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Chemical Structure| 1119-62-6 Chemical Structure| 1119-62-6
Chemical Structure| 1119-62-6

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Dithiodipropionic acid can form nanostructures (CPUL1-DA NAs) with CPUL1 (a TrxR inhibitor), which are more effective than free CPUL1 in generating reactive oxygen species (ROS), inducing apoptosis, and enhancing the antitumor effect on HUH7 cancer cells.

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

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Product Details of Dithiodipropionic acid

CAS No. :1119-62-6
Formula : C6H10O4S2
M.W : 210.27
SMILES Code : O=C(O)CCSSCCC(O)=O
English Name :3,3-Dithiodipropionic Acid
MDL No. :MFCD00002780
InChI Key :YCLSOMLVSHPPFV-UHFFFAOYSA-N
Pubchem ID :95116

Safety of Dithiodipropionic acid

Application In Synthesis of Dithiodipropionic acid

* 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 [ 1119-62-6 ]

[ 1119-62-6 ] Synthesis Path-Downstream   1~14

  • 2
  • [ 6414-69-3 ]
  • [ 1119-62-6 ]
  • 6
  • [ 30453-21-5 ]
  • [ 1119-62-6 ]
  • [ 663199-00-6 ]
YieldReaction ConditionsOperation in experiment
80% In water at 40℃; for 3h;
  • 7
  • [ 25249-16-5 ]
  • [ 1119-62-6 ]
  • [ 1190876-88-0 ]
YieldReaction ConditionsOperation in experiment
41% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice; 1 Synthesis of DTMA 3,3'-dihydrooxoline acid (DTDPA) (20g, 95mmol),Hydroxyethyl methacrylate (HEMA) (13.6g, 100mmol) and 4-N,N-dimethylaminopyridine (DMAP) (1.74g, 14mmol) are blended in 200mL of anhydrous dichloromethane (DCM), take 1 -(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) (20g, 100mmol) was dissolved in 200mL anhydrous DCM, and the EDC·HCl solution was dropped under ice bath conditions Add to the above reaction solution and stir overnight at room temperature. The reaction solution was washed with water three times (100mL×3), 1M hydrochloric acid solution washed three times (100mL×3), saturated sodium chloride solution washed once (100mL×1), dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product. The product was purified by silica gel column with n-hexane/ethyl acetate eluent to obtain colorless and transparent liquid DTMA (12.6 g, yield 41%).
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Cooling with ice; 2 Synthesis of intermediate product DTMA: Take 3,3′-Dithiodipropionic acid(DTDPA) 20g (0.095mol),Hydroxyethyl methacrylate (HEMA) 13.6g (0.1mol)And 1.74 g (0.014 mol) of 4-dimethylaminopyridine in 200 mL of dichloromethane,20 g of 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride was dissolved in 200 mL of dichloromethane,Add dropwise to the mixture under ice-bath conditions and stir overnight at room temperature.The reaction solution was washed three times with water, three times with 1M HCl solution, and two times with saturated NaCl solution.Dry over anhydrous sodium sulfate and concentrate under reduced pressure to obtain the crude product.The crude product was purified through a column with n-hexane / ethyl acetate eluent to obtain the product, named DTMA.
Stage #1: 2-Hydroxyethyl methacrylate; 3,3'-Dithiodipropionic acid With dmap In tetrahydrofuran at 20℃; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; 2.2a (2a) Synthetic monomer MASSMI Accurately weigh (1g, 7.68mmol) hydroxyethyl methacrylate HEMA, (6.45g, 30.72mmol) 3,3'-dithiodipropionic acid DTDPA and (85.29mg, 0.7mmol) DMAP and mix them, add 60mL After freshly removing water from THF and reacting at room temperature for 12 h, a reaction mixture was obtained. The reaction mixture was then cooled in an ice bath at 0°C for 1 h. Dissolve (1.74g, 8.44mmol) dicyclohexylcarbodiimide (DCC) in 20 mL of freshly dehydrated THF and drop it into the reaction mixture, stir vigorously, and react at room temperature for 24 h. After the reaction is completed, use a Buchner funnel to filter, collect the filtrate and perform rotary evaporation, add 50 mL CHCl3 to dissolve and filter.After washing three times with brine, the product was obtained by rotary evaporation, which was recorded as MASSCOOH. Its NMR spectrum is shown in Figure 2. As can be seen from Figure 2, the obtained product is MASSCOOH.
Stage #1: 2-Hydroxyethyl methacrylate; 3,3'-Dithiodipropionic acid With dmap In tetrahydrofuran at 20℃; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; 2.2a (2a) Synthetic monomer MASSMI Accurately weigh (1g, 7.68mmol) hydroxyethyl methacrylate HEMA, (6.45g, 30.72mmol) 3,3'-dithiodipropionic acid DTDPA and (85.29mg, 0.7mmol) DMAP and mix them, add 60mL After freshly removing water from THF and reacting at room temperature for 12 h, a reaction mixture was obtained. The reaction mixture was then cooled in an ice bath at 0°C for 1 h. Dissolve (1.74g, 8.44mmol) dicyclohexylcarbodiimide (DCC) in 20 mL of freshly dehydrated THF and drop it into the reaction mixture, stir vigorously, and react at room temperature for 24 h. After the reaction is completed, use a Buchner funnel to filter, collect the filtrate and perform rotary evaporation, add 50 mL CHCl3 to dissolve and filter.After washing three times with brine, the product was obtained by rotary evaporation, which was recorded as MASSCOOH. Its NMR spectrum is shown in Figure 2. As can be seen from Figure 2, the obtained product is MASSCOOH.

  • 8
  • [ 1653-40-3 ]
  • [ 1119-62-6 ]
  • [ 500542-19-8 ]
YieldReaction ConditionsOperation in experiment
99.2% With 1-propyl-3-methylimidazolium methanesulfonate at 100℃; for 5h; Inert atmosphere; 1-4; 1-7 100 g (0.4756 mol) of 3,3'-dithiodipropionic acid, 173.46 g (1.332 mol) of isooctanol, and 1 g of 1-propyl-3-methylimidazolium methanesulfonate were added to a reaction vessel. The molar ratio of 3,3'-dithiodipropionic acid to isooctanol was 1:2.8. The air in the reaction vessel was replaced with nitrogen. The mixture was heated to 100°C under stirring and maintained at this temperature for 5 hours for the esterification reaction. The reaction mixture was cooled to 70°C, 20 g of water was added and stirred for 10 minutes. After standing, the mixture separated into two layers: the upper layer was the isooctanol phase containing the product, and the lower layer was the aqueous phase containing the 1-propyl-3-methylimidazolium methanesulfonate. The lower aqueous layer was separated and removed. Another 20 g of water was added and stirred for 15 minutes, followed by standing to allow separation of the layers. The lower aqueous layer was again separated and removed. The remaining isooctanol was recovered by vacuum distillation. Gas chromatography analysis of the residue showed that it contained 205.09 g (0.4718 mol) of 3,3'-dithiodipropionic acid bis(isooctyl ester), with a yield of 99.2%.
90.3% With phosphoric acid at 120℃; 1B; 3B; 4B; 5B; 6A; 6B Example 1B 60 g (0.285 mol) of 3,3'-dithiodipropionic acid was added to the reaction vessel.Isooctanol 100 g (0.768 mol) and catalyst phosphoric acid 2 g (0.02 mol).Stir and warm until the starting material is completely dissolved, maintaining the temperature to 120 ° C until the end of the reaction.Reduce the temperature to 60 ° C, add 10g of 10% aqueous sodium hydroxide solution to adjust the pH,After stirring the reaction, it was allowed to stand.The lower aqueous phase is separated to give the upper organic phase. Add 10g (0.56mol) of deionized water,Stir for 10 minutes.Rest,After separating the lower aqueous phase, an upper organic phase is obtained, and the remaining raw material isooctyl alcohol is recovered by reduced pressure.Get the product3,3'-dithiodipropionate bis(isooctanyl ester)112 g (0.258 mol), yield 90.3%.
  • 9
  • [ 1119-62-6 ]
  • [ 19008-43-6 ]
  • dibenzyl 4,4’-((3,3’-disulfanediylbis(propanoyl))bis(azanediyl))dibenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 10 - 50℃; for 12h; To a solution of 3-(2-carboxyethyldisulfanyl)propanoic acid (6.01 g, 28.60 mmol, I eq) and pyridine ( 14.93 g, 188.77 mmol, 15.24 mL, 6.6 eq) in DMF ( 120 L) was added EDCI ( 12.06 g, 62.92 mmol, 2.2 eq) and <strong>[19008-43-6]benzyl 4-aminobenzoate</strong> ( 13 g, 57.20 mmol, 2 eq) at 10C. Then, the mixture was stirred at 50C for 12 hrs. The residue was poured into ice-water (200 mL) and stirred for 20 min. The aqueous phase was extracted with ethyl acetate (200 mL*3). The combined organic phase was washed with sat. NaCI (200 mL*3), dried with anhydrous Na SCfi, filtered and concentrated in vacuum. Then, the residue was recrystallized from Petroleum ether:DCM = 50: 1 to get the solid. The solid was washed petroleum three times ( 150 ml * 3), and then dried in vacuum to give benzyl 4-[3-[[3-(4-benzyloxycarbonylanilino)-3-oxo-propyl]disulfanyl] propanoylamino]benzoate (14 g, crude) as a white solid; NMR (400MHz, DMSO-d6) d = 10.37 (s, 2H), 8.02 - 7.83 (m, 4H), 7.72 (d, J=8.8 Hz, 4H), 7.48 - 7.32 (m, 1 OH), 5.31 (s, 4H), 3.05 - 2.98 (m. 4H), 2.81 - 2.75 (m, 4H).
  • 10
  • [ 1438-91-1 ]
  • [ 1119-62-6 ]
  • [ 138148-59-1 ]
YieldReaction ConditionsOperation in experiment
40 % With N-Bromosuccinimide In acetonitrile at 25℃; Schlenk technique; Sealed tube;
  • 11
  • [ 1119-62-6 ]
  • [ 7333-67-7 ]
  • [ 3022261-58-8 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In methanol at 50℃; 7 Example 7 The present embodiment relates to the preparation process of bisphosphine cationic ionic liquid propane-1,3-diyl bis(triphenylphosphino)3,3'-dithiodipropionate ([PPh 3 PrPPh3] [DA]) containing sulfide, the specific preparation method is as follows: (1) Dissolve 0.01mol [1,10-(propane-1,4-diyl)-bis(triphenylphosphino)] dibromide salt, 0.01mol 3,3'-dithiodipropionic acid and 4mL sodium methoxide with 150mL of anhydrous methanol, stirring at 50 °C for 24h; (2) Put the mixed solution obtained in step (1) into the rotary evaporator, and use the rotary evaporator to spin the reacted liquid at 90 °C for enough time to remove anhydrous methanol and obtain a solid precipitate. (3) Add 50mL chloroform and 30mL of ultrapure water to the flask for extraction, the liquid in the flask is divided into two layers, the upper layer is the aqueous phase, the lower layer is the organic phase, the liquid of the lower layer is separated, and the ultrapure water is washed three times; (4) Use a rotary evaporator to spin steam the washed liquid at 80 °C for enough time to remove chloroform and obtain a crude product; (5) After the crude product is put into a vacuum drying oven with phosphorus pentoxide and dried at room temperature, propane-1,3-diylbis(triphenylphosphino)3,3'-dithiodipropionate is obtained.
  • 12
  • [ 1119-62-6 ]
  • [ 184719-80-0 ]
  • [ 2839365-34-1 ]
YieldReaction ConditionsOperation in experiment
1.06 g With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; 1-7-1 (1-7-1) Synthesis of Linker Intermediate (48) 3,3′-dithiodipropionic acid (608 mg, 2.89 mmol) was dissolved in dichloromethane (15 mL), and D-proline tert-butylhydrochloride (1.32 g, 6.36 mmol), WSC·HCl (1.39 mg, 2.72 mmol), 1-hydroxy-7-azabenzotriazole (78.7 mg, 0.578 mmol) and triarylamine (2.00 mL, 14.5 mmol) were added, and the mixture was stirred at room temperature overnight. After concentration under reduced pressure, the solution was diluted by adding ethyl acetate, the mixture was washed with water and brine, and then sodium sulfate was added. Sodium sulfate was removed by filtration, the solution was concentrated under reduced pressure, and the reactant was purified by column chromatography (hexane:ethyl acetate=1:1). The fraction containing the product was collected and concentrated in vacuo to give the linker intermediate (48) (1.06 g, 2.04 mmol). (0603) 1H NMR (400 MHz, Chloroform-d) δ4.40 (dd, J=8.6, 3.5 Hz, 2H), 3.64-3.49 (m, J=8.5, 7.9, 4H), 3.08-2.86 (m, 4H), 2.77 (td, J=8.1, 7.6, 3.3 Hz, 4H), 2.23-1.87 (m, 8H), 1.68 (s, 2H), 1.47 (s, 16H), 1.40-1.24 (m, 2H), 0.90 (t, J=6.6 Hz, 2H). (0604) MS(ESI) m/z: 517 [M+H]+
1.06 g With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 1-7-1 (1-7-1) Synthesis of Linker Intermediate (48) 3,3′-dithiodipropionic acid (608 mg, 2.89 mmol) was dissolved in dichloromethane (15 mL), and D-proline tert-butylhydrochloride (1.32 g, 6.36 mmol), WSC·HCl (1.39 mg, 2.72 mmol), 1-hydroxy-7-azabenzotriazole (78.7 mg, 0.578 mmol) and triarylamine (2.00 mL, 14.5 mmol) were added, and the mixture was stirred at room temperature overnight. After concentration under reduced pressure, the solution was diluted by adding ethyl acetate, the mixture was washed with water and brine, and then sodium sulfate was added. Sodium sulfate was removed by filtration, the solution was concentrated under reduced pressure, and the reactant was purified by column chromatography (hexane:ethyl acetate=1:1). The fraction containing the product was collected and concentrated in vacuo to give the linker intermediate (48) (1.06 g, 2.04 mmol). (0603) 1H NMR (400 MHz, Chloroform-d) δ4.40 (dd, J=8.6, 3.5 Hz, 2H), 3.64-3.49 (m, J=8.5, 7.9, 4H), 3.08-2.86 (m, 4H), 2.77 (td, J=8.1, 7.6, 3.3 Hz, 4H), 2.23-1.87 (m, 8H), 1.68 (s, 2H), 1.47 (s, 16H), 1.40-1.24 (m, 2H), 0.90 (t, J=6.6 Hz, 2H). (0604) MS(ESI) m/z: 517 [M+H]+
  • 13
  • [ 1119-62-6 ]
  • [ 184719-80-0 ]
  • [ 2839365-38-5 ]
YieldReaction ConditionsOperation in experiment
1.09 g With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; 1-8-1 (1-8-1) Synthesis of Linker Intermediate (54) Dithioglycolic acid (613 mg, 3.36 mmol) was dissolved in dichloromethane (17 mL), and D-proline tert-butylhydrochloride (1.53 g, 7.40 mmol), WSC·HCl (1.61 mg, 8.40 mmol), 1-hydroxy-7-azabenzotriazole (91.4 mg, 0.672 mmol), and triarylamine (2.33 mL, 16.8 mmol) were added, and the mixture was stirred at room temperature overnight. After concentration under reduced pressure, ethyl acetate was added and diluted, the solution was washed with water and brine, and then sodium sulfate was added. Sodium sulfate was removed by filtration, the solution was concentrated under reduced pressure, and the reactant was purified by column chromatography (hexane:ethyl acetate=1:1). The fraction containing the product was collected and concentrated in vacuo to give the linker intermediate (54) (1.09 g, 2.23 mmol). (0624) 1H NMR (400 MHz, Chloroform-d) δ4.39 (dt, J=8.3, 3.6 Hz, 2H), 3.79-3.60 (m, 8H), 2.35-2.14 (m, 2H), 2.14-1.85 (m, 6H), 1.47 (s, 18H). (0625) MS(ESI) m/z: 489 [M+H]+
1.09 g With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; 1-8-1 (1-8-1) Synthesis of Linker Intermediate (54) Dithioglycolic acid (613 mg, 3.36 mmol) was dissolved in dichloromethane (17 mL), and D-proline tert-butylhydrochloride (1.53 g, 7.40 mmol), WSC·HCl (1.61 mg, 8.40 mmol), 1-hydroxy-7-azabenzotriazole (91.4 mg, 0.672 mmol), and triarylamine (2.33 mL, 16.8 mmol) were added, and the mixture was stirred at room temperature overnight. After concentration under reduced pressure, ethyl acetate was added and diluted, the solution was washed with water and brine, and then sodium sulfate was added. Sodium sulfate was removed by filtration, the solution was concentrated under reduced pressure, and the reactant was purified by column chromatography (hexane:ethyl acetate=1:1). The fraction containing the product was collected and concentrated in vacuo to give the linker intermediate (54) (1.09 g, 2.23 mmol). (0624) 1H NMR (400 MHz, Chloroform-d) δ4.39 (dt, J=8.3, 3.6 Hz, 2H), 3.79-3.60 (m, 8H), 2.35-2.14 (m, 2H), 2.14-1.85 (m, 6H), 1.47 (s, 18H). (0625) MS(ESI) m/z: 489 [M+H]+
  • 14
  • [ 1119-62-6 ]
  • [ 67385-09-5 ]
  • [ 485800-27-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In methanol at 21℃; for 15h; 1.2.1.1 Synthesis of Compound 4: Take a 40 mL sample vial, weigh compound 3 (1 g), dissolve it in methanol (10 mL), then add triethylamine (1.93 g) and compound 2 (1.26 g), and stir electromagnetically at 21 °C for 15 hours. Concentrate the reaction solution under reduced pressure to obtain a crude product, which is then purified using a Biotage automated column chromatography system (silica gel, dichloromethane/methanol as the developing solvent = 1/0 to 10/1) to obtain compound 4.
 

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