In:
Acta Crystallographica Section C Structural Chemistry, International Union of Crystallography (IUCr), Vol. 74, No. 7 ( 2018-07-01), p. 839-846
Abstract:
The syntheses of nine new 5-iodosalicylic acid-based 1,3,4-oxadiazoline derivatives starting from methyl salicylate are described. These compounds are 2-[4-acetyl-5-methyl-5-(3-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate ( 6a ), 2-[4-acetyl-5-methyl-5-(4-nitrophenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate ( 6b ), 2-(4-acetyl-5-methyl-5-phenyl-4,5-dihydro-1,3,4-oxadiazol-2-yl)-4-iodophenyl acetate, C 19 H 17 IN 2 O 4 ( 6c ), 2-[4-acetyl-5-(4-fluorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C 19 H 16 FIN 2 O 4 ( 6d ), 2-[4-acetyl-5-(4-chlorophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate, C 19 H 16 ClIN 2 O 4 ( 6e ), 2-[4-acetyl-5-(3-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate ( 6f ), 2-[4-acetyl-5-(4-bromophenyl)-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate ( 6g ), 2-[4-acetyl-5-methyl-5-(4-methylphenyl)-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate ( 6h ) and 2-[5-(4-acetamidophenyl)-4-acetyl-5-methyl-4,5-dihydro-1,3,4-oxadiazol-2-yl]-4-iodophenyl acetate ( 6i ). The compounds were characterized by mass, 1 H NMR and 13 C NMR spectroscopies. Single-crystal X-ray diffraction studies were also carried out for 6c , 6d and 6e . Compounds 6c and 6d are isomorphous, with the 1,3,4-oxadiazoline ring having an envelope conformation, where the disubstituted C atom is the flap. The packing is determined by C—H...O, C—H...π and I...π interactions. For 6e , the 1,3,4-oxadiazoline ring is almost planar. In the packing, Cl...π interactions are observed, while the I atom is not involved in short interactions. Compounds 6d , 6e , 6f and 6h show good inhibiting abilities on the human cancer cell lines KB and Hep-G2, with IC 50 values of 0.9–4.5 µ M .
Type of Medium:
Online Resource
ISSN:
2053-2296
DOI:
10.1107/S2053229618008719
DOI:
10.1107/S2053229618008719/sk3693sup1.cif
DOI:
10.1107/S2053229618008719/sk36936csup2.hkl
DOI:
10.1107/S2053229618008719/sk36936dsup3.hkl
DOI:
10.1107/S2053229618008719/sk36936esup4.hkl
DOI:
10.1107/S2053229618008719/sk36936csup5.cml
DOI:
10.1107/S2053229618008719/sk36936dsup6.cml
DOI:
10.1107/S2053229618008719/sk36936esup7.cml
DOI:
10.1107/S2053229618008719/sk3693sup8.pdf
Language:
Unknown
Publisher:
International Union of Crystallography (IUCr)
Publication Date:
2018
detail.hit.zdb_id:
2025703-X
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