Structure of 1600-44-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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CAS No. : | 1600-44-8 |
Formula : | C4H8OS |
M.W : | 104.17 |
SMILES Code : | O=S1CCCC1 |
MDL No. : | MFCD00005477 |
InChI Key : | ISXOBTBCNRIIQO-UHFFFAOYSA-N |
Pubchem ID : | 1128 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302 |
Precautionary Statements: | P264-P270-P301+P312-P330-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.14 - 83% | With peroxynitrous acid; at 25℃; for 0.166667 - 4h;pH 7.4 - 12.7;phosphate buffer;Reactivity; | Example 1. The corrole metal complexes prevent oxidation and nitration of small molecules by ROS and RNS. Table 1 summarizes the results obtained by treating five different molecules with peroxynitrite, with and without catalytic amounts of 1-Fe or 1-Mn. These particular molecules were specifically chosen because they represent targets of hydroxy 1 radical, nitrogen dioxide, and of oxygen transfer reagents. In addition, their reaction products are easily identified and quantified by established methods. The results were very illuminative: both complexes rescued the simple molecule DMSO, as well as the more sophisticated one, deoxyribose, from peroxynitrite-derived hydroxyl radical. The situation with regard to nitration by reactive nitrogen species originating from peroxynitrite was quite different: 1-Mn completely eliminated the reactions of both relevant molecules, while 1-Fe had no effect on the nitration of tyrosine, and was only partially effective in avoiding that of fluorescein. This is perfectly consistent with the mode of action of the complexes on peroxynitrite, as dilute nitrite obtained from 1-Mn (Scheme 2, equation 2) is not a nitrating agent while nitrate (from the action of 1-Fe, Scheme 2, equation 1) is. Both complexes were quite (but not absolutely) effective with regard to arresting the oxidation of tetramethylenesulfoxide to sulfone, in a way which is most likely an oxygen atom transfer reaction, with 1-Fe displaying some larger efficiency. Additional experiments were carried out by using CuSO4/ascorbate as the initiator of reactive oxygen species (by the complex Fenton-type oxidation that produces hydroxyl radical via the involvement of superoxide anion radical and <n="26"/>Hydrogen peroxide), as to bridge between the results of the small molecules and those obtained by oxidation of LDL. 1-Fe eliminated the oxidation of DMSO to malonaldehyde completely and 1-Mn did it only partially (65% inhibition), which is consistent with the faster decomposition of hydrogen peroxide by 1-Fe relative to 1- Mn.These investigations clearly point toward the following conclusions: a) both complexes serve very well for preventing the formation of hydroxyl radical from peroxynitrite; b) the iron complex is more efficient in avoiding the formation of metal-induced hydroxyl radical; c) the manganese complex is more efficient in inhibiting the formation of reactive nitrogen species from peroxynitrite.; (i) Oxidation of small molecules by peroxynitrite; c) Sulfolane from tetramethylene sulfoxide: Peroxynitrite (6 mM) was added to a solution of tetramethylene sulfoxide (0.038 mM) in phosphate buffer solution pH 7.4 and T= 25 0C, both in the presence and absence of 38 muM 1-Fe or 1-Mn. The sulfolane was extracted into diethyl ether after 10 min of stirring and quantified by GC analysis. The same experiment was done at pH 12.7, with a reaction time of 4 hr. |
0.1 - 0.4% | With peroxynitrous acid;[iron(III)(C19H6N2(C6F5)3(SO3H)2]; at 25℃; for 0.166667 - 4h;pH 7.4 - 12.7;phosphate buffer;Reactivity; | Example 1. The corrole metal complexes prevent oxidation and nitration of small molecules by ROS and RNS. Table 1 summarizes the results obtained by treating five different molecules with peroxynitrite, with and without catalytic amounts of 1-Fe or 1-Mn. These particular molecules were specifically chosen because they represent targets of hydroxy 1 radical, nitrogen dioxide, and of oxygen transfer reagents. In addition, their reaction products are easily identified and quantified by established methods. The results were very illuminative: both complexes rescued the simple molecule DMSO, as well as the more sophisticated one, deoxyribose, from peroxynitrite-derived hydroxyl radical. The situation with regard to nitration by reactive nitrogen species originating from peroxynitrite was quite different: 1-Mn completely eliminated the reactions of both relevant molecules, while 1-Fe had no effect on the nitration of tyrosine, and was only partially effective in avoiding that of fluorescein. This is perfectly consistent with the mode of action of the complexes on peroxynitrite, as dilute nitrite obtained from 1-Mn (Scheme 2, equation 2) is not a nitrating agent while nitrate (from the action of 1-Fe, Scheme 2, equation 1) is. Both complexes were quite (but not absolutely) effective with regard to arresting the oxidation of tetramethylenesulfoxide to sulfone, in a way which is most likely an oxygen atom transfer reaction, with 1-Fe displaying some larger efficiency. Additional experiments were carried out by using CuSO4/ascorbate as the initiator of reactive oxygen species (by the complex Fenton-type oxidation that produces hydroxyl radical via the involvement of superoxide anion radical and <n="26"/>Hydrogen peroxide), as to bridge between the results of the small molecules and those obtained by oxidation of LDL. 1-Fe eliminated the oxidation of DMSO to malonaldehyde completely and 1-Mn did it only partially (65% inhibition), which is consistent with the faster decomposition of hydrogen peroxide by 1-Fe relative to 1- Mn.These investigations clearly point toward the following conclusions: a) both complexes serve very well for preventing the formation of hydroxyl radical from peroxynitrite; b) the iron complex is more efficient in avoiding the formation of metal-induced hydroxyl radical; c) the manganese complex is more efficient in inhibiting the formation of reactive nitrogen species from peroxynitrite.; (i) Oxidation of small molecules by peroxynitrite; c) Sulfolane from tetramethylene sulfoxide: Peroxynitrite (6 mM) was added to a solution of tetramethylene sulfoxide (0.038 mM) in phosphate buffer solution pH 7.4 and T= 25 0C, both in the presence and absence of 38 muM 1-Fe or 1-Mn. The sulfolane was extracted into diethyl ether after 10 min of stirring and quantified by GC analysis. The same experiment was done at pH 12.7, with a reaction time of 4 hr. |
0.18 - 0.6% | With peroxynitrous acid;[manganese(III)(C19H6N2(C6F5)3(SO3H)2]; at 25℃; for 0.166667 - 4h;pH 7.4 - 12.7;phosphate buffer;Reactivity; | Example 1. The corrole metal complexes prevent oxidation and nitration of small molecules by ROS and RNS. Table 1 summarizes the results obtained by treating five different molecules with peroxynitrite, with and without catalytic amounts of 1-Fe or 1-Mn. These particular molecules were specifically chosen because they represent targets of hydroxy 1 radical, nitrogen dioxide, and of oxygen transfer reagents. In addition, their reaction products are easily identified and quantified by established methods. The results were very illuminative: both complexes rescued the simple molecule DMSO, as well as the more sophisticated one, deoxyribose, from peroxynitrite-derived hydroxyl radical. The situation with regard to nitration by reactive nitrogen species originating from peroxynitrite was quite different: 1-Mn completely eliminated the reactions of both relevant molecules, while 1-Fe had no effect on the nitration of tyrosine, and was only partially effective in avoiding that of fluorescein. This is perfectly consistent with the mode of action of the complexes on peroxynitrite, as dilute nitrite obtained from 1-Mn (Scheme 2, equation 2) is not a nitrating agent while nitrate (from the action of 1-Fe, Scheme 2, equation 1) is. Both complexes were quite (but not absolutely) effective with regard to arresting the oxidation of tetramethylenesulfoxide to sulfone, in a way which is most likely an oxygen atom transfer reaction, with 1-Fe displaying some larger efficiency. Additional experiments were carried out by using CuSO4/ascorbate as the initiator of reactive oxygen species (by the complex Fenton-type oxidation that produces hydroxyl radical via the involvement of superoxide anion radical and <n="26"/>Hydrogen peroxide), as to bridge between the results of the small molecules and those obtained by oxidation of LDL. 1-Fe eliminated the oxidation of DMSO to malonaldehyde completely and 1-Mn did it only partially (65% inhibition), which is consistent with the faster decomposition of hydrogen peroxide by 1-Fe relative to 1- Mn.These investigations clearly point toward the following conclusions: a) both complexes serve very well for preventing the formation of hydroxyl radical from peroxynitrite; b) the iron complex is more efficient in avoiding the formation of metal-induced hydroxyl radical; c) the manganese complex is more efficient in inhibiting the formation of reactive nitrogen species from peroxynitrite.; (i) Oxidation of small molecules by peroxynitrite; c) Sulfolane from tetramethylene sulfoxide: Peroxynitrite (6 mM) was added to a solution of tetramethylene sulfoxide (0.038 mM) in phosphate buffer solution pH 7.4 and T= 25 0C, both in the presence and absence of 38 muM 1-Fe or 1-Mn. The sulfolane was extracted into diethyl ether after 10 min of stirring and quantified by GC analysis. The same experiment was done at pH 12.7, with a reaction time of 4 hr. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66%; 60% | With dihydrogen peroxide; In water; at 30 - 35℃; for 24h;Sealed tube; Green chemistry; | General procedure: A mixture of sulfide (1 mmol) and H2O (2 mL) wastaken in a stoppered tube. Then 1.2/2.5equiv. of 50%H2O2 was added slowly to it. The reaction mixture wasstirred at room temperature. The progress of the reactionwas monitored by TLC or GC. After 24 h, the productwas extracted with ethyl acetate (3 x5 mL). The organiclayer was separated, dried (Na2SO4), and concentratedunder vacuum. The crude products were purified bycolumn chromatography using silica gel (60-120 mesh)with petroleum ether and ethyl acetate as solvent to getthe pure product. The pure products were analyzed by13C, 1H NMR spectra and gas chromatography massspectrometer (GCMS). |