39093-93-1

Basic information

• Product Name: Thiomorpholine-1,1-dioxide
• Synonyms: THIOMORPHOLINE DIOXIDE;THIOMORPHOLINE 1,1-DIOXIDE;TIMTEC-BB SBB010267;1,1-DIOXOTHIOMORPHOLINE;1,1-DIOXIDE-4-THIOMORPHOLINE;Thiomorpholine-1,1-oxide;thiomorpholine 1,1-dioxide(SALTDATA: HCl);ThioMorpholine-1,1-dioxid
• CAS NO: 39093-93-1
• Molecular Formula: C₄H₉NO₂S
• Molecular Weight: 135.18
• EINECS: 1308068-626-2
• Product Categories: Heterocycles series
• Mol File: 39093-93-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 0°C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: light yellow solid
• Density: 1.239 g/cm³
• Vapor Pressure: 0.413mmHg at 25°C
• Refractive Index: 1.549
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 6.48±0.20(Predicted)
• CAS DataBase Reference: Thiomorpholine-1,1-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: Thiomorpholine-1,1-dioxide(39093-93-1)
• EPA Substance Registry System: Thiomorpholine-1,1-dioxide(39093-93-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 39093-93-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Thiomorpholine-1,1-dioxide is used as a synthetic building block for the development of antibacterial agents, specifically biaryloxazolidinone analogues. These analogues are designed to combat bacterial infections by targeting essential bacterial processes, thereby contributing to the treatment and prevention of various diseases caused by bacterial pathogens.
Additionally, Thiomorpholine-1,1-dioxide is used as a synthetic building block for the creation of isothiazolo-pyridine derivatives. These derivatives have potential applications as cyclin G-associated kinase inhibitors, which can play a crucial role in regulating cellular processes and may have implications in the treatment of certain diseases.
Furthermore, Thiomorpholine-1,1-dioxide is utilized in the synthesis of antiviral agents, particularly isothiazolo-pyridine derivatives. These agents can help in the development of treatments for viral infections by inhibiting essential viral replication processes, thus providing a valuable contribution to the field of antiviral drug development.

InChI:InChI=1/C4H5NO2S/c6-3-1-5-2-4(7)8-3/h5H,1-2H2

Upstream product

• 17688-68-5 4-Phenyltetrahydro-1,4-thiazine 1,1-dioxide 
• 107-61-9 1,4-oxathiane-4,4-dioxide 
• 5967-90-8 thiamorpholine hydrochloride 
• 220655-09-4 tert-butyl thiomorpholine-4-carboxylate 
• 123-90-0 Thiomorpholin 
• 215791-95-0 tert-butyl thiomorpholine-4-carboxylic acid-1,1-dioxide 

Downstream Products

• 67214-88-4 2-chloro-4-(1,1-dioxo-1λ⁶-thiomorpholine-4-sulfonyl)-benzenesulfonamide 
• 59801-63-7 1,1-dioxo-thiomorpholine-4-carboxylic acid toluene-4-sulfonylamide 
• 39093-81-7 (1,1-dioxo-1λ⁶-thiomorpholin-4-yl)-acetic acid hydrazide 
• 59801-64-8 1,1-dioxo-thiomorpholine-4-carbothioic acid 2,6-dichloro-anilide 
• 78235-27-5 {2,3-Dichloro-4-[3-(1,1-dioxo-1λ⁶-thiomorpholin-4-ylmethyl)-4-hydroxy-benzoyl]-phenoxy}-acetic acid ethyl ester 
• 78235-41-3 {4-[3,5-Bis-(1,1-dioxo-1λ⁶-thiomorpholin-4-ylmethyl)-4-hydroxy-benzoyl]-2,3-dichloro-phenoxy}-acetic acid ethyl ester 
• 79207-43-5 4-Cyanomethyl-thiomorpholin-S-dioxid 
• 155392-50-0 α-(S,S-dioxothiomorpholino)acetophenone 
• 79207-42-4 4-Allyl-thiomorpholin-S-dioxid 
• 922142-73-2 4-(2-fluoro-4-nitrophenyl)thiomorpholine 1,1-dioxide 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 215791-95-0 tert-butyl thiomorpholine-4-carboxylic acid-1,1-dioxide 
• 939810-68-1 (1,1-dioxo-1lambda*6*-thiomorpholin-4-yl)-(4-fluoro-phenyl)-acetonitrile 

Relevant articles and documents

Design, synthesis and biological evaluation of protease inhibitors containing morpholine cores with remarkable potency against both HIV-1 subtypes B and C

By following up on the design vector of optimizing amine-based HIV-1 protease inhibitors, we have designed and biologically evaluated a novel class of inhibitors with the free nitrogen or sulphone in morpholine cores as P2 ligands in combination with diverse substituted phenylsulfonamide P2′ ligands. As it turns out, a majority of these inhibitors exhibit prominent enzymatic inhibitory activity in low nanomolar ranges with relatively low cytotoxicity. Particularly, inhibitor 1e containing a morpholine carboxamide P2 ligand and a 4-hydroxyphenylsulfonamide P2′ ligand illustrates a robust enzyme inhibitory IC50 value of 90 pM. Furthermore, 1e demonstrates impressive in vivo antiviral activity with EC50 value of 89 nM and a degree of inhibitory potency against the DRV-resistant variant. More importantly, 1e exhibits remarkable activity with EC50 values of 13.59 nM and 8.23 nM against subtype C HIV-1 strains ZM246 and Indie, respectively. Furthermore, the in silico studies provide molecular insights into binding features of inhibitors with HIV-1 protease, and furnish a valuable forecast on further process.

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.

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.

Synthesis, Characterization and Catalytic Activity of a Tungsten(VI) Amino Triphenolate Complex

Abstract: Synthesis, characterization and catalytic activity of a novel tungsten(VI) amino triphenolate complex have been investigated. In particular, a tungsten(VI) amino triphenolate complex has been synthesized and tested in the oxidation of sulfides and cyclooctene, using hydrogen peroxide as terminal oxidant. The catalyst has proved to be air and water tolerant, also showing a good efficiency in terms of yields and selectivity. Moreover, an upgrade of our previous ligand synthesis is herein reported. The new developed procedure allows to obtain the triphenolamine in large scale without the use of chromatography for the intermediates purification. Graphical Abstract: [Figure not available: see fulltext.].

Quinolinone-carboxamide compounds

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Indazole-carboxamide compounds

The invention provides novel indazole-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

5-HT4 receptor agonist compounds

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Quinolinone compounds as 5-HT4 receptor agonists

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

INDAZOLE-CARBOXAMIDE COMPOUNDS AS 5-HT4 RECEPTOR AGONISTS

The invention provides novel indazole-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

AZAARENE DERIVATIVES

A compound represented by the general formula: wherein X1 represents a nitrogen atom or a group represented by the formula -CR10=; X2 represents a nitrogen atom or a group represented by the formula -CR11=; Y represents an oxygen atom or the like; R1 represents a C1-6 alkoxy group, an optionally substituted C6-10 aryloxy group, a group represented by the formula -NR12aR12b or the like; R2 represents a hydrogen atom, an optionally substituted C1-6 alkyl group, or the like; R3, R4, R5, R6, R7, R8, R10 and R11 each independently represent a hydrogen atom, a halogen atom, an optionally substituted C1-6 alkyl group, or the like; R9 represents a group represented by the formula -NR16aR16b or the like; and R12a, R12b, R16a and R16b each independently represent a hydrogen atom, an optionally substituted C1-6 alkyl group, or the like, a salt thereof, or a hydrate of the foregoing.