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[ CAS No. 2591-17-5 ] {[proInfo.proName]}

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Chemical Structure| 2591-17-5
Chemical Structure| 2591-17-5
Structure of 2591-17-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2591-17-5 ]

CAS No. :2591-17-5 MDL No. :
Formula : C11H8N2O3S2 Boiling Point : -
Linear Structure Formula :- InChI Key :BJGNCJDXODQBOB-SSDOTTSWSA-N
M.W : 280.32 Pubchem ID :92934
Synonyms :
Firefly luciferin;Beetle Luciferin;D-(-)-Luciferin

Calculated chemistry of [ 2591-17-5 ]

Physicochemical Properties

Num. heavy atoms : 18
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.18
Num. rotatable bonds : 2
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 75.29
TPSA : 136.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.49
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 1.57
Log Po/w (MLOGP) : 0.45
Log Po/w (SILICOS-IT) : 3.1
Consensus Log Po/w : 1.77

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -3.22
Solubility : 0.169 mg/ml ; 0.000601 mol/l
Class : Soluble
Log S (Ali) : -4.73
Solubility : 0.00524 mg/ml ; 0.0000187 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -2.51
Solubility : 0.866 mg/ml ; 0.00309 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.68

Safety of [ 2591-17-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2591-17-5 ]

* 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 [ 2591-17-5 ]

[ 2591-17-5 ] Synthesis Path-Downstream   1~73

  • 2
  • [ 349-46-2 ]
  • [ 939-69-5 ]
  • [ 2591-17-5 ]
  • 3
  • [ 32443-99-5 ]
  • [ 939-69-5 ]
  • [ 2591-17-5 ]
YieldReaction ConditionsOperation in experiment
22.76g With potassium carbonate; In methanol; for 8h;Inert atmosphere; Under an inert gas atmosphere, the 100 ml methanol is added to the above-mentioned product 1 in, stirring to dissolve, weighing D-cysteine hydrochloride monohydrate 23g (130.93mmol) is added to the above-mentioned system, lucifugous conditions adding anhydrous potassium carbonate 36.2g (261.86mmol), stirring 8 hours. After the reaction, the methanol is removed under reduced pressure, the concentration of 10percent aqueous solution of hydrochloric acid for pH adjustment system 2, a solid precipitated, filtered, the filter cake is washed with water 200 ml water back-washing 3 times, filtering the white solid obtained, the final product is obtained by freezing and drying 22.76g (93percent, m.p.187-188 °C, nuclear magnetism hydrogen spectrogram see Figure 2).
  • 7
  • [ 2591-17-5 ]
  • (S)-2-(6-Hydroxy-7-iodo-benzothiazol-2-yl)-4,5-dihydro-thiazole-4-carboxylic acid [ No CAS ]
  • 8
  • [ 2591-17-5 ]
  • D-(-)-2-(6'-hydroxy-7'-[123I]iodobenzothiazolyl)-Δ2-thiazoline-4-carboxylic acid [ No CAS ]
  • 9
  • [ 2591-17-5 ]
  • [ 145577-00-0 ]
  • C11(11)CH10N2O3S2 [ No CAS ]
  • 10
  • [ 918400-82-5 ]
  • [ 70-18-8 ]
  • 2-amino-4-[1-(carboxymethyl-carbamoyl)-2-(5-methyl-2-nitro-phenylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
  • [ 2591-17-5 ]
  • 11
  • [ 918400-81-4 ]
  • [ 70-18-8 ]
  • 2-amino-4-[1-(carboxymethyl-carbamoyl)-2-(4-methyl-2-nitro-phenylsulfanyl)-ethylcarbamoyl]-butyric acid [ No CAS ]
  • [ 2591-17-5 ]
  • 16
  • [ 2591-17-5 ]
  • 2-(6-acetoxy-benzothiazol-2-yl)-thiazole-4-carboxylic acid methyl ester [ No CAS ]
  • 17
  • [ 2591-17-5 ]
  • [ 63565-77-5 ]
  • 19
  • [ 91634-13-8 ]
  • [ 2591-17-5 ]
  • 23
  • C27H22N4O8S3 [ No CAS ]
  • C16H16N2O6S [ No CAS ]
  • [ 2591-17-5 ]
  • 24
  • [ 892402-96-9 ]
  • [ 2591-17-5 ]
  • [ 892402-99-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In water; at 4℃; for 4h; To an oven dried flask equipped with a stir bar and a Teflon cap under argon was added 2a (44.0 mg, 0.235 mmol), triphosgene (25.0 mg, 0.0842 mmol), and pyridine (18.0 mul, 0.222 mmol) in methylene chloride (3 ml) at room temperature. The solution remained clear. This was allowed to stir for 30 minutes then the solvent was evaporated in vacuo to afford a white bubbly solid. To this was added luciferin (30.0 mg, 94.3 mumol) and NaOH (547 mul of 0.5 M, 0.273 mmol) in water (3 ml) that had been chilled in brine and ice. The solution turned cloudy white, purple then cloudy yellow. The reaction was stirred for 4 hours at 4 C, quenched with 1% TFA and water (15 ml) and extracted three times with methylene chloride. The solvent was evaporated in vacuo the compound was purified using flash chromatography with 20% ethyl acetate, 1% acetic acid, and methylene chloride. The appropriate fractions were isolated then further purified by RP-HPLC. Appropriate fractions were lyophilized to afford a yellow solid (27 mg, 54.5 mumol, 58%), which was homogeneous (one spot) by TLC Rf = 0.4 (20% EtOAc, 1% acetic acid, DCM). 1H NMR (400 MHz, CDCl3) delta 8.59-8.58 (m, IH), 8.15 (d, IH5 J= 9 Hz), 7.85-7.77 (m, 3H), 7.36 (dd, IH, J = 9 Hz), 7.23-7.23 (m, IH), 5.46 (t, IH, J = 8.4 Hz), 4.55 (t, 2H, J= 8.4 Hz), 3.84-3.81 (m, 2H), 3.18 (t, 2H, J = 8.4 Hz). 13C NMR (500 MHz, CDCl3): delta 172.9, 167.5, 161.0, 159.2, 153.3, 151.3, 150.0, 148.8, 139.0, 137.9, 130.6, 125.6, 122.0, 121.2, 114.5, 78.2, 66.5, 37.3, 35.4. IR (thin film): 3350, 2952, 2360, 1761, 1587, 1448, 1418, 1201, 1196, 1043 cm'1. EI-MS (m/z): [M+l] calculated for Ci9Hi6N3O5S4493.9; (H+) found 493.9.
  • 25
  • [ 1186015-41-7 ]
  • [ 2591-17-5 ]
  • 26
  • [ 1186015-42-8 ]
  • [ 2591-17-5 ]
  • 27
  • [ 1186015-43-9 ]
  • [ 2591-17-5 ]
  • 28
  • [ 921-01-7 ]
  • [ 939-69-5 ]
  • [ 2591-17-5 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In water; at 20℃; for 3h; General procedure: The hydroxy- or methoxycarbonitrile derivative (1 eq) was added to the cysteine derivative (1.05 eq) and sodium carbonate (3 eq) in 5 ml water. The mixture was stirred at room temperature for three hours before addition of dilute HCl (1 M) to pH ? 3.5 - 4.0. The product was isolated by extraction with diethyl ether, washed by water, followed by evaporation
  • 29
  • [ 2591-17-5 ]
  • [ 676460-20-1 ]
YieldReaction ConditionsOperation in experiment
Luciferol: A suspension of <strong>[2591-17-5]D-luciferin</strong> free acid (0.43 g, 1.53 mmol) in THF (15 mL) was cooled in a -20 C. bath (dry ice-isopropanol). To the suspension was added dropwise via syringe a solution of borane-THF (1.8 mL of a 1 M solution in THF, 1.8 mmol). The pale yellow solution was allowed to warm to ambient temperature overnight (about 15 h) under nitrogen. Additional borane-THF (2.5 mL of a 1 M solution in THF, 2.5 mmol) was added and the reaction went an additional 24 h. The excess borane-THF was quenched by the addition of 10% aqueous acetic acid solution and the resulting bilayer was extracted with ethyl acetate (3×75 mL). Combined extracts were dried and evaporated to give an orange solid that was purified by chromatography on silica gel (70 g) using 4:1 dichloromethane-methanol. This operation separated the remaining <strong>[2591-17-5]D-luciferin</strong> free acid from a less polar product mixture. The less polar product mixture was separated by reverse-phase HPLC on a 1-inch Synergi 4mu MAX-RP 80A column (100×21.20 mm) using a methanol-water gradient. Appropriate fractions were pooled and evaporated to provide 10 mg (3% yield) of the desired product as a pale yellow solid. This product was 95.4% pure by HPLC analysis. MS (ESI-): m/z 264.4 (M-H)-; calc'd: 265.01.
  • 30
  • C17H24NO4Pol [ No CAS ]
  • [ 2591-17-5 ]
  • C28H30N3O6PolS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: A solution of amino acid monomer (1.25 mmol), 1-methylimidazole (75 muL, 0.75 mmol), and 1-(2-mesitylenesulfonyl)-3-nitro-1H-1,2,4-triazole (370 mg, 1.0 mmol) in DCM (3.75 mL) was stirred for 10 min at room temperature and added to Wang resin (338 mg, 0.2 mmol) in DCM. The suspension was vertexed for 2.5 h. The supernatant was removed and a fresh amino acid reaction solution was added to react for another 2.5 hr. The resin was then washed with DMF and DCM. The resin was treated with 25% piperidine in DMF for 30 min at room temperature twice to remove the Fmoc group. The resin was then washed with DMF and DCM. A solution of quinylylluciferin or luciferin (0.50 mmol), HOBt (74 mg, 0.55 mmol), HBTU (208 mg, 0.55 mmol), and DIPEA (175 muL, 1.0 mmol) in DCM (5.0 mL) was stirred for 30 min at room temperature and then added to the resin. The reaction mixture was vertexed for 3 h. After washing, the brown colored resin was treated with TFA/H2O/TIS (10 mL, 38/1/1) for 2 h. The supernatant was filtered and dried under reduced pressure to give the crude compound. The residue was purified by HPLC to give a yellow solid (52 mg, 60%): 1H NMR (300 MHz, DMSO-d6) delta 8.29 (m, 1 H), 7.99 (m, 3 H), 7.40 (m, 1 H), 7.24 (m, 1 H), 6.99 (m, 2 H), 6.69 (d, J = 8.4 Hz, 1 H), 6.56 (m, 1 H), 5.35 (m, 1 H), 4.45 (m, 2 H), 3.29 (dd, J = 11.1, 9.0 Hz, 1 H), 2.92 (m, 3 H); 13C NMR (500 MHz, DMSO-d6) delta 173.0, 172.5, 170.5, 157.6, 156.5, 156.4, 147.6, 147.4, 135.5, 131.3, 130.9, 130.6, 127.6, 115.3, 109.7, 109.0, 63.6; ESI-MS (ES+) m/z calcd for C22H19N3O5S 437.1, found 438.2 (M + H+); HRMS calcd for C22H20N3O5S (M+ + H+) 438.1123, found 438.1131.
  • 31
  • [ 2591-17-5 ]
  • C11H8N2O3S2*Mg(2+) [ No CAS ]
  • 32
  • [ 2591-17-5 ]
  • C11H8N2O3S2*Ca(2+) [ No CAS ]
  • 33
  • [ 2591-17-5 ]
  • Ba(2+)*C11H8N2O3S2 [ No CAS ]
  • 34
  • CoA [ No CAS ]
  • [ 2591-17-5 ]
  • [ 541-41-3 ]
  • dehydroluciferyl-coenzyme A [ No CAS ]
  • 35
  • [ 2591-17-5 ]
  • [ 56-65-5 ]
  • oxyluciferin [ No CAS ]
  • [ 61-19-8 ]
  • 39
  • [ 2591-17-5 ]
  • [ 67670-69-3 ]
  • luciferyl N-acetylneuraminic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% A solution of luciferin (365 mg, 1.3 mmol) in 1 M NaOH (1.2 mL) in a 100 mL four-necked flask was stirred for 10 min at 0 C under N2 in the dark. Then, the ice bath was removed and the reaction solution was allowed to warm up to the room temperature. Meanwhile a solution of the crude product iii and NaI·2H2O (242 mg, 1.3 mmol) in acetone (8 mL) was stirred at room temperature for 15 min, then, the mixture of iii and another 1 M NaOH (2.5 mL) were simultaneously added dropwise to the above solution of luciferin within 15 min to ensure pH 9-10. The mixture was saturated with nitrogen continuously and stirred for another 2 h in the dark, and evaporated to dryness under diminished pressure. The residue was dissolved in methanol (8 mL), and an addition of NaOH (2 mL) was added to the above mixture solution, which was kept stirring for 1 h. The reaction mixture was neutralized with 3 M HCl to pH 4.5-5.0 and then extracted with CH2Cl2 (15 mL * 3). The recovered water layer was purified by reverse phase HPLC (Rt = 13.6 min) and lyophilized to afford white powder 1 (491 mg, 43%). Mp 199-200 C. +160.7 (c 1.0, CH3OH. 1H NMR (600 MHz, CD3OD) delta 1.87-1.94 (m, 1H, H-3ax), 2.04 (s, 3H, NAc), 3.05 (d, 1H, J = 10.7 Hz, H-3eq), 3.57-3.59 (m, 1H, H-thiazolyl SCH2), 3.67-3.68 (m, 1H, H-thiazolyl SCH2), 3.77-3.92 (m, 7H, H-4, 5, 6, 7, 8, 9, 9'), 5.27-5.30 (m, 1H, H-thiazolyl NCH), 7.47 (d, 1H, J = 7.9 Hz, H-phenyl 5'), 7.91-7.96 (m, 2H, H-phenyl 4', 7'). 13C NMR (151 MHz, CD3OD) delta 23.18 (Me-NAc), 37.30 (thiazolyl SCH2), 43.38 (C-3), 54.64 (C-5), 65.07 (C-9), 69.91 (C-7), 70.85 (C-6), 73.77 (C-4), 75.84 (C-8), 82.39 (thiazolyl NCH), 104.90 (C-2), 115.73, 124.22, 125.46, 138.23, 151.20, 156.39, 162.01, 166.76 (phenyl and thiazolyl), 173.66 (CO-NAc), 176.09 (COOH). MS (m/z): 570.2 [M-H]-. Anal. Calcd for C22H25N3O11S2: C, 46.23; H, 4.41; N, 7.35; S, 11.22. Found: C, 46.36; H, 4.45; N, 7.31; S, 11.12.
  • 40
  • [ 1400692-83-2 ]
  • [ 2591-17-5 ]
  • luciferyl 4,7-di-O-methyl-N-acetylneuraminic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
28% To a solution of viii in acetone (15 mL) was added NaI·2H2O (483 mg, 2.6 mmol), and the mixture was stirred at room temperature for 15 min. Meanwhile, luciferin (730 mg, 2.6 mmol) was dissolved in 1 M NaOH (2.4 mL) in a 100 mL four-necked flask at 0 C under N2 in the dark. After 10 min, the ice bath was removed and the reaction solution was allowed to warm up to the room temperature. Then the above mixture of viii and 5 mL of 1 M NaOH were simultaneously added dropwise to the solution of luciferin within 25 min to make pH 9-10. The mixture was saturated continuously with nitrogen and stirred at room temperature for 2 h in the dark, then evaporated to dryness under diminished pressure. The addition of 1 M NaOH solution (4 mL) and methanol (15 mL) were added to the residue, which was kept stirring for another 1 h, and then neutralized with 3 M HCl to pH 4.5-5.0. The mixture was extracted with CH2Cl2 (30 mL * 3) to eliminate impurities. The product was purified by reverse phase HPLC (Rt = 22.4 min) and lyophilized to afford white powder 2 (436 mg, 28%). Mp 204-205 C. +167.7 (c 1.0, CH3OH)1H NMR (600 MHz, CD3OD) delta 1.78 (t, 1H, J = 11.8 Hz, H-3ax), 1.99 (s, 3H, NAc), 3.07 (dd, 1H, J = 12.2, 4.3 Hz, H-3eq), 3.30-3.32 (m, 3H, H-4, thiazolyl SCH2), 3.39-3.42 (m, 4H, OMe-7, H-7), 3.44 (s, 3H, OMe-4), 3.64 (dd, 1H, J = 11.4, 4.8 Hz, H-9'), 3.72 (d, 1H, J = 9.3 Hz, H-9), 3.84 (dd, 1H, J = 10.4, 1.0 Hz, H-8), 3.90 (s, 1H, H-6), 4.06-4.12 (m, 1H, H-5), 5.19 (t, 1H, J = 9.1 Hz, H-thiazolyl NCH), 7.41 (d, 1H, J = 8.9 Hz, H-phenyl 5'), 7.85 (s, 1H, H-phenyl 7'), 7.91 (d, 1H, J = 8.9 Hz, H-phenyl 4').13C NMR (151 MHz, CD3OD) delta 23.63 (Me-NAc), 37.80 (thiazolyl SCH2), 39.51 (C-3), 51.88 (C-5), 57.80 (OMe-4), 61.61 (OMe-7), 64.43 (C-9), 73.63 (C-7), 75.17 (C-6), 80.45 (C-8), 80.90 (C-4), 83.67 (thiazolyl NCH), 104.95 (C-2), 115.39, 123.93, 125.39, 138.18, 151.07, 156.35, 162.20, 165.95 (phenyl and thiazolyl), 173.97 (CO-NAc), 178.01 (COOH). MS (m/z): 598.2 [M-H]-. Anal. Calcd for C24H29N3O11S2: C, 48.07; H, 4.87; N, 7.01; S, 10.69. Found: C, 48.10; H, 4.89; N, 7.04; S, 10.64.
  • 41
  • [ 1622311-98-1 ]
  • [ 2591-17-5 ]
YieldReaction ConditionsOperation in experiment
With water; 3-morpholinosydnonymine; 2-amino-2-hydroxymethyl-1,3-propanediol; In aq. buffer; at 37℃; for 1h;pH 8.5;Kinetics; General procedure: Example 4: Bioluminescence[0090] Figure 1 shows plots of total bioluminescence upon treatment of PCL-1 or PCL-F (5 muMu) with a minimal amount of SIN-1 (2.5 muMu) or H202(25 muMu) for 60 minutes at 37C. Recombinant luciferase was added to the reaction mixture and bioluminescence was detected at 612 nm for 60 minutes. D-Luciferin (5 muMu) was used as a determinant of maximum yield. Figure 1 demonstrates that PCL-F is resistant to hydrolysis in comparison to PCL-1 , and when subject to trace amounts of oxidant, and is more selective than PCL-1 in detecting peroxynitrite vs. hydrogen peroxide.[0091] Figure 2 shows kinetic plots of formation of D-Luciferin (measured by absorbance at 385 nm) upon treatment of 5 muMu PCL-1 (Figure 2A) or PCL-F (Figure 2B) in TBS, pH 8.5, at 37C with 100 muMu SIN-1 or H202over the course of 90 minutes. Figures 2C and 2D show the maximum yield of D-Luciferin obtained upon treatment of 5 muMu PCL-1 or PCL-F, respectively, with 100 muMu SIN-1 or H202in the presence of increasing concentrations of glutathione (a competing scavenger of peroxynitrite) over the course of 90 minutes. Little reactivity with H202was observed with PCL-F compared to PCL-1. In addition, reactivity of PCL-F with SIN-1 was retained until concentrations of 1 -5 mM glutathione were used.These data demonstrate remarkable selectivity improvement in PCL-F over PCL-1 in detection of peroxynitrite over hydrogen peroxide, as well as fast enough reactivity to achieve significant conversion to D-Luciferin in the presence of milieu competition such as active thiols. While it was expected that a decrease in overall reactivity would be observed in PCL-F over PCL-1 , it was surprising that introduction of an electron-withdrawing fluorine atom in the aryl ring of the boronic acid resulted in a compound with ablated reactivity with hydrogen peroxide, yet still detected peroxynitrite in the presence of biologically relevant amounts of competing thiols (glutathione).
  • 42
  • (S)-2-(6-(4-boronobenzyloxy)benzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid [ No CAS ]
  • [ 2591-17-5 ]
YieldReaction ConditionsOperation in experiment
With water; 3-morpholinosydnonymine; 2-amino-2-hydroxymethyl-1,3-propanediol; In aq. buffer; at 37℃; for 1.5h;pH 8.5;Kinetics; General procedure: Example 4: Bioluminescence[0090] Figure 1 shows plots of total bioluminescence upon treatment of PCL-1 or PCL-F (5 muMu) with a minimal amount of SIN-1 (2.5 muMu) or H202(25 muMu) for 60 minutes at 37C. Recombinant luciferase was added to the reaction mixture and bioluminescence was detected at 612 nm for 60 minutes. D-Luciferin (5 muMu) was used as a determinant of maximum yield. Figure 1 demonstrates that PCL-F is resistant to hydrolysis in comparison to PCL-1 , and when subject to trace amounts of oxidant, and is more selective than PCL-1 in detecting peroxynitrite vs. hydrogen peroxide.[0091] Figure 2 shows kinetic plots of formation of D-Luciferin (measured by absorbance at 385 nm) upon treatment of 5 muMu PCL-1 (Figure 2A) or PCL-F (Figure 2B) in TBS, pH 8.5, at 37C with 100 muMu SIN-1 or H202over the course of 90 minutes. Figures 2C and 2D show the maximum yield of D-Luciferin obtained upon treatment of 5 muMu PCL-1 or PCL-F, respectively, with 100 muMu SIN-1 or H202in the presence of increasing concentrations of glutathione (a competing scavenger of peroxynitrite) over the course of 90 minutes. Little reactivity with H202was observed with PCL-F compared to PCL-1. In addition, reactivity of PCL-F with SIN-1 was retained until concentrations of 1 -5 mM glutathione were used.These data demonstrate remarkable selectivity improvement in PCL-F over PCL-1 in detection of peroxynitrite over hydrogen peroxide, as well as fast enough reactivity to achieve significant conversion to D-Luciferin in the presence of milieu competition such as active thiols. While it was expected that a decrease in overall reactivity would be observed in PCL-F over PCL-1 , it was surprising that introduction of an electron-withdrawing fluorine atom in the aryl ring of the boronic acid resulted in a compound with ablated reactivity with hydrogen peroxide, yet still detected peroxynitrite in the presence of biologically relevant amounts of competing thiols (glutathione).
  • 44
  • [ 2591-17-5 ]
  • [ 68957-94-8 ]
  • C20H28N2O9P3S2(1-) [ No CAS ]
  • 46
  • [ 67-56-1 ]
  • [ 2591-17-5 ]
  • [ 73918-26-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; at 20℃; for 1h; General procedure: The condensation product (1,3-thiazole-4-carboxylic acid derivative) was dissolved in methanol before thionyl chloride was added. The reaction mixture was stirred for 1h before the product was recovered under vacuum.
  • 47
  • [ 2591-17-5 ]
  • [ 61-19-8 ]
  • D-luciferyl adenylate [ No CAS ]
  • [ 17002-50-5 ]
  • 48
  • [ 2591-17-5 ]
  • [ 36727-10-3 ]
  • C12H10N2O5S2 [ No CAS ]
  • [ 73918-27-1 ]
  • 49
  • [ 2591-17-5 ]
  • 4-hydroxyluciferin [ No CAS ]
  • 50
  • [ 2591-17-5 ]
  • 4-hydroxyluciferin [ No CAS ]
  • 4-hydroxyluciferyl adenylate [ No CAS ]
  • 51
  • [ 939-69-5 ]
  • C14H12N2O4S2 [ No CAS ]
  • C14H14N2O5S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 52
  • 2-cyano-6-(3-butenyloxy)benzothiazole [ No CAS ]
  • C14H12N2O4S2 [ No CAS ]
  • C14H14N2O5S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 53
  • 2-cyano-6-(3-butenyloxy)benzothiazole [ No CAS ]
  • [ 2591-17-5 ]
  • 54
  • C15H14N2O3S2 [ No CAS ]
  • C14H12N2O4S2 [ No CAS ]
  • C14H14N2O5S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 55
  • C15H14N2O3S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 56
  • C18H13N3O5S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 57
  • [ 73918-26-0 ]
  • [ 2591-17-5 ]
  • 58
  • [ 2591-17-5 ]
  • [ 20115-09-7 ]
  • [ 17002-50-5 ]
  • 59
  • benzoylhydrazine luciferin [ No CAS ]
  • [ 2591-17-5 ]
  • 60
  • [ 2591-17-5 ]
  • [ 18107-18-1 ]
  • [ 73918-26-0 ]
  • 61
  • C22H22N2O5S3 [ No CAS ]
  • [ 2591-17-5 ]
  • 62
  • C15H16N2O4S3 [ No CAS ]
  • [ 2591-17-5 ]
  • 63
  • 4-(bromomethyl)phenyl 2-methylpropane-2-sulfinate [ No CAS ]
  • [ 2591-17-5 ]
  • C22H22N2O5S3 [ No CAS ]
  • 64
  • [ 31562-43-3 ]
  • [ 2591-17-5 ]
  • C15H16N2O4S3 [ No CAS ]
  • 65
  • C26H25N5O4S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 66
  • C23H21N5O2S [ No CAS ]
  • [ 2591-17-5 ]
  • 67
  • acrylic ester luciferin [ No CAS ]
  • [ 2591-17-5 ]
  • 68
  • C18H14N2O4S2 [ No CAS ]
  • [ 2591-17-5 ]
  • 69
  • [ 52-89-1 ]
  • [ 939-69-5 ]
  • [ 2591-17-5 ]
YieldReaction ConditionsOperation in experiment
86% D-Cysteine hydrochloride monohydrate (30.0 mg, 0.171 mmcl, 1.04 eq) and 2-cyano-6-hydroxy- benzothiazole (29.0 mg, 0.163 mmol, 1 eq) were dissolved in 2:1 MeOH:H20 (1 mL). The resultingsolution was allowed to stir at room temperature for 5 mm under a nitrogen atmosphere, after which potassium carbonate (23.0 mg, 0.164 mmol 1.01 eq) was added. The resulting bright yellow-green solution was allowed to stir for an additional 20 mm, at room temperature, while maintaining the inert atmosphere. Upon consumption of <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong>, as evidenced by TLC analysis, the methanol was removed in vacuo and the remaining aqueoussolution cooled to 0 °C and acidified to pH 3 with 3 M HCI. The aqueous layer was then extracted with EtOAc (5 x 10 mL) and the combined organ ics were dried over Na2SO4, filtered, concentrated in vacuo and purified with column chromatography 3:6:1 DCM:EtOAc:MeOH to provide D-luciferin as a pale yellow solid (39.0 mg, 86 percent). [c]ObS = 290, DMF, c = 1 ([a]1. = -34°, DMF, c = 1). Mp:197-199°C (lit. 196 °C).3 1H-NMR (400 MHz, MeOD) (57.93 (1H, d, J= 8.9 Hz, H-7), 7.35 (iH, d,J= 2.3 Hz, H-b), 7.10 (1H, dd, J= 8.9, 2.3 Hz, H-8), 5.40 (iH, appt, J= 9.0 Hz, H-2), 3.79 (2H, m, H-3) ppm. 13C-NMR (100.6 MHz, CDCI3) oe 172.1 (C-i), 166.2 (C-4), 157.6 (C-9), 157.1 (C-5), 146.8 (C-6), 137.7 (C-il), 124.5 (C-7), 116.8 (C-b), 105.9 (C-8), 78.2 (C-2), 34.5 (C-3) ppm. HAMS (ESI+): m/zCalculated for C11H8N20352 [M+Na] 302.9874, found 302.9868.
80% With potassium carbonate; In methanol; dichloromethane; water; for 0.166667h;Cooling with ice; <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong> (100 mg, 0.57 mmol) was dissolved in DCM:MeOH = 2:3 (10 mL: 15 mL).And pass N2 to the solution.D-cysteine hydrochloride (136 mg, 0.86 mmol) and K2CO3 (119 mg, 0.86 mmol) were dissolved in DI H2O:MeOH = 1:1 (3 mL).The solution was added dropwise to the above <strong>[939-69-5]2-cyano-6-hydroxybenzothiazole</strong>, and the reaction was carried out in the ice bath for 10 min.After the reaction was completed, DCM and MeOH were distilled off under reduced pressure.The pH was then adjusted to 2-3 with a solution of hydrochloric acid (1M) and a yellow precipitate precipitated.The precipitate was filtered and washed with DI H 2 O until the pH became neutral to give D-luciferin crude product.By column chromatography (silica, DCM: MeOH: AcOH, 10:1:1 v/v/v)Purification gave 128 mg of a pale yellow solid.The yield was 80percent.
  • 70
  • [ 2591-17-5 ]
  • [ 70-34-8 ]
  • C17H10N4O7S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25℃; for 2h; <strong>[2591-17-5]D-luciferin</strong> (50 mg, 0.18 mmol), 2,4-dinitrofluorobenzene (49.8 mg, 0.27 mmol) and DIPEA (23 mg, 0.18 mmol) were dissolved in anhydrous CH2Cl2 (15 mL).The reaction was carried out at 25 C for 2 h.The solvent was distilled off under reduced pressure to give a crude yellow material.The crude product was purified by column chromatography (silica, DCM:MeOH, 60:1 v/v)Purification gave 24 mg of a white solid.The yield was 30%.
  • 71
  • C25H16N2O5S3 [ No CAS ]
  • [ 2591-17-5 ]
  • 73
  • [ 2591-17-5 ]
  • [ 116271-34-2 ]
  • C19H15N3O5S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Ca. 69.4% Compound 1 (1 mmol) was dissolved in dry dichloromethane (10 mL, the solution was pale yellow), and manganese dioxide (1.2 mmol) was added under stirring at -20 C. After stirring for 1 hour, the manganese dioxide. was filtered off. Collect the filtrate (red) and set aside. Take the compound of formula II (<strong>[2591-17-5]D-luciferin</strong>, 0.4 mmol) was dissolved in methanol - dichloromethane mixture (12 mL, a volume ratio of 1: 1) was stirred under an ice bath, added to the above filtrate, the reaction was stirred overnight, TLC the The reaction was complete after concentration under reduced pressure, silica gel column chromatography (ethyl acetate / petroleum ether = 1 / 6-1 / 4) gave a white solid (119mg, yielding about 69.4%).
Same Skeleton Products
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