358732-56-6

Basic information

• Product Name: N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one
• Synonyms: N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one
• CAS NO: 358732-56-6
• Molecular Weight: 307.414
• Mol File: 358732-56-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one(358732-56-6)
• EPA Substance Registry System: N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one(358732-56-6)

Safety Data

• Hazardous Substances Data: 358732-56-6(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 675-20-7 piperidin-2-one 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 1415152-91-8 1-[(2E)-3-phenylprop-2-enoyl]-5,6-dihydropyridin-2(1H)-one 
• 1415686-34-8 (E)-1-(3-mesitylacryloyl)-5,6-dihydropyridin-2(1H)-one 
• 1415686-30-4 (E)-1-(3-(4-bromophenyl)prop-2-enoyl)-5,6-dihydropyridin-2(1H)-one 
• 1415152-85-0 (E)-1-(3-(4-methoxyphenyl)prop-2-enoyl)-5,6-dihydropyridin-2(1H)-one 
• 6052-73-9 5,6-dihydro-2(1H)-pyridinone 
• 20069-09-4 piperlongumine 
• 358732-55-5 4-oxo-4,5,6,7-tetrahydro-2H-pyrrolo[3,4-c]pyridine-1-carbaldehyde 
• 128372-89-4 6-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

Design, synthesis, and biological evaluation of a novel indoleamine 2,3-dioxigenase 1 (IDO1) and thioredoxin reductase (TrxR) dual inhibitor

Targeting the Trp-Kyn pathway is an attractive approach for cancer immunotherapy. Thioredoxin reductase (TrxR) enzymes are reactive oxygen species (ROS) modulators that are involved in the tumor cell growth and survival processes. The 4-phenylimidazole scaffold is well-established as useful for indoleamine 2,3-dioxygenase 1 (IDO1) inhibition, while piperlongumine (PL) and its derivatives have been reported to be inhibitors of TrxR. To take advantage of both immunotherapy and TrxR inhibition, we designed a first-generation dual IDO1 and TrxR inhibitor (ZC0101) using the structural combination of 4-phenylimidazole and PL scaffolds. ZC0101 exhibited better dual inhibition against IDO1 and TrxR in vitro and in cell enzyme assays than the uncombined forms of 4-phenylimidazole and PL. It also showed antiproliferative activity in various cancer cell lines, and a selective killing effect between normal and cancer cells. Furthermore, ZC0101 effectively induced apoptosis and ROS accumulation in cancer cells. Knockdown of TrxR1 and IDO1 expression induced cellular enzyme inhibition and ROS accumulation effects during ZC0101 treatment, but only reduced TrxR1 expression was able to improve ZC0101′s antiproliferation effect. This proof-of-concept study provides a novel strategy for cancer treatment. ZC0101 represents a promising lead compound for the development of novel antitumor agents that can also be used as a valuable probe to clarify the relationships and mechanisms of cancer immunotherapy and ROS modulators.

Novel pyrrolyllactone and pyrrolyllactam indolinones as potent cyclin-dependent kinase 2 inhibitors

Cyclin-dependent kinases (CDKs) are essential in the control of cell cycle progression. Inhibition of CDKs represents a new approach for pharmacological intervention in the treatment of a variety of proliferative diseases, especially cancer. Based on the crystal structure of CDK2 in complex with an imidazole indolinone compound 1 (SU9516), lead optimization through modeling, synthesis, and SAR studies has led to the discovery of a novel series of pyrrolyllactone and pyrrolyllactam indolinones as potent CDK2 inhibitors.