28948-60-9

Basic information

• Product Name: 2-Bromothieno[3,2-c]pyridin-4(5H)-one
• Synonyms: 2-Bromothieno[3,2-c]pyridin-4(5H)-one;2-broMo-4H,5H-thieno[3,2-c]pyridin-4-one;2-BroMothieno[3,2-c]pyridin-4-ol;2-Bromo-5H-thieno[3,2-c]pyridin-4-one
• CAS NO: 28948-60-9
• Molecular Formula: C₇H₄BrNOS
• Molecular Weight: 230.085
• EINECS: 604-604-1
• Mol File: 28948-60-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 461.674 °C at 760 mmHg
• Flash Point: 233.012 °C
• Appearance: /
• Density: 1.801 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.12±0.20(Predicted)
• CAS DataBase Reference: 2-Bromothieno[3,2-c]pyridin-4(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromothieno[3,2-c]pyridin-4(5H)-one(28948-60-9)
• EPA Substance Registry System: 2-Bromothieno[3,2-c]pyridin-4(5H)-one(28948-60-9)

Safety Data

• Hazardous Substances Data: 28948-60-9(Hazardous Substances Data)

Usage

General Description

2-bromothieno[3,2-c]pyridin-4(5H)-one is a chemical compound with the formula C7H4BrNOS. It is a heterocyclic compound containing a thieno-pyridinone structure. 2-bromothieno[3,2-c]pyridin-4(5H)-one has potential applications in pharmaceuticals and materials science due to its unique structure and properties. It may also be used as a building block in the synthesis of other organic compounds. Additionally, its bromine atom provides reactivity and potential for further functionalization, making it a versatile and valuable compound in organic chemistry research and industry.

Upstream product

• 541-41-3 chloroformic acid ethyl ester 
• 50868-68-3 (E)-3-(5-bromo-2-thienyl)-2-propenoic acid 
• 29079-97-8 3-(5-Bromo-2-thienyl)acrylic acid 
• 4701-17-1 5-bromo-2-thiophencarboxaldehyde 
• 636999-00-3 (2E)-3-(5-bromothien-2-yl)acryloyl azide 

Downstream Products

• 28948-61-0 2-bromo-4-chlorothieno[3,2-c]pyridine 
• 690636-03-4 2-phenylthieno[3,2-c]pyridin-4(5H)-one 
• 1333107-87-1 C₁₂H₈N₂OS 
• 1333107-77-9 C₁₉H₁₀FN₃OS 
• 1333107-78-0 C₂₀H₁₄N₂O₃S 
• 1333107-79-1 C₂₀H₁₃N₃OS 
• 1333107-80-4 C₁₇H₁₀ClN₃OS 
• 1333107-81-5 C₁₇H₉N₃OS₂ 
• 1333107-82-6 C₂₀H₁₆N₂O₂S 
• 1333107-83-7 C₁₉H₁₅N₃O₂S 
• 1333107-84-8 C₁₉H₁₃FN₂O₂S 
• 1333107-85-9 C₂₁H₁₇N₃O₂S 
• 1333107-86-0 C₂₁H₁₃N₃OS 
• 1333107-70-2 7-bromo-2-pyridin-4-yl-5h-thieno[3,2-c]pyridin-4-one 

Relevant articles and documents

Synthesis and evaluation of bifunctional PTP4A3 phosphatase inhibitors activating the ER stress pathway

We developed JMS-053, a potent inhibitor of the dual specificity phosphatase PTP4A3 that is potentially suitable for cancer therapy. Due to the emerging role of the unfolded protein response (UPR) in cancer pathology, we sought to identify derivatives that combine PTP4A3 inhibition with induction of endoplasmatic reticulum (ER) stress, with the goal to generate more potent anticancer agents. We have now generated bifunctional analogs that link the JMS-053 pharmacophore to an adamantyl moiety and act in concert with the phosphatase inhibitor to induce ER stress and cell death. The most potent compound in this series, 7a, demonstrated a ca. 5-fold increase in cytotoxicity in a breast cancer cell line and strong activation of UPR and ER stress response genes in spite of a ca. 13-fold decrease in PTP4A3 inhibition. These results demonstrate that the combination of phosphatase inhibition with UPR/ER-stress upregulation potentiates efficacy.

In-flow photooxygenation of aminothienopyridinones generates iminopyridinedione PTP4A3 phosphatase inhibitors

A continuous flow photooxygenation of 7-aminothieno[3,2-c]pyridin-4(5H)-ones to produce 7-iminothieno[3,2-c]pyridine-4,6(5H,7H)-diones has been developed, utilizing ambient air as the sole reactant. N-H Imines are formed as the major products, and excellent functional group tolerance and conversion on gram-scale without the need for chromatographic purification allow for facile late-stage diversification of the aminothienopyridinone scaffold. Several analogs exhibit potent in vitro inhibition of the cancer-associated protein tyrosine phosphatase PTP4A3, and the SAR supports an exploratory docking model.

Identification of 2-(4-pyridyl)thienopyridinones as GSK-3β inhibitors

The discovery of a novel series of 2-(4-pyridyl)thienopyridinone GSK-3β inhibitors is reported. X-ray crystallography reveals its binding mode and enables rationalization of the SAR. The initial optimization of the template for improved cellular activity and predicted CNS penetration is also presented.