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[ CAS No. 491-30-5 ] {[proInfo.proName]}

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Chemical Structure| 491-30-5
Chemical Structure| 491-30-5
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Product Details of [ 491-30-5 ]

CAS No. :491-30-5 MDL No. :MFCD00006899
Formula : C9H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :VDBNYAPERZTOOF-UHFFFAOYSA-N
M.W : 145.16 Pubchem ID :10284
Synonyms :

Calculated chemistry of [ 491-30-5 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 44.57
TPSA : 32.86 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) : -6.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 1.33
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 1.65
Log Po/w (SILICOS-IT) : 2.64
Consensus Log Po/w : 1.73

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.25
Solubility : 0.815 mg/ml ; 0.00562 mol/l
Class : Soluble
Log S (Ali) : -1.62
Solubility : 3.47 mg/ml ; 0.0239 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.58
Solubility : 0.0378 mg/ml ; 0.000261 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.36

Safety of [ 491-30-5 ]

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 [ 491-30-5 ]

* 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.

  • Upstream synthesis route of [ 491-30-5 ]
  • Downstream synthetic route of [ 491-30-5 ]

[ 491-30-5 ] Synthesis Path-Upstream   1~23

  • 1
  • [ 491-30-5 ]
  • [ 19493-44-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1992, vol. 35, # 22, p. 4105 - 4117
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 3, p. 383 - 391
[3] Heterocycles, 2012, vol. 86, # 2, p. 1583 - 1590
[4] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3199 - 3203
  • 2
  • [ 491-30-5 ]
  • [ 19493-44-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 740 - 743
[2] Chemische Berichte, 1900, vol. 33, p. 987[3] Chemische Berichte, 1901, vol. 34, p. 1654
  • 3
  • [ 1532-84-9 ]
  • [ 491-30-5 ]
  • [ 19493-44-8 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 544[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1023
  • 4
  • [ 1532-72-5 ]
  • [ 116833-54-6 ]
  • [ 1532-94-1 ]
  • [ 19493-44-8 ]
  • [ 491-30-5 ]
Reference: [1] Tetrahedron Letters, 1993, vol. 34, # 45, p. 7247 - 7250
  • 5
  • [ 491-30-5 ]
  • [ 10025-87-3 ]
  • [ 19493-44-8 ]
Reference: [1] Chemische Berichte, 1900, vol. 33, p. 987[2] Chemische Berichte, 1901, vol. 34, p. 1654
  • 6
  • [ 119-65-3 ]
  • [ 136918-14-4 ]
  • [ 491-30-5 ]
  • [ 2439-04-5 ]
  • [ 643-79-8 ]
Reference: [1] Journal of Physical Chemistry A, 1998, vol. 102, # 34, p. 6760 - 6765
  • 7
  • [ 491-30-5 ]
  • [ 119-65-3 ]
  • [ 394-67-2 ]
Reference: [1] Patent: JP2018/70562, 2018, A,
[2] Patent: JP2018/70562, 2018, A,
[3] Patent: JP2018/70562, 2018, A,
[4] Patent: JP2018/70562, 2018, A,
  • 8
  • [ 491-30-5 ]
  • [ 394-67-2 ]
Reference: [1] Patent: CN108558758, 2018, A,
  • 9
  • [ 491-30-5 ]
  • [ 1532-71-4 ]
Reference: [1] Yakugaku Zasshi, 1931, vol. 51, p. 542,571; dtsch. Ref. S. 73, 76[2] Chem.Abstr., 1931, p. 5427
[3] Recueil des Travaux Chimiques des Pays-Bas, 1943, vol. 62, p. 466
[4] Patent: EP446604, 1991, A2,
  • 10
  • [ 491-30-5 ]
  • [ 15298-58-5 ]
Reference: [1] Journal of Organic Chemistry, 1958, vol. 23, p. 1071
  • 11
  • [ 491-30-5 ]
  • [ 66728-98-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 2, p. 217 - 222
  • 12
  • [ 491-30-5 ]
  • [ 51206-40-7 ]
YieldReaction ConditionsOperation in experiment
96% at 140℃; for 0.166667 h; A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 °C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
96% at 140℃; for 0.166667 h; Preparation of Intermediate A: A mixture of 2.90 g, 19.07mMol of isocarbostyril and 14.40 g, 33.68mMol of phosphorus pentabromide were allowed to melt together at 140 0C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried, wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
71.3% at 125 - 140℃; In a 250ml three neck flask fitted with overhead stirrer and condenser which is also connected to a scrubber solution, 1-hydroxyisoquinoline (lO.g, 68.89mmol) and PBrs (53.38g, 124 mmol) were taken. The reaction mixture was gradually heated to 140°C. At about 125°C - 130°C the solid melts and a deep read solution obtained which on further heating converts to yellowish solid at ~135°C. The reaction mixture was heated at this temperature for lOmin then allowed to cool to room temperature. The pale yellow solid was crushed and added in portions into ice with stirring to obtain a pale yellow powder which was filtered and washed with water (150ml) and dried in an oven at 50°C under vacuum. The crude solid was purified by recrystallisation from EtOAc/heptane (14. lg, 99.93percent HPLC, 71.3percent yield). 1H-NMR (600MHz, CDCI3, TMS): S= 8.47 (s, 1H), 8.32(d, 1H), 8.19 (m, 1H), 7.72(m, 1H).
Reference: [1] Patent: EP1228063, 2009, B1, . Location in patent: Page/Page column 32
[2] Patent: WO2007/118602, 2007, A1, . Location in patent: Page/Page column 51
[3] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 8029 - 8047
[4] Patent: WO2017/103586, 2017, A1, . Location in patent: Page/Page column 38
[5] Patent: US2010/222345, 2010, A1, . Location in patent: Page/Page column 97
  • 13
  • [ 491-30-5 ]
  • [ 51206-40-7 ]
YieldReaction ConditionsOperation in experiment
96% at 140℃; for 0.166667 h; Neat (no solvent) A mixture of 2.90 g, 19.07 mMol of isocarbostyril and 14.40 g, 33.68 mMol of phosphorus pentabromide were allowed to melt together at 140° C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was cooled. The reaction mixture was crushed up and dumped into ice water. The resulting solid was filtered and air-dried. wt. 5.50 g, 96percent yield, mp.=94-96°. Rf=0.66 in 40percent ethyl acetate in hexanes.
Reference: [1] Patent: US6689883, 2004, B1, . Location in patent: Page column 43
  • 14
  • [ 491-30-5 ]
  • [ 58142-97-5 ]
Reference: [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 3, p. 740 - 743
  • 15
  • [ 67-56-1 ]
  • [ 7742-74-7 ]
  • [ 5597-04-6 ]
  • [ 491-30-5 ]
  • [ 59048-50-9 ]
Reference: [1] Heterocycles, 1982, vol. 19, # 12, p. 2275 - 2278
  • 16
  • [ 67-56-1 ]
  • [ 24623-16-3 ]
  • [ 5597-04-6 ]
  • [ 491-30-5 ]
  • [ 59048-50-9 ]
Reference: [1] Heterocycles, 1982, vol. 19, # 12, p. 2275 - 2278
  • 17
  • [ 491-30-5 ]
  • [ 59139-93-4 ]
Reference: [1] Patent: WO2013/92979, 2013, A1,
[2] European Journal of Medicinal Chemistry, 2014, vol. 83, p. 1 - 14
  • 18
  • [ 491-30-5 ]
  • [ 223671-80-5 ]
  • [ 56241-09-9 ]
Reference: [1] Patent: US6248738, 2001, B1,
[2] Patent: US2003/199440, 2003, A1,
[3] Patent: EP1077945, 2003, B1,
  • 19
  • [ 491-30-5 ]
  • [ 56241-09-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 10, p. 2341 - 2351
[2] Patent: US6093731, 2000, A,
  • 20
  • [ 491-30-5 ]
  • [ 3951-95-9 ]
YieldReaction ConditionsOperation in experiment
68% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Intermediate 6 4-bromoisoquinolin-1(2H)-one [0497] [0498] To a solution of isoquinolin-1(2H)-one (105 mg, 0.723 mmol) in DMF (2 mL), was added NBS (142 mg, 0.796 mmol). The mixture was stirred at rt for 2 h, then was concentrated. The crude product was purified via preparative HPLC to afford 110 mg (68percent) of Intermediate 6. [0499] MS (ESI) m/z: 223.9 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 11.57 (br. s., 1H), 8.24 (dd, J=8.0, 0.8 Hz, 1H), 7.88-7.83 (m, 1H), 7.79-7.75 (m, 1H), 7.61 (ddd, J=8.0, 7.1, 1.1 Hz, 1H), 7.55 (s, 1H).
Reference: [1] Journal of Medicinal Chemistry, 2014, vol. 57, # 4, p. 1299 - 1322
[2] Angewandte Chemie - International Edition, 2011, vol. 50, # 36, p. 8416 - 8419
[3] Synthetic Communications, 2007, vol. 37, # 23, p. 4199 - 4208
[4] Patent: US2014/206686, 2014, A1, . Location in patent: Paragraph 0497-0499
[5] Patent: WO2016/69976, 2016, A1, . Location in patent: Page/Page column 91
  • 21
  • [ 491-30-5 ]
  • [ 3951-95-9 ]
Reference: [1] Patent: US6093731, 2000, A,
  • 22
  • [ 491-30-5 ]
  • [ 256478-05-4 ]
  • [ 3951-95-9 ]
Reference: [1] Patent: EP1077945, 2003, B1,
  • 23
  • [ 110-85-0 ]
  • [ 491-30-5 ]
  • [ 110-17-8 ]
  • [ 126653-00-7 ]
Reference: [1] Patent: US4950670, 1990, A,
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