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Chemical Structure| 7365-82-4 Chemical Structure| 7365-82-4
Chemical Structure| 7365-82-4

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ACES is an effective physiological buffer used to stabilize the pH of biological systems.

Synonyms: N-(2-Acetamido)-2-aminoethanesulfonic acid

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of ACES

CAS No. :7365-82-4
Formula : C4H10N2O4S
M.W : 182.20
SMILES Code : NC(=O)CNCCS(O)(=O)=O
Synonyms :
N-(2-Acetamido)-2-aminoethanesulfonic acid
English Name :N-(Carbamoylmethyl)-2-aminoethanesulfonic Acid
MDL No. :MFCD00008030
InChI Key :DBXNUXBLKRLWFA-UHFFFAOYSA-N
Pubchem ID :81832

Safety of ACES

Application In Synthesis of ACES

* 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.

  • Downstream synthetic route of [ 7365-82-4 ]

[ 7365-82-4 ] Synthesis Path-Downstream   1~5

YieldReaction ConditionsOperation in experiment
Natriumbromethansulfonat, Glycinamidhydrochlorid;
wherein the biological buffer is selected from the group consisting of: N-2-acetamido-2-aminoethanesulfonic acid (ACES); N-2-acetamido-2-iminodiacetic acid (ADA); amino methyl propanediol (AMP); 3-1,1-dimethyl-2-hydroxyethylamino-2-hydroxy propanesulfonic acid (AMPSO); N,N-bis2-hydroxyethyl-2-aminoethanesulfonic acid (BES); N,N-bis-2-hydroxyethylglycine (BICINE); 1,3-bistrishydroxymethylmethylaminopropane (Bis-Tris Propane); 4-cyclohexylamino-1-butane sulfonic acid (CABS); 3-cyclohexylamino-1-propane sulfonic acid (CAPS); ...
Zwitterionic compounds selected from: taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido)iminodiacetic acid (ADA), N-(2-acetamido)-2-aminoethanesulphonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulphonic acid (BES), N-N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid (TES), N-2-hydroxyethylpiperazine-N'-2-ethanesulphonic acid (HEPES), 2-(cyclohexylamino)ethanesulphonic acid (CHES) or 3-(cyclohexylamino)propanesulphonic acid (CAPS),
...g a chronic progressive inflammatory condition or disease by stimulating myeloperoxidase activity comprising systemically administering to a patient in need thereof an effective amount of taurine and at least one N-halo derivative of a zwitterionic compound selected from the group consisting of: taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido)iminodiacetic acid (ADA), N-(2-acetamido)-2-aminoethanesulphonic acid) (ACES), N,N-bis(2-hydroxylethyl)-2-aminoethanesulphonic acid) (BES), N,N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid) (TES), N,2-hydroxyethylpiperazine-N'-2-ethanesulphonic acid) (HEPES), N,2-hydroxyethylpiperazine-N'-3-propanesulphonic acid) ((H)EPPS), 2-(cyclohexylamino)ethanesulphonic acid) (CHES), and
The present invention provides a method of stimulating myeloperoxidase activity in a patient in need of such stimulation, which comprises administering to said patient as active agent an effective amount of a zwitterionic compound selected from: taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido)iminodiacetic acid (ADA), N-(2-acetamido)-2-aminoethanesulphonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulphonic acid (BES), N-N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid (TES), N-2-hydroxyethylpiperazine-N'-2-ethanesulphonic acid (HEPES), N-2-hydroxyethylpiperazine-N'3-propanesulphonic acid ((H)EPPS), 2-(cyclohexylamino)ethanesulphonic acid (CHES) or 3-(cyclohexylamino)propanesulphonic acid (CAPS),
Method of claim 4, further comprising administering an N-halo derivative of a compound selected from the group consisting of taurine (2-aminoethanesulphonic acid), 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido)iminodiacetic acid (ADA), N-(2-acetamido)-2-aminoethanesulphonic acid) (ACES), N,N-bis(2-hydroxylethyl)-2-aminoethanesulphonic acid) (BES), N,N[tris(hydroxymethyl)-methyl]-2-aminoethanesulphonic acid) (TES), N,2-hydroxyethylpiperazine-N'-2-ethanesulphonic acid) (HEPES), N,2-hydroxyethylpiperazine-N'-3-propanesulphonic acid) ((H)EPPS), 2-(cyclohexylamino)ethanesulphonic acid) (CHES) and ...
Use of a zwitterionic compound selected from: ... 2(N-morpholino)ethanesulphonic acid (MES), N-(2-acetamido) iminodiacetic acid (ADA), N-(2-acetamido)-2-aminoethanesulphonic acid (ACES), N,N-bis(2-hydroxyethyl)-2-aminoethanesulphonic acid (BES), ...
, wherein the plurality of positively charged groups are provided by a biological buffer which is selected from the group consisting of: N-2-acetamido-2-aminoethanesulfonic acid (ACES); N-2-acetamido-2-iminodiacetic acid (ADA); N,N-bis2-hydroxyethyl-2-aminoethanesulfonic acid (BES); N,N-bis-2-hydroxyethylglycine (BICINE); 1,3-bistrishydroxymethylmethylaminopropane (Bis-Tris Propane); 3-N,N-bis-2-hydroxyethylamino-2-hydroxypropanesulfonic acid (DIPSO); -2-hydroxyethylpiperazine-N-3-propanesulfonic acid (EPPS); -2-hydroxyethylpiperazine-N-4-butanesulfonic acid (HEPBS); -2-hydroxyethylpiperazine-N-2-ethanesulfonic acid (HEPES); ...
...econd, higher, pH at which the charge on the ionizable groups is negative, neutral or less positive, wherein said plurality of positively ionizable groups have a pKa between about 4.5 and about 8.5, the ionizable groups being provided by a biological buffer selected from the group consisting of: N-2-acetamido-2-aminoethanesulfonic acid (ACES); N-2-acetamido-2-iminodiacetic acid (ADA); N,N-bis2-hydroxyethyl-2-aminoethanesulfonic acid (BES); N,N-bis-2-hydroxyethylglycine (BICINE); 1,3-bistrishydroxymethylmethylaminopropane (Bis-Tris Propane); 3-N,N-bis-2-hydroxyethylamino-2-hydroxypropanesulfonic acid (DIPSO); -2-hydroxyethylpiperazine-N-3-propanesulfonic acid (EPPS); -2-hydroxyethylpiperazine-N-4-butanesulfonic acid (HEPBS); -2-hydroxyethylpiperazine-N-2-ethanesulfonic acid (HEPES); ...
Examples of the Good's buffer include, but are not limited to, N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid (BES), 2-morpholinoethanesulfonic acid (MES), N-(2-acetamide) iminodiacetic acid (ADA), piperazine-N,N'-bis(2-ethanesulfonic acid) (PIPES), N-(2-acetamide)-2-aminoethanesulfonic acid (ACES), 3-morpholino-2-hydroxypropanesulfonic acid (MOPSO), 3-morpholinopropanesulfonic acid (MOPS), N-[tris(hydroxymethyl)methyl]-2-aminoethanesulfonic acid (TES), 2-[4-(2-hydroxyethyl)-1-piperazinyl]ethanesulfonic acid (HEPES), ...

  • 2
  • [ 55850-75-4 ]
  • [ 7365-82-4 ]
YieldReaction ConditionsOperation in experiment
82% With ammonia In tetrahydrofuran at 60℃; for 8h; 2.3-2.4 In the presence of the reaction solvent tetrahydrofuran, add nitrogen-containing reagent ammonia into the reactor to react with the second intermediate product obtained in step 2, wherein the molar ratio of ammonia to the second intermediate product is 1:1, The reaction temperature is 60°C, the reaction pressure is 1 MPa (gauge pressure), and the reaction time is 8 hours. After the reaction is completed, it is acidified to generate ACES, as shown below:Then spin off the solvent tetrahydrofuran, add ethyl acetate, wash twice with water, dry with anhydrous sodium sulfate, and spin off the ethyl acetate to obtain the crude ACES. The calculated yield of the crude ACES is 70%.Step 4: Purification stepIn the reactor, the purified solvent tetrahydrofuran was added to dissolve the crude ACES, recrystallized at low temperature, the insoluble matter was removed by suction, and the filtrate was rotary evaporated to remove tetrahydrofuran to obtain refined ACES with a purification yield of 82%.The NMR analysis test of the refined ACES obtained in step 4 was carried out with the AVANCE 400 Mega NMR spectrometer of Bruker (Bruker).The above-mentioned NMR results are consistent with those of commercially available ACES standards.Through acid-base titration analysis, the purity of the ACES product in this example is 99.5%.
  • 3
  • [ 1671069-26-3 ]
  • [ 7365-82-4 ]
YieldReaction ConditionsOperation in experiment
80% With ammonia In acetonitrile at 60℃; for 8h; 3.3-3.4 In the presence of the reaction solvent acetonitrile, add nitrogen-containing reagent ammonia to the reactor to react with the second intermediate product obtained in step 2, wherein the molar ratio of ammonia to the second intermediate product is 1:1, and the reaction temperature The temperature is 60°C, the reaction pressure is 0.5MPa (gauge pressure), and the reaction time is 8h. After the reaction is completed, it is acidified to generate ACES, as shown below:Then spin off the solvent, add ethyl acetate, wash twice with water, dry with anhydrous sodium sulfate, and spin off the ethyl acetate to obtain the crude ACES. The calculated yield of the crude ACES is 72%.Step 4: Purification stepIn the reactor, the purified solvent methanol is added to dissolve the crude ACES, recrystallization is performed at low temperature, the insoluble matter is removed by suction filtration, and the filtrate is rotary evaporated to remove methanol to obtain refined ACES with a purification yield of 80%.The NMR analysis test of the refined ACES obtained in step 4 was carried out with the AVANCE 400 Mega NMR spectrometer of Bruker (Bruker).The above-mentioned NMR results are consistent with those of commercially available ACES standards.Through acid-base titration analysis, the purity of the ACES product in this example was 99.0%.
  • 4
  • [ 2538453-22-2 ]
  • [ 7365-82-4 ]
YieldReaction ConditionsOperation in experiment
82% With ammonia In tetrahydrofuran at 60℃; for 8h; 1.3-1.4; 4.3-4.4 In the presence of the reaction solvent acetonitrile, add nitrogen-containing reagent ammonia to the reactor to react with the second intermediate product obtained in step 2, wherein the molar ratio of ammonia to the second intermediate product is 1:1, and the reaction temperature The temperature is 60°C, the reaction pressure is 0.5MPa (gauge pressure), and the reaction time is 8h. After the reaction is completed, it is acidified to generate ACES as shown below:Then spin off the solvent acetonitrile, add ethyl acetate, wash twice with water, dry with anhydrous sodium sulfate, and spin off the ethyl acetate to obtain the crude ACES. The calculated yield of the crude ACES is 74%.; In the reactor, the purified solvent acetonitrile was added to dissolve the crude ACES, recrystallized at low temperature, the insoluble matter was removed by suction filtration, and the filtrate was rotary evaporated to remove the acetonitrile to obtain refined ACES with a purification yield of 80%.
  • 5
  • [ 54757-46-9 ]
  • [ 7365-82-4 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
240 mg With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15 - 25℃; 5.1 5.1 Synthesis of compound 5 Acitretin (250 mg, 0.77 mmol) was suspended in DMF (2.5 mL) and N-(2-acetamido)-taurine (140 mg, 0.77 mmol) was added followed by DIPEA (400 pL, 2.3 mmol). The yellow suspension was cooled to 15°C and PyBOP (478 mg, 0.9 mmol) was added. The resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into cold water (10 mL), acidified with IM HCI to pH 1 and extracted with EtOAc (3 x 15 mL). As UPLC showed that no product was present in the organic extracts, the organic layer was discarded. The aqueous layer was saturated with solid NaCI. After several minutes a yellow solid precipitated. The suspension was sonicated for 1 minute and then stirred at room temperature for 15 minutes. The solid was filtered off, washed with a small amount of water and dried under vacuum to give 240 mg of the product as a yellow solid (purity 99.9%). (0161) 235 mg of solid was dissolved in MeOH (5 mL) and a solution of NaOH (19 mg) in MeOH (0.5 mL) was then added. The solution was stirred for 1 hour and a yellow solid precipitated. The mixture was concentrated to ca. 3 mL, stirred for 30 minutes and then filtered. The solid was washed with a small amount of MeOH and dried. Yield: 41% (160 mg). XH NMR (300 MHz, DMSO-d6): 6 7.51 (d, J = 9.5 Hz, 1H), 7.14-6.79 (m, 2H), 6.66 (d, J = 19.1 Hz, 2H), 6.45-5.94 (m, 4H), 3.90 (d, J = 31.6 Hz, 2H), 3.76 (s, 3H), 3.56 (dt, J = 23.1, 7.4 Hz, 2H), 2.66 (dt, J = 13.9, 7.0 Hz, 2H), 2.26 (s, 3H), 2.19 (s, 3H), 2.06 (d, J = 6.8 Hz, 9H). m/z = 513.19; 491.41.
 

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