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Synthesis, X-ray molecular structure, biological evaluation and molecular docking studies of some N4-benzyl substituted 5-nitroisatin-3-thiosemicarbazones.

Abstract：

:A series of fifteen N4-benzyl substituted 5-nitroisatin-3-thiosemicarbazones 5a-o was synthesized and evaluated for urease inhibitory, phytotoxic and cytotoxic influences. All the compounds proved to be highly potent inhibitors of the enzyme, showing inhibitory activity (IC50=0.87±0.25-8.09±0.23μM) much better than the reference inhibitor, thiourea (IC50=22.3±1.12μM) and may thus act as persuasive leads for further studies. In phytotoxicity assay, twelve out of fifteen thiosemicarbazones tested i.e. 5a-e, 5g, 5i and 5k-o appeared to be active, exhibiting weak or non-significant (5-35%) growth inhibition at the highest tested concentrations (1000 or 500μg/mL). In contrast, only one compound i.e. 5i was active in the brine shrimp (Artemia salina) lethality bioassay, demonstrating cytotoxic activity with LD50 value 2.55×10-5M. Molecular docking studies of compounds 5a-o were also performed to identify their probable binding modes in the active site of the enzyme.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Pervez H,Khan N,Zaib S,Yaqub M,Naseer MM,Tahir MN,Iqbal J

doi

10.1016/j.bmc.2016.12.012

subject

Has Abstract

pub_date

2017-02-01 00:00:00

pages

1022-1029

issue

3

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(16)31048-3

journal_volume

25

pub_type

杂志文章

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