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.
Cytowania
-
1 7
CrossRef
-
0
Web of Science
-
1 9
Scopus
Autorzy (9)
Cytuj jako
Pełna treść
- Wersja publikacji
- Accepted albo Published Version
- Licencja
- otwiera się w nowej karcie
Słowa kluczowe
Informacje szczegółowe
- 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
-
- 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
- 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.
- 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
- HRMS (ESI-TOF) otwiera się w nowej karcie
- C, H, N.
- 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
- HRMS (ESI-TOF) otwiera się w nowej karcie
- C, H, N.
- 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
- 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;
- HRMS (ESI-TOF) otwiera się w nowej karcie
- C, H, N.
- 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
- 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
- C, H, N.
- 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
- 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;
- 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
- 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
- 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;
- 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;
- 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
- 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
- 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;
- 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
- C, H, N.
- 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
- 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
- , 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
- HRMS (ESI-TOF) otwiera się w nowej karcie
- C, H, N.
- 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
- (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
- 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
- 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
- E.J. Freireich, Can we conquer cancer in the twenty-first century? Cancer Chemother. Pharmacol. 48 (Suppl 1) (2001) S4eS10. otwiera się w nowej karcie
- Y. Yamada, N. Yamamoto, T. Shimoyama, A. Horiike, Y. Fujisaka, K. Takayama, T. Sakamoto, Y. Nishioka, S. Yasuda, T. Tamura, Phase I pharmacokinetic and pharmacogenomic study of E7070 administered once every 21 days, Cancer Sci. 96 (2005) 721e728. otwiera się w nowej karcie
- J.F. Smyth, S. Aamdal, A. Awada, C. Dittrich, F. Caponigro, P. Sch€ offski, M. Gore, T. Lesimple, N. Djurasinovic, B. Baron, M. Ravic, P. Fumoleau, C.J. Punt, EORTC new drug development and melanoma groups, phase II study of E7070 in patients with metastatic melanoma, Ann. Oncol. 16 (2005) 158e161. otwiera się w nowej karcie
- M. Baur, M. Gneist, T. Owa, C. Dittrich, Clinical complete long-term remission of a patient with metastatic malignant melanoma under therapy with indis- ulam (E7070), Melanoma Res. 17 (2007) 329e331. otwiera się w nowej karcie
- Y. Ozawa, N.H. Sugi, T. Nagasu, T. Owa, T. Watanabe, N. Koyanagi, H. Yoshino, K. Kitoh, K. Yoshimatsu, E7070, a novel sulphonamide agent with potent antitumour activity in vitro and in vivo, Eur. J. Cancer 37 (2001) 2275e2282. otwiera się w nowej karcie
- A.M. Pick, K.K. Nystrom, Pazopanib for the treatment of metastatic renal cell carcinoma, Clin. Ther. 34 (2012) 511e520. otwiera się w nowej karcie
- D.T. Nguyen, S. Shayahi, Pazopanib: approval for soft-tissue sarcoma, J. Adv. Pract. Oncol. 4 (2013) 53e57.
- P. Sch€ offski, Pazopanib in the treatment of soft tissue sarcoma, Expert Rev. Anticancer Ther. 12 (2012) 711e723.
- J. McLachlan, S. Banerjee, Pazopanib in ovarian cancer, Expert Rev. Anticancer Ther. 15 (2015) 995e1005. otwiera się w nowej karcie
- B. Milojkovic Kerklaan, M.P.J. Lolkema, L.A. Devriese, E.E. Voest, A. Nol-Boekel, M. Mergui-Roelvink, M. Langenberg, K. Mykulowycz, J. Stoebenau, S. Lane, P. Legenne, P. Wissel, D.A. Smith, B.J. Giantonio, J.H.M. Schellens, P.O. Witteveen, Phase I and pharmacological study of pazopanib in combi- nation with oral topotecan in patients with advanced solid tumours, Br. J. Cancer 113 (2015) 706e715.
- S. Gupta, P.E. Spiess, The prospects of pazopanib in advanced renal cell car- cinoma, Ther. Adv. Urol. 5 (2013) 223e232. otwiera się w nowej karcie
- T. Medina, M.N. Amaria, A. Jimeno, Dabrafenib in the treatment of advanced melanoma, Drugs Today (Barc) 49 (2013) 377e385.
- H.Z. Lee, V.E. Kwitkowski, P.L. Del Valle, M.S. Ricci, H. Saber, B.A. Habtemariam, J. Bullock, E. Bloomquist, Y. Li Shen, X.H. Chen, J. Brown, N. Mehrotra, S. Dorff, R. Charlab, R.C. Kane, E. Kaminskas, R. Justice, A.T. Farrell, R. Pazdur, FDA approval: belinostat for the treatment of patients with relapsed or refractory peripheral t-cell lymphoma, Clin. Cancer Res. 21 (2015) 2666e2670. otwiera się w nowej karcie
- L.H. Camacho, S.L. Moulder, P.M. LoRusso, G.R. Blumenschein, P.J. Bristow, R. Kurzrock, S. Fu, K. Schlienger, D.A. Bergstrom, First in human phase I study of MK-2461, a small molecule inhibitor of c-Met, for patients with advanced solid tumors, J. Clin. Onc 26 (Suppl) (2008) 639s. Abstract 14657. otwiera się w nowej karcie
- A.M. Tsimberidou, C. Vaklavas, S. Wen, D. Hong, J. Wheler, C. Ng, A. Naing, S. Tse, N. Busaidy, M. Markman, S.I. Sherman, R. Kurzrock, Phase I clinical trials in 56 patients with thyroid cancer: the M. D. Anderson cancer center expe- rience, J. Clin. Endocrinol. Metab. 94 (2009) 4423e4432. otwiera się w nowej karcie
- W. DePinto, X.J. Chu, X. Yin, M. Smith, K. Packman, P. Goelzer, A. Lovey, Y. Chen, H. Qian, R. Hamid, Q. Xiang, C. Tovar, R. Blain, T. Nevins, B. Higgins, L. Luistro, K. Kolinsky, B. Felix, S. Hussain, D. Heimbrook, In vitro and in vivo activity of R547: a potent and selective cyclin-dependent kinase inhibitor currently in phase I clinical trials, Mol. Cancer Ther. 5 (2006) 2644e2658. otwiera się w nowej karcie
- G.I. Shapiro, J. Rodon, C. Bedell, E.L. Kwak, J. Baselga, I. Braña, S.S. Pandya, C. Scheffold, A.D. Laird, L.T. Nguyen, Y. Xu, C. Egile, G. Edelman, Phase I safety, pharmacokinetic, and pharmacodynamic study of SAR245408 (XL147), an oral pan-class I PI3K inhibitor, in patients with advanced solid tumors, Clin. Cancer Res. 20 (2014) 233e245. otwiera się w nowej karcie
- U. Matulonis, I. Vergote, F. Backes, L.P. Martin, S. McMeekin, M. Birrer, F. Campana, Y. Xu, C. Egile, S. Ghamande, Phase II study of the PI3K inhibitor pilaralisib (SAR245408; XL147) in patients with advanced or recurrent endometrial carcinoma, Gynecol. Oncol. 136 (2015) 246e253. otwiera się w nowej karcie
- B.S. Pan, G.K. Chan, M. Chenard, A. Chi, L.J. Davis, S.V. Deshmukh, J.B. Gibbs, S. Gil, G. Hang, H. Hatch, J.P. Jewell, I. Kariv, J.D. Katz, K. Kunii, W. Lu, B.A. Lutterbach, C.P. Paweletz, X. Qu, J.F. Reilly, A.A. Szewczak, Q. Zeng, N.E. Kohl, C.J. Dinsmore, MK-2461, a novel multitargeted kinase inhibitor, preferentially inhibits the activated c-Met receptor, Cancer Res. 15 (2010) 1524e1533. otwiera się w nowej karcie
- P. Foster, K. Yamaguchi, P.P. Hsu, F. Qian, X. Du, J. Wu, K.A. Won, P. Yu, C.T. Jaeger, W. Zhang, C.K. Marlowe, P. Keast, W. Abulafia, J. Chen, J. Young, A. Plonowski, F.M. Yakes, F. Chu, K. Engell, F. Bentzien, S.T. Lam, S. Dale, O. Yturralde, D.J. Matthews, P. Lamb, A.D. Laird, The selective PI3K inhibitor XL147 (SAR245408) inhibits tumor growth and survival and potentiates the activity of chemotherapeutic agents in preclinical tumor models, Mol. Cancer Ther. 14 (2015) 931e940. otwiera się w nowej karcie
- Clinical Trials. Available online: http://clinicaltrials.gov (accessed on April 29, 2016).. otwiera się w nowej karcie
- Z. Brzozowski, F. Są czewski, J. Sławi nski, Synthesis of novel 3-amino-2-(4- chloro-2-mercaptobenzenesulfonyl)-guanidine derivatives as potential anti- tumor agents, Eur. J. Med. Chem. 42 (2007) 1218e1225. otwiera się w nowej karcie
- B. _ Zołnowska, J. Sławi nski, A. Pogorzelska, J. Chojnacki, D. Vullo, C.T. Supuran, Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N'-[2-arylmethylthio-4-chloro-5- methylbenzenesulfonyl)guanidine and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII, Eur. J. Med. Chem. 71 (2014) 135e147. otwiera się w nowej karcie
- J. Sławi nski, A. Pogorzelska, B. _ Zołnowska, K. Bro _ zewicz, D. Vullo, C.T. Supuran, Carbonic anhydrase inhibitors. Synthesis of a novel series 5-substituted 2,4- dichlorobenzenesulfonamides and their inhibition of human cytosolic iso- zymes I and II and the transmembrane tumor-associated isozymes IX and XII, Eur. J. Med. Chem. 82 (2014) 47e55. otwiera się w nowej karcie
- J. Sławi nski, Z. Brzozowski, B. _ Zołnowska, K. Szafra nski, A. Pogorzelska, D. Vullo, C.T. Supuran, Synthesis of new series N 4 -substituted 4-(2- aminoethyl)benzenesulfonamides and their inhibitory effect of human car- bonic anhydrase cytosolic isozymes I and II and the transmembrane tumor- associated isozymes IX and XII, Eur. J. Med. Chem. 84 (2014) 59e67. otwiera się w nowej karcie
- K. Bro _ zewicz, J. Sławi nski, 1-(2-Mercaptobenzenesulfonyl)-3- hydroxyguanidines e novel potent antiproliferatives, synthesis and in vitro biological activity, Eur. J. Med. Chem. 55 (2012) 384e394.
- M. Pless, K. Belhadj, H.D. Menssen, W. Kern, B. Coiffier, J. Wolf, R. Herrmann, E. Thiel, D. Bootle, I. Sklenar, C. Müller, L. Choi, C. Porter, R. Capdeville, Clinical efficacy, tolerability, and safety of SAM486A, a novel polyamine biosynthesis inhibitor, in patients with relapsed or refractory non-Hodgkin's lymphoma: results from a phase II multicenter study, Clin. Cancer Res. 15 (2004) 1299e1305. otwiera się w nowej karcie
- R. Romagnoli, P.G. Baraldi, O. Cruz-Lopez, M. Tolomeo, A. Di Cristina, R.M. Pipitone, S. Grimaudo, J. Balzarini, A. Brancale, E. Hamel, Synthesis of novel antimitotic agents based on 2-amino-3-aroyl-5-(hetero)arylethynyl thiophene derivatives, Bioorg. Med. Chem. Lett. 21 (2011) 2746e2751. otwiera się w nowej karcie
- S. Meike, T. Yamamori, H. Yasui, M. Eitaki, A. Matsuda, M. Morimatsu, M. Fukushima, Y. Yamasaki, O. Inanami, A nucleoside anticancer drug, 1-(3-C- ethynyl-b-D-ribo-pentofuranosyl)cytosine (TAS106), sensitizes cells to radia- tion by suppressing BRCA2 expression, Mol. Cancer 10 (2011) 92e100. otwiera się w nowej karcie
- J. Wan, Y. Xia, Y. Liu, M. Wang, P. Rocchi, J. Yao, F. Qu, J. Neyts, J.L. Iovanna, L. Peng, Discovery of novel arylethynyltriazole ribonucleosides with selective and effective antiviral and antiproliferative activity, J. Med. Chem. 52 (2009) 1144e1155. otwiera się w nowej karcie
- B.M. Ku, S.J. Kim, N. Kim, D. Hong, Y.B. Choi, S.H. Lee, Y.D. Gong, S.Y. Kim, Transglutaminase 2 inhibitor abrogates renal cell carcinoma in xenograft models, J. Cancer Res. Clin. Oncol. 140 (2014) 757e767. otwiera się w nowej karcie
- J. Sławi nski, Syntheses and some reactions of 3-amino-6-chloro-7-methyl- 1,1-dioxo-1,4,2-benzodithiazine, Pol. J. Chem. 75 (2001) 1309e1316.
- J. Sławi nski, A. Pogorzelska, B. _ Zołnowska, A. Kę dzia, M. Zi ołkowska-Klinkosz, otwiera się w nowej karcie
- E. Kwapisz, Synthesis and anti-yeast evaluation of novel 2-alkylthio-4-chloro- 5-methyl-N-[imino-(1-oxo-(1H)-phthalazin-2-yl)methyl]benzenesulfona- mide derivatives, Molecules 19 (2014) 13704e13723.
- J. Sławi nski, B. _ Zołnowska, C. Orlewska, J. Chojnacki, Synthesis and molecular structure of novel 2-(alkylthio)-4-chloro-N-(4,5-dihydro-5-oxo-1H-1,2,4- triazol-3-yl)-5-methylbenzenesulfonamides with potential anticancer activ- ity, Monatsh. Chem. 143 (2012) 1705e1718. otwiera się w nowej karcie
- B. _ Zołnowska, J. Sławi nski, A. Pogorzelska, J. Chojnacki, D. Vullo, C.T. Supuran, Carbonic anhydrase inhibitors. Synthesis, and molecular structure of novel series N-substituted N 0 -(2-arylmethylthio-4-chloro-5- methylbenzenesyulfonyl)guanidines and their inhibition of human cytosolic isozymes I and II and the transmembrane tumor-associated isozymes IX and XII, Eur. J. Med. Chem. 17 (2014) 135e147. otwiera się w nowej karcie
- J. Sławi nski, P. Bednarski, R. Grünert, P. Reszka, Syntheses of a new series of N- amino-N 00 -(benzenesulphonyl)guanidine derivatives with potential antitumor activity, Pol. J. Chem. 77 (2003) 53e64. otwiera się w nowej karcie
- B. _ Zołnowska, J. Sławi nski, A. Pogorzelska, K. Szafra nski, A. Kawiak, G. Stasiłoj c, M. Belka, S. Ulenberg, T. Bą czek, J. Chojnacki, Novel 5-substituted 2-(aryl- methylthio)-4-chloro-N-(5-aryl-1,2,4-triazin-3-yl)benzenesulfonamides: syn- thesis, molecular structure, anticancer activity, apoptosis-inducing activity, and metabolic stability, Molecules 21 (2016) 808. otwiera się w nowej karcie
- M.C. Etter, Encoding and decoding hydrogen-bond patterns of organic com- pounds, Acc. Chem. Res. 23 (1990) 120e126. otwiera się w nowej karcie
- STOE, G.M.B.H. Cie, X-Area 1.75, Software Package for Collecting Single-crystal Data on STOE Area-detector Diffractometers, for Image Processing, Scaling Reflection Intensities and for Outlier Rejection, 2005. Darmstadt, Germany.
- R.H. Blessing, Outlier treatment in data merging, J. Appl. Cryst. 30 (1997) 421e426. otwiera się w nowej karcie
- W. Herrendorf, HABITUS, a Program for the Optimization of the Crystal Description for the Numerical Absorption Correction by Means of Suitable, Psi Scanned Reflections, dissertation, 1994. Karlsruhe, extension 1998, Gießen, Germany.
- G.M. Sheldrick, A short history of SHELX, Acta Cryst. A64 (2008) 112e122. otwiera się w nowej karcie
- L.J. Farrugia, WinGX and ORTEP for Windows: an update, J. Appl. Cryst. 45 (2012) 849e854. otwiera się w nowej karcie
- M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. F, M. A. R. Gaussian 03, Revision C.02..
- V. Vapnik, The Nature of Statistical Learning Theory, Springer, 2000. otwiera się w nowej karcie
- D. Basak, S. Pal, D.C. Patranabis, C, Support vector regression, Neural Inf. process. Rev. 11 (2007) 203e224.
- Weryfikacja:
- Politechnika Gdańska
wyświetlono 123 razy
Publikacje, które mogą cię zainteresować
Synthesis, Molecular Structure, Metabolic Stability and QSAR Studies of a Novel Series of Anticancer N-Acylbenzenesulfonamides
- B. Żołnowska,
- J. Sławiński,
- M. Belka
- + 5 autorów
Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)Benzenesulfonamide Derivatives
- B. Żołnowska,
- J. Sławiński,
- Z. Brzozowski
- + 5 autorów
Synthesis, molecular structure, and metabolic stability of new series of N' -(2-alkylthio-4-chloro-5-methylbenzenesulfonyl)-1-(5-phenyl-1 H -pyrazol-1-yl)amidine as potential anti-cancer agents
- A. Pogorzelska,
- J. Sławiński,
- A. Kawiak
- + 6 autorów
Novel 5-Substituted 2-(Aylmethylthio)-4-chloro-N-(5-aryl-1,2,4-triazin-3-yl)benzenesulfonamides: Synthesis, Molecular Structure, Anticancer Activity, Apoptosis-Inducing Activity and Metabolic Stability
- B. Żołnowska,
- J. Sławiński,
- A. Pogorzelska
- + 7 autorów