Organotin (IV) derivative of Piperic acid and Phenylthioacetic acid: Synthesis, Crystal structure, Spectroscopic characterizations and Biological activities

Three new organotin (IV) derivatives have been prepared from piperic and phenylthio acetic acids, the former is obtained by hydrolysis of piperine, which is extracted from black pepper. The three complexes {[n-Bu 2 SnO 2 C-(CH=CH) 2 -C 7 H 5 O 2 ] 2 O} 2 1 , {[n-Bu 2 SnO 2 C-CH 2 -S-C 6 H 4 ] 2 O} 2 2 , and [Ph 3 SnO 2 C-(CH=CH) 2 -C 7 H 5 O 2 ] n 3 , have been characterized by IR, 1 H and 13 C NMR spectroscopic techniques. Single crystal diffraction studies were made to determine the structures of the three compounds 1 , 2 and 3 . Compounds 1 and 2 crystallize in the triclinic system ( P\- 1), and the respective cell parameters (A, °) [ a = 10.4427 (19), b = 12.881 (2), c = 15.991 (3), a= 76.840 (7), b= 85.130 (6), g= 87.278 (6), and [ a = 12.237 (3),  b = 12.580 (3),  c = 13.507 (3), a= 91.146 (8),  b= 104.916 (8), g= 111.307 (8)]. Compound 3 crystallizes in the Monoclinic system ( P 2 1 / c) with the cell parameters (A, °) [a= 12.982 (3), b= 11.282 (2), c= 18.528 (4) and b (°) = 108.572 (7)]. The title compounds were evaluated for their biological activities against a range of cancer cell lines (BT-474, MDA-MB-231, AU565), Chronic myeloid leukemia cell line (K562), Lung cancer cell line (H460) and normal cell line 3T3 mouse fibroblast. Especially complexes 1 and 3 (derivatives of the piperic acid), i.e. Pipericcarboxylate triphenyltin [Ph 3 SnO 2 C-(CH=CH) 2 -C 7 H 5 O 2 ] n and {[n-Bu 2 SnO 2 C-(CH=CH) 2 -C 7 H 5 O 2 ] 2 O} 2 were most active against all cancer cell lines. These compounds were also active against 3T3 normal cell line, but the IC 50 values were high as compared to cancer cell lines.