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[ CAS No. 1628-29-1 ] {[proInfo.proName]}

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Chemical Structure| 1628-29-1
Chemical Structure| 1628-29-1
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Product Details of [ 1628-29-1 ]

CAS No. :1628-29-1 MDL No. :MFCD00022264
Formula : C14H11NOS Boiling Point : -
Linear Structure Formula :- InChI Key :DNVNQWUERFZASD-UHFFFAOYSA-N
M.W : 241.31 Pubchem ID :74200
Synonyms :

Calculated chemistry of [ 1628-29-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 72.95
TPSA : 45.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.57
Log Po/w (XLOGP3) : 2.99
Log Po/w (WLOGP) : 3.46
Log Po/w (MLOGP) : 3.42
Log Po/w (SILICOS-IT) : 2.98
Consensus Log Po/w : 3.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.0509 mg/ml ; 0.000211 mol/l
Class : Soluble
Log S (Ali) : -3.61
Solubility : 0.059 mg/ml ; 0.000244 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.7
Solubility : 0.00485 mg/ml ; 0.0000201 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.64

Safety of [ 1628-29-1 ]

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

Application In Synthesis of [ 1628-29-1 ]

* 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 [ 1628-29-1 ]
  • Downstream synthetic route of [ 1628-29-1 ]

[ 1628-29-1 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 92-84-2 ]
  • [ 75-36-5 ]
  • [ 1628-29-1 ]
YieldReaction ConditionsOperation in experiment
100% at 50℃; for 1 h; 19.1)
10-acetyl-10H-phenothiazine:
20 g (0.1 mol) of phenothiazine followed by 14.3 ml (2 eq.) of acetyl chloride are added to a 500 ml flask containing 200 ml of toluene.
The heterogeneous reaction mixture is stirred for 1 hour at 50° C.
After concentration to dryness, the precipitate is taken up in a minimum of isopentane and filtered.
After drying, 24 g of a beige solid is obtained with a quantitative yield.
Melting point: 210-211° C.
96%
Stage #1: With zinc(II) chloride In dichloromethane at 0℃; for 0.333333 h;
Stage #2: at 0 - 20℃; for 24 h;
A mixture of zinc chloride (0.75g, 5.50mmol), acetyl chloride (0.8mL, 5.62mmol) in dichloromethane (25mL) at 0°C was stirred for 20min. Phenothiazine 16 (1.00g, 5.02mmol) was added to the solution and stirred at rt for 24h before reaction mixture was diluted with ice-cold H2O and extracted with dichloromethane (3×20 mL). The organic layers were dried with Na2SO4, filtered off and concentrated under reduced pressure. The product 17 was obtained as a green solid in 96percent (1.146g) yield; mp: 191–195°C (dichloromethane); IR (ATR diamond, cm-1) ν: 1668, 1459, 1315, 1257; 1H NMR (400MHz, CDCl3) δ: 2.20 (s, 3H, CH3), 7.22 (t, J=6Hz, 2H, H-7, H-3), 7.32 (t, J=6Hz, 2H, H-2, H-8), 7.43 (d, J=6Hz, 2H, H-4, H-6), 7.50 (d, J=6Hz, 2H, H-1, H-9); 13C NMR (100MHz, CDCl3) δ: 23.4 (CH3), 127.1 (2CH), 127.3 (2CH), 127.5 (2CH), 128.3 (2CH), 133.4 (2Cq), 139.3 (2Cq), 169.6 (Cq). HRMS (ESI): calcd for C14H12NOS [M+H]+: 242.0640 found 242.0638.
94.5% for 0.166667 h; Microwave irradiation General procedure: To a solution of 10H-phenothiazine (2.62 mmol) in dry toluene (5 mL) was added drop by drop the corresponding acyl chloride (0.5 mL; 6.2 mmol). The reaction was irradiate with MW (500 Watts) during 10 min, then was washed with NaOH 5percent (2 .x. 5 mL) and the organic phase was dry with anhydrous Na2SO4. Finally the solvent was remove in vacuo.
93% for 1 h; Reflux To 1 mmole of 10-H PTZ was added an equivalent quantity of glacial acetic acid. 10-H PTZ is stirred in solvent for 1 hr to get clear solution. To the resultant solution, 10 mL of acetyl chloride was added. During the addition of acetyl chloride, the internal temperature was maintained at 5°C. The resulting mixture was refluxed for 1 h. The mixture was kept for overnight; the formation of white crystals was taken place. Filter the residue and recrystallized from hot ethanol.[10] Yield: 93percent; m.p.: 172 °C; IR (KBr, υmax/cm−1): 2899.19 (CH3, str), 1363.51 (C-N of PTZ ring, str), 1655(C=O, str). 1H NMR (DMSO-d6, 500 MHz, δ/ppm): 8.20–8.18 (d, 2H, J= 5Hz, Ar-H), 7.42–7.40 (d, 2H, J = 5Hz, Ar-H), 7.21–7.19 (d, 2H, J = 5Hz, Ar-H), 6.50-6.48 (d, 2H, J = 5Hz, Ar-H), 3.189 (s, 3H, CH3).

Reference: [1] Patent: US2005/222045, 2005, A1, . Location in patent: Page/Page column 13
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4113 - 4126
[3] European Journal of Medicinal Chemistry, 2011, vol. 46, # 1, p. 101 - 105
[4] Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 2, p. 221 - 226
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 1, p. 157 - 161
[6] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 1, p. 211 - 222
[7] Journal of the American Chemical Society, 1953, vol. 75, p. 5422,5425
[8] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1953, vol. 236, p. 1569
[9] Bulletin de la Societe Chimique de France, 1960, p. 1049 - 1066
[10] Journal of Medicinal Chemistry, 1998, vol. 41, # 2, p. 148 - 156
[11] Chemistry Letters, 2018, vol. 47, # 7, p. 825 - 828
  • 2
  • [ 1408316-55-1 ]
  • [ 1628-29-1 ]
YieldReaction ConditionsOperation in experiment
90% for 24 h; Reflux The hydrazine 6 (10 mmol) was stirred in absolute EtOH at reflux for 24 h. A white precipitate formed during the reaction progress and, after cooling to room temperature, it was collected by filtration and washed with ethanol to afford pure compound 15 as a white solid with the same physico-chemical properties as described in the literature;28 90percent yield. 1H NMR (CDCl3, 400 MHz) δ 2.19 (s, 3H), 7.19 (dt, J = 7.6, 1.2 Hz, 2H), 7.30 (dt, J = 7.6, 1.2 Hz, 2H), 7.41 (dd, J = 7.6, 1.2 Hz, 2H), 7.49 (d, J = 7.6 Hz, 2H).
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 45, p. 6127 - 6131
  • 3
  • [ 92-84-2 ]
  • [ 108-24-7 ]
  • [ 1628-29-1 ]
Reference: [1] Canadian Journal of Chemistry, 2010, vol. 88, # 1, p. 42 - 49
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2568 - 2581
[3] Chemische Berichte, 1978, vol. 111, p. 1453 - 1463
[4] Journal of Pharmaceutical Sciences, 1976, vol. 65, # 11, p. 1699 - 1701
[5] Patent: WO2007/20932, 2007, A1, . Location in patent: Page/Page column 10
[6] Patent: US9198916, 2015, B1, . Location in patent: Page/Page column 12
  • 4
  • [ 61214-99-1 ]
  • [ 1628-29-1 ]
Reference: [1] Heterocycles, 1993, vol. 36, # 7, p. 1641 - 1644
  • 5
  • [ 92-84-2 ]
  • [ 75-36-5 ]
  • [ 1628-29-1 ]
  • [ 6632-11-7 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2673,2677
  • 6
  • [ 786-50-5 ]
  • [ 1628-29-1 ]
Reference: [1] Tetrahedron Letters, 2012, vol. 53, # 45, p. 6127 - 6131
[2] Tetrahedron Letters, 2012, vol. 53, # 45, p. 6127 - 6131
[3] Tetrahedron Letters, 2012, vol. 53, # 45, p. 6127 - 6131
  • 7
  • [ 63107-77-7 ]
  • [ 1628-29-1 ]
Reference: [1] Chemistry Letters, 2018, vol. 47, # 7, p. 825 - 828
  • 8
  • [ 244205-40-1 ]
  • [ 1628-29-1 ]
Reference: [1] Chemistry Letters, 2018, vol. 47, # 7, p. 825 - 828
  • 9
  • [ 19614-16-5 ]
  • [ 1628-29-1 ]
Reference: [1] Chemistry Letters, 2018, vol. 47, # 7, p. 825 - 828
  • 10
  • [ 122-39-4 ]
  • [ 1628-29-1 ]
Reference: [1] Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 2, p. 221 - 226
  • 11
  • [ 98546-66-8 ]
  • [ 108-24-7 ]
  • [ 1628-29-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1885, vol. 230, p. 169,170[2] Chemische Berichte, 1906, vol. 39, p. 1808
  • 12
  • [ 1628-29-1 ]
  • [ 6631-94-3 ]
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 2, p. 148 - 156
[2] Bulletin de la Societe Chimique de France, 1955, p. 768,781
  • 13
  • [ 1628-29-1 ]
  • [ 75-36-5 ]
  • [ 6631-94-3 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2673,2677
[2] Journal of Organic Chemistry, 1956, vol. 21, p. 1006
  • 14
  • [ 1628-29-1 ]
  • [ 506-96-7 ]
  • [ 6631-94-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1962, vol. 10, p. 1 - 8
  • 15
  • [ 1628-29-1 ]
  • [ 108-24-7 ]
  • [ 6631-94-3 ]
Reference: [1] J. Gen. Chem. USSR (Engl. Transl.), 1960, vol. 30, p. 2622 - 2626[2] Zhurnal Obshchei Khimii, 1960, vol. 30, p. 2640 - 2645
  • 16
  • [ 1628-29-1 ]
  • [ 124-63-0 ]
  • [ 23503-68-6 ]
YieldReaction ConditionsOperation in experiment
28%
Stage #1: With aluminum (III) chloride In dichloromethane at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 24 h;
A mixture of 131 aluminium trichloride (0.17g, 1.24mmol) and 139 methanesulfonyl chloride (0.17mL, 2.34mmol) in 133 dichloromethane (20mL) at 0°C was stirred for 15min before compound 17 (0.30g, 1.24mmol) was added. The reaction mixture was stirred at rt for 24h before it was diluted with ice-cold H2O and extracted with dichloromethane (3×20 mL). The organic layers were dried with Na2SO4, filtered off and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography using 129 Hexane:140 EtOAc (0.65:0.35) as eluent. The product 118 18 was obtained as a green solid in 28percent (96mg) yield; mp: 211–215°C (hexane/ethyl acetate); IR (ATR diamond, cm-1) ν: 3351, 1567, 1310, 1297; 1H NMR (400MHz, acetona-d6) δ: 3.22 (s, 3H, CH3), 6.90 (d, J=9Hz, 1H, H-9), 6.98 (d, J=9Hz, 1H, H-6), 7.03 (t, J=9Hz, 1H, H-7), 7.13 (d, J=6Hz, 1H, H-3), 7.20 (t, J=9Hz, 1H, H-8), 7.58 (s, 1H, H-1), 7.66 (d, J=6Hz, 1H, H-4), 8.55 (bs, 1H, NH–); 13C NMR (100MHz, acetone-d6) δ: 44.2 (CH3), 114.5 (CH), 115.6 (CH), 116.9 (Cq), 118.7 (Cq), 123.8 (CH), 125.9 (CH), 126.8 (CH), 127.8 (CH), 128.4 (CH), 134.7 (Cq), 140.9 (Cq), 147.2 (Cq). HRMS (ESI): calcd for C13H12NO2S2 [M+H]+: 278.0309 found 278.0310.
Reference: [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 14, p. 4113 - 4126
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