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Senevirathne, Prasadini ; Sterling, Alyssa ; Anne Refaei, Mary , et al. DOI:

Abstract: NADPH oxidases (NOXs) are newly identified enzymes that generate intracellular reactive oxygen species (ROS) in skin cells. Recent studies demonstrated that NOX1 holoenzyme is expressed in human keratinocytes and melanocytes, which are implicated in skin photo-carcinogenesis due to the high amounts of ROS produced. Holoenzyme activation requires a ternary complex comprised of NOX1, cytochrome B alpha chain (CYBA), and cytoplasmic NADPH Oxidase Organizer 1 (NOXO1) to properly form. By inhibiting this assembly process, an opportunity for reducing the production of catalytic ROS is possible, especially during high ROS conditions that occur under prolonged UV exposure. We designed a series of small mols. and evaluated their inhibitory effects on NOXO2 using in-silico docking methods in the 1WLP crystal structure. We show that the NOX_inh_5 inhibitor was successful in a variety of experiments using primary skin models from various skin tones. NOX_inh_5 proved to be non-cytotoxic while also improving the viability of primary human skin primary cells under UV exposure. Biophys. studies with NOX_inh_5 using an Isothermal calorimetric (ITC) binding and heteronuclear single quantum coherence (HSQC-NMR) exhibited inhibition of complex formation between NOXO2 and CYBA. Authentic human skin explants, treated with and without NOX_inh_5 and UV exposure, decreased p53 stabilization and decreased UV-induced DNA damage as quantified through cyclobutane dimer formation.

Keywords: Reactive oxygen species ; Apocynin ; UV ; Melanoma ; Sunscreen ; NOXO1 ; CYBA

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Product Details of [ 111-24-0 ]

CAS No. :111-24-0 MDL No. :MFCD00000268
Formula : C5H10Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :IBODDUNKEPPBKW-UHFFFAOYSA-N
M.W : 229.94 Pubchem ID :8100
Synonyms :

Calculated chemistry of [ 111-24-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.89
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.7 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.51
Log Po/w (XLOGP3) : 2.82
Log Po/w (WLOGP) : 2.95
Log Po/w (MLOGP) : 3.29
Log Po/w (SILICOS-IT) : 2.68
Consensus Log Po/w : 2.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.78
Solubility : 0.383 mg/ml ; 0.00167 mol/l
Class : Soluble
Log S (Ali) : -2.48
Solubility : 0.766 mg/ml ; 0.00333 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.62
Solubility : 0.0558 mg/ml ; 0.000243 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.56

Safety of [ 111-24-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P210-P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319 Packing Group:N/A
GHS Pictogram:

Applications of [ 111-24-0 ]

1,5-Dibromopentane (CAS: 111-24-0) can be used in the preparation of ETC-1002 (CAS: 738606-46-7). Bempedoic acid is a first-in-class adenosine triphosphate-citrate lyase (ACL) inhibitor.

Application In Synthesis of [ 111-24-0 ]

* 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.

  • Upstream synthesis route of [ 111-24-0 ]
  • Downstream synthetic route of [ 111-24-0 ]

[ 111-24-0 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 111-24-0 ]
  • [ 4801-58-5 ]
Reference: [1] Gazzetta Chimica Italiana, 1997, vol. 127, # 1, p. 25 - 30
  • 2
  • [ 111-24-0 ]
  • [ 106-50-3 ]
  • [ 2359-60-6 ]
Reference: [1] Patent: DE858551, 1951, ,
  • 3
  • [ 111-24-0 ]
  • [ 591-27-5 ]
  • [ 27292-50-8 ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydrogencarbonate In toluene for 17 h; Heating / reflux 10.91 g (100 mmol) of 3-aminophenol was dissolved in 100 ml of toluene, and 18.5 g (220 mmol) of sodium bicarbonate and 16.0 ml (110 mmol) of 1,5-dibromopentane were added thereto, followed by refluxing the resulting mixture for 17 hours. The reaction mixture was cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate were added thereto. The water layer was separated, extracted twice with 100 ml portions of ethyl acetate, and the organic layers were combined, dried over anhydrous MgS04, and concentrated under a reduced pressure. The concentrate was subjected to column chromatography using 20percent ethyl acetate/hexane as an eluent to obtain 12.9 g (yield 73percent) of 3- (piperidin-1-yl)phenol a solid. M.P. : 112-114°C; (at)H NMR (300 MHz, CDC13) No. 7.09 (t, 1H, J= 7.9 Hz), 6.52 (dd, 1H, J= 8.3,2.3 Hz), 6.41 (t, 1H, J = 2.3 Hz), 6.26 (dd, 1H, J = 8.2,2.4 Hz), 4.60 (s, 1H), 3.17-3.12 (m, 4H), 1.69-1.55 (m, 6H); MS (EI) M+ calc. 177.1154 for C10H15NO, found 177
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 24, p. 13626 - 13631
[2] Patent: WO2005/123054, 2005, A1, . Location in patent: Page/Page column 31
  • 4
  • [ 111-24-0 ]
  • [ 27292-50-8 ]
Reference: [1] Journal of the American Chemical Society, 1953, vol. 75, p. 5280,5282
  • 5
  • [ 111-24-0 ]
  • [ 1074-82-4 ]
  • [ 954-81-4 ]
YieldReaction ConditionsOperation in experiment
73.5% With potassium carbonate In acetone at 60 - 65℃; Inert atmosphere General procedure: The appropriate dibromoalkane derivative 2a-2e (11.9 mmol) was added slowly to a mixture of the starting material phthalimide potassium salt (1) (1g, 5.4 mmol) and anhydrous K2CO3 (0.82 g, 5.94 mmol) in acetone (15 mL). The reaction mixture was heated to 60-65 °C and stirred for 6-10 h under an argon atmosphere. After complete reaction, the solvent was evaporated under reduced pressure. Water (50 mL) was added to the residue and the mixture was extracted with dichloromethane (30 mL × 3). The combined organic phases were washed with saturated aqueous NaCl, dried over Na2SO4, and filtered. The solvent was evaporated to dryness under reduced pressure. The crude product was purified on a silica gel chromatography using dichloromethane/acetone (50:1) as eluent to give the intermediates 3a-3e.
73% for 24 h; Reflux General procedure: A mixture of phthalimide10(6.8 mmol) dissolved in EtOH (20 mL) was gently boiled for about 1h. The hot solution was decanted from any solid into 1.25 mL of a specially prepared solution of KOH (15.25 g KOH dissolved in 15 mL of H2O and 45 mL of EtOH). A precipitate of potassium phthalimide separates at once. The mixture was stirred and cooled quickly to room temperature, and the precipitate was filtered under vacuum. To the alcoholic mother liquors a second 1 g portion of phthalimide was added, and the entire process was repeated. The two crops of crystals were united and washed with acetone to remove any unchanged phthalimide. After air-dried pure potassium phthalimidewas obtained as white crystals (yield 30percent). In a second step, a mixture of potassium phthalimide (2.2 mmol),the appropriate dibromoalkane derivative (2.9 mmol) and 2.5 mL of acetone was stirred and refluxed for 24h, and then cooled to 15 °C. After filtering off the precipitated potassium bromide, the cake was washed with acetone and the solvent evaporated to give pure compound.
72% for 10.25 h; Reflux General procedure: Acetone (150mL) and dibromoalkyl (30mol) were added to a 250mL three-necked round-bottom flask fitted with a mechanical stirrer and reflux condenser. Potassium phthalimide (11.85g, 10 mol) was added slowly over a 15-min period, and then the reaction mixture was heated under reflux for 10h. The reaction mixture was filtered via suction, and the acetone was removed via rotary evaporation. The crude product was purified by flash chromatography on silica gel (EtOAc:petroleum ether=1:14) to afford 2–5 as white solid.
65% at 20 - 90℃; for 18.5 h; To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90°C for 1 8 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered anad concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10percent EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65percent yield).H NMR (400 MHz, CDCI3): d 7.82 (dd,J= 5.5, 3.1 Hz, 2H), 7.69 (dd,J= 5.5, 3.0 Hz, 2H),3.68 (t, J= 7.2 Hz, 2H), 3..38 (t, J= 6.8 i-iz, 2Ff). 1.93-1.85 (n:i, 2H), 1.70 (p, J= 7,5 Hz, 2H),1.53-1.43 (m, 2H).
65% at 20 - 90℃; o a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90°C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10percent EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65percent yield).1H NMR (400 MHz, CDC13): δ 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J= 5.5, 3.0 Hz, 2H), 3.68 (t, J= 7.2 Hz, 2H), 3.38 (t, J= 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H), 1.53-1.43 (m, 2H).
65% at 20 - 90℃; for 18.5 h; To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90°C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10percent EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65percent yield). ‘HNMR (400 IVIFIz, CDC13): 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J 5.5, 3.0 Hz, 2H), 3.68 (t, J 7.2 Hz, 2H), 3.38 (t, J 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H),1.53-1.43 (m, 2H).
65% at 20 - 90℃; for 18.5 h; To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90°C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10percent EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65percent yield). 1H NMR (400 MHz, CDC13): δ 7.82 (dd, J= 5.5, 3.1 Hz, 2H), 7.69 (dd, J= 5.5, 3.0 Hz, 2H), 3.68 (t, J= 7.2 Hz, 2H), 3.38 (t, J= 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H), 1.53-1.43 (m, 2H).
65% at 20 - 90℃; for 18.5 h; To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 mm at room temperature. After complete addition, the reaction mixture was stirred at 90°C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10percent EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65percent yield).‘H NMR (400 MHz, CDC13): 7.82 (dd,J= 5.5, 3.1 Hz, 2H), 7.69 (dd,J= 5.5, 3.0 Hz, 2H), 3.68 (t, J 7.2 Hz, 2H), 3.38 (t, J 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J= 7.5 Hz, 2H),1.53-1.43 (m, 2H).
65% at 20 - 90℃; [0714] Step 11: Synthesis of 2-(5-bromopentyl) isoindoline-1,3-dione (14-k) To a stirred solution of 1,5-dibromopentane (13-k) (170.58 mL, 1.26 mol) in DMF (1.5 L) was added potassium phthalate (12-k) (78.0 g, 0.42 mol) portion-wise over 30 min at room temperature. After complete addition, the reaction mixture was stirred at 90°C for 18 h, then quenched with water (3 L) and extracted with diethyl ether (500 mL x 4). The combined organic extracts were washed with water (500 mL x 2), followed by brine (500 mL x 2) and dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude. The residue was purified by silica gel column chromatography (60-120 mesh) using 5-10percent EtOAc / hexanes to afford 14-k as an off-white solid (81 g, 65percent yield). 1H NMR (400 MHz, CDCl3): δ 7.82 (dd, J = 5.5, 3.1Hz, 2H), 7.69 (dd, J = 5.5, 3.0 Hz, 2H), 3.68 (t, J = 7.2 Hz, 2H), 3.38 (t, J = 6.8 Hz, 2H), 1.93-1.85 (m, 2H), 1.70 (p, J = 7.5 Hz, 2H), 1.53-1.43 (m, 2H).
55% at 20℃; for 24 h; [65] To a solution of 1,5-dibromopentane (9.00 ml, 65.22 mmol) dissolved in DMF (100 ml) was added potassium phthalimide (12.08 g, 65.22 mmol) at room temperature, and the reaction mixture was stirred for 24 hours. After the reaction was completed, distilled water was added, and the resulting reaction mixture was stirred for 10 minutes and extracted with ethyl acetate three times. Then, the organic phase was washed with a saline solution, dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane = 1:3) to give the target compound (10.6 g, 55 percent).[66] 1H-NMR (400 MHz, CDCl3) δ 7.85-7.70 (m, 4H, aromatic), 3.71-3.67 (t, 2H, -CH2 -CH2-CH2-CH2-CH2-Br), 3.4-3.38 (t, 2H, -CH^-CH2-CH2-CH2-Qi2-Br), 1.94-1.87 (m, 2H, -CH2-CIl2-CH2-CH2-CH2-Br), 1.73-1.67 (m, 2H, -CH2-CH2-CH2-CH2-CH2-Br), 1.53-1.47 (m, 2H, -CH2-CH2-CH2-CH2-CH2-Br).[67]
6.9 g at 20℃; for 15 h; 8.7ml (6 · 5 X 102 moles) 1,5-dibromopentane with6 g (3. 2 X 10 2 moles) Phthalimide potassium salt dissolved in 100ml of N, N- dimethylformamide andunder room temperatureit was stirred for 15hours.The solvent was distilled off under reduced pressure, The residue usingn-hexane: ethyl acetate with a volumeratio of 10: 1 eluent to carry out column chromatography, gradually increasingthe polarity to hexane: ethyl acetate with a volume ratio of 5: 1 to give a product of 6.9g(2.3X102 mol) a bromogroup substituted by Phthalimide. The product with 5. 9g (4. 7X 102 mol) of sodium sulfite, 140ml water and 85ml95percent ethanol mixed reactionwas heated to 95 ° C for18h, the remainingsolvent was drained, and the resulting residue was mixed with 73ml ofconcentrated hydrochloric acidthen was heated to 110 ° C thefor 18H, it was drained, with water - 95percent ethanol on the residue to carry out recrystallization to give 5-amino-1-pentylSulfonic acid 2. 7g (total yield 50percent).

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  • 6
  • [ 136918-14-4 ]
  • [ 111-24-0 ]
  • [ 954-81-4 ]
YieldReaction ConditionsOperation in experiment
80.4% With potassium carbonate In acetonitrile for 24 h; Reflux General procedure: Compound 6–9 was prepared according the literature reported by Cheng L etal. [34] and with some modifications. Namely, phthalimide (2.9g, 20mmol) and the appropriate dibromoalkanes (80mmol) were added into MeCN (50mL). After an addition of K2CO3 (11g, 80mmol), the mixture was refluxed for 24h and followed by TLC (Thin Layer Chromatography). The solvent was evaporated under reduced pressure, and then the residuum was dissolved in ethyl acetate (200mL) and washed by water (3×100 mL). The organic phase was dried by MgSO4, and then was evaporated. The crude product was purified by column chromatography (PE/EtOAc=10:1, Rf=0.4) to give 6–9.
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Reference: [1] Journal of the American Chemical Society, 1924, vol. 46, p. 2841
  • 20
  • [ 111-24-0 ]
  • [ 140-29-4 ]
  • [ 2201-23-2 ]
YieldReaction ConditionsOperation in experiment
65.76% With sodium hydride In diethyl ether; dimethyl sulfoxide at 0℃; for 2 h; To a suspension of NaH (42.7 g, 1067.0 mmol, 60percent) in dimethyl sulfoxide (600.0 mL) were added drop-wise a mixture of phenylacetonitrile (50.0 g, 426.8 mmol) and 1,5-dibromopentane (58.1 mL, 426.8 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (200.0 mL) at 0° C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water and a 10percent HCl solution were added to the mixture and the mixture was extracted with ethyl acetate. The combined organic layer was then washed with water and brine and dried over sodium sulfate and concentrated under reduced pressure to obtain a crude product. This crude product was then purified by normal silica gel column chromatography (using hexane) to get 1-phenyl-cyclohexanecarbonitrile (249) (52.0 g, 65.76percent) as a colorless oil. [0942] GC-MS: 185.0 (m/z).
37% With sodium hydride In diethyl ether; dimethyl sulfoxide; mineral oil at 15 - 20℃; for 25 h; Inert atmosphere General procedure: To a stirred suspension of NaH (60percent dispersed in oil) (0.14 g, 3.4 mmol) in DMSO (20 mL) under nitrogen at 15° C, a solution of the appropriate acetonitrile (1.8 mmol) and 1,5-dibromopentane (0.41 g, 1.8 mmol) in Et2O (4 mL) and DMSO (1 mL) was added dropwise over 1 h. The mixture was allowed to warm to room temperature and stirred for an additional 24 h under nitrogen. The reaction mixture was carefully quenched by the addition dropwise of isopropanol (5 mL), followed by H2O (5 mL) 10 min later. The mixture was diluted with AcOEt and washed with H2O. The aqueous layer was re-extracted with AcOEt, and the two organic layers were combined, dried (Na2SO4), and concentrated in vacuo. The crude residue was chromatographed (n-hexane/AcOEt, 4:1, as eluent) to give the desired compound as a colorless oil.
3.370 g With sodium hydride In N,N-dimethyl-formamide at 0 - 50℃; for 17.5 h; A solution of phenylacetonitrile (2.000 g, 17.072 mmol) and 1,5-dibromopentane (2.036 ml, 17.072 mmol) in N,N-dimethylformamide (100 ml) was stirred at 0 °C for 30 minutes then sodium hydride (60.00percent, 1.502 g, 37.559 mmol) was added and stirred at 50 °C for additional 17 hours, then the temperature was reduced to room temperature to terminate the reaction. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, and water was removed with anhydrous magnesium sulfate, followed by filtration and concentration under reduced pressure. The title compound was used without further purification (3.370 g, 115.3percent, brown oil).
Reference: [1] Patent: US2014/194431, 2014, A1, . Location in patent: Paragraph 0940-0942
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3913 - 3924
[3] Journal of Organic Chemistry, 1971, vol. 36, p. 1308 - 1309
[4] Chemische Berichte, 1973, vol. 106, p. 2890 - 2903
[5] Bulletin de la Societe Chimique de France, 1965, p. 2030 - 2037
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 5, p. 1438 - 1441
[7] Patent: KR2017/43091, 2017, A, . Location in patent: Paragraph 0255-0258
  • 21
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  • [ 865-48-5 ]
  • [ 2201-23-2 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 4059,4062
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  • [ 111-24-0 ]
  • [ 829-85-6 ]
  • [ 27721-02-4 ]
Reference: [1] Tetrahedron Letters, 2003, vol. 44, # 46, p. 8373 - 7377
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 2004, vol. 179, # 2, p. 277 - 283
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  • [ 111-24-0 ]
  • [ 100-33-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1990, vol. 33, # 4, p. 1252 - 1257
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 2, p. 592 - 608
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  • [ 111-24-0 ]
  • [ 63203-48-5 ]
Reference: [1] Organic and Biomolecular Chemistry, 2005, vol. 3, # 17, p. 3188 - 3193
  • 25
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  • [ 112-18-5 ]
  • [ 18464-25-0 ]
Reference: [1] Molecules, 2011, vol. 16, # 1, p. 319 - 335
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 24, p. 5824 - 5828
[3] Pharmaceutical Chemistry Journal, 1968, # 5, p. 247 - 250[4] Khimiko-Farmatsevticheskii Zhurnal, 1968, # 5, p. 15 - 18
[5] Canadian Journal of Chemistry, 2010, vol. 88, # 2, p. 124 - 134
  • 26
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  • [ 591-19-5 ]
  • [ 84964-24-9 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 11, p. 3094 - 3113
[2] Journal of Organic Chemistry, 2009, vol. 74, # 19, p. 7464 - 7469
[3] Journal of Organic Chemistry, 2011, vol. 76, # 1, p. 342 - 345
[4] Patent: WO2015/42397, 2015, A1, . Location in patent: Paragraph 000909
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