Synthesis of Tin‐Containing Cyclodextrins as Potential Enzyme Models

Abstract

The synthesis and the characterization of two types of water‐soluble β‐cyclodextrin‐supported organotin derivatives is described. These new tin‐containing macromolecules were prepared through a free radical bishydrostannylation of the corresponding β‐cyclodextrin propargylic ethers using Me2SnClH prepared in situ with AIBN as initiator. The tin moieties were attached both on the primary and on the secondary rim of β‐cyclodextrin in excellent yield.

Structure–reactivity studies of chloro and isothiocyanato diorganotin (IV) complexes based on multidentate N‐donor ligands: Synthesis, spectral characterization and crystal structures

“…Furthermore, the Sn─N SCN bond lengths (Sn1─N1 = 2.295 (7) and Sn1─N2 = 2.274(6) Å) are less than the Sn─N ftpy bond lengths (Sn1─N5 = 2.483(6), Sn1─N3 = 2.495 (6) [46] Surprisingly, the N─C─S bond angles are 146.6(6)°and 167.5 (6)°which reveals that the NCS groups deviate significantly from linearly. The aromatic rings of ftpy ligand are not co-planar, the dihedral angles of 20.63°, 19.93°and 30.01°are found between the Cg(4)─Cg (5), Cg(4)─Cg (6) and Cg(5)─ Cg(6) planes, respectively. The furyl ring is twisted in relation to the following Cg(4), Cg (5) and Cg(6) planes (4) is N3-C16-C15-C10-C9-C3, Cg(5) is N4-C4-C8-C7-C6-C5 and Cg (6) is N5-C18-C19-C20-C21-C17} by 1.91°, 22.43°and 20.44°, respectively.…”

“…The aromatic rings of ftpy ligand are not co-planar, the dihedral angles of 20.63°, 19.93°and 30.01°are found between the Cg(4)─Cg (5), Cg(4)─Cg (6) and Cg(5)─ Cg(6) planes, respectively. The furyl ring is twisted in relation to the following Cg(4), Cg (5) and Cg(6) planes (4) is N3-C16-C15-C10-C9-C3, Cg(5) is N4-C4-C8-C7-C6-C5 and Cg (6) is N5-C18-C19-C20-C21-C17} by 1.91°, 22.43°and 20.44°, respectively. The axial sites are occupied by the methyl groups which deviate slightly from 180°(174.4(2)°).…”

“…The coordination chemistry of organotin (IV) complexes has received increasing attention in the past few decades due to their widespread biological and industrial applications, catalytic activities and supramolecular architectures. [1][2][3][4][5][6][7] Among them, the organotin (IV) complexes featuring a Sn-N bond have been extensively investigated due to their anticancer activity. [8][9][10][11] There are several reports of the existence of penta-and hexa-coordinated tin (IV) complexes in trigonal bipyramidal or octahedral geometries containing various nitrogen ligands.…”

Monosubstituted Cyclodextrins as Precursors for Further Use

“…Unfortunately, this signal is thus overlapped with other peracetylated CD signals. However, this shift causes a decrease in the integral intensity of the H-3 signals by one ( Figure 5 [82] 2 α-CD cinnamyl 3.38 [82] 3 α-CD formylmethyl 3.34 [82] 4 α-CD carboxymethyl 3.43 [82] 5 -CD allyl 3.27 [83] 6 -CD allyl 3.28 [55] 7 -CD propargyl 3.55 [84] 8 -CD carboxymethyl 3.38 [83] 9 -CD 3,3-bis(chlorodimethylstannyl)propanyl 3.59 [84] 10 -CD 4-(1,2-dicarbadodecaboran-1-yl)but-2-en-1-yl 3.34 [56] 11 [56] dicarbaundecaborate)]-8-yl}but-2-en-1-yl 12 -CD 4-{8,8′-μ-(sulfido)-[3,3′-commocobalt(III)-bis(1,2-di-3.24 [56] carbaundecaborate)]-8-yl}but-2-en-1-yl 13 -CD 5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodec-2-en-3.30 [55] 1-yl 14 γ-CD allyl 3.28 [85] 15 γ-CD propargyl 3.48 [85] 16 γ-CD formylmethyl 3.30 [85] 17 γ-CD carboxymethyl 3.43 [85] If none of the changes described above is observed, then the isomer is substituted in position 6. This could be confirmed by the measurement of APT or DEPT spectra.…”

“…A literature survey (of cases in which sufficient NMR spectroscopic data are given) confirmed that this method is usable with all known peracetylated mono-O-substituted α-, -and γ-CD derivatives ( Table 1, Table 2, and Table 3). H-2 A signals are shifted to the 3.2-3.6 ppm region, the integral inten- 1 α-CD allyl [82] 2 α-CD cinnamyl [82] 3 α-CD formylmethyl [82] 4 α-CD carboxymethyl [82] 5 α-CD 2-bromoprop-2-en-1-yl [82] 6 -CD allyl [83] 7 -CD allyl [56] 8 -CD cinnamyl [78] 9 -CD propargyl [84] 10 -CD carboxymethyl [78] 11 -CD 3,3-bis(chlorodimethylstannyl)propanyl [84] 12 -CD 4-(1,2-dicarbadodecaboran-1-yl)but-2-en-1-yl [56] 13 γ-CD allyl [85] 14 γ-CD propargyl [85] 15 γ-CD formylmethyl [85] 16 γ-CD carboxymethyl [85] [55] 2 α-CD cinnamyl 68.05 [82] 3 α-CD formylmethyl 70.20 [82] 4 α-CD 5,5,6,6,7,7,7-heptafluorohept-2-en-1-yl 68.33 [55] 5 α-CD 5,6,6,6-tetrafluoro-5-(trifluoromethyl)hex-2-en-1-yl 68.32 [55] 6 α-CD 5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodec-2-en-1-yl 68.34 [55] 7 -CD allyl 67.6 [78] 8 -CD propargyl 67.67 [84] 9 -CD carboxymethyl 70.5 [78] 10 -CD 3,3-bis(chlorodimethylstannyl)propanyl 69.07 [84] 11 -CD 4-(1,2-dicarbadodecaboran-1-yl)but-2-en-1-yl 68.12 [56] 12…”