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[ CAS No. 140-75-0 ] {[proInfo.proName]}

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Chemical Structure| 140-75-0
Chemical Structure| 140-75-0
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Product Citations

Product Citations

Dube, Phelelisiwe S. ; Angula, Klaudia T. ; Legoabe, Lesetja J. , et al. DOI: PubMed ID:

Abstract: Herein, we describe 39 novel quinolone compounds bearing a hydrophilic amine chain and varied substituted benzyloxy units. These compounds demonstrate broad-spectrum activities against acid-fast bacterium, Gram-pos. and -neg. bacteria, fungi, and leishmania parasite. Compound 30 maintained antitubercular activity against moxifloxacin-, isoniazid-, and rifampicin-resistant Mycobacterium tuberculosis, while 37 exhibited low micromolar activities (<1 μg/mL) against World Health Organization (WHO) critical pathogens: Cryptococcus neoformans, Acinetobacter baumannii, and Pseudomonas aeruginosa. Compounds in this study are metabolically robust, demonstrating % remnant of >98% after 30 min in the presence of human, rat, and mouse liver microsomes. Several compounds thus reported here are promising leads for the treatment of diseases caused by infectious agents.

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Product Details of [ 140-75-0 ]

CAS No. :140-75-0 MDL No. :MFCD00008120
Formula : C7H8FN Boiling Point : -
Linear Structure Formula :- InChI Key :IIFVWLUQBAIPMJ-UHFFFAOYSA-N
M.W : 125.14 Pubchem ID :67326
Synonyms :

Calculated chemistry of [ 140-75-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 34.07
TPSA : 26.02 ?2

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) : -6.21 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.56
Log Po/w (XLOGP3) : 1.2
Log Po/w (WLOGP) : 1.55
Log Po/w (MLOGP) : 1.97
Log Po/w (SILICOS-IT) : 1.88
Consensus Log Po/w : 1.63

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.8
Solubility : 1.99 mg/ml ; 0.0159 mol/l
Class : Very soluble
Log S (Ali) : -1.34
Solubility : 5.68 mg/ml ; 0.0454 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.262 mg/ml ; 0.00209 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 140-75-0 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:2735
Hazard Statements:H227-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 140-75-0 ]

* 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.

  • Downstream synthetic route of [ 140-75-0 ]

[ 140-75-0 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 27048-04-0 ]
  • [ 140-75-0 ]
  • [ 33400-49-6 ]
YieldReaction ConditionsOperation in experiment
97.2% With triethylamine; In methanol; at 80℃; for 10h; To a reaction flask, 200 mL of methanol, 52.08 g of compound 1, 37.54 g of p-fluorobenzylamine and 50.0 mL of triethylamine werea added. The reaction mixture was heated to 80 C for 10 hours, and the reaction solution was added with 10 times of water to give 76.47 g of compound 3 in a yield of 97.2% and a purity of 99.62% (HPLC).
96.8% With triethylamine; In isopropyl alcohol; for 14h;Inert atmosphere; Reflux; Industry scale; 2-Amino-6-chloro-3-nitropyridine (ACNP, 10.0 kg) was suspended in isopropanol (49 L) under stirring and a nitrogen blanket. 4-Fluorobenzylamine (7.7 kg) and triethylamine (8.4 kg) were added and the mixture was heated to reflux. Stirring at reflux was maintained for 14 h. The reaction mixture was cooled to 50C and samples were taken for checking completion of the reaction by HPLC (amount of residual ACNP: 0.02%). Water (163 kg) was added and the mixture was stirred for 5 min, then cooled to 5C and stirred for 30 minutes. The precipitate was filtered off, washed with water (41 L) and dried under reduced pressure at 50C. Yield: 14.6 kg (96.8% of theory).
96.6% With triethylamine; In isopropyl alcohol; at 70 - 80℃; for 12h;Large scale; Was added to the reaction kettle 3.04kg and 10kg of isopropanol fluorobenzylamine, with stirring, was added 4kg2- amino-3-nitro-6-chloropyridine and 8.67kg of triethylamine, and heated at reflux temperature for 12h 70-80 , cooled to 60 , reaction was monitored sampling is complete, add 4% sodium hydroxide aqueous solution prepared 1.07kg, 55 concentrated under reduced pressure until no solvent flows, centrifuged solids, temperature 50-60 , dried 10-12 hours to give flupirtine maleate intermediate (2-amino-3-nitro-6- (p-fluoro-benzylamino) pyridine) 5.86kg, a yield of 96.6%
88% With triethylamine; In isopropyl alcohol; at 90℃; for 0.666667h;Microwave irradiation; To a solution of Intermediate 5 (500 mg, 2.9 mmol) in isopropanol was added 4- fluorobenzylamine (463 iil, 4.06 mmol) and triethylamine (805 iil, 5.8 mmol). This mixture was stirred at 90C for 40 minutes in the microwave. Water was added to the mixture and the resulting precipitate was filtered off, washed with water and then driedover vacuum for an hour. Intermediate 6 was isolated as a bright yellow solid (661 mg,88%).LCMS (m/z): [IVIH] calcd. for C12H11FN4O2, 262.24; found 263.00.
79.4% With triethylamine; In isopropyl alcohol; at 5℃; for 0.5h; 2-Amino-3-nitro-6-chloropyridine (Compound 1) (50.0 g, 288 mmol, 1.00 eq) was dissolved in isopropyl alcohol (500 mL).p-Fluorobenzylamine (39.7 g, 317 mmol, 1.10 eq) and TEA (32.0 g, 317 mmol, 1.10 eq.Thereafter, the reaction solution was poured into water (1.5 L), and slowly cooled to 5 C and stirred for 30 minutes.Filter and filter cake was washed with water (500 mL).The filter cake was collected and dried to give a yellow solid (Compound 2) 60 g, yield 79.4%.
150 g With triethylamine; In water; at 20 - 85℃; 100 gm of 2-amino-3-nitro-6-chloro-pyridine is taken in 800 ml of water. 90 gm of p-fluorobenzylamine is added dropwise into the reaction mixture at 20-25C. Then 87 gm triethylamine is also added dropwise into the reaction mixture at 20-25C. After complete addition, the reaction mass is stirred at 40-45C for half an hour again the reaction mass is heated to 80-85C and stirred at this temperature for 3-4 hours. After completion of the reaction, the reaction mass is cooled to 20-25C and stirred at this temperature for 2-3 hours and then stirred at 15-20C for 3-4 hours. The solid mass is filtered and then washed with 200 ml of water and 100 ml isopropyl alcohol and then dried in air oven till constant weight to get 140-150 gm. of 2-amino-3-nitro-6-p- fluorobenzylamino-py ridine.
With potassium carbonate; In butan-1-ol; for 2h;Reflux; Step-2: Synthesis of Compound 4: 2-Amino-6-chloro-3-nitropyridine 2 (17.35 g, 0.10 mol), 4-fluoro benzyl amine (0.10 mol) and powdered potassium carbonate (10.4 g, 0.035 mol) in n-butanol (100 mL) were heated under reflux for 2 hours. The suspension was filtered and after cooling to room temperature the solid 4 was collected by filtration, washed with butanol, and dried.
at 60 - 65℃; for 6h;Large scale; 2,6-dichloro-3-nitropyridine (5 kg, 25.9 mol) was added to a reaction vessel containing 20 kg of ethanol, and 25% aqueous ammonia (9.07 kg, 64.8 mol) was added at room temperature to control the internal temperature. 30~35 C, heat preservation reaction for about 6h, TLC monitoring the raw material reaction completely stop the reaction, adding p-fluorobenzylamine (3.8kg, 31.1mol), heating to 60~65 C reaction for about 6h, TLC monitoring the raw material reaction is complete The reaction was stopped, and the temperature was lowered to 5 to 10 C for crystallization for 1 to 2 hours and then filtered. The obtained wet product was added to 60 kg of isopropyl alcohol, heated to reflux, and cooled to room temperature for 2 hours, filtered, and the wet product was kept in the reaction vessel. 75 kg of isopropanol, 5% Pd/C 0.3 kg and ethyl chloroformate (3 kg, 27.6 mol) were added to the reaction vessel, and hydrogen pressure was maintained at 1.2 to 1.5 MPa, and the temperature was controlled at 60 to 70 C for 5 hours. Filtration, the filtrate was cooled to 0~5 C and stirred for 2 h, and dried under reduced pressure at 60 C for 4 h to obtain white flupirtine hydrochloride 6.48 kg, the yield was 73.4%, and the chromatographic purity was 99.62%. The nuclear magnetic data is basically consistent with the data of Example 1.

  • 2
  • [ 140-75-0 ]
  • [ 518048-03-8 ]
  • 3
  • [ 444731-75-3 ]
  • [ 140-75-0 ]
  • [ 1572439-57-6 ]
  • 4
  • [ 876343-10-1 ]
  • [ 140-75-0 ]
  • [ 1637569-25-5 ]
YieldReaction ConditionsOperation in experiment
In butan-1-ol; at 145℃; General procedure: Compound 1a-d or 54 (1 mmol) was mixed with the selected amine, 2-25, (3 mmol) and n-butanol (5 ml) and agitated at145 C for 14-24 h. Then the mixture was cooled to 22 C, dilutedwith water (15 ml) and ethyl acetate (40 ml). After phase separation,the water phase was back extracted with more ethyl acetate(2 10 ml). The combined organic phases were washed with brine(10 ml), dried over anhydrous Na2SO4, filtered and concentrated invacuo, before the crude mixture was purified as specified for eachindividual compound
  • 5
  • [ 6624-49-3 ]
  • [ 140-75-0 ]
  • C17H13FN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; N,N-dimethyl-formamide; at -15 - 20℃; for 1.5h;Inert atmosphere; General procedure: Compounds 1-13 were synthesized using the mixed anhydrides method of peptide synthesis (10). Suitable acid (10 mmol) was dissolved in DMF (15 mL) and THF (15 mL) was added. Next, N-methylmorpholine (10 mmol, 1.1 mL) was added and the mixture was stirred under nitrogen and chilled to -15°C. Isobutyl chloroformate (10 mmol, 1.3 mL) was added dropwise to keep the temperature below -15°C. Then, benzylamine or halogenated benzylamine (10 mmol) in THF was added in small portions and the reaction mixture was stirred at -15°C for 30 min, at room temperature for 1 h. The solution was concentrated in vacuo and the residue was dissolved in EtOAc (20 mL). This solution was washed with 20 mL portions of 1 M HCl, saturated NaHCO3 solution and saturated NaCl solution, then dried with anhydrous MgSO4, filtered and concentrated in vacuo. The obtained compounds were purified by crystallization with EtOAc/hexane o MeOH/Et2O. All stages of the synthesis were controlled by TLC. The purity of the final compound was determined by HPLC and identity by 1H NMR. The pathway for the synthesis of the obtained compounds is shown in Scheme 1.
  • 6
  • [ 140-75-0 ]
  • [ 27398-39-6 ]
  • C12H10FN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
80.6% With potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 140℃; for 16h;Inert atmosphere; [00142] A mixture of 19 (1.50 g, 9.49 mmols, 1.0 eq), 1-(4-fluorophenyl)ethanamine (2.64 g, 19.0 mmols, 2.0 eq) and K2C03 (3.93 g, 28.5 mmols, 3.0 eq) in NMP (30 mL) was degassed, purged with nitrogen, and stirred at 140 °C for 16 hours. The mixture was diluted with ethyl acetate (100 mL) and washed with 2 N aqueous HC1 (30 mL x 3). The organic layer was dried over Na2SO4, filtered, and concentrated, the residue was purified by recrystallization (Petroleum ether/ethyl acetate) to give the desired product 20 (2.00 g, 7.66 mmols, 80.6percent) as a white solid.[00143] LCMS: ESI-MS: m/z: 262.2 [M+H1 RT = 1.87 mm. (Method A).
  • 7
  • C10H15N3O4 [ No CAS ]
  • [ 140-75-0 ]
  • [ 518048-03-8 ]
YieldReaction ConditionsOperation in experiment
In methanol; at 65℃; for 3h; 0.75 g of compound e was placed in 10 mL of anhydrous methanol, followed by the addition of 0.4 g of p-fluorobenzylamine, and the system was heated to reflux at 65 C for 3 hours.After the reaction is completed, the solvent of the system is rotated.The obtained oil was dissolved in 10 mL of THF (tetrahydrofuran).The system is then cooled to 0 C in a low temperature reactor.Then add 2mL NMM (N-methylmorpholine),Further adding the CH3CN solution of the compound d prepared above,Note that the system temperature is kept below 5 C during the addition.After the addition is completed,The system was continued at 0 C for 2 hours.After that, it was heated to reflux at 65 C for 2 hours.After cooling to room temperature,Add 1.3 g of KOH in 10 mL of water,Stir for 30 minutes,Then adjust to pH=4 with 2M HCl at room temperature.The system continued to stir for 15 minutes.Add 10 mL of water and 10 mL of EA (ethyl acetate).Continue to stir for 15 minutes.After the liquid separation,The aqueous phase was re-extracted with 10 mL of EA.Collect organic phase,Wash twice with saturated 200 mL saturated NaCl solution.The organic phase was then collected and concentrated under reduced pressure to give a white solid.That is, compound h,The yield was 76.5%.
  • 8
  • [ 5900-59-4 ]
  • [ 140-75-0 ]
  • 7-chloro-2-(4-fluorophenyl)quinazolin-4(3H)-one [ No CAS ]
  • 9
  • [ 33742-70-0 ]
  • [ 140-75-0 ]
  • N<SUP>6</SUP>-(4-fluorobenzyl)-N<SUP>2</SUP>-methyl-3-nitropyridine-2,6-diamine [ No CAS ]
  • 10
  • [ 202217-19-4 ]
  • [ 140-75-0 ]
  • N<SUP>2</SUP>-(4-fluorobenzyl)-3-methyl-5-nitropyridine-2,6-diamine [ No CAS ]
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