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CAS No. : | 2715-70-0 | MDL No. : | MFCD18843695 |
Formula : | C9H13N5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BKXMJMZKKNIYRD-UHFFFAOYSA-N |
M.W : | 191.23 g/mol | Pubchem ID : | 75929 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.44 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 55.41 |
TPSA : | 69.62 Ų |
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) : | -6.58 cm/s |
Log Po/w (iLOGP) : | 1.84 |
Log Po/w (XLOGP3) : | 1.25 |
Log Po/w (WLOGP) : | 1.22 |
Log Po/w (MLOGP) : | 0.56 |
Log Po/w (SILICOS-IT) : | 0.64 |
Consensus Log Po/w : | 1.1 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.09 |
Solubility : | 1.55 mg/ml ; 0.00811 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.31 |
Solubility : | 0.936 mg/ml ; 0.00489 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.59 |
Solubility : | 0.496 mg/ml ; 0.00259 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.95 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
GHS Pictogram: |
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* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ethanol; ammonia |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With pyridine In dichloromethane for 2h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; | |
85% | With potassium carbonate In N,N-dimethyl-formamide at 20℃; | |
85% | With potassium carbonate In N,N-dimethyl-formamide |
81% | With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 96h; Inert atmosphere; | |
64% | Stage #1: adenine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 1-bromo-butane In N,N-dimethyl-formamide at 20℃; Inert atmosphere; | 4.1.1.1 General procedure used for preparing 9-alkylated adenine General procedure: To a suspension of adenine in dry DMF, NaH (1.1equiv) was added under argon. The mixture was stirred at rt for 1h then the alkylating agent (1.05equiv) was added and the mixture was stirred until complete reaction. |
With sodium hydride 1.) DMF, 1 h, 2.) DMF, 16 h; Yield given. Multistep reaction; | ||
With potassium carbonate In dimethyl sulfoxide at 23℃; for 48h; | 2.7 Synthesis of n-butyl adenine (nBA) guest molecule Adenine (6.05 g, 44.8 mmol), 1-bromobutane (6.16 g, 45.0 mmol), potassium carbonate (8.33 g, 60.3 mmol), and DMSO (60 mL) were added to a 250-mL round-bottomed flask. The resulting solution was stirred for 48 h at 23 °C and then poured into 600 mL water. The aqueous solution was extracted three times with 100 mL DCM and then the organic layer was washed three times with 100 mL water. The organic layer was dried over magnesium sulfate and concentrated in vacuo to obtain a solid. The product was obtained as a white solid after recrystallization from chloroform:hexanes. 1H NMR (400 MHz, CDCl3): 0.96 ppm (t, 3H, Ha), 1.37 ppm (m, 2H, Hb), 1.88 ppm (p, 2H, Hc), 4.20 ppm (t, 2H, Hd), 5.67 ppm (s, 2H, He), 7.79 ppm (s, 1H, Hf), 8.37 ppm (s, 1H, Hg) (Fig. S5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; tert-butylhypochlorite In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | In pyridine at 100℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride 1.) reflux, 0.5 h, 2.) pyridine, 90 deg C, 1 h; Yield given; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | With bromine; sodium acetate; acetic acid In tetrahydrofuran; methanol at 20℃; for 0.5h; | |
41% | With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 40h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With caesium carbonate In N,N-dimethyl-formamide for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
9% | Stage #1: 9-butyladenine With sodium hydride In tetrahydrofuran for 3h; Heating; Stage #2: 9,1-bis(chloromethyl)anthracene In tetrahydrofuran for 10h; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: 9-butyladenine With sodium hydride In tetrahydrofuran for 3h; Heating; Stage #2: anthracenylmethyl chloride In tetrahydrofuran for 6h; Heating; Further stages.; | |
60% | With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 78 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 86 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 77 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 72 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 75 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 73 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 79 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 80 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 76 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 80 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 81 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 81 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 77 percent / HOAc; Br2; NaOAc / tetrahydrofuran; methanol / 0.5 h / 20 °C 2.1: potassium tert-butoxide / dimethylformamide / 0.25 h / 20 °C 2.2: 78 percent / dimethylformamide / 6 h / 130 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) t-BuOCl; 2.) aq. NaOH / methanol 2: (DHQ)2PHAL, K2OsO2(OH)4 / methanol; propan-1-ol / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) t-BuOCl; 2.) aq. NaOH / methanol 2: (DHQ)2PHAL, K2OsO2(OH)4 / methanol; propan-1-ol / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) t-BuOCl; 2.) aq. NaOH / methanol 2: (DHQ)2PHAL, K2OsO2(OH)4 / methanol; propan-1-ol / 50 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With caesium carbonate In N,N-dimethyl-formamide at 50℃; | |
51% | With caesium carbonate In N,N-dimethyl-formamide at 50℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | In tetrahydrofuran Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With copper(I) bromide; Trimethylacetic acid In dimethyl sulfoxide at 130℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | In water at 50℃; for 48h; Inert atmosphere; | 4.1.2.1 General procedure used for preparing methylglyoxal adducts General procedure: To the commercial concentrated aqueous solution of methylglyoxal (MG) (40%) (8equiv), the α-aminoazaheterocycle was added. In some cases, the reaction mixture was diluted by addition of water. Argon was flushed through the solution and the mixture was heated at 50°C until complete reaction under argon. After evaporation under reduced pressure, the residue was chromatographed on Sep-Pak C18 cartridges (10g) eluting with H2O and then H2O-MeOH (95:5) giving the major isomers adducts a except for compound 17, which for the two isomers were isolated. Compounds 15a, 17a, 18a, and 21a were also crystallized from propan-2-ol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 9-butyladenine; dimethylsulfide With N-chloro-succinimide In dichloromethane at -20 - 20℃; for 2h; Stage #2: With sodium methylate In methanol; dichloromethane at 20℃; for 0.166667h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: N-chloro-succinimide / dichloromethane / 2 h / -20 - 20 °C 1.2: 0.17 h / 20 °C 2.1: dichloro(2-picolinato)gold(III) / toluene / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With trans-bis(triphenylphosphine)palladium dichloride; caesium carbonate; triphenylphosphine In toluene at 110℃; Inert atmosphere; | 2.2.2. Synthesis of 1 Compound 4 (0.1 g, 0.30 mmol), 9-butyl adenine (0.058 g,0.3 mmol), Cs2CO3 (0.49 g, 1.50 mmol), PdCl2(PPh3)2 (0.06 g,0.09 mmol) and PPh3 (0.05 g, 0.19 mmol) were taken in a 50 mL twonecked round bottom flask and 20 mL dry toluene was added. Theflask was vacuumed and purged with dry nitrogen under stirring [11].Then the reaction mixture was allowed to reflux at 110 °C under N2 atmospherefor 8 h. The reactionmixturewas cooled to roomtemperaturefollowed by addition of H2O.The aqueous partwas extractedwith CHCl3for two times (2 × 50 mL). The organic parts were collected and driedover anhydrous Na2SO4. The solvent was evaporated under vacuum toobtain crude productwhichwas further purified by column chromatographyusing petroleum ether and ethyl acetate in 3:2 (v/v) ratio as eluent.Compound 1 (0.045 g, yield 45%, m.p: 160 °C) was obtained asyellow powder. 1H NMR (d6-DMSO, 400 MHz): δ 10.47 (s, 1H),8.57-8.49 (m, 3H), 8.42 (s, 1H), 8.37 (s, 1H), 8.15 (d, 1H, J = 8 Hz),7.82 (t, H, J = 8 Hz), 4.24 (t, 2H, J = 8 Hz), 4.07 (t, 2H, J = 8 Hz),1.88-1.80 (m, 2H), 1.67-1.60 (m, 2H), 1.39-1.34 (m, 4H), 1.31-1.25(m, 6H); 13C NMR (d6-DMSO, 100 MHz) δ: 163.9, 163.4, 152.8, 152.1,151.1, 143.1, 142.2, 131.7, 131.3, 130.8, 128.9, 126.7, 126.5, 122.6,122.1, 120.6, 118.1, 43.3, 31.8, 30.1, 20.2, 19.7, 14.2, 13.8 (one carbonin the aliphatic region is buried under the signal of d6-DMSO); FT-IR:ν in cm-1 (KBr): 3420, 3098, 2955, 1696, 1657, 1624, 1572, 1386,1358, 1232; HRMS (ESI): m/z Calcd. 443.2195 (M + H)+, found443.1959 (M + H)+. |
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