215791-95-0

Basic information

• Product Name: tert-Butyl thiomorpholine-4-carboxylate
• Synonyms: tert-butyl 1,1-dioxothiomorpholine-4-carboxylate
• CAS NO: 215791-95-0
• Molecular Formula: C₉H₁₇NO₄S
• Molecular Weight: 203.30178
• Mol File: 215791-95-0.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 390.7±35.0 °C(Predicted)
• Appearance: /
• Density: 1.230±0.06 g/cm3(Predicted)
• PKA: -1.87±0.20(Predicted)
• CAS DataBase Reference: tert-Butyl thiomorpholine-4-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-Butyl thiomorpholine-4-carboxylate(215791-95-0)
• EPA Substance Registry System: tert-Butyl thiomorpholine-4-carboxylate(215791-95-0)

Safety Data

• Hazardous Substances Data: 215791-95-0(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 59801-62-6 1,1-dioxothiomorpholine hydrochloride 
• 220655-09-4 tert-butyl thiomorpholine-4-carboxylate 
• 39093-93-1 thiomorpholine 1,1-dioxide 

Downstream Products

• 73286-70-1 N-(tert-butoxycarbonyl)-3-pyrroline 
• 39093-93-1 thiomorpholine 1,1-dioxide 
• 59801-62-6 1,1-dioxothiomorpholine hydrochloride 

Relevant articles and documents

Optimization of biaryloxazolidinone as promising antibacterial agents against antibiotic-susceptible and antibiotic-resistant gram-positive bacteria

We previously discovered a series of novel biaryloxazolidinone analogues bearing a hydrazone moiety with potent antibacterial activity. However, the most potent compound OB-104 exhibited undesirable chemical and metabolic instability. Herein, novel biaryloxazolidinone analogues were designed and synthesized to improve the chemical and metabolic stability. Compounds 6a-1, 6a-3, 14a-1, 14a-3 and 14a-7 showed significant antibacterial activity against the tested Gram-positive bacteria as compared to radezolid and linezolid. Further studies indicated that most of them exhibited improved water solubility and chemical stability. Compound 14a-7 had MIC values of 0.125–0.25 μg/mL against all tested Gram-positive bacteria, and showed excellent antibacterial activity against clinical isolates of antibiotic-susceptible and antibiotic-resistant bacteria. Moreover, it was stable in human liver microsome. From a safety viewpoint, it showed non-cytotoxic activity against hepatic cell and exhibited lower inhibitory activity against human MAO-A compared to linezolid. The potent antibacterial activity and all these improved drug-likeness properties and safety profile suggested that compound 14a-7 might be a promising drug candidate for further investigation.

HETEROCYCLIC COMPOUNDS

Provided herein are compounds of formula (I) which comprise a thiomorpholine 1,1-dioxide or 1-imino-thiomorpholine 1-oxide moiety, or pharmaceutically acceptable salts of any of the foregoing, pharmaceutical compositions that include a compound described herein (including salts of the compound) and methods of synthesizing the same. Also provided are methods of treating Hepatitis B viral (HBV) infections using a compound of formula (I), or pharmaceutically acceptable salts thereof.

Synthesis and antibacterial activity evaluation of novel biaryloxazolidinone analogues containing a hydrazone moiety as promising antibacterial agents

A series of linezolid analogues containing a hydrazone moiety were designed, synthesized and evaluated for their antibacterial activity. Most compounds exhibited more potent antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens as compared with linezolid and radezolid. Compounds 9a, 9c, 9f, 9g, 10m and 10t were more potent against tested clinical isolates of MRSA, MSSA, VRE and LREF as compared to linezolid. Compound 9a exhibited comparable activity with linezolid against human MAO-A for safety evaluation and showed moderate metabolism in human liver microsome. The most promising compound 9a showed remarkable antibacterial activity against S.aureus, MRSA, MSSA, LREF and VRE pathogens with MIC value of 0.0675 mg/mL, respectively, which was 15- to 30-fold more potent than linezolid.