PMID: 6405034May 1, 1983Paper

Inhibition of prostaglandin synthetase by di- and triphenylethylene derivatives: a structure-activity study

Journal of Medicinal Chemistry
J GilbertA C Crastes de Paulet

Abstract

The syntheses of new di- and triphenylethylene derivatives are described along with their X-ray analysis and NMR study, which have helped to establish their conformation. Screening of over 50 derivatives for inhibition of prostaglandin synthetase (PGS) activity in bovine seminal vesicle microsomes has revealed that many of the triphenylethylene derivatives are potent inhibitors of PGS. Several even show marked activity at the extremely low concentration (IC50) of about 4 X 10(-8) M, which is two orders of magnitude lower than the active concentration of the majority of known nonsteroidal antiinflammatory agents (IC50 approximately equal to 10(-6) M). Unlike the latter, these compounds are not carboxylic acids. Furthermore, in contrast to biphenyl, diphenylmethane, or unsymmetrical, alpha, alpha'-diphenylethylene PGS inhibitors, the presence of a beta-phenyl ring was an essential requirement for high potency. The best inhibitors possessed a cyanide group (acids, amides, and amines were poor inhibitors), methoxy in preference to hydroxy groups on the alpha-phenyl rings, and a halogen (F or Cl) in a para position on the beta-phenyl ring. These data provide additional insight into the nature of the PGS binding site.

Citations

Jan 1, 1990·Journal of Tongji Medical University = Tong Ji Yi Ke Da Xue Xue Bao·W P DingX R Wu
Nov 1, 1986·Journal of Steroid Biochemistry·J P Raynaud, T Ojasoo
Nov 15, 1986·Thrombosis Research·G H RaoT J Holmes
Aug 18, 2017·Angewandte Chemie·Alejandro G BarradoManuel Alcarazo

❮ 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.