s, 2H, N-CH2); 5.68(m, 1H, 16- H); 6.69(d, 1H, J=2.2Hz, 4-H); 6.77(dd, 1H; J=2.2Hz, J=8.6Hz, 2-H); 6.89(m, 1H, NH); (overlapping multiplets, 5H, 1-H, 2 -H, 3 -H, 5 -H, 6 -H); 7.31(t, 1H, J=7.3Hz, 4 -H); 7.37(t, 2H, J=7.3Hz, 3 -H, 5 -H); 7,42(d, 2H, J=7.3Hz, 2 -H, 6 -H); 7.50(C=CH). 13 C NMR δ [ppm] = 15.2(C-18); 23.9(2C: CH(CH3)2); 25.9; 27.2; 30.2; 33.9(CH(CH3)2); 34.6; 35.2; 37.8; 41.0; 42.9; 45.5; 47.3; 54.3; 69.9(OCH3); 112.4(C-2); 114.3(C-16a); 114.5(C-4); 122.4(C=CH); 126.3(C-1); 127.2(2C) and 127.4(2C) and 128.3(2C) and 128.5(2C): C-2, C- 3, C-5, C-6, C-2, C-3, C-5, C-6 ; 127.8(C-4 ); 131.4(C-1 ); 132.5(C-10); 137.3(C-1 ); 137.9(C-5); 138.7(C-16); 145.0(C=CH); 149.8(C-4 ); 156.8(C-3); 178.0(C-17). MS m/z (%): 603 (100), 542 and 604 (42). Anal. Calcd. for C39H46N4O2: C, 77.71; H, Found: C, 77.95; H, 7.58%. 3-Benzyloxy-N-{[1-(4-tert-butylbenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)- des-d-estra-1,3,5(10)-trien-13α-carboxamide (11e)
8 From compound 6 (427 mg, 1.00 mmol). Yield: 597 mg (97%), mp C, Rf = 0.53 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.15(s, 3H, 18- H3); 1.31(s, 9H, C(CH3)3); 2.81(m, 2H, 6-H2); 4.45(m, 2H, HN-CH2); 4.78(m, 2H, 16a-H2); 5.02(s, 2H, OCH2); 5.45(s, 2H, N-CH2); 5.71(m, 1H, 16-H); 6.70(d, 1H, J=2.2Hz, 4-H); 6.77(dd, 1H; J=8.6Hz, J=2.2Hz, 2-H); 7.16(d, 1H, J=8.6Hz, 1-H); 7.20(d, 2H, J=8.2Hz, 2 -H, 6 -H); 7.31(t, 1H, J=7.3Hz, 4 -H); (overlapping multiplets, 6H, 2 -H, 3 -H,5 -H, 6 - H, 3 -H, 5 -H); 7.50(C=CH). 13 C NMR δ [ppm] = 15.2(C-18); 31.2(3C: C(CH3)3); 25.9; 27.2; 29.7; 30.2; 34.7; 35.2; 37.8(C(CH3)3); 40.9; 42.9; 45.5; 47.3; 54.2; 69.9(OCH2); 112.4(C-2); 114.6(C-4); 114.6(C-16a); 122.5(C=CH); 126.1(2C: C-3, C-5 ); 126.3(C-1); 127.4(2C: C-2, C-6 ); 127.8(C-4'); 128.0(2C: C-2, C-6 ); 128.5(2C, C-3', C-5'); 131.1(C-1 ); 132.5(C-10); 137.2(C-1 ); 137.9(C-5); 138.9(C-16); 145.0; 152.1; 156.8(C-3); 178.4(C-17). MS m/z (%): 617 (100), 618 (44). Anal. Calcd. for C40H48N4O2: C, 77.89; H, Found: C, 78.02; H, 7.73%. 3-Methyloxy-N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-14β-(prop-2-en-yl)-des-D-estra- 1,3,5(10)-trien-13β-carboxamide (12a) From compound 7 (351 mg, 1.00 mmol). Yield: 474 mg (98%), mp C, Rf = 0.54 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.26(s, 3H, 18- H3); 2.81(m, 2H, 6-H2); 3.77(s, 3H, OCH3); 4.40(m, 2H, HN-CH2); 4.94(m, 2H, 16a-H2); 5.44(m, 2H, N-CH2); 5.82(m, 1H, 16-H); 6.35(m, 1H, NH); 6.61(d, 1H, J=2.2Hz, 4-H); 6.67(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.12(d, 1H, J=8.6Hz, 1-H); 7.20(m, 2H) and 7.32(m, 3H): 2 -H, 3 -H, 4 -H, 5 -H, 6 -H); 7.40(s, 1H, C=CH). 13 C NMR δ [ppm] = 27.1(C-18); 27.3; 27.8; 30.4; 34.7; 35.1; 39.7; 42.5; 43.6; 46.5; 51.7; 54.1(N-CH2); 55.2(OCH3); 111.5(C- 2); 113.3(C-4); 113.8(C-16a); 122.1(C=CH); 126.2(C-1); 128.0(2C: C-2, C-6 ); 128.7(C-
9 4 ); 129.1(2C: C-3, C-5 ); 132.5(C-10); 134.4(C-1 ); 138.1(C-5); 141.0(C-16); 145.3(C=CH); 157.4(C-3); 176.2(C-17). MS m/z (%): 485 (100), 486 and 507 (30). Anal. Calcd. for C30H36N4O2: C, 74.35; H, Found: C, 74.52; H, 7.55%. 3-Methyloxy-N-{[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des-Destra-1,3,5(10)-trien-13β-carboxamide (12b) From compound 7 (351 mg, 1.00 mmol). Yield: 524 mg (99%), mp C, Rf = 0.31 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.27(s, 3H, 18- H3); 2.82(m, 2H, 6-H2); 3.76(s, 3H, OCH3); 4.42(m, 2H, HN-CH2); 4.92(m, 2H, 16a-H2); 5.55(s, 2H, N-CH2); 5.81(m, 2H, 16-H); 6.36(m, 1H, NH); 6.62(s, 1H, J=2.2Hz, 4-H); 6.67(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.10(d, 1H, J=8.6Hz, 1-H); 7.31(d, 2H, J=8.6Hz, 2 -H, 6 -H); 7.49(s, 1H, C=CH); 7.66(d, 2H, J=2.2Hz, 3 -H, 5 -H). 13 C NMR δ [ppm] = 27.2(C- 18); 27.4; 27.8; 30.4; 34.7; 35.2; 39.7; 42.5; 43.5; 46.7; 51.7; 53.1; 55.2(OCH3); 111.5(C-2); 113.4(C-4); 114.0(C-16a); 122.6(C=CH); 124.3(2C: C-2, C-6 ); 126.2(C-1); 128.5(2C: C- 3, C-5 ); 132.3(C-10); 137.9(C-5); 139.5(C-1 ); 140.9(C-16); 141.3(C-4 ); 146.3(C=CH); 157.4(C-3); 176.4(C-17). MS m/z (%): 530 (100), 552 (84), 531 (38). Anal. Calcd. for C30H35N5O4: C, 68.03; H, Found: C, 67.91; H, 6.73%. 3-Methyloxy-N-{[1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des- D-estra-1,3,5(10)-trien-13β-carboxamide (12c) From compound 7 (351 mg, 1.00 mmol). Yield: 488 mg (98%), C, Rf = 0.37 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.26(s, 3H, 18- H3); 2.33(s, 3H, 4 -CH3); 2.82(m, 2H, 6-H2); 3.76(s, 3H, OCH3); 4.40(m, 2H, HN-CH2);
10 4.92(m, 2H, 16a-H2); 5.40(m, 2H, N-CH2); 5.83(m, 1H, 16-H); 6.40(m, 1H, NH); 6.60(d, 1H, J=2.2Hz, 4-H); 6.67(d, 1H, J=8.6Hz, J=2.2Hz, 2-H); 7.10(overlapping multiplets, 5H, 1-H, 2 -H, 3,-H, 5 -H, 6 -H); 7.37(s, 1H, C=CH). 13 C NMR δ [ppm] = 21.2(4 -CH3); 27.1(C-18); 27.3; 27.8; 30.4; 34.6; 35.2; 39.7; 42.5; 43.6; 46.5; 51.7; 54.0; 55.2(OCH3); 111.5(C-2); 113.3(C-4); 113.8(C-16a); 122.0(C=CH); 126.3(C-1); 128.1(2C: C-3, C-5 ); 129.7(2C: C- 2, C-6 ); 131.6(C-1 ); 132.5(C-10); 138.1(C-5); 138.6(C-4 ); 141.0(C-16); 145.9(C=CH); 156.3(C-3), 175.8(C-17). MS m/z (%): 499 (100), 521 (64), 500 (36). Anal. Calcd. for C31H38N4O2: C, 74.67; H, Found: C, 74.78; H, 7.54%. 3-Benzyloxy-N-[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]-14β-(prop-2-en-yl)-des-D-estra- 1,3,5(10)-trien-13β-carboxamide (13a) From compound 8 (427 mg, 1.00 mmol). Yield: 549 mg (98%), oil, Rf = 0.67 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, CDCl3): δ [ppm] = 1.26(s, 3H, 18-H3); 2.80(m, 2H, 6-H2); 4.67(m, 2H, HN-CH2); 4.91(m, 2H, 16a-H2); 5.02(s, 2H, OCH2); 5.44(s, 2H, N-CH2); 5.82(m, 1H, 16-H); 6.36(m, 1H, NH); 6.69(d, 1H, J=2.2Hz, 4-H); 6.74(dd, 1H, J=8.6Hz,J=2.2Hz, 2-H); 7.11(d, 1H, J=8.6Hz, 1-H); 7.20(m, 2H) and 7.32(m, 3H) and 7.37(m, 3H) and 7.41(m, 3H): benzylic aromatic protons and C=CH. 13 C NMR δ [ppm] = 27.2(C-18); 27.3; 27.8; 30.4; 34.6; 35.2; 39.7; 42.4; 43.6; 46.6; 51.7; 54.3; 62.9; 69.9(OCH2); 112.3(C-2); 113.9(C-16a); 114.4(C-4); 127.4(2C) and and 128.0(2C) and 128.5(2C) and 128.8; 129.1; 129.7: C-1, C-2, C-3, C-4, C-5, C-6 C-2, C-3, C5, C-6 ; 126.3(C=CH); 132.8(C-10); 134.3(C-1 ); 134.5(C-1 ); 138.1(C-5); 140.9(C-16); 145.3(C=CH); 156.7(C-3); 176.3(C-17). MS m/z (%): 485 (100). Anal. Calcd. for C36H40N4O2: C, 77.11; H, Found: C, 77.28; H, 7.31%.
11 3-Benzyloxy-N-{[1-(4-nitrobenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des-Destra-1,3,5(10)-trien-13β-carboxamide (13b) From compound 8 (427 mg, 1.00 mmol). Yield: 599 mg (99%), mp C, Rf = 0.42 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, DMSO-d6): δ [ppm] = 1.21(s, 3H, 18-H3); 2.74(m, 2H, 6-H2); 4.25(m, 2H, HN-CH2); 4.91(m, 2H, 16a-H2); 5.03(s, 2H, OCH2); 5.72(s, 2H, N-CH2); 5.80(m, 1H, 16-H); 6.68(d, 1H, J=2.2Hz, 4-H); 6.71(dd, 1H, J=8.6Hz,J=2.2Hz, 2-H); 7.08(d; 1H, J=8.6Hz, 1-H); 7.31(t, 1H, J=7.3Hz, 4'-H); (overlapping multiplets, 6H, 2 -H, 3 -H, 4 -H, 5 -H, 6 -H, 2 -H, 6 -H); 7.89(s, 1H, C=CH); 8.00(m, 1H, HN); 8.17(d, 2H, J=8.5Hz, 3 -H, 5 -H). 13 C NMR δ [ppm] = 26.3(C- 18); 26.7; 27.4; 29.8; 34.2; 35.1; 38.7; 41.9; 42.9; 46.1; 51.2; 51.6; 68.9(OCH2); 112.1(C-2); 113.5(C-16a); 114.1(C-4); 123.7(2C) and 127.4(2C) and and 128.3(2C) and and 128.7(2C): C-1, C-2, C-3, C-4, C-5, C-6 C-2, C-3, C5, C-6 ; 126.0(C=CH); 132.6(C- 10); 137.3(C-1 ); 137.4(C-5); 141.5(C-16); 143.6; 147.1; 153.5; 156.0(C-3); 175.4(C-17). MS m/z (%): 236 (100), 606 (77), 159 (50), 279 (42). Anal. Calcd. for C36H39N5O4: C, 71.38; H, Found: C, 71.49; H, 6.63%. 3-Benzyloxy-N-{[1-(4-methylbenzyl)-1H-1,2,3-triazol-4-yl]methyl}-14β-(prop-2-en-yl)-des- D-estra-1,3,5(10)-trien-13β-carboxamide (13c) From compound 8 (427 mg, 1.00 mmol). Yield: 557 mg (97%), mp C, Rf = 0.63 (50% ethyl acetate/50% dichloromethane). 1 H NMR (500 MHz, C6D6): δ [ppm] = 1.07(s, 3H, 18- H3); 2.02(s, 3H, 4 -CH3); 2.71(m, 2H, 6-H2); 4.40(m, 2H, NH-CH2); 4,72(s, 2H, N-CH2); 4.79(s, 2H, OCH2); 4.95(m, 2H, 16a-H2); 5.84(m, 1H, 16-H); 6.53(m, 1H, NH); 6.71(overlapping multiplets, 3H, 4-H and 2 -H, 6 -H); 6.80(d, 2H, J=7.8Hz, 3 -H and 5 -H); 6.85(dd, 1H, J=8.6Hz, J=2.2Hz, 2-H); 6.96(s, 1H, C=CH); 7.08(t, 1H, J=7.4Hz, 4 -H); 7.12-
12 7.17(overlapping multiplets, 3H, 1-H and 3 -H and 5 -H); 7.32(d, 2H, J=7.4Hz, 2 -H, 6 -H). 13 C NMR δ [ppm] = 21.0(4 -CH3); 27.0(C-18); 27.8; 28.5; 30.8; 35.0; 35.9; 40.0; 42.9; 44.1; 46.7; 52.2; 53.4; 69.9(OCH2); 113.0(C-2); 113.8(C-16a); 114.9(C-4); 122.3(C=CH); 126.7(C- 1); 127.6(2C, C-2 and C-6 ); 128.1(2C, C-3 and C-5 ); 128.3(C-4 ); 128.6(2C, C-2 and C- 6 ); 129.7(2C, C-3 and C-5 ); 132.5(C-1 ); 133.3(C-10); 138.2(C-4 ); 138.4(2C, C-1 and C-5); 141.8(C-16); 146.0(C=CH); 157.4(C-3); 175.9(C-17).MS m/z (%): 575 (100), 597 (65), 576 (34). Anal. Calcd. for C37H42N4O2: C, 77.32; H, Found: C, 77.55; H, 7.23%.
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