Synthesis, structural characterization and cytotoxic activity of diorganotin(IV) complexes of N‐(5‐halosalicylidene)tryptophane

Synthesis, structure and cytotoxic activity of diethyltin N‐[(2‐oxyphenyl)methylene]phenylalaninates

“…Complexes 1 , 2 , 3 , 4 all display in vitro activity against A549 and CoLo205, in which the activity of 3 is the best, but their activity is weaker than clinically used cisplatin. This result is similar to that of our previously reported diethyltin analogues Et 2 Sn(5‐Cl‐2‐OC 6 H 3 CHNCH(CH 2 Ind)COO), Et 2 Sn(5‐Br‐2‐OC 6 H 3 CHNCH(CH 2 Ind)COO) and Et 2 Sn(3,5‐Br 2 ‐2‐OC 6 H 2 CHNCH(CH 2 Ind)COO) . Several groups have reported that the dibutyltin and diphenyltin complexes of the Schiff base ligand derived from substituted salicylaldehyde and α‐amino acid have potentially good inhibition activity for some tumor cells, namely MCF‐7, EVSA‐T, WiDr, IGROV, MI9 MEL, A498, H226, HeLa, CoLo205, HCT‐15 and NCI‐522, and the IC 50 values of some of them against the cell lines are less than 0.05 µg ml −1 .…”

“…This is quantified by the value of τ (=0.10), which compares with τ = 0.00 for an ideal square pyramid and τ = 1.00 for an ideal trigonal bipyramid . The Sn(1)O(1) (2.2073(19) Å) and Sn(1)O(3) (2.1761(18) Å) bond distances are consistent with those found in the analogues Et 2 Sn(5‐Cl‐2‐OC 6 H 3 CHNCH(CH 2 Ind)COO) (2.1754(15) and 2.1022(16) Å) and Et 2 Sn(3,5‐Br 2 ‐2‐OC 6 H 2 CHNCH(CH 2 Ind)COO) (2.191(5) and 2.142(5) Å) …”

“…With respect to the six‐membered ring defined by the Sn(1)–N(1)–C(14)–C(15)–C(16)–O(1) fragments, the maximum deviation from the mean planes at O(1) atom is 0.271(3) Å. The Sn(1)O(1) (2.089(3) Å) and Sn(1)O(2) (2.159(3) Å) bond distances are comparable with those found in the analogues Bu 2 Sn(3,5‐Br 2 ‐2‐OC 6 H 2 CHNCH(CH 2 Ph)COO) (2.110(4) and 2.174(4) Å) and Et 2 Sn(3,5‐Br 2 ‐2‐OC 6 H 2 CHNCH(CH 2 Ind)COO) (2.142(5) and 2.191(5) Å) . The axial bond angles O(1)–Sn(1)–O(2) (154.77(13)°) in 4 are similar to those of the above two analogues (154.9(2)° and 151.72(19)°).…”

“…Bioassay studies showed that the diorganotin complexes possess significant cytotoxic activity against some human tumor cell lines . To expand the chemistry and therapeutic potential of the diorganotin complexes of the ligand, we previously reported the synthesis, structure and biological activity of some diorganotin complexes with N ‐(substituted salicylidene)‐α‐amino acid . In those investigations, more attention was paid to the di‐ n ‐butyl‐ and diphenyltin complexes, and less to the diethyltin complexes.…”

Synthesis, characterization and cytotoxic activity of new diorganotin(IV) complexes of N‐(3,5‐dibromosalicylidene)tryptophane

“…The organotin moiety, the ligand and the number of tin atoms appear to play an important role in determining their cytotoxicity activity 3–5. In order to continue to expand the chemistry and therapeutic potential of the diorganotin(IV) complexes of the ligands, recently we synthesized and characterized some diorganotin(IV) complexes with N ‐(halosalicylidene)‐α‐amino acid 15–18. As a continuation of our work, here we selected N ‐(3,5‐dibromosalicylidene)tryptophane as a ligand, synthesized four new diorganotin complexes, R 2 Sn[3,5‐Br 2 ‐2‐OC 6 H 2 CHNCH(CH 2 Ind)COO] [Ind = 3‐indolyl; R = Et ( 1 ); n ‐Bu ( 2 ); Cy ( 3 ); Ph ( 4 ); Scheme ], and determined their cytotoxic activity.…”