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[ CAS No. 72033-13-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 72033-13-7
Chemical Structure| 72033-13-7
Chemical Structure| 72033-13-7
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Product Details of [ 72033-13-7 ]

CAS No. :72033-13-7 MDL No. :MFCD11040749
Formula : C11H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :FBDXNIMSTUCEIF-UHFFFAOYSA-N
M.W : 187.19 Pubchem ID :53403762
Synonyms :

Calculated chemistry of [ 72033-13-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 53.29
TPSA : 50.19 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : 1.78
Log Po/w (WLOGP) : 1.86
Log Po/w (MLOGP) : 1.1
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 1.64

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -2.52
Solubility : 0.567 mg/ml ; 0.00303 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.661 mg/ml ; 0.00353 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.48
Solubility : 0.062 mg/ml ; 0.000331 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.55

Safety of [ 72033-13-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 72033-13-7 ]

* 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 [ 72033-13-7 ]

[ 72033-13-7 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 69391-35-1 ]
  • [ 72033-13-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: C11H9NO3 With trichlorophosphate Stage #2: Stage #3: With sodium hydrogencarbonate
  • 2
  • [ 72033-13-7 ]
  • [ 63463-06-9 ]
  • [ 1236037-34-5 ]
YieldReaction ConditionsOperation in experiment
70% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; Molecular sieve; Cooling with ice; Inert atmosphere; 1.2 General procedure for amide coupling/hydrolysis reaction. General procedure: On an ice-water bath, to thesolution of acid (3 eq) in anhydrous DMF (7 mL), was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI, 3 equiv), hydrobenzotriazole (HOBt, 3 equiv), 4 Åmolecular sieves, and TEA (8.0 eq) with N2 protection. Fifteen minutes later, a solution of 6α-naltrexamine hydrochloride (12, 1.0 eq) in DMF (5 mL) was added dropwise. The resultedmixture was allowed to warm up to ambient temperature gradually. Upon completion of thereaction, the mixture was then filtered through celite. The filtrate was concentrated to removeDMF. Methanol (10 mL), and K2CO3 (3 eq) were then added to the residue and stirred at ambient temperature overnight. The mixture was then filtered through celite again. The filtrate wasconcentrated to remove methanol. The residue was partitioned between CH2Cl2 (50 mL) and brine (50 mL). The organic layer was separated and dried over anhydrous MgSO4, concentratedunder reduced pressure. The residue was then purified by column chromatography, eluting withCH2Cl2/MeOH (1% NH3·H2O) to afford the corresponding compound as free base. Uponconfirmation by 1H NMR and 13C NMR, the free base was then transformed into hydrochloridesalt by dissolving in MeOH (0.1 mL) and DCM (2 mL), adding HCl methanol solution (1.25 M,4 eq) with an ice-water bath, and stirred for 5 min. Diethyl ether (10 mL) was then added. Twohours later, the precipitate was collected by filtration, dried in vacuum to give the targetcompound as hydrochloride salt, which was used in the HPLC, LC-MS, and elemental analysis.1.3 Experimental procedures1.3.1 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-[2-(isoquinolin-3-yl)acetamido)morphinan (1). The title compound was prepared following the general procedure1.2 in 70% yield. Hydrochloride salt: 1H NMR (400 MHz, DMSO-d6) 9.67 (s, 1H), 9.31 (brs,1H, exchangeable), 8.84 (brs, 1H, exchangeable), 8.37 (d, J = 8.56 Hz, 1H), 8.33 (d, J = 8.04 Hz,1H), 8.178.15 (m, 2H), 8.04 (t, J = 7.58 Hz, 1H), 7.87 (t, J = 7.46 Hz, 1H), 6.75 (d, J = 8.12 Hz,1H), 6.58 (d, J = 8.16 Hz, 1H), 6.29 (brs, 1H), 4.64 (d, J = 3.88 Hz, 1H), 4.45 (m, 1H), 4.06 (s,2H), 3.90 (d, J = 6.64 Hz, 1H), 3.34 (d, J = 19.96 Hz, 1H), 3.26 (m, 1H), 3.092.97 (m, 2H),2.94 (m, 1H), 2.70 (m, 1H), 2.43 (m, 1H), 1.87 (m, 1H), 1.62 (m, 1H), 1.501.35 (m, 2H),1.080.95 (m, 2H), 0.67 (m, 1H), 0.61 (m, 1H), 0.47 (m, 1H), 0.39 (m, 1H); 13C NMR (100 MHz,DMSO-d6) δ 169.19, 148.48, 147.37, 141.37, 140.74, 140.50, 138.04, 131.87, 131.35, 130.11,128.49, 127.87, 126.71, 123.43, 121.08, 119.65, 89.12, 71.00, 63.70, 59.21, 47.52, 47.17, 47.11,40.01, 31.67, 30.62, 25.02, 21.02, 6.86, 6.24, 3.42. MS m/z found 512.2699 (M + H)+. IR (Diamond, cm-1) νmax 3232.8, 1651.9, 1615.6, 1236.4, 1117.6, 765.6, 747.5. mp 203 °C dec.
70% Stage #1: 2-(isoquinolin-3-yl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 0.25h; Cooling with ice; Molecular sieve; Inert atmosphere; Stage #2: alpha-Naltrexamine dihydrochloride at 20℃; Cooling with ice; Stage #3: With potassium carbonate In methanol at 20℃; 17-Cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-[2-(isoquinolin-3-yl)acetamido)morphinan (1) General procedure: On an ice-water bath, to the solution of acid (3equiv, prepared in house, see Supplementary data for details) in anhydrous DMF (7mL), was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 3equiv), hydrobenzotriazole (HOBt, 3equiv), 4Å molecular sieves, and TEA (8.0equiv) under N2 protection. Fifteen minutes later, a solution of 6α-naltrexamine hydrochloride (19, 1.0equiv) in DMF (5mL) was added dropwise. The resulted mixture was allowed to warm up to ambient temperature gradually. Upon completion of the reaction, the mixture was then filtered through celite. The filtrate was concentrated to remove DMF. Methanol (10mL), and K2CO3 (3equiv) were then added to the residue and stirred at ambient temperature overnight. The mixture was then filtered through celite again. The filtrate was concentrated to remove methanol. The residue was partitioned between CH2Cl2 (50mL) and brine (50mL). The organic layer was separated and dried over anhydrous MgSO4, concentrated under reduced pressure. The residue was then purified by column chromatography, eluting with CH2Cl2/MeOH (1% NH3·H2O) to afford the corresponding compound as free base. Upon confirmation of the structure by 1H NMR and 13C NMR, the compound was then transformed into hydrochloride salt by dissolving the free base in MeOH (0.1mL) and DCM (2mL), adding HCl methanol solution (1.25M, 4equiv) under an ice-water bath, and stirred for 5min. Diethyl ether (10mL) was then added. Two hours later, the precipitate was collected by filtration, dried in vacuum to give the target compound as hydrochloride salt, which was then used in the HPLC, LC-MS, elemental analysis, and biological screenings. The title compound was prepared in 70% yield. Hydrochloride salt: 1H NMR (400MHz, DMSO-d6) δ 9.67 (s, 1H), 9.31 (br s, 1H, exchangeable), 8.84 (br s, 1H, exchangeable), 8.37 (d, J=8.56Hz, 1H), 8.33 (d, J=8.04Hz, 1H), 8.17-8.15 (m, 2H), 8.04 (t, J=7.58Hz, 1H), 7.87 (t, J=7.46Hz, 1H), 6.75 (d, J=8.12Hz, 1H), 6.58 (d, J=8.16Hz, 1H), 6.29 (br s, 1H), 4.64 (d, J=3.88Hz, 1H), 4.45 (m, 1H), 4.06 (s, 2H), 3.90 (d, J=6.64Hz, 1H), 3.34 (d, J=19.96Hz, 1H), 3.26 (m, 1H), 3.09-2.97 (m, 2H), 2.94 (m, 1H), 2.70 (m, 1H), 2.43 (m, 1H), 1.87 (m, 1H), 1.62 (m, 1H), 1.50-1.35 (m, 2H), 1.08-0.95 (m, 2H), 0.67 (m, 1H), 0.61 (m, 1H), 0.47 (m, 1H), 0.39 (m, 1H); 13C NMR (100MHz, DMSO-d6) δ 169.19, 148.48, 147.37, 141.37, 140.74, 140.50, 138.04, 131.87, 131.35, 130.11, 128.49, 127.87, 126.71, 123.43, 121.08, 119.65, 89.12, 71.00, 63.70, 59.21, 47.52, 47.17, 47.11, 40.01, 31.67, 30.62, 25.02, 21.02, 6.86, 6.24, 3.42. HRMS m/z found 512.2699, calculated 512.2544 (M+H)+. IR (Diamond, cm-1) νmax 3232.8, 1651.9, 1615.6, 1236.4, 1117.6, 765.6, 747.5. Mp 203°C dec.
  • 3
  • [ 72033-13-7 ]
  • [ 63463-06-9 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-[2-(isoquinolin-3-yl)acetamido]morphinan hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 20 °C / Molecular sieve; Cooling with ice; Inert atmosphere 2: hydrogenchloride / methanol; dichloromethane / 0.08 h / Cooling with ice
  • 4
  • [ 1125-80-0 ]
  • [ 72033-13-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / Reflux 2: sodium iodide / ethanol; water / 1 h / 100 °C 3: sodium hydroxide / ethanol / 1 h / Reflux
Multi-step reaction with 3 steps 1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / Reflux 2: sodium iodide / ethanol; water / 1 h / 100 °C 3: sodium hydroxide / ethanol; water / 1 h / Reflux
  • 5
  • [ 54804-44-3 ]
  • [ 72033-13-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium iodide / ethanol; water / 1 h / 100 °C 2: sodium hydroxide / ethanol / 1 h / Reflux
Multi-step reaction with 2 steps 1: sodium iodide / ethanol; water / 1 h / 100 °C 2: sodium hydroxide / ethanol; water / 1 h / Reflux
  • 6
  • [ 58130-44-2 ]
  • [ 72033-13-7 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In ethanol for 1h; Reflux; 2-(Isoquinolin-3-yl)acetic acid (13). The 15 (237 mg, 1.41 mmol) in EtOH (6 mL) and 2 NNaOH (4.2 mL) was refluxed for 1 h. After cooled down, the mixture was concentrated toremove most of the EtOH, and adjusted pH to 3 with 6 N HCl. The resultant mixture was driedunder reduced pressure. To the residue was added EtOH (20 mL) and refluxed for 5 min. Then itwas subjected to hot filtration. The collected solid was added EtOH (20 mL) and subjected torefluxing and hot filtration twice. The combined filtration was concentrated and crystallized withMeOH/EtOH to give light yellow solid in quantitative yield. 1H NMR (400 MHz, DMSO-d6) 1312.48 (brs, 1H), 9.24 (s, 1H), 8.10 (d, J = 8.12 Hz, 1H), 7.92 (d, J = 8.24 Hz, 1H), 7.787.75 (m,2H), 7.64 (m, 1H), 3.86 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 172.16, 151.78, 148.92,135.72, 130.60, 127.42, 127.00, 126.87, 126.16, 119.46, 43.44. MS m/z found 188.0866 (M +H)+. IR (Diamond, cm-1) νmax 1705.7, 1224.6, 1164.6, 974.0, 757.0. mp 180 - 181 °C.
100% With sodium hydroxide In ethanol; water for 1h; Reflux; 2-(Isoquinolin-3-yl)acetic acid (20) Compound 22 (237 mg, 1.41 mmol) in EtOH (6mL) and 2 N NaOH (4.2 mL) was refluxed for 1 h. After cooled down, the mixturewas concentrated to remove most of the EtOH, and adjusted pH to 3 with 6 N HCl.The resultant mixture was dried under reduced pressure. To the residue wasadded EtOH (20 mL) and refluxed for 5 min. Then it was subjected to hotfiltration. The collected solid was added EtOH (20 mL) and subjected torefluxing and hot filtration twice. The combined filtration was concentratedand crystallized with MeOH/EtOH to give light yellow solid in quantitativeyield. 1H NMR (400 MHz, DMSO-d6)d 12.48 (brs, 1H), 9.24 (s,1H), 8.10 (d, J = 8.12 Hz, 1H), 7.92 (d, J = 8.24 Hz, 1H), 7.78-7.75 (m, 2H), 7.64 (m, 1H),3.86 (s, 2H); 13C NMR (100 MHz, DMSO-d6) δ 172.16,151.78, 148.92, 135.72, 130.60, 127.42, 127.00, 126.87, 126.16, 119.46, 43.44. MSm/z found188.0866 (M + H)+. IR(Diamond, cm-1) νmax 1705.7, 1224.6, 1164.6, 974.0, 757.0. mp 180-181°C
  • 7
  • [ 72033-13-7 ]
  • [ 63463-06-9 ]
  • 17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6α-[2-(isoquinolin-3-yl)acetamido]morphinan hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / N,N-dimethyl-formamide / 0.25 h / Cooling with ice; Molecular sieve; Inert atmosphere 1.2: 20 °C / Cooling with ice 1.3: 20 °C 2.1: hydrogenchloride / methanol; dichloromethane / 0.08 h / Cooling with ice
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