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[ CAS No. 16064-15-6 ] {[proInfo.proName]}

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Chemical Structure| 16064-15-6
Chemical Structure| 16064-15-6
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Product Details of [ 16064-15-6 ]

CAS No. :16064-15-6 MDL No. :MFCD14583012
Formula : C8H6N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :NDHAHRQOSZIMIN-UHFFFAOYSA-N
M.W : 178.14 Pubchem ID :135742258
Synonyms :

Calculated chemistry of [ 16064-15-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 46.41
TPSA : 86.21 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.34 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.6
Log Po/w (XLOGP3) : 0.06
Log Po/w (WLOGP) : 0.33
Log Po/w (MLOGP) : -0.02
Log Po/w (SILICOS-IT) : 1.09
Consensus Log Po/w : 0.41

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.55
Solubility : 5.0 mg/ml ; 0.0281 mol/l
Class : Very soluble
Log S (Ali) : -1.42
Solubility : 6.71 mg/ml ; 0.0377 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.08
Solubility : 1.47 mg/ml ; 0.00826 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.61

Safety of [ 16064-15-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16064-15-6 ]

* 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 [ 16064-15-6 ]

[ 16064-15-6 ] Synthesis Path-Downstream   1~17

  • 2
  • [ 108-24-7 ]
  • [ 16064-15-6 ]
  • [ 765249-38-5 ]
YieldReaction ConditionsOperation in experiment
92.5% With pyridine; at 120 - 125℃; for 2h; (ii) Preparation of 6,7-diacetoxy-4 (3H)-quinazolinone of formula (10)Into a 1.0 L four necked round bottomed flask equipped with a mechanical stirrer, reflux condenser and thermometer socket are charged acetic anhydride (600 g), pyridine (4 ml) followed by 6,7-dihydroxy-4 (3H)-quinazolinone (100 g) obtained by the process described in step (i) above. The reaction mass was heated to 120 C. and maintained for 2 hours at 120-125 C. After completion of the maintenance period, distilled off the solvent under vacuum. Cooled the reaction mass to 25-35 and water (1000 ml) was added, stirred for 1 hour, filtered the product and washed the cake with water and dried to get 136.2 g (92.5% by theory) of 6,7-diacetoxy-4 (3H)-quinazolinone as off-white crystalline solid.Purity: 99.0% (by HPLC).Melting range: 235-237 C.IR ((KBr): 3128, 3044, 2930, 2882, 1779, 1693, 1660, 1620, 1479, 1372, 1280, 1209, 1163, 929, and 914 cm-1.1H NMR (300 MHz, DMSO-d6): 2.3-2.32 (s, 6H); 7.58 (s, 1H); 7.95 (s, 1H); 8.12 (d, 1H); 12.39 (br. s, 1H).13C NMR (75 MHz, DMSO-d6): 20.14, 20.31, 115.8, 118.5, 124, 140.9, 144.2, 145.7, 150.1, 160.4, and 168.6.Mass: (M+1): 263.
83.4% With pyridine; at 20 - 25℃;Inert atmosphere; (2)Compound b (5 g, 1.0 eq) and pyridine (50 ml) were added to a three-neck bottle.Acetic anhydride (2.5 eq) was added under controlled nitrogen at a controlled temperature of less than 20 C.After the addition, the reaction was kept for 1 h, and the temperature was raised to 25 C for 4-6 h.After the reaction was completed, the reaction solution was poured into ice water, and 3N hydrochloric acid was adjusted to pH 6-7.Extracted with DCM and dried over anhydrous sodium sulfate.The organic phase was concentrated to dryness over a flash column to afford 6.14 g of Compound C.
83.4% With pyridine; at 20 - 25℃;Inert atmosphere; (2) Compound b (5 g, 1.0 eq) and pyridine (50 ml) were added to a three-necked flask, and acetic anhydride (2.5 eq) was added under a nitrogen atmosphere at a controlled temperature of less than 20 C. After the addition, the reaction was incubated for 1 h, and the temperature was raised to 25 C for 4-6 h. After the reaction was completed, the reaction solution was poured into ice water, and 3N hydrochloric acid was adjusted to pH 6-7, extracted with DCM, dried over anhydrous sodium sulfate and concentrated organic. To dryness, over a flash column gave 6.14 g of Compound C. Yield: 83.4%.
80% With pyridine; at 130℃; for 6h; 7.6 g of the resulting product 6,7-dihydrox- yquinazolinone synthesized in step 2 was added with 40 ml of acetic anhydride and 1 ml of pyridine, and then the system was heated to 130 C., refluxed and reacted for 6 hrs and cooled to room temperature. The reaction solution was poured into 100 ml of water andstirred, and a large amount of grey solids was precipitated. The mixture was filtered. The filter cake was washed with a small amount of water and dried to obtain 9 g of the resulting product 6,7-diacetoxylquinazolinone (80%).10093] ?H NMR (400 MHz, DM50) oe 12.41 (s, 1H), 8.13 (s, 1H), 7.97 (s, 1H), 7.60 (s, 1H), 2.34 (s, 3H), 2.32 (s, 3H)
53% With pyridine; at 120℃; for 2h;Heating / reflux; To 6,7-dihydroxy- 4(3H)-quinazolinone, 11 (2.20 g, 12.2 mmol) was added Ac2O (13.3 ml) and a drop of pyridine and the reaction mixture was heated to reflux at 12O0C for 2 h. The reaction mixture was cooled to room temperature and the solvent was distilled off under reduced pressure. The residue was taken up in water and stirred for an hour at room <n="31"/>temperature. The solid obtained was filtered and dried to give 6,7-diacetoxy-4(3H)- quinazolinone 12 as an off-white crystalline solid (1.70 g, 53%).
53% pyridine; at 120℃; for 2h; Step 2. 6,7-Diacetoxy-4(3H)-quinazolinone (12). To 6,7-dihydroxy-4(3H)- quinazolinone 11 (2.2O g, 12.2 mmol) was added Ac2O (13.3 ml) and a drop of pyridine and the resulting reaction mixture was heated to reflux at 120 0C for 2 hours. The reaction mixture was cooled to room temperature and the solvent was removed under reduced pressure. The residue was taken up in water and the mixture stirred for 1 hour at room temperature. The resulting precipitate was filtered and dried to give 6,7-diacetoxy-4(3H)-quinazolinone 12 as an off-white crystalline solid (1.70 g, 53%).

  • 3
  • [ 13794-72-4 ]
  • [ 16064-15-6 ]
YieldReaction ConditionsOperation in experiment
98.62% (i) Preparation of 6,7-dihydroxy-4 (3H)-quinazolinone of formula (9)Into a 2.0 Lt four necked round bottomed flask equipped with a mechanical stirrer, reflux condenser and thermometer socket are charged 48% (w/w) hydrobromic acid (1000 g) and 6,7-dimethoxy-4 (3H)-quinazolinone (100 g). Slowly heated the reaction mass to reach 110 C. and maintained for 1 hour at the same temperature. Then raised mass temperature to reach reflux condition and refluxed for 12 hours. Monitored the completion of the reaction by TLC. Then cooled the reaction mass to 25-35 C. and filtered the mass. Transferred the wet cake into another 2.0 Lt round bottomed flask containing 1000 ml of DM water. Stirred for 10-15 minutes and adjusted the pH to 7.0-7.5, by adding aqueous ammonia solution. Filtered the resulting product and washed the cake with DM water and dried to get 85.2 g (98.62% by theory) of 6,7-dihydroxy-4 (3H)-quinazolinone as off-white crystalline solid.Purity: 99.25% (by HPLC)Melting point: >250 C.IR (KBr): 3208.7, 1679.0, 1614.5, 1514.7, 1427.7, 1374.3, 1316.2, 1293.9, 1261.0, 1214.5, 1195.5, 866.0, 845.3, 780.7, 523.8, and 449.2 cm-1.1H NMR (300 MHz, DMSO-D6): 6.93 (s, 1H); 7.35 (s, 1H); 7.84 (s, 1H); 9.75 (s, 1H); 10.13 (s, 1H); 11.2-12.4 (s, 1H).Mass: 179 (M+1), 177 (M-1).
97% With hydrogen bromide; at 120℃; 6,7-dimethoxy-3H-quinazolin-4-one (25 g, 124 mmol) was stirred in HBr, 48% (150 mL) at 120 O overnight. The mixture was cooled to room temperature and filtered. The filter cake was stirred in water and treated with ammonium hydroxide to pH = 8 and the mixture was filtered. The filter cake was stirred in acetone and the resulting mixture was filtered. The filter cake was washed with diethyl ether and dried giving the desired product as a fine, pale powder (21 g, 97 %). 1H NMR (d6-DMSO) O 11.82 (brs, 1H), 10.13 (5, 1 H), 9.75 (5, 1 H), 7.84 (5, 1 H), 7.34 (5, 1 H), 6.92 (5, 1 H).
84% With hydrogen bromide; In water; at 120℃; for 12h;Heating / reflux; To 6,7-dimethoxy- 4(3H)-quinazolinone, 10 (3.0 g, 14.5 mmol) was added 48% HBr (36 mL) and the solution was heated to reflux at 100 0C for 12 h. The reaction mixture was cooled to room temperature and the solids were filtered. The solid obtained was neutralized with aq. NH3 (pH = 8) and the solution was filtered and washed with water and dried to give 6,7-dihydroxy-4(3H)-quinazolinone, 11 as a off-white crystalline solid (2.20 g, 84%).
84% Step 1. 6,7-Dihvdroxy-4(3H)-quinazorinone (11). A solution of 6,7- dimethoxy-4(3H)-quinazolinone 10 (3.0 g, 14.5 mmol) and 48% HBr (36 mL) was heated to reflux at 100 0C for 12 hours. The reaction mixture was cooled to room temperature and the solids were removed by filtration then neutralized with aqueous NH3 (pH = 8). The resulting solution was filtered and the solids were washed with water and dried to give 6,7-dihydroxy-4(3H)-quinazolinone 11 as an off-white crystalline solid (2.20 g, 84%).
80.5% With boron tribromide; In dichloromethane; at -78 - 25℃;Inert atmosphere; (1)Compound a (10 g, 1.0 eq) and dichloromethane (100 ml) were added to a three-necked flask under nitrogen.The temperature was lowered to -78 C, and a solution of boron tribromide (10 eq) in dichloromethane (1 g / 3 ml) was added.After the addition, the reaction was kept for 1 h, and the temperature was raised to 25 C for 4-6 h.After the reaction is over,Wash with 10 ml of water and dry over anhydrous sodium sulfate.Concentrate the organic phase to dryness,Over the fast column,Yielding 6.97 g of compound b,Yield: 80.5%.
80.5% With boron tribromide; In dichloromethane; at -78 - 25℃;Inert atmosphere; (1) Compound a (10 g, 1.0 eq) and dichloromethane (100 ml) were added to a three-necked flask, cooled to -78 C under nitrogen atmosphere, and a solution of boron tribromide (10 eq) in dichloromethane (1 g) was added. /3ml). Plus,Insulation reaction for 1 h,The temperature was raised to 25 C for 4-6 h. After the reaction was completed, it was washed with 10 ml of water, dried over anhydrous sodium sulfate, and the organic layer was concentrated to dryness to yield 6.97 g of compound b, yield: 80.5%.
75% With hydrogen bromide; acetic anhydride; at 110 - 140℃; for 31h; 10 g of the resulting product synthesized in step 1 was added in 85 ml of 40% H13r solution, and then the mixture was slowly added with 30 ml of acetic anhydride in a water bath. The water bath is removed, and the system was heated to 110 C. in an oil bath, reacted for 1 hr, then heated to 140 C. and reacted for 30 hrs. A large amount of white solids was precipitated in the flask. The reaction solution was filtered after cooled. The filter cake was dissolved in 75 ml of water, and the mixture was added with aqua ammonia until the pH value was adjusted to 9 and then filtered. The filter cake was washed with 75 ml of 1M NaHCO3 solution and dried to obtain 6.5 g of the resulting product (75%). ?H NMR (400 MHz, DMSO) oe 7.78 (s, 1H), 7.29 (s, 1H), 6.84 (s, 1H)

  • 4
  • [ 3282-30-2 ]
  • [ 16064-15-6 ]
  • [ 1174662-16-8 ]
YieldReaction ConditionsOperation in experiment
71% With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; 4-Oxo-3,4-dihydroquinazoline-6 7-diyl bis(2,2-dimethylpropanoate) To a stirred suspension of <strong>[16064-15-6]6,7-dihydroxyquinazolinone</strong> (2) (38.0 g, 213.3 mmol) and TEA (89.1 ml, 640 mmol) in DMF (200 ml), was added dropwise trimethylacetyl chloride (78.8 ml, 640 mmol). The resulting suspension was stirred at room temperature for 1 hour , diluted with EtOAc (500 ml) and washed with water (5 x 20 ml). The organic phase was concentrated to dryness and the residue triturated with water and the resulting precipitate was collected by filtration, washed with water (5 x 20 ml) and dried to a constant weight to afford the title compound (52.3 g, 71%) as a pale pink solid: LCMS (retention time = 3.65 min., purity = 100%), ESI+ mJz 347.33 (M+H)+; 'H-NMR (DMSO-d6) delta (ppm) 1.32 (s, 18H), 7.59 (s, 1H), 7.92 (s, 1H), 8.14 (s, 1H).
  • 5
  • [ 179688-53-0 ]
  • [ 16064-15-6 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine hydrochloride; at 180℃; for 4h; 6,7-Dihydroxyquinazolinone (2) To an excess of stirred molten pyridinium hydrochloride at 180 C was added portionwise 6-acetoxy-7-methoxy-quinazolone (1) (49.5 g, 211.35 mmol) and the resulting solution was stirred at 180 C for 4 hours. After cooling to room temperature, water (500 ml) was added and the pH adjusted to 7 with aqueous ammonia. The resulting precipitate was collected by filtration, washed with water (5 x 20 ml), ether (5 x 20 ml) and dried to a constant weight in a vacuum oven at 40 C to afford 6,7-dihydroxyquinazolinone (2) (38 g, 100%) as a beige solid: LCMS (retention time = 0.97 min., purity = 98%), ESI+ m/z 179.18 (M+H)+; 'H- NMR (DMSO-d6) delta (ppm) 6.95 (s, 1H), 7.41 (s, 1H), 7.91 (s, 1H), 9.78 (s, 1H), 10.23 (s, 1H), 11.7 (br s, 1H).
  • 6
  • [ 4101-33-1 ]
  • [ 16064-15-6 ]
YieldReaction ConditionsOperation in experiment
97% With hydrogen bromide; In water; at 110 - 140℃; for 16h; In a 250 ml_ flask, a mixture of 6,7-dimethoxy-4-(3H)-quinazoline (20.00 g, 97.0 mmol) and 48% HBr (200 g, 133 ml_) was heated at 1 10 C and was stirred for 1 h. The mixture was heated to 140 C and was stirred for 15 h. The resulting suspension was cooled to 20 C and was filtered. The collected solid was suspended in H2O (150 ml_) and NH4OH was added to pH 9. The suspension was filtered and the resulting solid was suspended in 1 MNaHCO3 (150 ml_). The solid was filtered, was washed with H2O (50 ml_) and was dried to give the title compound as a white solid (16.82 g, 97% yield). 1H NMR (d6-DMSO, ppm): delta 7.79 (s, 1 H), 7.32 (s, 1 H), 6.88 (s, 1 H).
97% Example 1: Preparation of 6,7-dihydroxyauinazolinone In a 250 mL flask, a mixture of 6,7-dimethoxy-4-(3H)-quinazoline (20.00 g, 97.0 mmol) and 48% HBr (200 g, 133 mL) was heated at 110 C and was stirred for 1 h. The mixture was heated to 140 C and was stirred for 15 h. The resulting suspension was cooled to 20 C and was filtered. The collected solid was suspended in H2O (150 mL) and NH4OH was added to pH 9. The suspension was filtered and the resulting solid was suspended in 1 M NaHCO3 (150 mL). The solid was filtered, was washed with H2O (5 mL) and was dried to give the title compound as a white solid (16.82 g, 97% yield). 1H NMR (d6-DMSO, ppm): delta 7.79 (s, 1 H), 7.32 (s, 1 H), 6.88 (s, 1 H).
  • 7
  • [ 16064-15-6 ]
  • [ 183321-74-6 ]
  • 9
  • [ 16064-15-6 ]
  • N-[(3-ethynylphenyl)-(2-methoxyethyl)]-6,7-bis(2-methoxyethoxy)-4-quinazolinamine [ No CAS ]
  • C25H29N3O5 [ No CAS ]
  • C25H29N3O5 [ No CAS ]
  • 10
  • [ 16064-15-6 ]
  • [ 1312937-41-9 ]
  • 11
  • [ 67-56-1 ]
  • [ 16064-15-6 ]
  • [ 1312937-40-8 ]
YieldReaction ConditionsOperation in experiment
79% In a 250 ml_ flask, a mixture of <strong>[16064-15-6]6,7-dihydroxyquinazolinone</strong> (15.00 g, 84.2 mmol) and DMF (1 .70 ml_, 21 .9 mmol, 0.26 eq.) in POCI3 (38.5 ml_, 421 mmol, 5 eq.) was stirred at 120 C for 3 h or until total dissolution of the solid is observed. POCI3 was distilled under vacuum and to the resulting foam was added toluene (50.0 ml_) and K2CO3 (1 1 .63 g, 84.2 mmol, 1 eq.). The mixture was cooled to 0 C and methanol (70.0 ml_) was added carefully slowly keeping the temperature under 40 C. The resulting suspension was stirred at room temperature for 45 min and the solvents were removed under vacuum to provide a solid foam. H2O (150 ml_) was added slowly and 50% NaOH (18 ml_) was added at 0 C to pH 5. The resulting solid was filtered and was washed with H2O (20 ml_) to give the title compound as a yellow solid (12.81 g, 79% yield). 1H NMR (d6-DMSO, ppm): delta 8.47 (s, 1 H), 7.27 (s, 1 H), 7.1 1 (s, 1 H), 4.02 (s, 3H).
79% Example 2: Preparation of 4-methoxyguinazoline-6,7-diol In a 250 mL flask, a mixture of <strong>[16064-15-6]6,7-dihydroxyquinazolinone</strong> (15.00 g, 84.2 mmol) and DMF (1.70 mL, 21.9 mmol, 0.26 eq.) in POCl3 (38.5 mL, 421 mmol, 5 eq.) was stirred at 120 C for 3 h or until total dissolution of the solid is observed. POCl3 was distilled under vacuum and to the resulting foam were added toluene (50.0 mL) and K2CO3 (11.63 g, 84.2 mmol, 1 eq.). The mixture was cooled to 0 C and methanol (70.0 mL) was added carefully slowly keeping the temperature under 40 C. The resulting suspension was stirred at room temperature for 45 min and the solvents were removed under vacuum to provide a solid foam. H2O (150 mL) was added slowly and 50% NaOH (18 mL) was added at 0 C to pH 5. The resulting solid was filtered and was washed with H2O (20 mL) to give the title compound as a yellow solid (12.81 g, 79% yield). 1H NMR (d6-DMSO, ppm): delta 8.47 (s, 1 H), 7.27 (s, 1 H), 7.11 (s, 1H), 4.02(s,3H)
  • 12
  • [ 16064-15-6 ]
  • N-[(3-ethynylphenyl)-(2-methoxyethyl)]-6,7-bis(2-methoxyethoxy)-4-quinazolinamine [ No CAS ]
  • C25H31N3O5 [ No CAS ]
  • C25H31N3O5 [ No CAS ]
  • 13
  • [ 16064-15-6 ]
  • (2-{2-[4-(3-ethynyl-phenylamino)-7-(2-methoxy-ethoxy)quinazolin-6-yloxy]ethoxy}ethyl)carbamic acid tert-butyl ester [ No CAS ]
  • 14
  • [ 16064-15-6 ]
  • [6-[2-(2-amino-ethoxy)ethoxy]-7-(2-methoxy-ethoxy)quinazolin-4-yl]-(3-ethynyl-phenyl)amine dihydrochloride [ No CAS ]
  • 15
  • [ 16064-15-6 ]
  • C40H39N5O9 [ No CAS ]
  • 16
  • [ 16064-15-6 ]
  • [ 1145671-34-6 ]
  • 17
  • [ 16064-15-6 ]
  • [ 1145671-36-8 ]
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; ;