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[ CAS No. 74115-13-2 ] {[proInfo.proName]}

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Chemical Structure| 74115-13-2
Chemical Structure| 74115-13-2
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Product Citations

Product Citations

Ouellette, Vincent ; Bouzriba, Chahrazed ; Alvarez, Atziri Corin Chavez , et al. DOI:

Abstract: We developed first-in-class antimitotic prodrugs phenyl 4-(2-oxo-alkylimidazolidin-1-yl)benzenesulfonates (PAIB-SOs) bioactivated by cytochrome (CYP) 1A1 that are highly selective toward several breast cancer cells. However, they show sparingly water solubility. Therefore, we replaced their phenyl ring B with a substituted pyridinyl group preparing novel pyridinyl 4-(2-oxo-3-alkylimidazolidin-1-yl)benzenesulfonates (PYRAIB-SOs) and their hydrochloride salts. Our results evidence that PYRAIB-SO hydrochloride salts show higher water solubility compared to their neutral and PAIB-SO counterparts by up to 625-fold. PYRAIB-SOs with a nitrogen atom at position 3 of the pyridinyl ring exhibited strong antiproliferative activity (IC50: 0.03-3.3 μM) and high selectivity (8-> 1250) toward sensitive CYP1A1-positive breast cancer cells and cells stably transfected with CYP1A1. They induce cell cycle arrest in the G2/M phase and disrupt microtubule dynamic assembly. Enzymatic assays confirmed that CYP1A1 metabolizes PYRAIB-SOs into their active form with in vitro hepatic half-lives (55-120 min) in rodent and human liver microsomes. Overall, this will allow to increase drug concentration for in vivo studies.

Keywords: Anticancer agents ; Antimitotics ; Antimicrotubule agents ; CYP1A1-activated prodrugs ; Pyridinyl 4-(2-oxo-alkylimidazolidin-1-yl)benzenesulfonates ; PYRAIB-SOs ; Pyridinyl 4-(2-oxoimidazolidin-1-yl)benzenesulfonates ; PYRIB-SOs ; Phenyl 4-(2-oxo-alkylimidazolidin-1-yl)benzenesulfonates ; PAIB-SOs

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Product Details of [ 74115-13-2 ]

CAS No. :74115-13-2 MDL No. :MFCD00661305
Formula : C5H4BrNO Boiling Point : -
Linear Structure Formula :- InChI Key :VNYBIBSZZDAEOK-UHFFFAOYSA-N
M.W : 174.00 Pubchem ID :599529
Synonyms :

Calculated chemistry of [ 74115-13-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 33.96
TPSA : 33.12 ?2

Pharmacokinetics

GI absorption : High
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) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 1.19
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 0.58
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 1.25

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.22
Solubility : 1.04 mg/ml ; 0.00598 mol/l
Class : Soluble
Log S (Ali) : -1.48
Solubility : 5.74 mg/ml ; 0.033 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.3
Solubility : 0.876 mg/ml ; 0.00504 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.47

Safety of [ 74115-13-2 ]

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 [ 74115-13-2 ]

* 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.

  • Downstream synthetic route of [ 74115-13-2 ]

[ 74115-13-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 74115-13-2 ]
  • [ 161511-85-9 ]
  • [ 186593-31-7 ]
YieldReaction ConditionsOperation in experiment
85% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 48h; To a stirred solution of 1-tert-butoxycarbonyl-2 (5)-AZETIDINE (800 mg, 4.3 mmol) and 3-bromo-5- hydroxypyridine (800 mg, 4.6 mmol), and PPh3 (1.69 g, 6.45 mmol) in THF (50 mL) was slowly added DEAD (1.02 mL, 6.45 mmol). The reaction mixture was stirred at room temperature for 48 h, and concentrated in vacuo. The residue was purified by chromatography with hexane-EtOAc (4: 1) to give a light yellow oil (1.25 g, 85%). H NMR (CDC13) 6 8.29 (d, 1H, J= 2.1 Hz), 8. 28 (d, 1H, J= 2.7 Hz), 7.43 (t, 1H, J= 2.4 Hz), 4.51 (M, 1H), 4.34 (M, 1H), 4. 13 (dd, 1H, J= 10.2, 3.0 Hz), 3. 89 (t, 2H, J= 7.5 Hz), 2.42-2. 22 (M, 2H), 1.43 (s, 9H) ; 13C NMR (CDC13) 8 156.05, 155.35, 143.07, 136.58, 123.96, 120.25, 79.75, 68. 90,59. 84, 47.02, 28. 31,18. 88.
70% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; A gram-scale synthesis of sazetidine A is outlined in Figure Ia. The Boc-protected azidityl methyl alcohol 2 and 3 -bromo-5 -hydroxy pyridine (3) are both commercially available. Treatment with PPh3 and DEAD according to the Mitsunobu protocol formed ether derivative 4 in 70% yield. Palladium-mediated coupling of the bromo-substituted pyridine 4 with 5-hexyn-l-ol under modified Sonogashira conditions furnished Boc- protected sazetidine A in 73% yield. Deprotection of the Boc-group with HCl was expected to give sazetidine A in salt form as published in the literature. However, after several <n="43"/>AtIy Docket No.: GUX-023.25 attempts, it was found that the HCl salt, especially on larger scale, was a white solid that could be obtained in only moderate yield by a tedious filtration under an inert atmosphere. Exposure of the material to air immediately resulted in decomposition of the material to a yellow-brown wet solid. Therefore, in order to obtain gram quantities of pure sazetidine A, it was found that it was necessary to treat the deprotected material immediately with NH4OH and then isolated the free base of sazetidine A. This product was then taken up in an aqueous solution of HCl to give a solution of the HCl salt of sazetidine A. This modified method gives purer material and was indeed found to be more potent than that reported in the literature.
64% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 0 - 20℃;Inert atmosphere; Under N2 stream, triphenylphosphine (7.8 g, 29.7 mmol), 40% diethyl azodicarboxylate (40% solution in toluene, 5.2 mL), and 5-bromo-3-hydroxynicotinic acid (5.2 g, 29.7 mmol) at 0 C were added to a solution of 1 (3.6 g, 19.8 mmol) in THF (20 mL). The mixture was stirred at 0 C for 10 min and then warmed to room temperature and stirred overnight. After the reaction, the solvent was removed under reduced pressure followed by silica gel chromatography (petroleum ether/ethylacetate=1/1) to yield 8 (4.35 g, 12.7 mmol, 64%) as a colorless oil. 1HNMR (500 MHz, CDCl3) δ; 8.29 (t, J=2.6 Hz, 2H), 7.45-7.42 (m, 1H),4.55-4.48 (m, 1H), 4.33 (broad s, 1H), 4.13 (dd, J=7.5, 2.9 Hz, 1H),3.89 (m, 2H), 2.39-2.24 (m, 2H), 1.43 (s, 9H). 13C NMR (125 MHz,CDCl3) δ; 156.1, 155.4, 143.2, 136.7, 124.1, 120.3, 79.9, 69.0, 64.2,59.5, 28.4, 19.0. MS (EI+) m/z; 344 ([M+2]+, 1.97), 342 (M+, 1.92),271 (5.59), 269 (5.81), 243 (5.83), 241 (6.09), 156 (28), 113 (22), 100(34), 57 (1 0 0). HRMS (EI+) m/z; 342.0585 (Calcd: 342.0578 forC14H19N2O3Br). [α]D20=-59.63 (c=2.24, CHCl3).
55% With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 10 - 20℃; for 48h;Inert atmosphere; General procedure for Mitsunobu Reaction (Method A). To a mixture of 5-Bromo-3- pyridinol (1.2 equiv) and Ph3P (1.6 equiv) in anhydrous THF taken in a flame-dried flask under N2, N-Boc protected alcohol (1 equiv) was added and the mixture was cooled to - 10 C. Diethyl azodicarboxylate (40% w/v) in toluene (1.6 equiv) was added dropwise to the mixture and was warmed gradually to the room temperature. After 48 h, the reaction mixture was quenched with 1 mL of water and the solvent was removed under reduced pressure. The resulting yellow oil was purified by column chromatography on silica gel to yield 55-60% as a white solid. Example 3(S)-tei"i-butyl-2-((5-bromopyridin-3-yloxy)methyl)azetidine-l-carboxylate (VMY-2-3): Method A was used. Yield 55% (white solid). 1H NMR (400 MHz, CDC13) ? 8.25 - 8.19 (m, 2H), 7.36 (s, 1H), 4.44 (d, J= 5.3, 1H), 4.32 - 4.20 (m, 1H), 4.06 (dd, J = 2.8, 10.1, 1H), 3.81 (t, J= 7.5, 2H), 2.36 - 2.14 (m, 2H), 1.36 (s, 9H). 13C NMR (100 MHz, CDC13 ) ? 156.07,155.41, 143.13, 136.65, 124.02, 120.28, 79.76, 69.00, 59.92,47.14, 28.37, 18.95.HRMS (ESI): exact mass calcd for Ci4Hi9BrN203 [M+H]+, 343.0657, found 343.0670.
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 12a. 5-((2S)-Azetidinylmethyloxy)-3-bromopyridine dibenzoate Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mnol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for 10 minutes. Samples of 1-t-butyloxycarbonyl-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol, Step 7c above) and 3-bromo-5-hydroxypyridine.(1.51 g, 10.2 mmol, Step 10c above) were added, and the mixture was stirred for 40 hours at room temperature. The volatile components were removed under vacuum, and the residue was triturated with hexane. The separated hexane fraction was concentrated, and the residue was chromatographed (silica gel; hexane/ether, 10:1 to 10:2) to afford 5-bromo-3-((1-t-butyloxycarbonyl-(2S)-azetidinyl)methoxy)pyridine as a colorless oil (1.669 g): 1 H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1 H), 4.322 (m, 1 H), 4.52 (m, 1 H), 7.43 (m, 1 H), 8.29 (m, 2H); MS (CI/NH3) m/z 344 (M+H)+.

  • 2
  • [ 74115-13-2 ]
  • [ 79069-15-1 ]
  • [ 552331-47-2 ]
  • 3
  • [ 74115-13-2 ]
  • [ 161511-85-9 ]
  • 3-((1-BOC-2-(S)-azetidinyl)methoxy)-5-bromopyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 54b. 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mmol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for for 10 minutes. Samples of 1-BOC-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol), prepared as described above, and 5-bromo-3-hydroxypyridine (1.505 g, 10.2 mmol) were added, and the reaction rnixture was stirred for 40 hours at room temperature. The volatiles were removed under vacuum, and the residue was triturated with hexane. The hexane was removed, and the residue was chromatographed on a silica gel column, eluding with hexane:Et2 O 10:1 to 10:2 to afford the title compound as a colorless oil (1.669 g). MS (CI/NH3) m/z 344 (M+H)+. 1 H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1H), 4.322 (m, 1H), 4.52 (m, 1H), 7.43 (m, 1H), 8.29 (m, 2H).
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 54b. 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mmol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for for 10 minutes. Samples of 1-BOC-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol), prepared as described above, and 5-bromo-3-hydroxypyridine (1.505 g, 10.2 mmol) were added, and the reaction mixture was stirred for 40 hours at room temperature. The volatiles were removed under vacuum, and the residue was triturated with hexane. The hexane was removed, and the residue was chromatographed on a silica gel column, eluding with hexane:ether 10:1 to 10:2 to afford the title compound as a colorless oil (1.669 g). MS (CI/NH3) m/z 344 (M+H)+. 1 H NMR (CDCl3, 300 MHz) δ1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1H), 4.322 (m, 1H), 4.52 (m, 1H), 7.43 (m, 1H), 8.29 (m, 2H).
  • 4
  • [ 74115-13-2 ]
  • [ 73183-34-3 ]
  • [ 1171891-35-2 ]
  • [ 1208308-11-5 ]
YieldReaction ConditionsOperation in experiment
With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80.0℃; for 2.0h;Inert atmosphere; General procedure: 5-Bromo-2-methoxypyridin-3-amine (1.73 g, 6.82 mmol) was dissolved in 50 mL dioxane. Bis(pinacolato)diboron (4.4 g, 17.33 mmol), potassium acetate (2.5 g, 25.47 mmol) were added and the mixture was submitted to three vacuum-argon cycles. Finally, bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (0.9 g, 0.16 mmol) was added under argon conditions. The mixture was then heated at 80C for 2h. The crude was partitioned between ethyl acetate and water and then filtered through a plug of celite. The organic phase was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was purified using SP1 Purification System (0% to 20%, hexane-ethyl acetate) to obtain 1.43g. This solid was triturated with hexane, filtered and dried in the oven to give 0.94 g (55% yield) of the desired product as a solid. 5-(4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridin-3-ol 5-Bromopyridin-3-ol (3.70 g, 21.26 mmol) was treated with bis(pinacolato)diboron (10.80 g, 42.53 mmol), potassium acetate (6.26 g, 63.79 mmol) and bis(diphenylphosphino)ferrocene-palladium(ll)dichloride dichloromethane complex (1 .74 g, 2.13 mmol), 1 ,1 -bis(diphenylphosphino)ferrocene (1.18 g, 2.13 mmol) according to the method described in Preparation 42a to give 2.5 g (53 % yield) of the title compound as a mixture of boronate and boronic acid. Purity 100%. LRMS (m/z): 222 (M+1 )+.
  • 5
  • [ 74115-13-2 ]
  • [ 352359-22-9 ]
  • [ 1202552-02-0 ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 110℃; for 1.5h;Microwave irradiation; Inert atmosphere; A microwave flask is charged with 6-chloro-1-Boc-indole-2-boronic acid (1.91 g, 6.46 mmol), 3-hydroxy-5-bromopyridine (0.750 g, 4.31 mmol), potassium phosphate (1.83 g, 8.62 mmol) and DMF (15 ml_). The flask is evacuated and filled with nitrogen thrice and <n="164"/>Pd(PPh3)4 (0.250 g, 0.215 mmol) is added. The flask is evacuated and filled with nitrogen thrice again, and heated to 110 C under microwave irradiation for 45 min. Pd(PPh3)4 (0.100 g, 0.086 mmol) is added and the vial is heated again to 110 0C under microwave irradiation for 45 min. The mixture is then diluted with ethyl acetate and washed with water thrice. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel flash chromatography (dichloromethane-methanol, 19:1 ) to afford 6-chloro-2-(5-hydroxy-pyridin-3-yl)-indole-1- carboxylic acid tert-butyl ester as a solid. MS (ESI) m/z 345.06 (M+H)+
  • 6
  • [ 74115-13-2 ]
  • [ 1064194-10-0 ]
  • [ 1374144-65-6 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; To a solution of 5-bromopyridin-3-ol (0.285 g, 1.64 mmol) in DMF (2.5 mL) was added K2CO3 (0.453 g, 3.28 mmol), followed by <strong>[1064194-10-0]3-bromo-azetidine-1-carboxylic acid tert-butyl ester</strong> (0.425 g, 1.8 mmol) in DMF (0.5 mL) and the reaction mixture was heated to 60° C. and stirred over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and the aqueous layer was extracted EtOAc (2×20 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 50percent EtOAc-heptane gradient to give the title compound (0.539 g, 100percent) as a colorless crystalline solid. MS: 329.1 (M+H+).
100% With potassium carbonate; In N,N-dimethyl-formamide; at 60℃; Intermediate A-283-(5-Bromopyridin-3-yloxy)-azetidine-l-carboxylic acid tert-butyl esterTo a solution of 5-bromopyridin-3-ol (0.285 g, 1.64 mmol) in DMF (2.5 mL) was added K2CO3 (0.453 g, 3.28 mmol), followed by 3-bromo-azetidine-l-carboxylic acid tert-butyl ester (0.425 g, 1.8 mmol) in DMF (0.5 mL) and the reaction mixture was heated to 60 °C and stirred over night. The reaction mixture was diluted with EtOAc, poured into sat. NaHCC"3 solution (10 mL) and the aqueous layer was extracted EtOAc (2 x 20 mL).Combined organics were washed with brine, dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 50percent EtO Ac-heptane gradient to give the title compound (0.539 g, 100percent) as a colorless crystalline solid. MS: 329.1 (M+H+).
  • 7
  • [ 74115-13-2 ]
  • [ 161511-85-9 ]
  • [ 186593-31-7 ]
YieldReaction ConditionsOperation in experiment
With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 54b. 5-Bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine Triphenylphosphine (4.01 g, 15.3 mmol) and DEAD (2.43 mL, 15.3 mmol) were dissolved in 30 mL of THF at 0 C., and the mixture was stirred for for 10 minutes. Samples of 1-BOC-2-(S)-azetidinemethanol (2.86 g, 15.3 mmol), prepared as described above, and 5-bromo-3-hydroxypyridine (1.505 g, 10.2 mmol) were added, and the reaction mixture was stirred for 40 hours at room temperature. The volatiles were removed under vacuum, and the residue was triturated with hexane. The hexane was removed, and the residue was chromatographed on a silica gel column, eluding with hexane:Et2O 10:1 to 10:2 to afford the title compound as a colorless oil (1.669 g). MS (CI/NH3) m/z 344 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.42 (s, 9H), 2.31 (m, 2H), 3.89 (m, 2H), 4.12 (m, 1H), 4.322 (m, 1H), 4.52 (m, 1H), 7.43 (m, 1H), 8.29 (m, 2H).
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