4079-26-9

Basic information

• Product Name: PD 146176
• Synonyms: 6,11-dihydrothiochromeno[4,3-b]indole
• CAS NO: 4079-26-9
• Molecular Formula: C₁₅H₁₁NS
• Molecular Weight: 237.325
• Mol File: 4079-26-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 160 °C
• Boiling Point: 485.4°Cat760mmHg
• Flash Point: 247.4°C
• Appearance: cream-colored/solid
• Density: 1.333g/cm³
• Vapor Pressure: 4.17E-09mmHg at 25°C
• Refractive Index: 1.773
• Storage Temp.: Store at +4°C
• Solubility: DMSO: 16 mg/mL, soluble
• PKA: 16.17±0.20(Predicted)
• CAS DataBase Reference: PD 146176(CAS DataBase Reference)
• NIST Chemistry Reference: PD 146176(4079-26-9)
• EPA Substance Registry System: PD 146176(4079-26-9)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 4079-26-9(Hazardous Substances Data)

Usage

Description

PD 146176 is a potent and selective inhibitor of reticulocyte 15-lipoxygenase-1. It limits hypercholesterolemia-induced atherosclerosis in New Zealand White rabbits and reduces oxidant stress-induced apoptosis in endothelial cells. PD 146176 inhibits amyloid β protein aggregate formation without changing total levels of amyloid β precursor protein (APP) in cells stably expressing APP. In addition, it lacks significant non-specific antioxidant properties.

Uses

PD 146176 has been used to study its influence on ex vivo leukotriene B4 (LTB4) and lipoxin A4 (LXA4) secretion in adipose tissue.

Biological Activity

Specific, non-competitve 15-lipoxygenase (15-LOX) inhibitor (K i = 197nM) that has no demonstrable effect on 5-LOX, 12-LOX, COX-1 or COX-2 (IC 50 = 0.54 μ M for 15-LOX in rabbit reticulocytes). Lacks non-specific antioxidant properties and prevents atherogenesis via regulation of monocyte-macrophage enrichment in vivo .

Biochem/physiol Actions

PD 146176 blocks neuroprotectin D1 (NPD1) and eicosanoid synthesis by inhibiting the 5-lipoxygenase-1 (15-LOX-1) enzyme.

InChI:InChI=1/C15H11NS/c1-3-7-13-10(5-1)12-9-17-14-8-4-2-6-11(14)15(12)16-13/h1-8,16H,9H2

Upstream product

• 121113-04-0 1-thiochroman-4-one phenylhydrazone 
• 5219-65-8 acide phenylthio-3 propanoique 
• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 100-63-0 phenylhydrazine 

Relevant articles and documents

Design and synthesis of new mass tags for matrix-free laser desorption ionization mass spectrometry (LDI-MS) based on 6,11-dihydrothiochromeno[4,3-b]indole

We have rationally designed and synthesized new mass tags that are heterolytically cleavable upon UV-irradiation; these tags are based on a 6,11-dihydrothiochromeno[4,3-b]indole skeleton. Unless exposed to UV light, the dithioacetal group maintained its stability under normal conditions. After chemical conjugation of the mass tags with biomolecules of interest, such as proteins, the resulting conjugates efficiently and selectively generated the corresponding mass-tag fragment ions without the aid of a matrix under laser desorption/ionization (LDI) conditions. We envision that these new dithioacetal-based tags would provide a new platform of the so-called matrix-free laser desorption ionization mass spectrometry (LDI-MS), that would allow multiple detection of biomarkers with high sensitivity and selectivity. The limit of detection (LOD) of these tags was measured to be 5?fmol in the case of non-conjugated mass tag themselves and 2.8?fmol in the case of mass-tag-conjugated myoglobin.

NOVEL TETRACYCLIC HETEROATOM CONTAINING DERIVATIVES USEFUL AS SEX STEROID HORMONE RECEPTOR MODULATORS

The present invention is directed to novel tetracyclic heteroatom containing derivatives, pharmaceutical compositions containing them, their use in the treatment of disorders mediated by one or more sex steroid hormone receptors and processes for their preparation.

Discovery of indole-containing tetracycles as a new scaffold for androgen receptor ligands

A novel series of tetracyclic indoles have been designed, synthesized and evaluated as androgen receptor (AR) ligands. Studies of structure-activity relationships (SARs) were investigated, which led to some compounds in this series as strong binders to an