5693-95-8

Usage

InChI:InChI=1/C5H7NOS/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)

Upstream product

• 1121-89-7 piperidine-2,6-dione 
• 325956-77-2 N-3,4-dimethyl-3-pentenylmonothioglutarimide 

Downstream Products

• 78312-57-9 2,3,5,6,7,8-Hexahydro-5-thioxo-indolizin-1-carbonsaeure-ethylester 
• 78312-54-6 4-(2-Oxo-5-thioxo-1-piperidinyl)-2-triphenylphosphorandiylbuttersaeure-ethylester 
• 77784-29-3 2,3,5,6,7,8-Hexahydro-5-oxo-indolizin-1-carbonsaeure-ethylester 
• 80362-98-7 2-(4-Chlorophenyl)-5,6,7,8-tetrahydro-3-hydroxythiazolo[3,2-a]-pyridinium bromide 

Relevant academic research and scientific papers

Lewis acid enhanced axial ligation of [Mo2]4+ complexes

We report here the syntheses, X-ray crystal structures, electrochemistry, and density functional theory (DFT) single-point calculations of three new complexes: tetrakis(monothiosuccinimidato)dimolybdenum(II) [Mo 2(SNO5)4, 1a], tetrakis(6-thioxo-2-piperidinonato) dimolybdenum(II) [Mo2(SNO6)4, 1b], and chlorotetrakis(monothiosuccinimidato)pyridinelithiumdimolybdenum(II) [pyLiMo2(SNO5)4Cl, 2-py]. X-ray crystallography shows unusually short axial Mo2-Cl bond lengths in 2-py, 2.6533(6) A, and dimeric 2-dim, 2.644(1) A, which we propose result from an increased Lewis acidity of the Mo2 unit in the presence of the proximal Li + ion. When 2-py is dissolved in MeCN, the lithium reversibly dissociates, forming an equilibrium mixture of (MeCNLiMo2(SNO5) 4Cl) (2-MeCN) and [Li(MeCN)4]+[Mo 2(SNO5)4Cl]- (3). Cyclic voltammetry was used to determine the equilibrium lithium binding constant (room temperature, K eq = 95 ± 1). From analysis of the temperature dependence of the equilibrium constant, thermodynamic parameters for the formation of 2-MeCN from 3 (ΔH = -6.96 ± 0.93 kJ mol-1 and ΔS = 13.9 ± 3.5 J mol-1 K-1) were extracted. DFT calculations indicate that Li+ affects the Mo-Cl bond length through polarization of metal-metal bonding/antibonding molecular orbitals when lithium and chloride are added to the dimolybdenum core.

A THIONATION PROCESS AND A THIONATING AGENT

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N

A thionation process and a thionating agent

A process for transforming a group >C=O (I) in a compound into a group >C=S (II) or into a tautomeric form of group (II) in a reaction giving a thionated reaction product, by use of crystalline P2S5·2 C5H5N as a thionating agent. A thionating agent which is crystalline P2S5·2 C5H5N.

Thionations using a P4S10-pyridine complex in solvents such as acetonitrile and dimethyl sulfone

Tetraphosphorus decasulfide (P4S10) in pyridine has been used as a thionating agent for a long period of time. The moisture-sensitive reagent has now been isolated in crystalline form, and the detailed structure has been determined by X-ray crystallography. The thionating power of this storable reagent has been studied and transferred to solvents such as acetonitrile in which it has proven to be synthetically useful and exceptionally selective. Its properties have been compared with the so-called Lawesson reagent (LR). Particularly interesting are the results from thionations at relatively high temperatures (165 °C) in dimethyl sulfone as solvent. Under these conditions, for instance, acridone and 3-acetylindole could quickly be transformed to the corresponding thionated derivatives. Glycylglycine similarly gave piperazinedithione. At these temperatures, LR is inefficient due to rapid decomposition. The thionated products are generally cleaner and more easy to obtain because in the crystalline reagent, impurities which invariably are present in the conventional reagents, P4S 10 in pyridine or LR, have been removed. 2011 American Chemical Society.

THALIDOMIDE ANALOGS

Thalidomide analogs that modulate tumor necrosis factor alpha (TNF-α) activity and angiogenesis are disclosed. In particularly disclosed embodiments, the thalidomide analogs are isosteric sulfur-containing analogs. Also disclosed are methods of treating a subject with the analogs.

Thiothalidomides: Novel Isosteric Analogues of Thalidomide with Enhanced TNF-α Inhibitory Activity

Thalidomide is being increasingly used in the clinical management of a wide spectrum of immunologically-mediated and infectious diseases, and cancers. However, the mechanisms underlying its pharmacological action are still under investigation. In this regard, oral thalidomide is clinically valuable in the treatment of erythema nodosum leprosum (ENL) and mutiple myeloma and effectively reduces tumor necrosis factor-α (TNF-α) levels and angiogenesis in vivo. This contrasts with its relatively weak effects on TNF-α and angiogenesis in in vitro studies and implies that active metabolites contribute to its in vivo pharmacologic action and that specific analogues would be endowed with potent activity. Our focus in the structural modification of thalidomide is toward the discovery of novel isosteric active analogues. In this regard, a series of thiothalidomides and analogues were synthesized and evaluated for their TNF-α inhibitory activity against lipopolysacharide (LPS)-stimulated peripheral blood mononuclear cells (PBMC), This was combined with a PBMC viability assay to differentiate reductions in TNF-α secretion from cellular toxicity. Two isosteric analogues of thalidomide, compounds 15 and 16, that mostly reflect the parent compound, together with the simple structure, dithioglutarimide 19, potently inhibited TNF-α secretion, compared to thalidomide, 1. The mechanism underpinning this most likely is posttranscriptional, as each of these compounds decreased TNF-α mRNA stability via its 3′-UTR. The potency of 19 warrants further study and suggests that replacement of the amide carbonyl with a thiocarbonyl may be beneficial for increased TNF-α inhibitory action. In addition, an intact phthalimido moiety appeared to be requisite for TNF-α inhibitory activity.

Photochemistry of N-3-butenyl- and N-4-pentenyl-glutarimides: Intramolecular thietane formation and the fission of thietane ring

Intramolecular photoreaction of N-3- or N-4-alkenylthioglutarimides (two or three methylenes) gave thietanes and their fission products.