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[ CAS No. 1226895-20-0 ] {[proInfo.proName]}

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Chemical Structure| 1226895-20-0
Chemical Structure| 1226895-20-0
Structure of 1226895-20-0 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1226895-20-0 ]

CAS No. :1226895-20-0 MDL No. :MFCD19443776
Formula : C21H19NO3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 365.45 Pubchem ID :-
Synonyms :
ATB-346
Chemical Name :4-Carbamothioylphenyl 2-(6-methoxynaphthalen-2-yl)propanoate

Safety of [ 1226895-20-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P270-P301+P312-P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1226895-20-0 ]

* 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 [ 1226895-20-0 ]

[ 1226895-20-0 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 1000700-40-2 ]
  • [ 1226895-20-0 ]
YieldReaction ConditionsOperation in experiment
61% With Lawessons reagent In benzene at 60℃; for 4h; 10 Synthesis of 4-thiocarbamoylphenyl 2-(2-methoxynaphthalen-6-yl)propanoate (6) Synthesis of 4-thiocarbamoylphenyl 2-(2-methoxynaphthalen-6-yl)propanoate (6)4-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate, 5 (1.80 g, 4.34 mmol) and Lawesson reagent (1.75 g, 4.34 mmol) were dissolved in 130 ml of anhydrous benzene. The reaction was warmed to 60 C. and stirred for 4 h. The solvent was removed under reduced pressure; the crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.75:0.25) to furnish 2.9 g of crude compound 6. The obtained compound was purified by a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5)) giving the pure compound 6 (970 mg, 61% yield).1H NMR (DMSO-d6): ? 1.59 (d, 3H), 3.86 (s, 3H, OCH3), 4.24 (dd, 1H), 7.06 (d, 2H), 7.18 (d, 1H), 7.31 (s, 1H), 7.50 (d, 1H), 7.84 (s, 1H) 7.85 (d, 1H), 7.86 (s, 1H), 7.89 (d, 2H), 9.47 and 9.84 (s, 2H, NH2).13C NMR (DMSO-d6): ? 19.1, 45.2, 55.9, 106.5, 119.6, 121.6, 126.6, 126.9, 128.0, 129.4, 129.9, 134.2, 135.6, 137.8, 153.4, 158.1, 173.3, 199.7.MS (EI), m/e 366 (M+);m.p.: 196-198 C.
  • 2
  • [ 1226895-20-0 ]
  • [ 2757-23-5 ]
  • [ 2369985-58-8 ]
YieldReaction ConditionsOperation in experiment
87% In tetrahydrofuran at 20℃; for 2h; 15 Example 15 (0309) In this example, GSH-triggered H2S release from compound 900 was evaluated. ATB-346 has been demonstrated to exhibit promising anti-inflammatory effect with much reduced side effects in the Gl system, presumably due to H2S release, although the H2S release from thioamide is inefficient. To improve the H2S releasing capacity of ATB-346, compound 900 was made by reacting ATB-346 with chlorocarbonyl sulfenyl chloride reagent (see Scheme 9). The resultant compound 900 was then added to PBS containing GSH and CA. A promising H2S release was observed (see FIG. 16), which was not detected from ATB-346 under the identical conditions. This experiment indicates that compound 900 is a potent H2S donor and may have potential anti-inflammatory effects.
87% In tetrahydrofuran at 0 - 20℃; for 1.16667h;
  • 3
  • [ 2369985-58-8 ]
  • [ 1226895-20-0 ]
YieldReaction ConditionsOperation in experiment
With GLUTATHIONE In aq. phosphate buffer; dimethyl sulfoxide at 20℃; 15 Example 15 (0309) In this example, GSH-triggered H2S release from compound 900 was evaluated. ATB-346 has been demonstrated to exhibit promising anti-inflammatory effect with much reduced side effects in the Gl system, presumably due to H2S release, although the H2S release from thioamide is inefficient. To improve the H2S releasing capacity of ATB-346, compound 900 was made by reacting ATB-346 with chlorocarbonyl sulfenyl chloride reagent (see Scheme 9). The resultant compound 900 was then added to PBS containing GSH and CA. A promising H2S release was observed (see FIG. 16), which was not detected from ATB-346 under the identical conditions. This experiment indicates that compound 900 is a potent H2S donor and may have potential anti-inflammatory effects. (0310)
  • 4
  • [ 1226895-20-0 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation in experiment
With carbonic anhydrase from bovine erythrocytes; GLUTATHIONE; cetyltrimethylammonim bromide In aq. phosphate buffer at 20℃; for 4h; Enzymatic reaction;
  • 5
  • [ 619-57-8 ]
  • [ 22204-53-1 ]
  • [ 1226895-20-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 1 h / 0 °C 1.2: 3 h / 0 - 20 °C 2.1: Lawessons reagent / benzene / 4 h / 60 °C
  • 6
  • [ CAS Unavailable ]
  • [ 1226895-20-0 ]
YieldReaction ConditionsOperation in experiment
61% With Lawessons reagent In benzene at 60℃; for 4h; 1A.2 Step 2: Synthesis of 4-thiocarbamoylphenyl 2-(2-methoxynaphthalen-6- yl)propanoate 4-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate, 5 (1.80 g, 4.34 mmol) and Lawesson reagent (1.75 g, 4.34 mmol) were dissolved in 130 ml of anhydrous benzene. The reaction was warmed to 60° C. and stirred for 4 h. The solvent was removed under reduced pressure; the crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.75:0.25) to furnish 2.9 g of crude compound.[00188] The obtained compound was purified by a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5)) giving the pure compound 6 (970 mg, 61 % yield).[00189]1H NMR (DMSO-d6): 8 1.59 (d, 3H), 3.86 (s, 3H, OCH3), 4.24 (dd, 1 H), 7.06 (d, 2H), 7.18 (d, 1 H), 7.31 (s, 1 H), 7.50 (d,1 H), 7.84 (s, 1 H) 7.85 (d, 1 H), 7.86 (s, 1 H), 7.89 (d, 2H), 9.47 and 9.84 (s, 2H, NH2).13C NMR (DMSO-d6): 8 19.1 , 45.2, 55.9, 106.5, 119.6, 121.6, 126.6, 126.9, 128.0, 129.4, 129.9, 134.2, 135.6, 137.8, 153.4, 158.1 , 173.3, 199.7.[00190] MS (El), m/e 366 (M+); [00191] m.p.: 196-198° C
61% With Lawessons reagent In benzene at 60℃; for 4h; 1A.2 Step 2: Synthesis of 4-thiocarbamoylphenyl 2-(2-methoxynaphthalen-6- yl)propanoate 4-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate, 5 (1.80 g, 4.34 mmol) and Lawesson reagent (1.75 g, 4.34 mmol) were dissolved in 130 ml of anhydrous benzene. The reaction was warmed to 60° C. and stirred for 4 h. The solvent was removed under reduced pressure; the crude residue was purified by silica gel column (dichloromethane/methyl alcohol 9.75:0.25) to furnish 2.9 g of crude compound.[00188] The obtained compound was purified by a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5)) giving the pure compound 6 (970 mg, 61 % yield).[00189]1H NMR (DMSO-d6): 8 1.59 (d, 3H), 3.86 (s, 3H, OCH3), 4.24 (dd, 1 H), 7.06 (d, 2H), 7.18 (d, 1 H), 7.31 (s, 1 H), 7.50 (d,1 H), 7.84 (s, 1 H) 7.85 (d, 1 H), 7.86 (s, 1 H), 7.89 (d, 2H), 9.47 and 9.84 (s, 2H, NH2).13C NMR (DMSO-d6): 8 19.1 , 45.2, 55.9, 106.5, 119.6, 121.6, 126.6, 126.9, 128.0, 129.4, 129.9, 134.2, 135.6, 137.8, 153.4, 158.1 , 173.3, 199.7.[00190] MS (El), m/e 366 (M+); [00191] m.p.: 196-198° C
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