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[ CAS No. 29620-62-0 ] {[proInfo.proName]}

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Chemical Structure| 29620-62-0
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Product Details of [ 29620-62-0 ]

CAS No. :29620-62-0 MDL No. :MFCD00784841
Formula : C10H9N3O Boiling Point : -
Linear Structure Formula :- InChI Key :CPWKEFDYIVVJHG-UHFFFAOYSA-N
M.W : 187.20 Pubchem ID :3011577
Synonyms :

Calculated chemistry of [ 29620-62-0 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.64
TPSA : 68.01 Ų

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) : -7.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.32
Log Po/w (XLOGP3) : -0.53
Log Po/w (WLOGP) : 0.84
Log Po/w (MLOGP) : 0.9
Log Po/w (SILICOS-IT) : 0.77
Consensus Log Po/w : 0.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.06
Solubility : 16.2 mg/ml ; 0.0864 mol/l
Class : Very soluble
Log S (Ali) : -0.43
Solubility : 69.6 mg/ml ; 0.372 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.34
Solubility : 0.085 mg/ml ; 0.000454 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.37

Safety of [ 29620-62-0 ]

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

Application In Synthesis of [ 29620-62-0 ]

* 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 [ 29620-62-0 ]

[ 29620-62-0 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 698-63-5 ]
  • [ 29620-62-0 ]
  • [ 93866-40-1 ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid
  • 2
  • [ 21233-61-4 ]
  • [ 29620-62-0 ]
YieldReaction ConditionsOperation in experiment
99% With hydrazine hydrate monohydrate In ethanol at 80℃; for 8h;
65% With hydrazine In ethanol for 168h; Reflux;
With ethanol; hydrazine hydrate monohydrate
With hydrazine hydrate monohydrate Microwave irradiation;
5 g With 4-dimethylaminopyridine; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In methanol at 20℃; 1 Example 1 This example is the synthesis of the intermediate hydrazide compound (H) (quinoline-4-carboxylhydrazide),Can also be purchased directly.Add 100mL methanol and 20g EDCI to 15g methyl 4-quinolinecarboxylate,840mg DMAP and 15mL DIPEA, stirred at room temperature overnight,Concentrate under reduced pressure to obtain an oily substance, to which 200 mL of dichloromethane was added,Wash once with 100 mL of saturated saline, and once with 200 mL of saturated saline,After drying over anhydrous sodium sulfate, the organic layer was concentrated to dryness under reduced pressure. The concentrate was purified by silica gel chromatography, eluting with a gradient of petroleum ether-ethyl acetate 5:1 to 2:1, to obtain 8 g of a white solid. Dissolve the white solid with 50 mL of absolute ethanol, add 20 mL of hydrazine hydrate, and heat to reflux for 4 hours.Concentrate under reduced pressure to obtain an oil, to which was added 100 mL of ethyl acetate,Wash once with 100mL saturated saline, once with 200mL saturated saline,After drying over anhydrous sodium sulfate, the organic layer was concentrated to dryness under reduced pressure. The concentrate was purified by silica gel chromatography, eluting with a gradient of dichloromethane-methanol 50:1 to 20:1, to give 5 g of a white solid.

  • 4
  • [ 29620-62-0 ]
  • [ 122-85-0 ]
  • [ 108370-04-3 ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid
  • 5
  • [ 29620-62-0 ]
  • [ 100-52-7 ]
  • quinoline-4-carboxylic acid benzylidenehydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ethanol
  • 6
  • [ 29620-62-0 ]
  • [ 123-08-0 ]
  • [ 107413-58-1 ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid
  • 7
  • [ 29620-62-0 ]
  • [ 100-10-7 ]
  • [ 108477-75-4 ]
YieldReaction ConditionsOperation in experiment
With ethanol; acetic acid
  • 8
  • [ 29620-62-0 ]
  • [ 79-44-7 ]
  • 5-[4]quinolyl-3<i>H</i>-[1,3,4]oxadiazol-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With pyridine
  • 9
  • [ 29620-62-0 ]
  • [ 78151-28-7 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium nitrite
  • 10
  • [ 29620-62-0 ]
  • [ 62-53-3 ]
  • [ 92119-01-2 ]
YieldReaction ConditionsOperation in experiment
85% With mercury(II) oxide In benzene for 0.5h;
YieldReaction ConditionsOperation in experiment
Ester I, Hydrazinhydrat;
  • 13
  • [ 29620-62-0 ]
  • [ 107479-87-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: aqueous HCl; aqueous NaNO2
  • 15
  • [ 29620-62-0 ]
  • [ 24677-78-9 ]
  • N'-[(1E)-(2,3-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With acetic acid In water 6 4.1.1.3. Synthetic procedure for hydrazones preparation General procedure: A quinoline-2-carbohydrazide 4 (100 mg, 0.53 mmol) solution in water (2 mL) was sonicated for 2 min and then aldehyde 5 (0.53 mmol) and acetic acid (0.1 mL) were added dropwise to the reaction mixture. Upon completion of the reaction (20-30 min), the product was filtered, sequentially washed with water (20 mL) and ethyl ether (5 mL), dried in vacuo and recrystallized from ethanol to obtain the corresponding hydrazones in yields ranging from 40% to 85%. 4.1.1.3.6 N'-[(1E)-(2,3-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide (7a) Yield 70% (0.371 mmol, 114.0 mg); brown solid, M.p. 263-267 °C; IR (cm-1): νmax 3443 (Ar-OH), 3191 (N-H), 1654 (C=O), 1578 (C=N), 1471 (C=CAr), 1283 ((C=O)-N), 724 (C-HAr). 1H NMR (DMSO-d6): δ 6.76 (H16, tapparent, J = 7.84 Hz), 6.89 (H15, dd, J = 7.8, 1.3 Hz), 7.03 (H17, dd, J = 7.8, 1.3 Hz), 7.74 (H3, d, J = 4.2 Hz), 7.78-7.96 (H7, H8, m), 8.13 (H6, d, J = 8.4 Hz), 8.20 (H9, d, J = 8.2 Hz), 8.30 (OH), 8.52 (H11, s), 9.04 (H2, d, J = 4.4 Hz), 10.79 (OH), 12.34 (NH). 13C NMR (CDCl3): δ 119.20 (C12), 119.82 (C15), 120.16 (C3), 120.32 (C16), 124.61 (C17), 125.67 (C5), 128.30 (C5), 129.87 (C6, C9), 130.63 (C8), 140.18 (C4), 146.03 (C14), 148.30 (C10), 150.13 (C11), 150.74 (C2), 163.10 (C13), 168.76 (C=O). EIMS: m/z 308.1037 [M+H]+, Calcd for C17H13N3O3: 308.1035.
  • 16
  • [ 29620-62-0 ]
  • [ 95-01-2 ]
  • N'-[(1E)-(2,4-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With acetic acid In water 7 4.1.1.3. Synthetic procedure for hydrazones preparation General procedure: A quinoline-2-carbohydrazide 4 (100 mg, 0.53 mmol) solution in water (2 mL) was sonicated for 2 min and then aldehyde 5 (0.53 mmol) and acetic acid (0.1 mL) were added dropwise to the reaction mixture. Upon completion of the reaction (20-30 min), the product was filtered, sequentially washed with water (20 mL) and ethyl ether (5 mL), dried in vacuo and recrystallized from ethanol to obtain the corresponding hydrazones in yields ranging from 40% to 85%. 4.1.1.3.7 N'-[(1E)-(2,4-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide (7b) Yield 60% (0.318 mmol, 97.7 mg); yellow solid, M.p. 250-254 °C; IR (cm-1): νmax 3381 (Ar-OH), 2856 (N-H), 1632 (C=O), 1509 (C=N), 1466 (C=CAr), 1235 ((C=O)-N), 762 (C-HAr). 1H NMR (DMSO-d6): δ 6.35 (H14, d, J = 1.6 Hz), 6.38 (H16, dd, J = 8.5, 1.6 Hz), 7.36 (H17, d, J = 8.5 Hz), 7.71 (H3, d, J = 4.2 Hz), 7.77-7.89 (H7, H8, m), 8.12 (H6, d, J = 8.4 Hz), 8.19 (H9, d, J = 7.6 Hz), 8.42 (H11, s), 9.02 (H2, d, J = 4.2 Hz), 11.26 (OH), 12.22 (NH). 13C NMR (CDCl3): δ 103.1 (C14), 108.40 (C16), 110.82 (C12), 120.10 (C3), 124.70 (C5), 125.61 (C7), 128.22 (C8), 129.83 (C9), 130.57 (C6), 131.76 (C17), 140.36 (C4), 148.31 (C10), 150.36 (C11), 150.71 (C2), 159.95 (C15), 161.49 (C13), 162.76 (C=O). EIMS: m/z 308.1035 [M+H]+, Calcd for C17H13N3O3: 308.1035.
  • 17
  • [ 1194-98-5 ]
  • [ 29620-62-0 ]
  • N'-[(1E)-(2,5-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% With acetic acid In water 8 4.1.1.3. Synthetic procedure for hydrazones preparation General procedure: A quinoline-2-carbohydrazide 4 (100 mg, 0.53 mmol) solution in water (2 mL) was sonicated for 2 min and then aldehyde 5 (0.53 mmol) and acetic acid (0.1 mL) were added dropwise to the reaction mixture. Upon completion of the reaction (20-30 min), the product was filtered, sequentially washed with water (20 mL) and ethyl ether (5 mL), dried in vacuo and recrystallized from ethanol to obtain the corresponding hydrazones in yields ranging from 40% to 85%. 4.1.1.3.8 N'-[(1E)-(2,5-dihydroxyphenyl)methylidene]quinoline-4-carbohydrazide (7c) Yield 62% (0.329 mmol, 101.0 mg); light brown solid, M.p. 270-276 °C; IR (cm-1): νmax 3442 (Ar-OH), 3339 (N-H), 1661 (C=O), 1585 (C=N), 1466 (C=CAr), 1226 ((C=O)-N), 765 (C-HAr). 1H NMR (DMSO-d6): δ 6.77 (H14, H15, sapparent), 7.05 (H17, s), 7.72 (H3, d, J = 4.4 Hz), 7.78-7.89 (H7, H8, m), 8.12 (H6, d, J = 8.5 Hz), 8.19 (H9, d, J = 8.3 Hz), 8.27 (OH), 8.49 (H11, s), 9.03 (H2, d, J = 4.4 Hz), 10.22 (OH), 12.30 (NH). 13C NMR (CDCl3): δ 117.64 (C12), 119.43 (C14, C17), 119.90 (C15), 120.14 (C3), 124.60 (C5), 125.71 (C7), 128.22 (C9), 129.93 (C6), 130.60 (C8), 140.36 (C4), 148.33 (C11), 148.65 (C10), 150.36 (C16), 150.73 (C2), 163.10 (C13), 168.83 (C=O). EIMS: m/z 308.1034 [M+H]+, Calcd for C17H13N3O3: 308.1035.
  • 18
  • [ 29620-62-0 ]
  • [ 2144-08-3 ]
  • N'-[(1E)-(2,3,4-trihydroxyphenyl)methylidene]quinoline-4-carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With acetic acid In water 9 4.1.1.3. Synthetic procedure for hydrazones preparation General procedure: A quinoline-2-carbohydrazide 4 (100 mg, 0.53 mmol) solution in water (2 mL) was sonicated for 2 min and then aldehyde 5 (0.53 mmol) and acetic acid (0.1 mL) were added dropwise to the reaction mixture. Upon completion of the reaction (20-30 min), the product was filtered, sequentially washed with water (20 mL) and ethyl ether (5 mL), dried in vacuo and recrystallized from ethanol to obtain the corresponding hydrazones in yields ranging from 40% to 85%. 4.1.1.3.9 N'-[(1E)-(2,3,4-trihydroxyphenyl)methylidene]quinoline-4-carbohydrazide (7d) Yield 85% (0.450 mmol, 145.6 mg); light yellow solid, M.p. 285-286 °C; IR (cm-1): νmax 3496 (Ar-OH), 3190 (N-H), 1652 (C=O), 1517 (C=N), 1465 (C=CAr), 1250 ((C=O)-N), 797 (C-HAr). 1H NMR (DMSO-d6): δ 6.42 (H16, d, J = 8.6 Hz), 6.84 (H17, d, J = 8.6 Hz), 7.73 (H3, d, J = 4.3 Hz), 7.79-7.89 (H7, H8, m), 8.12 (H6, d, J = 8.4 Hz), 8.16 (OH), 8.20 (H9, d, J = 8.4 Hz), 8.38 (H11, s), 8.74 (OH), 9.04 (H2, d, J = 4.3 Hz), 11.21 (OH), 12.26 (NH). 13C NMR (CDCl3): δ 108.3 (C17), 111.16 (C3), 120.15 (C12), 121.72 (C16), 124.70 (C5), 125.71 (C7), 128.20 (C9), 129.91 (C6), 130.60 (C8), 133.2 (C14), 140.31 (C4), 148.0 (C10), 149.52 (C11), 150.74 (C15), 151.45 (C2), 162.73 (C13), 168.25 (C=O). EIMS: m/z 324.0983 [M+H]+, Calcd for C17H13N3O4: 324.0984.
  • 19
  • [ 29620-62-0 ]
  • [ 24677-78-9 ]
  • C17H13N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; acetic acid
  • 20
  • [ 29620-62-0 ]
  • [ 95-01-2 ]
  • C17H13N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; acetic acid
  • 21
  • [ 1194-98-5 ]
  • [ 29620-62-0 ]
  • C17H13N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; acetic acid
  • 22
  • [ 29620-62-0 ]
  • [ 2144-08-3 ]
  • C17H13N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In water; acetic acid
  • 23
  • [ 4363-93-3 ]
  • [ 29620-62-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium hydroxide; iodine 2: hydrazine hydrate / Microwave irradiation
  • 24
  • [ 29620-62-0 ]
  • [ 91-56-5 ]
  • N'‑(2‑oxoindolin‑3‑ylidene)quinoline‑4‑carbohydrazide [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With acetic acid In ethanol for 240h; Reflux;
  • 25
  • [ 67-52-7 ]
  • [ 29620-62-0 ]
  • [ 109-94-4 ]
  • 5-[(quinoline-4-carbohydrazido)methylene]pyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.2 g Stage #1: BARBITURIC ACID; ethyl formate With hydrogenchloride; sodium methoxide In ethyl acetate; N,N-dimethyl-formamide Stage #2: quinoline-4-carboxylic acid hydrazide In tetrahydrofuran for 3h; 7.a-7.b Example 7 The present embodiment is the hydrazide-substituted methylene pyrimidinetrione compound of structural formula (I)-5-[(quinoline-4-carboxyhydrazide)methylene]pyrimidine-2,4,6(1H,3H,5H)-trioneSynthesis Step a: Add 250 mL of ethyl formate to 500 mL of DMF, add 6 g under stirringPyrimidinetrioneReact with 2.5 g of sodium methoxide overnight, add dilute hydrochloric acid to quench, add 1000 mL of ethyl acetate and 500 mL of saturated brine, stir to separate the layers, extract the aqueous layer twice with 500 mL of ethyl acetate, combine the organic layers, wash with saturated brine, Dry over anhydrous sodium sulfate and filter.Step b: Concentrate the filtrate obtained in step a, add 500 ml of tetrahydrofuran and 2.5 g of quinoline-4-carboxylhydrazide, react for 3 hours, concentrate to remove the solvent, add 250 ml of acetonitrile and 250 ml of methanol, heat to reflux with stirring and then cool to room temperature, 3.2 g of solid product was obtained by filtration.
  • 26
  • [ 29620-62-0 ]
  • 1-cyclopropylpyrimidine-2,4,6(1H,3H,5H)-trione-5-carbaldehyde [ No CAS ]
  • 5-(quinoline-4-carbohydrazido)methylene-1-cyclopropylpyrimidine-2,4,6(1H,3H,5H)-trione [ No CAS ]
YieldReaction ConditionsOperation in experiment
720 mg In methanol at 20℃; for 0.5h; 6 Example 6 This embodiment is a hydrazide-substituted methylenepyrimidinetrione compound of structural formula (I)-5-(quinoline-4-carboxyhydrazide)methylene-1-cyclopropylpyrimidine-2,4,6 Synthesis of (1H,3H,5H)-triketoneAdd 500 mg of 1-cyclopropylpyrimidine-2,4,6(1H,3H,5H)-triketo-5-carbaldehyde to 5 mL of dry methanol, add 470 mg of quinoline-4-carboxyhydrazide, stir at room temperature for 30 minute,A white solid was precipitated, which was filtered off with suction, washed with a large amount of methanol, and dried to obtain 720 mg of the final product.
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