New chiral ebselen analogues with antioxidant and cytotoxic potential. *
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1 ew chiral ebselen analogues with antioxidant and cytotoxic potential A. J. Pacuła a, K. B. Kaczor b, J. Antosiewicz b,e, A. Janecka c, A. Długosz c, T. Janecki d, A. Wojtczak a and J. Ścianowski a* a Department of rganic Chemistry, Faculty of Chemistry, icolaus Copernicus University, Gagarina 7, Torun, Poland b Department of Bioenergetics and Physiology of Exercise, Medical University of Gdansk, Debinki 1, Gdansk, Poland c Department of Biomolecular Chemistry, Faculty of Medicine, Medical University of Lodz, Mazowiecka 6/8, Lodz, Poland dinstitute of rganic Chemistry, Lodz University of Technology, Zeromskiego 116, Lodz, Poland e Department of Biochemistry, Gdansk University of Physical Education and Sport, Kazimierza Gorskiego 1, Gdansk, Poland * jsch@chem.umk.pl Supporting Information: MR Spectra, Crystallografic data Index of content I. MR spectra a) (1R)- Camphor oxime (10) b) (1R)-Camphor -methyloxime (11) c) (R)-(-)-Isobornylamine (12) d) -Isobornyl-o-iodobenzamide (15) e) -Bornyl-o-iodobenzamide (16) f) 2,2 -Diselenobis(-isobornylbenzamide) (17) g) 2,2 -Diselenobis(-bornylbenzamide) (18) h) -Isobornyl-1,2-benzisoselenazol-3(2H)-one (19) i) -Bornyl-1,2-benzisoselenazol-3(2H)-one (20) j) 2,2-Diselenobis(benzoic acid) (6) k) 2-(Chloroseleno)benzoyl chloride (7) l) -(Glycine methyl ester)-benzisoselenazol-3(2h)-one (21) m) -(Alanine methyl ester)-benzisoselenazol-3(2h)-one (22) n) -(Leucine methyl ester)-benzisoselenazol-3(2h)-one (23) o) -(Phenylalanine methyl ester)-benzisoselenazol-3(2h)-one (24) p) -(Alanine carboxyl acid)-benzisoselenazol-3(2h)-one (25) II. Crystallographic data a) Table 1. Crystal data and structure refinement for -bornyl-1,2-benzisoselenazol-3(2h)-one 20 (e654a). b) Table 2. Selected bond lengths [Å] and angles [º] for -bornyl-1,2-benzisoselenazol-3(2h)-one 20 (e654a).
2 I. MR spectra (1R)- Camphor oxime (10) H
3 (1R)-Camphor -methyloxime (11) Me
4 (R)-(-)-Isobornylamine (12) H 2
5 -Isobornyl-o-iodobenzamide (15) H I
6 -Isobornyl-o-iodobenzamide (15) H I
7 -Bornyl-o-iodobenzamide (16) H I
8 -Bornyl-o-iodobenzamide (16) H I
9 2,2 -Diselenobis(-isobornylbenzamide) (17) H Se) 2
10 2,2 -Diselenobis(-isobornylbenzamide) (17) H Se) 2
11 2,2 -Diselenobis(-isobornylbenzamide) (17) H Se) 2
12 2,2 -Diselenobis(-bornylbenzamide) (18) H Se) 2
13 2,2 -Diselenobis(-bornylbenzamide) (18) H Se) 2
14 2,2 -Diselenobis(-bornylbenzamide) (18) H Se) 2
15 -Isobornyl-1,2-benzisoselenazol-3(2H)-one (19) Se
16 -Isobornyl-1,2-benzisoselenazol-3(2H)-one (19) Se
17 -Isobornyl-1,2-benzisoselenazol-3(2H)-one (19) Se
18 -Bornyl-1,2-benzisoselenazol-3(2H)-one (20) Se
19 -Bornyl-1,2-benzisoselenazol-3(2H)-one (20) Se
20 -Bornyl-1,2-benzisoselenazol-3(2H)-one (20) Se
21 2,2-Diselenobis(benzoic acid) (6) H Se) 2
22 2,2-Diselenobis(benzoic acid) (6) H Se) 2
23 2,2-Diselenobis(benzoic acid) (6) H Se) 2
24 2-(Chloroseleno)benzoyl chloride (7) Cl SeCl
25 2-(Chloroseleno)benzoyl chloride (7) Cl SeCl
26 2-(Chloroseleno)benzoyl chloride (7) Cl SeCl
27 -(Glycine methyl ester)-benzisoselenazol-3(2h)-one (21) Se
28 -(Glycine methyl ester)-benzisoselenazol-3(2h)-one (21) Se
29 -(Glycine methyl ester)-benzisoselenazol-3(2h)-one (21) Se
30 -(Alanine methyl ester)-benzisoselenazol-3(2h)-one (22) Se
31 -(Alanine methyl ester)-benzisoselenazol-3(2h)-one (22) Se
32 -(Alanine methyl ester)-benzisoselenazol-3(2h)-one (22) Se
33 -(Leucine methyl ester)-benzisoselenazol-3(2h)-one (23) Se
34 -(Leucine methyl ester)-benzisoselenazol-3(2h)-one (23) Se
35 -(Leucine methyl ester)-benzisoselenazol-3(2h)-one (23) Se
36 -(Phenylalanine methyl ester)-benzisoselenazol-3(2h)-one (24) Se
37 -(Phenylalanine methyl ester)-benzisoselenazol-3(2h)-one (24) Se
38 -(Phenylalanine methyl ester)-benzisoselenazol-3(2h)-one (24) Se
39 -(Alanine carboxyl acid)-benzisoselenazol-3(2h)-one (25) Se H
40 -(Alanine carboxyl acid)-benzisoselenazol-3(2h)-one (25) Se H
41 -(Alanine carboxyl acid)-benzisoselenazol-3(2h)-one (25) Se H
42 VI. Crystallographic data Table 1. Crystal data and structure refinement for -bornyl-1,2-benzisoselenazol-3(2h)-one 20 (e654a). Identification code e654a Empirical formula C17 H21 Se Formula weight Temperature; K 293(2) Wavelength; Å Crystal system, space group rthorhombic, P2(1)2(1)2(1) Unit cell dimensions; Å a = (10) b = (9) c = (10) Volume; Å (2) Z, Calculated density; Mg/m 3 4, Absorption coefficient; mm F(000) 688 Crystal size; mm 0.49 x 0.16 x 0.13 Theta range for data collection 2.45 to deg. Limiting indices -13<=h<=13, -14<=k<=15, -15<=l<=13 Reflections collected / unique 9666 / 3266 [R(int) = ] Completeness to theta % Absorption correction Analytical Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 3266 / 0 / 181 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Absolute structure parameter (4) Largest diff. peak and hole; e.a and Table 2. Selected bond lengths [Å] and angles [º] for -bornyl-1,2-benzisoselenazol-3(2h)-one 20 e654a. C1-C (4) C1-C (4) C1-C (4) C1-C (4) C (3)
43 C2-C (4) C3-C (4) C4-C (4) C4-C (4) C5-C (4) C7-C (4) C7-C (4) Se (2) Se1-C (2) 1-C (3) C (3) C11-C (3) C12-C (4) C12-C (4) C13-C (4) C14-C (4) C15-C (4) C16-C (3) C10-C1-C (2) C10-C1-C (2) C6-C1-C (2) C10-C1-C (2) C6-C1-C (2) C7-C1-C (2) 1-C2-C (2) 1-C2-C (2) C3-C2-C (2) C4-C3-C (2) C5-C4-C (2)
44 C5-C4-C (2) C3-C4-C (2) C4-C5-C (2) C1-C6-C (2) C9-C7-C (3) C9-C7-C (3) C8-C7-C (3) C9-C7-C (3) C8-C7-C (2) C4-C7-C1 93.6(2) 1-Se1-C (10) C11-1-C (2) C11-1-Se (16) C2-1-Se (16) 1-C (2) 1-C11-C (2) 1-C11-C (2) C17-C12-C (2) C17-C12-C (2) C13-C12-C (2) C14-C13-C (3) C13-C14-C (3) C16-C15-C (3) C15-C16-C (3) C12-C17-C (2) C12-C17-Se (19)
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