Novel 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives as potent anticancer agents – Synthesis, molecular structure, QSAR studies and metabolic stability - Publikacja - MOST Wiedzy

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Novel 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives as potent anticancer agents – Synthesis, molecular structure, QSAR studies and metabolic stability

Abstrakt

A series of new 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives have been synthesized and evaluated in vitro by MTT assays for their antiproliferative activity against cell lines of colon cancer HCT-116, cervical cancer HeLa and breast cancer MCF-7. The obtained results indicated that these compounds display prominent cytotoxic effect. The best anticancer properties have been observed for derivatives 44 (IC50 = 6-18 uM) and 45 (IC50 = 8-14 μM). Very good results of antiproliferative assays have been also shown for compounds 26, 36, and 46 and noticeable anticancer profile has been found for set of derivatives 34e39. Based on results of MTT assays the structure-activity relationships have been drawn. More in-depth biological research revealed that compounds 26, 33, 37, 39, 41 and 43 display cytotoxic effect only against cancer cells and do not inhibit the growth of nonmalignant HaCaT cells. Furthermore, the novel series of derivatives have shown good metabolic stability, especially among the pharmacologically active compounds. To obtain a deeper insight into the molecular description of compounds activity the QSAR studies have been applied. Support vector machines (SVM) have been used to developed QSAR models for predicting the anti-proliferative activity of novel derivatives. The obtained SVM models have shown prognostic ability for HCT-116 and HeLa cell lines and as a result these models may be useful for further development of structurally similar derivatives with better biological properties.

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Autorzy (9)

  • Zdjęcie użytkownika  Aneta Pogorzelska

    Aneta Pogorzelska

    • Medical University of Gdańsk Organic Chemistry
  • Zdjęcie użytkownika  Jarosław Sławiński

    Jarosław Sławiński

    • Medical University of Gdańsk Organic Chemistry
  • Zdjęcie użytkownika  Beata Żołnowska

    Beata Żołnowska

    • Medical University of Gdańsk Organic Chemistry
  • Zdjęcie użytkownika dr Krzysztof Szafrański

    Krzysztof Szafrański dr

    • Medical University of Gdańsk Organic Chemistry
  • Zdjęcie użytkownika  Anna Kawiak

    Anna Kawiak

    • Międzyuczelniany Wydział Biotechnologii UG i GUMed Wydział Biotechnologii
  • Zdjęcie użytkownika  Szymon Ulenberg

    Szymon Ulenberg

    • Medical University of Gdańsk Pharmaceutical Chemistry
  • Zdjęcie użytkownika  Joanna Zielińska

    Joanna Zielińska

    • Medical University of Gdańsk Pharmaceutical Chemistry
  • Zdjęcie użytkownika  Tomasz Bączek

    Tomasz Bączek

    • Medical University of Gdańsk Pharmaceutical Chemistry

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Kategoria:
Publikacja w czasopiśmie
Typ:
artykuł w czasopiśmie wyróżnionym w JCR
Opublikowano w:
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY nr 138, strony 357 - 370,
ISSN: 0223-5234
Język:
angielski
Rok wydania:
2017
Opis bibliograficzny:
Pogorzelska A., Sławiński J., Żołnowska B., Szafrański K., Kawiak A., Chojnacki J., Ulenberg S., Zielińska J., Bączek T.: Novel 2-(2-alkylthiobenzenesulfonyl)-3-(phenylprop-2-ynylideneamino)guanidine derivatives as potent anticancer agents – Synthesis, molecular structure, QSAR studies and metabolic stability// EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. -Vol. 138, (2017), s.357-370
DOI:
Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1016/j.ejmech.2017.06.059
Bibliografia: test
  1. 3H, arom.), 7.78 (brs, 1H, NH), 7.82 (s, 1H, H-6 arom.), 10.96 (s, 1H, NH) ppm; otwiera się w nowej karcie
  2. HRMS (ESI-TOF) þ ] 579.0898, found 579.0922. Anal. (C 26 H 22 ClF 3 N 4 O 2 S 2 ) C, H, N.
  3. 1.3.13. 2-{4-Chloro-5-methyl-2-[(4-trifluoromethylbenzyl)thio] benzenesulfonyl}-3-(3-phenylprop-2-ynylideneamino)guanidine (38). Starting from 20 (0.226 g) and phenylpropiolaldehyde diethyl acetal with stirring for 2 h, the title compound 38 was obtained (0.218 g, 77%): m.p. 176e179 C; IR (KBr): 3398, 3292, 3248 (NH), 2190 (C≡C), 1637 (NH), 1560, 1514, 1489, 1446 (C¼N, C¼C), 1323, 1177 (SO 2 ) cm À1 ; 1 H NMR (200 MHz, DMSO-d 6 ): d 2.26 (s, 3H, CH 3 ), 4.47 (s, 2H, SCH 2 ), 7.17 (s, 1H, N¼CH), 7.47e7.54 (m, 3H, H-3, arom.), 7.58 (m, 5H, arom.), 7.70e7.74 (m, 2H, arom.), 7.84e7.89 (m, 3H, 2 Â NH, H-6 arom.), 11.35 (s, 1H, NH) ppm; otwiera się w nowej karcie
  4. HRMS (ESI-TOF) otwiera się w nowej karcie
  5. C, H, N.
  6. 1.3.14. 2-{4-Chloro-5-methyl-2-[(4-trifluoromethylbenzyl)thio] benzenesulfonyl}-3-(1-methyl-3-phenylprop-2-ynylideneamino)gua- nidine (39). Starting from 20 (0.226 g) and 4-phenylbut-3-yn-2- one with stirring for 4 h, the title compound 39 was obtained (0.270 g, 94%): m.p. 187e190 C; IR (KBr): 3455, 3280, 3249 (NH), 2921 (CH), 2184 (C≡C), 1636 (NH), 1558, 1513, 1492, 1441 (C¼N, C¼C), 1324, 1162 (SO 2 ) cm À1 ; 1 H NMR (200 MHz, DMSO-d 6 ): d 2.18 (s, 3H, CH 3 ), 2.25 (s, 3H, CH 3 ), 4.45 (s, 2H, SCH 2 ), 7.47e7.54 (m, 3H, H-3, arom.), 7.57e7.70 (m, 6H, NH, arom.), 7.71e7.74 (m, 2H, arom.), 7.83e7.85 (m, 2H, NH, H-6 arom.), 11.03 (s, 1H, NH) ppm; otwiera się w nowej karcie
  7. HRMS (ESI-TOF) otwiera się w nowej karcie
  8. C, H, N.
  9. 1. 3 . 1 5 . 2 -{ 4 -C h l o r o -2 -[ ( 2 -c h l o r o b e n z y l ) t h i o ] -5 - methylbenzenesulfonyl}-3-(3-phenylprop-2-ynylideneamino)guani- dine (40). Starting from 21 (0.210 g) and phenylpropiolaldehyde diethyl acetal with stirring for 3 h, the title compound 40 was ob- tained (0.231 g, 87%): m.p. 190e193 C; otwiera się w nowej karcie
  10. IR (KBr): 3373, 3265 (NH), 2193 (C≡C), 1633 (NH), 1566, 1511, 1489, 1474 (C¼N, C¼C), 1330, 1168 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.27 (s, 3H, CH 3 ), 4.34 (s, 2H, SCH 2 ), 7.08 (s, 1H, N¼CH), 7.20e7.27 (m, 2H, arom.), 7.38e7.40 (m, 2H, arom.), 7.43e7.46 (m, 3H, NH, H-3, arom.), 7.48e7.51 (m, 1H, arom.), 7.67e7.68 (m, 3H, arom.), 7.80 (brs, 1H, NH), 7.87 (s, 1H, H-6 arom.), 11.23 (s, 1H, NH) ppm;
  11. HRMS (ESI-TOF) otwiera się w nowej karcie
  12. C, H, N.
  13. 1. 3 . 1 6 . 2 -{ 4 -C h l o r o -2 -[ ( 2 -c h l o r o b e n z y l ) t h i o ] -5 - m e t h y l b e n z e n e s u l f o n y l } -3 -( 1 -m e t h y l -3 -p h e n y l p r o p -2 - ynylideneamino)guanidine (41). Starting from 21 (0.210 g) and 4- phenylbut-3-yn-2-one with stirring for 6 h, the title compound 41 was obtained (0.186 g, 68%): m.p. 177e179 C; IR (KBr): 3396, 3291, 3244 (NH), 2181 (C≡C), 1633 (NH), 1567, 1508, 1491, 1474 (C¼N, C¼C), 1340, 1169 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): otwiera się w nowej karcie
  14. d 2.16 (s, 3H, CH 3 ), 2.25 (s, 3H, CH 3 ), 4.45 (s, 2H, SCH 2 ), 7.20e7.23 (m, 1H, arom.), 7.26e7.29 (m, 1H, arom.), 7.38e7.40 (m, 2H, arom.), 7.42e7.51 (m, 5H, NH, H-3, arom.), 7.67e7.69 (m, 2H, arom.), 7.73 (brs, 1H, NH), 7.85 (s, 1H, H-6 arom.), 10.93 (s, 1H, NH) ppm; HRMS (ESI-TOF) otwiera się w nowej karcie
  15. C, H, N.
  16. 1. 3 . 17 . 2 -{ 4 -C h l o r o -2 -[ ( 3 -c h l o r o b e n z y l ) t h i o ] -5 - methylbenzenesulfonyl}-3-(3-phenylprop-2-ynylideneamino)guani- dine (42). Starting from 22 (0.210 g) and phenylpropiolaldehyde diethyl acetal with stirring for 3 h, the title compound 42 was ob- tained (0.247 g, 93%): m.p. 195e197 C; otwiera się w nowej karcie
  17. IR (KBr): 3373, 3306 (NH), 2192 (C≡C), 1643 (NH), 1568, 1511, 1451 (C¼N, C¼C), 1331, 1154 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.25 (s, 3H, CH 3 ), 4.33 (s, 2H, SCH 2 ), 7.13 (s, 1H, N¼CH), 7.26e7.29 (m, 3H, arom.), 7.39 (s, 1H, arom.), 7.44e7.51 (m, 4H, H-3, arom.), 7.69e7.70 (m, 2H, arom.), 7.72 (brs, 1H, NH), 7.83 (brs, 1H, NH), 7.85 (s, 1H, H-6 arom.), 11.26 (s, 1H, NH) ppm;
  18. HRMS (ESI-TOF) m/z calcd for C 24 H 20 Cl 2 N 4 O 2 S 2 [M þ H þ ] 531.0477, found 531.0506. Anal. (C 24 H 20 Cl 2 N 4 O 2 S 2 ) C, H, N. 4 . 1. 3 . 18 . 2 -{ 4 -C h l o r o -2 -[ ( 3 -c h l o r o b e n z y l ) t h i o ] -5 - m e t h yl b e n z e n e s u l f o n yl } -3 -( 1 -m e t h yl -3 -p h e n y l p r o p -2 - ynylideneamino)guanidine (43). Starting from 22 (0.210 g) and 4- phenylbut-3-yn-2-one with stirring for 10 h, the title compound 43 was obtained (0.202 g, 76%): m.p. 175e178 C; IR (KBr): 3447, 3257, 3200 (NH), 2182 (C≡C), 1631 (NH), 1555, 1511, 1491, 1477 (C¼N, C¼C), 1341, 1173 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): otwiera się w nowej karcie
  19. d 2.18 (s, 3H, CH 3 ), 2.23 (s, 3H, CH 3 ), 4.32 (s, 2H, SCH 2 ), 7.25e7.31 (m, 3H, arom.), 7.39 (s, 1H, arom.), 7.44e7.46 (m, 2H, arom.), 7.49e7.51 (m, 2H, H-3, arom.), 7.55 (brs, 1H, NH), 7.70e7.72 (m, 2H, arom.), 7.79 (brs, 1H, NH), 7.83 (s, 1H, H-6 arom.), 10.98 (s, 1H, NH) ppm; 13 C NMR (125 MHz, DMSO-d 6 ): d 19.6, 22.9, 36.1, 80.9, 102.6, 120.6, 127.9, 128.4, 129.2, 129.5, 129.6, 130.8, 130.9, 131.3, 132.9, 133.2, 133.5, 133.6, 135.5, 137.4, 139.4, 140.6, 154.5 ppm; HRMS (ESI-TOF) otwiera się w nowej karcie
  20. m/z calcd for C 25 H 22 Cl 2 N 4 O 2 S 2 [M þ H þ ] 545.0634, found 545.0620. Anal. (C 25 H 22 Cl 2 N 4 O 2 S 2 ) C, H, N. 4 . 1. 3 . 1 9 . 2 -{ 4 -C h l o r o -2 -[ ( 4 -c h l o r o b e n z y l ) t h i o ] -5 - methylbenzenesulfonyl}-3-(3-phenylprop-2-ynylideneamino)guani- dine (44). Starting from 23 (0.210 g) and phenylpropiolaldehyde diethyl acetal with stirring for 12 h, the title compound 44 was obtained (0.237 g, 89%): m.p. 175e177 C; IR (KBr): 3386, 3302, 3220 (NH), 2191 (C≡C), 1639 (NH), 1567, 1507, 1491 (C¼N, C¼C), 1330, 1162 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.23 (s, 3H, CH 3 ), 4.31 (s, 2H, SCH 2 ), 7.14 (s, 1H, N¼CH), 7.25 (d, J ¼ 8.8 Hz, 2H, arom.), 7.34 (d, J ¼ 8.3 Hz, 2H, arom.), 7.43e7.49 (m, 2H, arom.), 7.50e7.52 (m, 1H, arom.), 7.53 (s, 1H, H-3 arom.), 7.68e7.70 (m, 2H, arom.), 7.77 (brs, 1H, NH), 7.82e7.83 (m, 2H, NH, H-6 arom.), 11.29 (s, 1H, NH) ppm;
  21. HRMS (ESI-TOF) m/z calcd for C 24 H 20 Cl 2 N 4 O 2 S 2 [M þ H þ ] 531.0477, found 531.0508. Anal. (C 24 H 20 Cl 2 N 4 O 2 S 2 ) C, H, N. 4 . 1. 3 . 2 0 . 2 -{ 4 -C h l o r o -2 -[ ( 4 -c h l o r o b e n z y l ) t h i o ] -5 - m e t h yl b e n z e n e s u l f o n yl } -3 -( 1 -m e t h yl -3 -p h e n y l p r o p -2 - ynylideneamino)guanidine (45). Starting from 23 (0.210 g) and 4- phenylbut-3-yn-2-one with stirring for 5 h, the title compound 45 was obtained (0.223 g, 84%): m.p. 202e205 C; IR (KBr): 3451, 3261 (NH), 2179 (C≡C), 1632 (NH), 1564, 1491, 1444 (C¼N, C¼C), 1342, 1175 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.17 (s, 3H, CH 3 ), 2.22 (s, 3H, CH 3 ), 4.30 (s, 2H, SCH 2 ), 7.27 (d, J ¼ 8.8 Hz, 2H, arom.), 7.33 (d, J ¼ 8.3 Hz, 2H, arom.), 7.43e7.46 (m, 2H, H-3, arom.), 7.48e7.51 (m, 2H, arom.), 7.55 (brs, 1H, NH), 7.69e7.70 (m, 2H, arom.), 7.77 (brs, 1H, NH), 7.81 (s, 1H, H-6 arom.), 10.97 (s, 1H, NH) ppm;
  22. HRMS (ESI-TOF) m/z calcd for C 25 H 22 Cl 2 N 4 O 2 S 2 [M þ H þ ] 545.0634, found 545.0637. Anal. (C 25 H 22 Cl 2 N 4 O 2 S 2 ) C, H, N. 4.1.3.21. 2-[4-Chloro-5-methyl-2-(naphthalene-1-ylmethylthio)ben- zenesulfonyl}-3-(3-phenylprop-2-ynylideneamino)guanidine (46). otwiera się w nowej karcie
  23. Starting from 24 (0.218 g) and phenylpropiolaldehyde diethyl acetal with stirring for 20 h, the title compound 46 was obtained (0.213 g, 78%): m.p. 191e194 C; otwiera się w nowej karcie
  24. IR (KBr): 3446, 3274 (NH), 3060, 2913, 2856 (CH), 2188 (C≡C), 1636 (NH), 1563, 1510, 1490, 1443 (C¼N, C¼C), 1343, 1168 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.27 (s, 3H, CH 3 ), 4.76 (s, 2H, SCH 2 ), 6.97 (s, 1H, N¼CH), 7.37e7.42 (m, 3H, arom.), 7.46e7.51 (m, 4H, NH, arom.), 7.58 (s, 1H, H-3 arom.), 7.61e7.63 (m, 3H, arom.), 7.78 (brs, 1H, NH), 7.83e7.84 (d, J ¼ 8.0 Hz, 1H, arom.), 7.88 (s, 1H, H-6 arom.), 7.91e7.92 (m, 1H, arom.), 8.16e8.18 (m, 1H, arom.), 11.18 (s, 1H, NH) ppm;
  25. HRMS (ESI-TOF) m/z calcd for C 28 H 23 ClN 4 O 2 S 2 [M þ H þ ] 547.1024, found 545.1029. Anal. otwiera się w nowej karcie
  26. C, H, N.
  27. 1.3.22. 2-[4-Chloro-5-methyl-2-(naphthalene-1-ylmethylthio)ben- zenesulfonyl}-3-(1-methyl-3-phenylprop-2-ynylideneamino)guani- dine (47). Starting from 24 (0.218 g) and 4-phenylbut-3-yn-2-one with stirring for 8 h, the title compound 47 was obtained (0.199 g, 71%): m.p. 177e180 C; IR (KBr): 3448, 3265 (NH), 2182 (C≡C), 1633 (NH), 1566, 1491, 1444 (C¼N, C¼C), 1342, 1171 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.05 (s, 3H, CH 3 ), 2.26 (s, 3H, CH 3 ), 4.75 (s, 2H, SCH 2 ), 7.37e7.41 (m, 4H, arom.), 7.45e7.51 (m, 4H, arom.), 7.59e7.63 (m, 3H, NH, H-3, arom.), 7.71 (brs, 1H, NH), 7.84e7.86 (m, 2H, H-6, arom.), 7.91e7.93 (m, 1H, arom.), 8.16 (d, J ¼ 8.3 Hz, 1H, arom.), 10.87 (s, 1H, NH) ppm; otwiera się w nowej karcie
  28. HRMS (ESI-TOF) m/z calcd for C 29 H 25 ClN 4 O 2 S 2 [M þ H þ ] 561.1180, found 561.1193. Anal. otwiera się w nowej karcie
  29. , 35%): m.p. 192e195 C; IR (KBr): 3430, 3329, 3236 (NH), 3062, 2902 (CH), 2190 (C≡C), 1633 (NH), 1567, 1502, 1487 (C¼N, C¼C), 1346, 1171 (SO 2 ) cm À1 ; 1 H NMR (500 MHz, DMSO-d 6 ): d 2.27 (s, 3H, CH 3 ), 4.23 (s, 2H, SCH 2 ), 6.02 (s, 2H, O-CH 2 -O), 6.91 (s, 1H, N¼CH), 6.97 (s, 1H, arom.), 7.09 (s, 1H, arom.), 7.42e7.50 (m, 4H, H-3, arom.), 7.66e7.68 (m, 3H, NH, arom.), 7.79 (brs, 1H, NH), 7.86 (s, 1H, H-6 arom.), 11.21 (s, 1H, NH) ppm; otwiera się w nowej karcie
  30. HRMS (ESI-TOF) otwiera się w nowej karcie
  31. C, H, N.
  32. 1. 3 . 24 . 2 -[ 4 -C h l o ro -2 -( 6 -ch l o ro b e n z o [ d ] [ 1, 3 ] d i o x o l -5 - ylmethylthio)-5-methylbenzenesulfonyl]-3-(1-methyl-3-phenylprop- 2-ynylideneamino)guanidine (49). Starting from 25 (0.232 g) and 4- phenylbut-3-yn-2-one with stirring for 14 h, the title compound 49 was obtained (0.092 g, 31%): m.p. 178e181 C; IR (KBr): 3454, 3258 (NH), 2180 (C≡C), 1639 (NH), 1552, 1471 (C¼N, C¼C), 1342, 1176 otwiera się w nowej karcie
  33. (SO 2 ) cm À1 ; 1 H NMR (200 MHz, DMSO-d 6 ): d 2.18 (s, 3H, CH 3 ), 2.27 (s, 3H, CH 3 ), 4.23 (s, 2H, SCH 2 ), 6.04 (s, 2H, O-CH 2 -O), 6.92 (s, 1H, arom.), 7.01 (s, 1H, arom.), 7.44e7.50 (m, 5H, NH, H-3, arom.), 7.66e7.71 (m, 3H, NH, arom.), 7.85 (s, 1H, H-6 arom.), 10.94 (s, 1H, NH) ppm; otwiera się w nowej karcie
  34. HRMS (ESI-TOF) m/z calcd for C 26 H 22 Cl 2 N 4 O 4 S 2 [M þ H þ ] 589.0532, found 589.0554. Anal. (C 26 H 22 Cl 2 N 4 O 4 S 2 ) C, H, N. otwiera się w nowej karcie
  35. X-ray structure determination Diffraction intensity data were collected on an IPDS 2T dual- beam diffractometer (STOE & Cie GmbH, Darmstadt, Germany) at 120.0(2) K with Mo-Ka (35, 42 and 43) or Cu-Ka (28) radiation of a microfocus x-ray source (GeniX 3D Mo High Flux, 50 kV, 1.0 mA, References otwiera się w nowej karcie
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