Design, synthesis and antiproliferative activity of novel aminosubstituted benzothiopyranoisoindoles

Antonios Christodoulou; Ioannis K Kostakis; Vassilios Kourafalos; Nicole Pouli; Panagiotis Marakos; Ioannis P Trougakos; Ourania E Tsitsilonis

doi:10.1016/j.bmcl.2011.03.021

Design, synthesis and antiproliferative activity of novel aminosubstituted benzothiopyranoisoindoles

Bioorg Med Chem Lett. 2011 May 15;21(10):3110-2. doi: 10.1016/j.bmcl.2011.03.021. Epub 2011 Mar 11.

Authors

Antonios Christodoulou¹, Ioannis K Kostakis, Vassilios Kourafalos, Nicole Pouli, Panagiotis Marakos, Ioannis P Trougakos, Ourania E Tsitsilonis

Affiliation

¹ Division of Pharmaceutical Chemistry, Department of Pharmacy, University of Athens, Panepistimiopolis-Zografou, Athens 15771, Greece.

PMID: 21444205
DOI: 10.1016/j.bmcl.2011.03.021

Abstract

The synthesis of a number of new benzothiopyrano[4,3,2-cd]isoindole aminoderivatives designed as structural analogues of the key metabolite of the anticancer agent Ledacrine (nitracrine) and their in vitro cytotoxic activity evaluation against HCT-116, MES-SA, and MES-SA/Dx cancer cell lines is reported. The majority of the derivatives possessed noticeable cytotoxicity in a low μM range indicating an interesting structure-activity relationship.

MeSH terms

Amines / chemical synthesis
Amines / chemistry*
Amines / pharmacology
Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Drug Design*
Humans
Indoles / chemical synthesis*
Indoles / chemistry
Indoles / pharmacology
Inhibitory Concentration 50
Molecular Structure
Nitracrine / chemistry
Pyrans / chemical synthesis
Pyrans / chemistry
Pyrans / pharmacology
Structure-Activity Relationship
Sulfhydryl Compounds / chemical synthesis
Sulfhydryl Compounds / chemistry
Sulfhydryl Compounds / pharmacology

Substances

Amines
Antineoplastic Agents
Indoles
Pyrans
Sulfhydryl Compounds
Nitracrine