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[ CAS No. 529-20-4 ] {[proInfo.proName]}

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Chemical Structure| 529-20-4
Chemical Structure| 529-20-4
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Product Citations

Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan , et al. DOI: PubMed ID:

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; chalcone ; drug likeliness properties ; imidazo[1,2-a]pyridine ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

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Product Details of [ 529-20-4 ]

CAS No. :529-20-4 MDL No. :MFCD00003338
Formula : C8H8O Boiling Point : -
Linear Structure Formula :- InChI Key :BTFQKIATRPGRBS-UHFFFAOYSA-N
M.W : 120.15 Pubchem ID :10722
Synonyms :

Calculated chemistry of [ 529-20-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 36.8
TPSA : 17.07 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) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.63
Log Po/w (XLOGP3) : 2.26
Log Po/w (WLOGP) : 1.81
Log Po/w (MLOGP) : 1.78
Log Po/w (SILICOS-IT) : 2.47
Consensus Log Po/w : 1.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.44 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 0.668 mg/ml ; 0.00556 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.249 mg/ml ; 0.00207 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 529-20-4 ]

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 [ 529-20-4 ]

* 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 [ 529-20-4 ]
  • Downstream synthetic route of [ 529-20-4 ]

[ 529-20-4 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 529-20-4 ]
  • [ 16732-80-2 ]
Reference: [1] Organic Process Research and Development, 2018, vol. 22, # 1, p. 97 - 102
  • 2
  • [ 529-20-4 ]
  • [ 89-92-9 ]
Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 27, p. 5161 - 5164
[2] Acta Pharmacologica Sinica, 2016, vol. 37, # 11, p. 1516 - 1524
  • 3
  • [ 79985-01-6 ]
  • [ 118-90-1 ]
  • [ 86128-85-0 ]
  • [ 529-20-4 ]
  • [ 89-92-9 ]
  • [ 91-13-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 10, p. 1857 - 1862
  • 4
  • [ 79985-01-6 ]
  • [ 118-90-1 ]
  • [ 86128-85-0 ]
  • [ 529-20-4 ]
  • [ 89-92-9 ]
  • [ 91-13-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1995, # 10, p. 1857 - 1862
  • 5
  • [ 529-20-4 ]
  • [ 59565-54-7 ]
Reference: [1] Catalysis Letters, 2018, vol. 148, # 11, p. 3486 - 3491
  • 6
  • [ 529-20-4 ]
  • [ 22364-68-7 ]
Reference: [1] European Journal of Organic Chemistry, 2017, vol. 2017, # 16, p. 2379 - 2384
  • 7
  • [ 529-20-4 ]
  • [ 24644-78-8 ]
Reference: [1] Patent: WO2013/74892, 2013, A1,
[2] Patent: US9125407, 2015, B2,
  • 8
  • [ 2259-30-5 ]
  • [ 529-20-4 ]
  • [ 2041-37-4 ]
Reference: [1] Canadian Journal of Chemistry, 1965, vol. 43, p. 498 - 509
  • 9
  • [ 529-20-4 ]
  • [ 90050-59-2 ]
YieldReaction ConditionsOperation in experiment
21% With aluminum (III) chloride; bromine In dichloromethane at 0 - 20℃; for 20.33 h; Intermediate 6: 5-Bromo-2-methylbenzaldehydeTo a solution of 15.1 g (113 mmol) AICI3 in 30 ml_ CH2CI2 at O0C was added dropwise over 20 min 7.50 ml_ (64.8 mmol) of 2-methylbenzaldehyde followed by the dropwise addition of 3.35 ml_ (64.8 mmol) Br2 in 30 ml_ CH2CI2 <n="54"/>over 8 hrs at O0C. The solution was allowed to warm to room temperature over 12 hours then was poured over 50Og ice. This mixture was extracted with 400 ml_ CH2CI2 and the organics washed with 250 ml_ 1.0 N HCI (aq), 250 ml_ sat. NaHCO3 (aq) and 250 ml_ brine then dried over Na2SO4. The solution was concentrated then the resulting solid was recrystallized twice from 50 ml_ hexanes to give 2.92 g (21 percent) of 5-bromo-2-methylbenzaldehyde as an off-white solid: 1 H NMR (400 MHz, CDCI3). δ 10.21 (s, 1 H), 7.94 (s, 1 H), 7.57 (d, 1 H, J = 8.5 Hz), 7.16 (d, 1 H, J = 8.5 Hz), 2.64 (s, 3H.)
5% With aluminum (III) chloride; bromine In dichloromethane at 0 - 20℃; for 18.5 h; Example 15E
5-Bromo-2-methylbenzaldehyde
77.7 g (583 mmol) of aluminium trichloride are suspended in 200 ml of dichloromethane and cooled to 0° C. 40.0 g (333 mmol) of 2-methylbenzaldehyde are added dropwise over the course of 30 min.
Then 53.2 g (333 mmol) of bromine are added at 0° C. over the course of 6 h, and the mixture is allowed to warm to RT and is stirred for 12 h.
The reaction solution is added to 500 ml of ice-water.
The aqueous phase is extracted several times with dichloromethane.
The combined organic phases are washed successively with 2N hydrochloric acid, a saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium chloride solution.
The organic phase is dried over sodium sulfate and concentrated in vacuo.
Purification is by silica gel chromatography and subsequently by crystallization from cyclohexane.
The precipitated product is filtered off.
Yield: 3.2 g (5percent of theory) LC-MS (method 9): Rt=3.26 min MS (EI): m/z=199 (M+H)+
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 29, p. 6935 - 6949
[2] Patent: WO2008/28118, 2008, A1, . Location in patent: Page/Page column 52-53
[3] Patent: US2007/99885, 2007, A1, . Location in patent: Page/Page column 23
[4] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 356
[5] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 356
[6] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 356
[7] Patent: EP2746301, 2014, A1, . Location in patent: Page/Page column
  • 10
  • [ 529-20-4 ]
  • [ 90050-59-2 ]
  • [ 83647-40-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
[2] Patent: WO2005/51911, 2005, A1, . Location in patent: Page/Page column 70
[3] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 68;69
  • 11
  • [ 529-20-4 ]
  • [ 2040-14-4 ]
Reference: [1] Journal of Organic Chemistry, 2003, vol. 68, # 4, p. 1594 - 1596
[2] Phytochemistry, 2013, vol. 96, p. 223 - 234
  • 12
  • [ 623-73-4 ]
  • [ 529-20-4 ]
  • [ 51725-82-7 ]
Reference: [1] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7599 - 7608
[2] Journal of Organic Chemistry, 2004, vol. 69, # 22, p. 7599 - 7608
  • 13
  • [ 529-20-4 ]
  • [ 51725-82-7 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 7, p. 1147 - 1149
  • 14
  • [ 529-20-4 ]
  • [ 16634-91-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 138 - 144
  • 15
  • [ 529-20-4 ]
  • [ 16634-91-6 ]
  • [ 23876-12-2 ]
Reference: [1] Journal of Medicinal Chemistry, 1988, vol. 31, # 1, p. 138 - 144
  • 16
  • [ 529-20-4 ]
  • [ 83647-43-2 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
  • 17
  • [ 529-20-4 ]
  • [ 90111-15-2 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 23, p. 6280 - 6283
  • 18
  • [ 529-20-4 ]
  • [ 74-89-5 ]
  • [ 874-33-9 ]
YieldReaction ConditionsOperation in experiment
93.2%
Stage #1: at 25℃; for 0.5 h;
Stage #2: With sodium tetrahydroborate In methanol; water at 0 - 25℃; for 1 h;
To a solution of 2-methylbenzaldehyde (10.0 g, 83.23 mmol) in MeOH at 25° C. was added methylamine (40 percent in H2O, 25.85 g, 332.9 mmol). The reaction mixture was stirred at 25° C. for 30 min after which time it was cooled to 0° C. and NaBH4 (6.30 g, 166.5 mmol) was added portion-wise. The reaction mixture was then warmed to 25° C. and stirred for an additional 1 hr. The solvent was removed under reduced pressure and water and CH2Cl2 were added. The organic layer was separated and washed with saturated NaHCO3 and brine. After drying over Na2SO4, organic phase was concentrated to afford desired methyl-(2-methyl-benzyl)-amine (10.49 g, 93.2percent) as an oil of sufficient purity for use in the next reaction: MS(APCI+) 136.3 m/z (M+H); H-NMR (CDCl3) δ 7.35-7.08 (m, 3 H), 3.73 (s, 2 H), 2.49 (s, 3 H), 2.34 (s, 3 H).
Reference: [1] Patent: US2006/111422, 2006, A1, . Location in patent: Page/Page column 53
[2] Journal of the American Chemical Society, 1940, vol. 62, p. 910
[3] Patent: US2006/52378, 2006, A1, . Location in patent: Page/Page column 111
[4] European Journal of Medicinal Chemistry, 2018, vol. 143, p. 390 - 401
  • 19
  • [ 529-20-4 ]
  • [ 874-33-9 ]
Reference: [1] Organic Letters, 2011, vol. 13, # 4, p. 600 - 603
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 23, p. 7219 - 7222
  • 20
  • [ 593-51-1 ]
  • [ 529-20-4 ]
  • [ 874-33-9 ]
Reference: [1] Archiv der Pharmazie (Weinheim, Germany), 1987, vol. 320, # 7, p. 647 - 654
  • 21
  • [ 529-20-4 ]
  • [ 90050-59-2 ]
  • [ 83647-40-9 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 6, p. 1645 - 1652
[2] Patent: WO2005/51911, 2005, A1, . Location in patent: Page/Page column 70
[3] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 68;69
  • 22
  • [ 529-20-4 ]
  • [ 342417-01-0 ]
Reference: [1] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
  • 23
  • [ 529-20-4 ]
  • [ 873443-66-4 ]
Reference: [1] Organic Process Research and Development, 2006, vol. 10, # 6, p. 1157 - 1166
  • 24
  • [ 529-20-4 ]
  • [ 914299-79-9 ]
  • [ 138713-44-7 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 37, p. 10884 - 10888[2] Angew. Chem., 2015, vol. 54, p. 10884 - 10888,5
  • 25
  • [ 529-20-4 ]
  • [ 1323140-59-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 2015, vol. 99, # 1, p. 82 - 91
  • 26
  • [ 529-20-4 ]
  • [ 1355326-35-0 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 10, p. 850 - 855
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