Synthesis, Molecular Structure, Anticancer Activity, and QSAR Study of N -(aryl/heteroaryl)-4-(1H -pyrrol-1-yl)Benzenesulfonamide Derivatives

International Journal of Molecular Sciences
Beata ŻołnowskaJarosław Chojnacki

Abstract

A series of N-(aryl/heteroaryl)-4-(1H-pyrrol-1-yl)benzenesulfonamides were synthesized from 4-amino-N-(aryl/heteroaryl)benzenesulfonamides and 2,5-dimethoxytetrahydrofuran. All the synthesized compounds were evaluated for their anticancer activity on HeLa, HCT-116, and MCF-7 human tumor cell lines. Compound 28, bearing 8-quinolinyl moiety, exhibited the most potent anticancer activity against the HCT-116, MCF-7, and HeLa cell lines, with IC50 values of 3, 5, and 7 µM, respectively. The apoptotic potential of the most active compound (28) was analyzed through various assays: phosphatidylserine translocation, cell cycle distribution, and caspase activation. Compound 28 promoted cell cycle arrest in G2/M phase in cancer cells, induced caspase activity, and increased the population of apoptotic cells. Relationships between structure and biological activity were determined by the QSAR (quantitative structure activity relationships) method. Analysis of quantitative structure activity relationships allowed us to generate OPLS (Orthogonal Projections to Latent Structure) models with verified predictive ability that point out key molecular descriptors influencing benzenosulfonamide's activity.

References

Apr 8, 2003·Current Medicinal Chemistry·Andrea ScozzafavaClaudiu T Supuran
Dec 22, 2007·Chemical Reviews·Hui FanJin-Feng Hu
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Mar 8, 2011·Cell·Douglas Hanahan, Robert A Weinberg
Feb 14, 2012·Expert Opinion on Investigational Drugs·Jamal Joudeh, David Claxton
Feb 22, 2012·Clinical Therapeutics·Amy M Pick, Kelly K Nystrom
Jun 19, 2013·Current Treatment Options in Oncology·Alessandro Gronchi, Paolo G Casali
May 27, 2014·Seminars in Cancer Biology·Simone Fulda
Mar 25, 2015·Clinical Cancer Research : an Official Journal of the American Association for Cancer Research·Hyon-Zu LeeRichard Pazdur
May 20, 2015·Alzheimer's & Dementia : the Journal of the Alzheimer's Association·UNKNOWN Alzheimer’s Association
Oct 28, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Beata ŻołnowskaKrzysztof Szafrański
Dec 17, 2015·Cancer Epidemiology, Biomarkers & Prevention : a Publication of the American Association for Cancer Research, Cosponsored by the American Society of Preventive Oncology·Lindsey A TorreAhmedin Jemal
Jan 26, 2016·European Journal of Medicinal Chemistry·Somnath S Gholap
Dec 3, 2016·Therapeutic Advances in Urology·Thomas A Schmid, Martin E Gore

❮ Previous
Next ❯

Citations


❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray
flow cytometry
NMR

Software Mentioned

Dragon
SHELXS
SHELXL
Flowing
SIMCA
WinGx
Area
Gaussian

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.