Cytotoxic activities of Mannich bases of chalcones and related compounds

Journal of Medicinal Chemistry
J R DimmockJan Balzarini

Abstract

Various Mannich bases of chalcones and related compounds displayed significant cytotoxicity toward murine P388 and L1210 leukemia cells as well as a number of human tumor cell lines. The most promising lead molecule was 21 that had the highest activity toward L1210 and human tumor cells. In addition, 21 exerted preferential toxicity to human tumor lines compared to transformed human T-lymphocytes. Other compounds of interest were 38, with a huge differential in cytotoxicity between P388 and L1210 cells, and 42, with a high therapeutic index when cytotoxicity to P388 cells and Molt 4/C8 T-lymphocytes were compared. In general, the Mannich bases were more cytotoxic than the corresponding chalcones toward L1210 but not P388 cells. A ClusCor analysis of the data obtained from the in vitro human tumor screen revealed that the mode of action of certain groups of compounds was similar. For some groups of compounds, cytotoxicity was correlated with the sigma, pi, or molar refractivity constants in the aryl ring attached to the olefinic group. In addition, the IC50 values in all three screens correlated with the redox potentials of a number of Mannich bases. X-ray crystallography and molecular modeling of representative compounds reveal...Continue Reading

References

Apr 1, 1977·Journal of Medicinal Chemistry·J G Topliss
Mar 1, 1977·Journal of Medicinal Chemistry·C C Lin, R J Dubois
Aug 1, 1989·Carcinogenesis·R H SchiestlP J Hastings
Jan 1, 1984·Cleveland Clinic Quarterly·R J PorterB G White
Sep 30, 1993·International Journal of Cancer. Journal International Du Cancer·Y Satomi

❮ Previous
Next ❯

Citations

Dec 25, 2012·Archives of Pharmacal Research·Loghman FiroozpourAlireza Foroumadi
May 17, 2005·Bioorganic & Medicinal Chemistry Letters·B A BhatG N Qazi
Jun 15, 2007·Bioorganic & Medicinal Chemistry Letters·Amitabh JhaJames P Stables
Jul 12, 2000·European Journal of Medicinal Chemistry·G DannhardtB Fiebich
Nov 26, 2002·European Journal of Medicinal Chemistry·Jonathan R DimmockJames P Stables
Mar 28, 2003·European Journal of Medicinal Chemistry·Jonathan R DimmockJames P Stables
Mar 1, 2002·Toxicology in Vitro : an International Journal Published in Association with BIBRA·M GulO Hänninen
Sep 24, 1999·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·S N PandeyaE DeClercq
Apr 27, 2000·Bioorganic & Medicinal Chemistry Letters·Y XiaK H Lee
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Huan-Mei GuoFang-Fang Jian
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Pu-Su ZhaoFang-Fang Jian
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Huan-Mei Guo
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Huan-Mei Guo
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Huan-Mei GuoFang-Fang Jian
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Zhi-Fang Pan
Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Kamini KapoorHitendra S Joshi
Sep 4, 2009·Journal of Hematology & Oncology·Subhash PadhyeFazlul H Sarkar
Dec 2, 2008·Chemical & Pharmaceutical Bulletin·Halise Inci GulJonathan Richard Dimmock
Dec 2, 2011·Chemical & Pharmaceutical Bulletin·Mopuru Vijaya Bhaskar ReddyTian-Shung Wu
Dec 3, 2014·European Journal of Medicinal Chemistry·Gheorghe Roman
Mar 24, 2015·Journal of Enzyme Inhibition and Medicinal Chemistry·Thalia LiargkovaConstantinos Avgoustakis
Jul 19, 2012·Journal of Enzyme Inhibition and Medicinal Chemistry·Sinan BilginerJonathan Richard Dimmock
Mar 22, 2007·Journal of Enzyme Inhibition and Medicinal Chemistry·Hari N PatiJonathan R Dimmock
Jul 15, 2015·Drug and Chemical Toxicology·Patrícia Albano MariñoFávero Reisdorfer Paula
Feb 4, 2016·Materials Science & Engineering. C, Materials for Biological Applications·Mohammad Hasanzadeh, Nasrin Shadjou
Jan 5, 2016·Journal of Medicinal Chemistry·Subhas S KarkiJonathan R Dimmock
Apr 29, 2011·European Journal of Medicinal Chemistry·Megan LeeMoses Lee
Mar 31, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran
Nov 5, 2005·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Xiang WuMei-Lin Go
May 26, 2015·European Journal of Medicinal Chemistry·Debarshi Kar MahapatraVivek Asati
Jun 20, 2016·European Journal of Medicinal Chemistry·Hassan Mirzaei, Saeed Emami
Jun 3, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Atulya K PandaJonathan R Dimmock
Sep 7, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Cem YamaliClaudiu T Supuran
Oct 25, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran
Oct 25, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran
Jul 21, 2016·Journal of Enzyme Inhibition and Medicinal Chemistry·Ebru MeteClaudiu T Supuran
Mar 7, 2017·Journal of Enzyme Inhibition and Medicinal Chemistry·Halise Inci GulClaudiu T Supuran
Jul 8, 2008·Bioorganic & Medicinal Chemistry·M Vijaya Bhaskar ReddyTian-Shung Wu
Sep 11, 2007·Bioorganic & Medicinal Chemistry Letters·Marlie JohnsonMoses Lee
Jan 1, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rui LiuJinyi Wang
Jan 10, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Thalia LiargkovaDimitra Hadjipavlou-Litina

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.