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Carbamate formation is one of the major chemical reactions that can occur in solution in the capture of CO2 by amine-based solvents, and carbamate formation makes a significant enthalpy contribution to the absorption-desorption of CO2 that occurs in the absorber/stripper columns of the PCC process. Consequently, the formation of carbamates of selected series of primary and secondary amines over the temperature range (288 to 318) K has been investigated by equilibrium H-1 NMR studies, and the stability constants (K-9) for the equilibrium: RNH2 + HCO3- reversible arrow(K9) RNHCOO- + H2O are reported. van’t Hoff analyses have resulted in standard molar enthalpies, Delta H-m(o), and entropies, Delta S-m(o), of carbamate formation. A Delta H-m(o) – Delta S-m(o) plot generates a linear correlation for carbamate formation (providing a mean standard molar free energy, Delta G(m)(o), for carbamate formation of about -7 kJ . mol (1)), and this relationship helps provide a guide to the selection of an amine(s) solvent for CO2 capture, in terms of enthalpy considerations. A linear Delta H-m(o) – Delta S-m(o) plot also occurs for carbamate protonation. The formation of the carbamates has been correlated with systematic changes in composition and structure, and steric effects have been identified by comparing molecular geometries obtained using density functional B3LYP/6-311++G(d,p) calculations. Trends in steric effects have been identified in the series of compounds monoethanolamine (MEA), 1-amino-2-propanol, 2-amino-1-propanol (AP) and 2-amino-2-methyl-1-propanol (AMP). In the case of 2-piperidinemethanol, 2-piperidineethanol and 3-piperidinemethanol, strong intramolecular hydrogen bonding is shown to be the likely cause for lack of carbamate formation, and in the ring systems of pyrrolidine, morpholine, piperidine and thiomorpholine trends in carbamate formation (as given by K-9) have been correlated with the internal ring angle at the amine nitrogen, as well as the planarity of the environment around the nitrogen atom. (C) 2012 Elsevier Ltd. All rights reserved.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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Cyclocondensation of alpha-halogenacetophenones with an original 4-morpholine thiosemicarbazide was used to synthesize a group of new Captions: of the 1,3,4-thiadiazine group, containing a thiomorpholine fragment at position 2 of the thiadiazine ring. Two members of this group of compounds were found to produce effective inhibition of nonenzymatic protein glycosylation in an in vitro model system. These test results allow compounds containing phenyl and fluorophenyl fragments IIIa and IIIb to be recommended for further study in in vivo experiments.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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The kinetics of the nitrosation of 2-hydroxyethylpiperidine have been studied in acidic (0.05-0.30 mol dm(-3) HClO4) aqueous media. The reaction rate is first order with respect to nitrite and amine and independent of acidity and shows an experimental isotope effect of 1.73. The most plausible mechanism involves the fast formation of an alkyl nitrite in the protonated amine (equilibrium constant estimated as 0.014 dm(3) mol(-1)). The loss of a proton from this intermediate is the rate-limiting step, and it is followed by a fast internal nitroso group transfer from the oxygen to the nitrogen atom to give the corresponding N-nitroso compound. A comparison of this nitrosation pathway of secondary amines in acid media with the nitrosation of thiomorpholine and piperidine, and with that of amines by alkyl nitrites in basic media is also discussed.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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The heme-enzyme soluble guanylyl cyclase (sGC) is an ubiquitous NO receptor, which mediates NO downstream signaling by the generation of cGMP. We studied the mechanism of action of the anthranilic acid derivatives 5-chloro-2-(5-chloro-thiophene-2-sulfonylamino-N-(4-(morpholine-4-sulfonyl)-phenyl)-benzamide sodium salt (HMR1766) (proposed international nonproprietary name, ataciguat sodium) and 2-(4-chloro-phenylsulfonylamino)4,5- dimethoxy-N-(4-(thiomorpholine-4-sulfonyl)-phenyl)-benzamide (S3448) as a new class of sGC agonists. Both compounds activated different sGC preparations (purified from bovine lung, or crude from human corpus cavernosum) in a concentration-dependent and quickly reversible fashion (EC50 = 0.5-10 mu M), with mixed-type activation kinetics. Activation of sGC by these compounds was additive to activation by NO donors, but instead of being inhibited, it was potentiated by the heme-iron oxidants 1H-[1,2,4]-oxdiazolo[3,4-a]quinoxalin-1-one (ODQ) and 4H-8-bromo-1,2,4-oxadiazolo(3,4-d) benz(b)(1,4) oxazin-1-one (NS2028), suggesting that the new compounds target the ferric heme sGC isoform. Protoporphyrin IX acted as a competitive activator, and zinc-protoporphyrin IX inhibited activation of heme-oxidized sGC by HMR1766 and S3448, whereas heme depletion of sGC by Tween 20 treatment reduced activation. Both compounds increased cGMP levels in cultured rat aortic smooth muscle cells; induced vasorelaxation of isolated endothelium-denuded rat aorta, porcine coronary arteries, and human corpus cavernosum (EC50 1 to 10 mu M); and elicited phosphorylation of the cGMP kinase substrate vasodilator-stimulated phosphoprotein at Ser239. HMR1766 intravenous bolus injection decreased arterial blood pressure in anesthetized pigs. All of these pharmacological responses to the new compounds were enhanced by ODQ and NS2028. Our findings suggest that HMR1766 and S3448 preferentially activate the NO-insensitive heme-oxidized form of sGC, which exists to a variable extent in vascular tissues, and is a pharmacological target for these new vasodilator drugs.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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Bacterial resistance to antibiotics is presently one of the most pressing healthcare challenges and necessitates the discovery of new antibacterials with unique chemical scaffolds. However, the determination of the optimal balance between structural requirements for pharmacological action and pharmacokinetic properties of novel antibacterial compounds is a significant challenge in drug development. The incorporation of lipophilic moieties within a compound’s core structure can enhance biological activity but have a deleterious effect on drug-like properties. In this Article, the lipophilicity of alkynylphenylthiazoles, previously identified as novel antibacterial agents, was reduced by introducing cyclic amines to the lipophilic side chain. In this regard, substitution with methylpiperidine (compounds 14-16) and thiomorpholine (compound 19) substituents significantly enhanced the aqueous solubility profile of the new compounds more than 150-fold compared to the first-generation lead compound 1b. Consequently, the pharmacokinetic profile of compound 15 was significantly enhanced with a notable improvement in both half-life and the time the compound’s plasma concentration remained above its minimum inhibitory concentration (MIC) against methicillin-resistant Staphylococcus aureus (MRSA). In addition, compounds 14-16 and 19 were found to exert a bactericidal mode of action against MRSA and were not susceptible to resistance formation after 14 serial passages. Moreover, these compounds (at 2X MIC) were superior to the antibiotic vancomycin in the disruption of the mature MRSA biofilm. The modifications to the alkynylphenylthiazoles reported herein successfully improved the pharmacokinetic profile of this new series while maintaining the compounds’ biological activity against MRSA.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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Cyclocondensation of alpha-halogenacetophenones with an original 4-morpholine thiosemicarbazide was used to synthesize a group of new Captions: of the 1,3,4-thiadiazine group, containing a thiomorpholine fragment at position 2 of the thiadiazine ring. Two members of this group of compounds were found to produce effective inhibition of nonenzymatic protein glycosylation in an in vitro model system. These test results allow compounds containing phenyl and fluorophenyl fragments IIIa and IIIb to be recommended for further study in in vivo experiments.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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The kinetics of the nitrosation of 2-hydroxyethylpiperidine have been studied in acidic (0.05-0.30 mol dm(-3) HClO4) aqueous media. The reaction rate is first order with respect to nitrite and amine and independent of acidity and shows an experimental isotope effect of 1.73. The most plausible mechanism involves the fast formation of an alkyl nitrite in the protonated amine (equilibrium constant estimated as 0.014 dm(3) mol(-1)). The loss of a proton from this intermediate is the rate-limiting step, and it is followed by a fast internal nitroso group transfer from the oxygen to the nitrogen atom to give the corresponding N-nitroso compound. A comparison of this nitrosation pathway of secondary amines in acid media with the nitrosation of thiomorpholine and piperidine, and with that of amines by alkyl nitrites in basic media is also discussed.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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The heme-enzyme soluble guanylyl cyclase (sGC) is an ubiquitous NO receptor, which mediates NO downstream signaling by the generation of cGMP. We studied the mechanism of action of the anthranilic acid derivatives 5-chloro-2-(5-chloro-thiophene-2-sulfonylamino-N-(4-(morpholine-4-sulfonyl)-phenyl)-benzamide sodium salt (HMR1766) (proposed international nonproprietary name, ataciguat sodium) and 2-(4-chloro-phenylsulfonylamino)4,5- dimethoxy-N-(4-(thiomorpholine-4-sulfonyl)-phenyl)-benzamide (S3448) as a new class of sGC agonists. Both compounds activated different sGC preparations (purified from bovine lung, or crude from human corpus cavernosum) in a concentration-dependent and quickly reversible fashion (EC50 = 0.5-10 mu M), with mixed-type activation kinetics. Activation of sGC by these compounds was additive to activation by NO donors, but instead of being inhibited, it was potentiated by the heme-iron oxidants 1H-[1,2,4]-oxdiazolo[3,4-a]quinoxalin-1-one (ODQ) and 4H-8-bromo-1,2,4-oxadiazolo(3,4-d) benz(b)(1,4) oxazin-1-one (NS2028), suggesting that the new compounds target the ferric heme sGC isoform. Protoporphyrin IX acted as a competitive activator, and zinc-protoporphyrin IX inhibited activation of heme-oxidized sGC by HMR1766 and S3448, whereas heme depletion of sGC by Tween 20 treatment reduced activation. Both compounds increased cGMP levels in cultured rat aortic smooth muscle cells; induced vasorelaxation of isolated endothelium-denuded rat aorta, porcine coronary arteries, and human corpus cavernosum (EC50 1 to 10 mu M); and elicited phosphorylation of the cGMP kinase substrate vasodilator-stimulated phosphoprotein at Ser239. HMR1766 intravenous bolus injection decreased arterial blood pressure in anesthetized pigs. All of these pharmacological responses to the new compounds were enhanced by ODQ and NS2028. Our findings suggest that HMR1766 and S3448 preferentially activate the NO-insensitive heme-oxidized form of sGC, which exists to a variable extent in vascular tissues, and is a pharmacological target for these new vasodilator drugs.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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Bacterial resistance to antibiotics is presently one of the most pressing healthcare challenges and necessitates the discovery of new antibacterials with unique chemical scaffolds. However, the determination of the optimal balance between structural requirements for pharmacological action and pharmacokinetic properties of novel antibacterial compounds is a significant challenge in drug development. The incorporation of lipophilic moieties within a compound’s core structure can enhance biological activity but have a deleterious effect on drug-like properties. In this Article, the lipophilicity of alkynylphenylthiazoles, previously identified as novel antibacterial agents, was reduced by introducing cyclic amines to the lipophilic side chain. In this regard, substitution with methylpiperidine (compounds 14-16) and thiomorpholine (compound 19) substituents significantly enhanced the aqueous solubility profile of the new compounds more than 150-fold compared to the first-generation lead compound 1b. Consequently, the pharmacokinetic profile of compound 15 was significantly enhanced with a notable improvement in both half-life and the time the compound’s plasma concentration remained above its minimum inhibitory concentration (MIC) against methicillin-resistant Staphylococcus aureus (MRSA). In addition, compounds 14-16 and 19 were found to exert a bactericidal mode of action against MRSA and were not susceptible to resistance formation after 14 serial passages. Moreover, these compounds (at 2X MIC) were superior to the antibiotic vancomycin in the disruption of the mature MRSA biofilm. The modifications to the alkynylphenylthiazoles reported herein successfully improved the pharmacokinetic profile of this new series while maintaining the compounds’ biological activity against MRSA.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem

 

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Reference of 103-67-3, New discoveries in chemical research and development in 2021.Chemistry can be defined as the study of matter and the changes it undergoes. 103-67-3, Name is N-Methyl-1-phenylmethanamine, SMILES is CNCC1=CC=CC=C1, belongs to thiomorpholine compound. In a article, author is Fernandes, Debra, introduce new discover of the category.

Carbamate formation is one of the major chemical reactions that can occur in solution in the capture of CO2 by amine-based solvents, and carbamate formation makes a significant enthalpy contribution to the absorption-desorption of CO2 that occurs in the absorber/stripper columns of the PCC process. Consequently, the formation of carbamates of selected series of primary and secondary amines over the temperature range (288 to 318) K has been investigated by equilibrium H-1 NMR studies, and the stability constants (K-9) for the equilibrium: RNH2 + HCO3- reversible arrow(K9) RNHCOO- + H2O are reported. van’t Hoff analyses have resulted in standard molar enthalpies, Delta H-m(o), and entropies, Delta S-m(o), of carbamate formation. A Delta H-m(o) – Delta S-m(o) plot generates a linear correlation for carbamate formation (providing a mean standard molar free energy, Delta G(m)(o), for carbamate formation of about -7 kJ . mol (1)), and this relationship helps provide a guide to the selection of an amine(s) solvent for CO2 capture, in terms of enthalpy considerations. A linear Delta H-m(o) – Delta S-m(o) plot also occurs for carbamate protonation. The formation of the carbamates has been correlated with systematic changes in composition and structure, and steric effects have been identified by comparing molecular geometries obtained using density functional B3LYP/6-311++G(d,p) calculations. Trends in steric effects have been identified in the series of compounds monoethanolamine (MEA), 1-amino-2-propanol, 2-amino-1-propanol (AP) and 2-amino-2-methyl-1-propanol (AMP). In the case of 2-piperidinemethanol, 2-piperidineethanol and 3-piperidinemethanol, strong intramolecular hydrogen bonding is shown to be the likely cause for lack of carbamate formation, and in the ring systems of pyrrolidine, morpholine, piperidine and thiomorpholine trends in carbamate formation (as given by K-9) have been correlated with the internal ring angle at the amine nitrogen, as well as the planarity of the environment around the nitrogen atom. (C) 2012 Elsevier Ltd. All rights reserved.

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Reference:
Thiomorpholine – Wikipedia,
,Thiomorpholine | C4H9NS – PubChem