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[ CAS No. 1207-69-8 ] {[proInfo.proName]}

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Chemical Structure| 1207-69-8
Chemical Structure| 1207-69-8
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Product Details of [ 1207-69-8 ]

CAS No. :1207-69-8 MDL No. :MFCD00022266
Formula : C13H8ClN Boiling Point : -
Linear Structure Formula :- InChI Key :BPXINCHFOLVVSG-UHFFFAOYSA-N
M.W : 213.66 Pubchem ID :71013
Synonyms :

Calculated chemistry of [ 1207-69-8 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 14
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 64.26
TPSA : 12.89 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.57
Log Po/w (XLOGP3) : 4.05
Log Po/w (WLOGP) : 4.04
Log Po/w (MLOGP) : 3.6
Log Po/w (SILICOS-IT) : 4.13
Consensus Log Po/w : 3.68

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.41
Solubility : 0.00837 mg/ml ; 0.0000392 mol/l
Class : Moderately soluble
Log S (Ali) : -4.02
Solubility : 0.0202 mg/ml ; 0.0000945 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.0
Solubility : 0.000214 mg/ml ; 0.000001 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.34

Safety of [ 1207-69-8 ]

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 [ 1207-69-8 ]

* 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 [ 1207-69-8 ]
  • Downstream synthetic route of [ 1207-69-8 ]

[ 1207-69-8 ] Synthesis Path-Upstream   1~16

  • 1
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  • [ 6574-15-8 ]
  • [ 2359-60-6 ]
Reference: [1] Patent: US2001/46991, 2001, A1,
  • 2
  • [ 578-95-0 ]
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YieldReaction ConditionsOperation in experiment
89% for 12 h; Reflux; Inert atmosphere A magnetically stirred solution of 9-acridanone (4.01 g, 21 mmol) in phosphorus oxychloride (105 mL, 1.13 mol) was brought to reflux for 12 h. The solution was cooled to rt, added slowly to cracked ice (650 g), and made slightly alkaline with concentrated ammoniumhydroxide. A light tan solid was collected by filtration, washed with water, and air dried for 24 h. Flash chromatography (silica gel/75percent hexane, 20percent THF, 5percent triethylamine) afforded 3.97 g (89percent yield)of 10 as fine yellow needles which was identical to material prepared by method A as judged by TLC, mp, and spectral data.
86% at 105℃; for 3 h; Inert atmosphere Add 3 mmol of acridone to a two-necked flask equipped with a condenser and a stir bar, fill with N2, add 6 ml of P0C13 in a nitrogen atmosphere, and reflux at 105 ° C for 3 h. After the reaction is completed, cool to room temperature. The reaction solution was slowly dropped into ice water while stirring, and a mixture of ice, concentrated aqueous ammonia and chloroform (volume ratio 1:1:1) was added to the above liquid, and the chloroform layer was separated and dried (anhydrous magnesium sulfate). Filtration gave a pale yellow liquid, which was purified by column chromatography using ethyl acetate: petroleum ether.White needle crystals were obtained with strong fluorescence. Intermediate Compound 1, yield 86percent.
47 g With thionyl chloride In N,N-dimethyl-formamide A mixture of 50 g (0.25 mol) of intermediate (d) and 35 g of thionyl chloride and 200 g of N, N-dimethylformamide,After completion of the reaction, the reaction mixture was poured into ice water, filtered and dried to obtain 47 g of a yellow solid powdery intermediate ()
Reference: [1] Pharmaceutical Sciences, 1997, vol. 3, # 5-6, p. 235 - 239
[2] European Journal of Inorganic Chemistry, 1999, # 3, p. 557 - 563
[3] Heterocycles, 2014, vol. 88, # 1, p. 535 - 546
[4] Patent: CN108640873, 2018, A, . Location in patent: Paragraph 0022; 0023
[5] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 926 - 935
[6] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 48
[7] Organic Syntheses, 1942, vol. 22, p. 5
[8] Chemische Berichte, 1900, vol. 33, p. 3770
[9] Patent: CN103755634, 2016, B, . Location in patent: Paragraph 0040
[10] Patent: WO2008/10984, 2008, A2, . Location in patent: Page/Page column 22
  • 3
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YieldReaction ConditionsOperation in experiment
84% for 12 h; Reflux; Inert atmosphere A magnetically stirred solution of N-phenylanthranilic acid (5.45 g,26 mmol) in phosphorus oxychloride (100 mL, 1.07 mol) was treated with concentrated sulfuric acid (0.5mL), then brought to reflux for 12 h. The solution was cooled to rt, added slowly to cracked ice (650 g), and made slightly alkaline with concentrated ammonium hydroxide. A light tan solid was collected by filtration, washed with water, and air dried for 24 h. Flash chromatography (silica gel/75percent hexane, 20percentTHF, 5percent triethylamine) afforded 4.67 g (84percent yield) of 10 as fine yellow needles having one medium Rf spot by TLC; mp 117–119 °C (lit.15 mp 119–120 °C); 1H NMR (CDCl3): 8.50–8.10 (m, 4H),7.95–7.50 (m, 4H); IR (THF): 3075, 1622, 1562, 1438, 1404, 1324, 1287, 1014, 831, 767, 647, 608cm-1; Vis (CHCl3): λmax (") 360.5 nm (10,000); MS EI: m/e (relative intensity) 215 (33, M++2), 213(100, M+), 178 (21), 177 (16). Anal. Calcd for C13H8ClN: C, 73.07; H, 3.77; N, 6.55; Cl, 16.59. Found: C, 72.99; H, 3.80; N, 6.55; Cl, 16.58.
69% Reflux General procedure: The phenyl amino benzoic acid derivatives (47 mmol) (2a–c) were cyclized intra molecularly to 9-chloroacridine derivatives(3a–c) by refluxing them in 60 mL of POCl3 for 4 h and the reaction was monitored by TLC. After completion, the excess POCl3 was removed by rota evaporator under reduced pressure to the crude reaction mass crushed ice was added, pH was adjusted 7 by adding saturated bicarbonate solution. The solid separated was filtered,dried and purified by flash column chromatography using 5–10percent ethyl acetate: hexane as eluent in 60–120 mesh silica gelto get the corresponding 9-chloroacridine derivatives in good yield. These intermediates were confirmed by mass analysis (ESI mode) and proceed to next step.
56% at 110℃; for 3 h; In a 100ml eggplant type bottle,N-phenylanthranilic acid (5.0 g, 23.5 mmol) was added,Phosphorus oxychloride (50 ml, 537 mmol). Put it in a 110°C oil bath and stir for 3 hours.TLC (developer: dichloromethane/methanol=20/1) detects complete disappearance of compound III-14.Withdraw from the oil bath and naturally cool to room temperature.The reaction mixture was slowly added to 150 g of ice and stirred vigorously. After the heat is released,The pH was adjusted with saturated sodium bicarbonate solution until bubbles ceased to form.After filtration, the filter cake is washed with water 2 or 3 times and drained.This gave the solid, 9-chlorohydrazine, 2.8 g (brown solid, yield 56percent).
Reference: [1] Journal of Physical Organic Chemistry, 2010, vol. 23, # 4, p. 382 - 389
[2] Journal of the American Chemical Society, 2010, vol. 132, # 40, p. 14006 - 14008
[3] Journal of Heterocyclic Chemistry, 1987, vol. 24, # 5, p. 1405 - 1408
[4] Heterocycles, 2014, vol. 88, # 1, p. 535 - 546
[5] Journal of Heterocyclic Chemistry, 2012, vol. 49, # 4, p. 748 - 754
[6] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 877 - 885
[7] Electrochimica Acta, 2010, vol. 55, # 9, p. 3348 - 3354
[8] Patent: CN107721925, 2018, A, . Location in patent: Paragraph 0092; 0093
[9] Organic Syntheses, 1942, vol. 22, p. 5
[10] Journal of the Indian Chemical Society, 1998, vol. 75, # 10-12, p. 716 - 724
[11] European Journal of Medicinal Chemistry, 2010, vol. 45, # 2, p. 745 - 751
[12] Archiv der Pharmazie, 2009, vol. 342, # 12, p. 699 - 709
[13] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 12, p. 3491 - 3494
[14] Heterocycles, 2010, vol. 80, # 2, p. 1047 - 1066
[15] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 217 - 224
[16] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4170 - 4177
[17] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3308 - 3311
[18] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 14, p. 3014 - 3017
[19] Medicinal Chemistry, 2014, vol. 10, # 5, p. 506 - 511
[20] Chinese Chemical Letters, 2014, vol. 25, # 7, p. 1021 - 1024
[21] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1800 - 1807
[22] Patent: CN103755634, 2016, B,
[23] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 1135 - 1146
[24] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 926 - 935
[25] RSC Advances, 2018, vol. 8, # 68, p. 38995 - 39004
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1901, vol. <2> 64, p. 192
[2] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 48
[3] Chemische Berichte, 1900, vol. 33, p. 3770
[4] European Journal of Medicinal Chemistry, 2016, vol. 122, p. 497 - 509
  • 5
  • [ 118-91-2 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 217 - 224
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4170 - 4177
[3] Medicinal Chemistry, 2014, vol. 10, # 5, p. 506 - 511
[4] Chinese Chemical Letters, 2014, vol. 25, # 7, p. 1021 - 1024
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1800 - 1807
[6] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 877 - 885
[7] Patent: CN103755634, 2016, B,
[8] European Journal of Medicinal Chemistry, 2017, vol. 138, p. 1135 - 1146
[9] Patent: CN107721925, 2018, A,
  • 6
  • [ 62-53-3 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 56, p. 217 - 224
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4170 - 4177
[3] Medicinal Chemistry, 2014, vol. 10, # 5, p. 506 - 511
[4] Chinese Chemical Letters, 2014, vol. 25, # 7, p. 1021 - 1024
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 8, p. 1800 - 1807
[6] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 877 - 885
[7] Patent: CN103755634, 2016, B,
[8] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 926 - 935
[9] Patent: CN107721925, 2018, A,
[10] RSC Advances, 2018, vol. 8, # 68, p. 38995 - 39004
  • 7
  • [ 6540-78-9 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1901, vol. <2> 64, p. 471
[2] Chemische Berichte, 1900, vol. 33, p. 3770
[3] Journal fuer Praktische Chemie (Leipzig), 1903, vol. <2> 68, p. 88
[4] Journal fuer Praktische Chemie (Leipzig), 1903, vol. <2> 68, p. 88
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 491
  • 8
  • [ 62-53-3 ]
  • [ 118-91-2 ]
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Reference: [1] Current Medicinal Chemistry, 2013, vol. 20, # 32, p. 4070 - 4079
[2] Journal of Heterocyclic Chemistry, 1986, vol. 23, # 3, p. 965 - 967
[3] Tetrahedron Letters, 2014, vol. 55, # 22, p. 3308 - 3311
  • 9
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Reference: [1] RSC Advances, 2018, vol. 8, # 68, p. 38995 - 39004
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Reference: [1] Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 926 - 935
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1903, vol. <2> 68, p. 88
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  • [ 85842-89-3 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1903, vol. <2> 68, p. 88
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Reference: [1] Justus Liebigs Annalen der Chemie, 1893, vol. 276, p. 48
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  • [ 10025-87-3 ]
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Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1901, vol. <2> 64, p. 471
[2] Chemische Berichte, 1900, vol. 33, p. 3770
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 491,492
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 6, p. 491
  • 15
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Reference: [1] Chemische Berichte, 1933, vol. 66, p. 866,869[2] Zhurnal Obshchei Khimii, 1933, vol. 3, p. 615,618
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Reference: [1] Justus Liebigs Annalen der Chemie, 1933, vol. 504, p. 297,302
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