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[ CAS No. 622-95-7 ] {[proInfo.proName]}

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Chemical Structure| 622-95-7
Chemical Structure| 622-95-7
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Product Citations

Product Citations      Expand+

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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Zehuan Huang ; Xiaoyi Chen ; Stephen J. K. O’Neill , et al. DOI: PubMed ID:

Abstract: Supramolecular polymer networks are non-covalently crosslinked soft materials that exhibit unique mechanical features such as self-healing, high toughness and stretchability. Previous studies have focused on optimizing such properties using fast-dissociative crosslinks (that is, for an aqueous system, dissociation rate constant kd?>?10?s?1). Herein, we describe non-covalent crosslinkers with slow, tuneable dissociation kinetics (kd?

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Product Details of [ 622-95-7 ]

CAS No. :622-95-7 MDL No. :MFCD00040714
Formula : C7H6BrCl Boiling Point : -
Linear Structure Formula :- InChI Key :KQNBRMUBPRGXSL-UHFFFAOYSA-N
M.W : 205.48 Pubchem ID :69329
Synonyms :
Chemical Name :1-(Bromomethyl)-4-chlorobenzene

Calculated chemistry of [ 622-95-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.29
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
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) : -5.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.32
Log Po/w (XLOGP3) : 3.35
Log Po/w (WLOGP) : 3.08
Log Po/w (MLOGP) : 3.68
Log Po/w (SILICOS-IT) : 3.49
Consensus Log Po/w : 3.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.65
Solubility : 0.0458 mg/ml ; 0.000223 mol/l
Class : Soluble
Log S (Ali) : -3.03
Solubility : 0.193 mg/ml ; 0.000939 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.28
Solubility : 0.0109 mg/ml ; 0.000053 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.52

Safety of [ 622-95-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:1759
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 622-95-7 ]

* 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 [ 622-95-7 ]

[ 622-95-7 ] Synthesis Path-Downstream   1~20

  • 1
  • [ 119838-38-9 ]
  • [ 622-95-7 ]
  • [ 123052-81-3 ]
  • 2
  • [ 622-95-7 ]
  • [ 116970-50-4 ]
  • [ 116970-58-2 ]
  • 3
  • [ 107819-90-9 ]
  • [ 622-95-7 ]
  • 1,3-bis-tert-butoxycarbonyl-1-(4'-chlorobenzyl)-2-methyl-2-thiopseudourea [ No CAS ]
  • 4
  • [ 106-43-4 ]
  • [ 57310-39-1 ]
  • [ 622-95-7 ]
  • 7
  • [ 622-95-7 ]
  • [ 190900-21-1 ]
  • [ 1076243-01-0 ]
YieldReaction ConditionsOperation in experiment
4-(4-Chloro-benzyl)-5-oxo-[l,4]diazepane-l-carboxylic acid t-butyl ester5-Oxo-[l,4]diazepane-l-carboxylic acid t-butyl ester (70 mg, 0.33 mmol) was added to a solution of KHMDS (91 mg, 0.46 mmol) in dry THF (1.6 ml) at app. -70 0C. After stirring <n="39"/>for 15 min the/?-chlorobenzyl bromide (74 mg, 0.36 mmol) was added to the reaction mixture. The reaction was quenched after 6 h at -75 0C by addition OfH2O and diluted with CH2Cl2. The organic phase was washed with H2O and filtered through an Extrelut tube.(R)., which was rinsed with CH2Cl2. The resulting organic phase was evaporated and purified by flash chromatography (SiO2, CH2Cl2-EtOAc) to give 50 mg of the subtitled compound as a semisolid.1R NMR (CD3OD) delta 7.31 (m, 4H), 4.58 (s, 2H), 3.59 (m, 2H), 3.44-3.50 (m, 4H), 2.75 (m,2H), 1.45 (s, 9H).
  • 8
  • [ 932-53-6 ]
  • [ 622-95-7 ]
  • [ 1207441-71-1 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydride; In dimethyl sulfoxide; mineral oil; at 20℃; for 0.25h;Inert atmosphere; According to Scheme 4 Step 1: To a solution of Azathymine (300 mg, 2.36 mmol) and 4-chlorobenzyl bromide (485 mg, 2.36 mmol) in DMSO (10 mL) was added portionwise NaH (55%) (103 mg, 2.36 mmol) at room temperature under nitrogen atmosphere. The mixture was stirred for 15 min at room temperature. Ethyl Acetate was then added (150 mL) and the organic layer was extracted thrice with water (100 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure to afford a yellow solid. The crude solid was purified by flash chromatography with silica gel using CH2Cl2/MeOH 98/2 as eluant to afford 4-(4-chlorobenzyl)-<strong>[932-53-6]6-methyl-1,2,4-triazine-3,5(2H,4H)-dione</strong> 8(A) (500 mg, 84%) as a white solid.LC1: Rt=3.66MS m/z (ES) [M-H]-=249
  • 9
  • [ 93247-78-0 ]
  • [ 622-95-7 ]
  • [ 1097196-86-5 ]
YieldReaction ConditionsOperation in experiment
A mixture of <strong>[93247-78-0]methyl indole-7-carboxylate</strong> (6.0 g) and DMF (60 mL) was ice-cooled, and potassium tert-butoxide (5.38 g) was added thereto, followed by stirring at the same temperature for 30 minutes. Then, 4-chlorobenzylbromide (7.39 g) was added thereto, followed by stirring at room temperature for 3 hours. The reaction mixture was ice-cooled, and water (60 mL) was added thereto, followed by extraction with ethyl acetate (80 mL). The organic layer was washed with 1 M hydrochloric acid, a saturated sodium bicarbonate solution, and saturated saline in this order, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was left to stand for 3 days for solidification, and washed with hexane-ethyl acetate (8:1, 18 mL) to obtain methyl 1-(4-chlorobenzyl)-1H-indole-7-carboxylate (4.94 g) as a pale yellow solid.
  • 10
  • [ 150008-24-5 ]
  • [ 622-95-7 ]
  • [ 224178-71-6 ]
  • 11
  • [ 71486-53-8 ]
  • [ 622-95-7 ]
  • [ 1225491-24-6 ]
YieldReaction ConditionsOperation in experiment
100% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h; 0.800 g of <strong>[71486-53-8]methyl 4-oxopiperidine-3-carboxylate hydrochloride</strong> (4.134 mmol), 1.44 mL (8.268 mmol) of diisopropylethylamine and 0.852 g (4.134 mmol) of 4-chloro-benzyl bromide were stirred at room temperature in 16.0 mL of anhydrous CH2C12.The reaction was monitored by HPLC and UPLC-MS. After 16 h at room temperature, brine was added to the reaction mixture.The organic phase was separated, dried over Na2SO4 and concentrated in vacuo to give pure methyl methyl 1-(4-chlorobenzyl)-4-oxopiperidine-3-carboxylate (1.164 g, 4.133 mmol, quantitative yield).The product was used for the next step without further manipulation. MS(ESI+): 282.1.
With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h; 0.800 g of <strong>[71486-53-8]methyl 4-oxopiperidine-3-carboxylate hydrochloride</strong> (4.134 mmol), 1.44 mL (8.268 mmol) of diisopropylethylamine and 0.852 g (4.134 mmol) of 4-chloro-benzyl bromide were stirred at room temperature in 16.0 mL of anhydrous CH2CI2. The reaction was monitored by HPLC and UPLC-MS. After 16 h at room temperature, brine was added to the reaction mixture. The organic phase was separated, dried over Na2S04 and concentrated in vacuo to give pure methyl methyl l-(4-chlorobenzyl)-4- oxopiperidine-3-carboxylate (1.164 g, 4.133 mmol, quantitative yield). The product was used for the next step without further manipulation.
  • 12
  • [ 57473-33-3 ]
  • [ 622-95-7 ]
  • C12H7Cl2N3O [ No CAS ]
  • 13
  • [ 622-95-7 ]
  • [ 208580-23-8 ]
  • [ 1359818-47-5 ]
YieldReaction ConditionsOperation in experiment
78% With potassium carbonate; In acetonitrile; for 7h;Reflux; Step 1 Potassium carbonate (0.7 g, 5.1 mmol) and 4-chlorobenzyl bromide (0.76 g, 3.7 mmol) were added to mixture of 7-bromo-3-(ethoxycarbonyl)quinolin-4(1H)-one (1.0 g, 3.4 mmol) and acetonitrile (20 mL), and stirred under heating at reflux for 7 hours. The insoluble matter was removed by filtering, and the filtrate was washed by ethyl acetate and concentrated in vacuo. The resulting solid was washed by water and hexane to give 7-bromo-1-(4-chlorobenzyl)-3-(ethoxycarbonyl)quinolin-4(1H)-one (1.11 g, yield: 78%) as colorless solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.29 (3H, t, J=6.0 Hz), 4.24 (2H, q, J=6.0 Hz), 5.69 (2H, s), 7.28 (2H, d, J=8.0 Hz), 7.44 (2H, d, J=8.0 Hz), 7.61 (1H, d, J=8.0 Hz), 7.85 (1H, s), 8.14 (1H, d, J=8.0 Hz), 8.89 (1H, s).
61% With potassium carbonate; In acetonitrile; at 100℃; for 5h; [Example 44] Preparation of 1-(4-chlorobenzyl)-7-(phenylamino)-3-(ethoxycarbonyl)quinoline-4(1H)-one (I-148) To a mixture of 7-bromo-3-(ethoxycarbonyl)quinoline-4(1H)-one (250 mg, 0.844 mmol) and acetonitrile (5 mL) were added potassium carbonate (175 mg, 1.27 mmol) and 4-chlorobenzylbromide (208 mg, 1.01 mmol), and the resulting mixture was stirred at 100C for 5 hours. The insoluble were removed by filtration and washed by ethyl acetate. The mother liquor was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 7-bromo-1-(4-chlorobenzyl)-3-(ethoxycarbonyl)quinoline-4(1H)-one (216 mg, Yield: 61%) as colorless solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.29 (3H, t, J=6.0 Hz), 4.24 (2H, q, J=6.0 Hz), 5.69 (2H, s), 7.28 (2H, d, J=8.0 Hz), 7.44 (2H, d, J=8.0 Hz), 7.61 (1H, d, J=8.0 Hz), 7.85 (1H, s), 8.14 (1H, d, J=8.0 Hz), 8.89 (1H, s).
61% With potassium carbonate; In acetonitrile; at 100℃; for 5h; EXAMPLE 44 Preparation of 1-(4-chlorobenzyl)-7-(phenylamino)-3-(ethoxycarbonyl)quinoline-4(1H)-one (I-148) To a mixture of 7-promo-3-(ethoxycarbonyl)quinoline-4(1H)-one (250 mg, 0.844 mmol) and acetonitrile (5 mL) were added potassium carbonate (175 mg, 1.27 mmol) and 4-chlorobenzylbromide (208 mg, 1.01 mmol), and the resulting mixture was stirred at 100 C. for 5 hours. The insoluble were removed by filtration and washed by ethyl acetate. The mother liquor was concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give 7-bromo-1-(4-chlorobenzyl)-3-(ethoxycarbonyl)quinoline-4(1H)-one (216 mg, Yield: 61%) as colorless solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.29 (3H, t, J=6.0 Hz), 4.24 (2H, q, J=6.0 Hz), 5.69 (2H, s), 7.28 (2H, d, J=8.0 Hz), 7.44 (2H, d, J=8.0 Hz), 7.61 (1H, d, J=8.0 Hz), 7.85 (1H, s), 8.14 (1H, d, J=8.0 Hz), 8.89 (1H, s).
  • 14
  • [ 1193-24-4 ]
  • [ 622-95-7 ]
  • [ 1447910-90-8 ]
YieldReaction ConditionsOperation in experiment
500 mg With silver carbonate; In tetrahydrofuran; for 2h;Reflux; B) 6- ( (4-Chlorobenzyl) oxy) pyrimidin-4 (3H) -one. To a stirred solution of pyrimidine-4 , 6-diol (2.5 g) in THF (25 ml) was added silver carbonate (15.3 g) at room temperature followed by dropwise addition of 4-chlorobenzyl bromide (4.58 g) , and the resultant mixture was heated at reflux for 2 h. The reaction mixture was then cooled to room temperature, filtered through Celite, and the filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM) to give the title compound (500 mg) as a white solid. MS (ESI+) : [M+H]+ 237.2.
  • 15
  • [ 622-95-7 ]
  • [ 208580-23-8 ]
  • [ 1359815-92-1 ]
  • 16
  • [ 95-54-5 ]
  • [ 622-95-7 ]
  • [ 1019-85-8 ]
YieldReaction ConditionsOperation in experiment
84% In acetonitrile;Irradiation; General procedure: A mixture of 1,2-Diaminobenzene 1 or 2-Mercaptoaniline 4(1 mmol), benzyl bromides (1 mmol) 2 and 4 % Cu:ZnS NPs (10 mol %)in 10 ml of CH3CN were irradiated in visible light (100W OSRAMTungsten Lamp, EFP 64627 HLX) with continuous stirring for the appropriatetime. Catalyst was separated by centrifugation after thecompletion of reaction. Evaporation of the above solution gave thecrude product which was purified using crystallization.
  • 17
  • [ 622-95-7 ]
  • [ 122-72-5 ]
  • 18
  • [ 1303587-99-6 ]
  • [ 622-95-7 ]
  • 2-chloro-8-(4-chlorobenzyl)-7,8-dihydro-6H-pyrimido[5,4-b][1,4]oxazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0℃; for 1h;Inert atmosphere; Synthesis of 2-chloro-8-(4-chlorobenzyl)-7 , 8-dihydro-6H-pyrimido [5, 4-b] [I, 4] oxazine [0450] To a stirred solution of 2-chloro-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (150 mg, 0.87 mmol) in DMF (3 mL) under argon atmosphere were added sodium hydride (40 mg, 1.75 mmol) and l-(bromomethyl)-4-chlorobenzene (215 mg, 1.05 mmol) at 0 C. The reaction mixture was stirred for 1 h at 0 C. After consumption of the starting materials (monitored by TLC), the reaction was diluted with water (50 mL) and extracted with EtOAc (2 x 50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was washed with n-pentane (2 x 5 mL) to afford 2- chloro-8-(4-chlorobenzyl)-7, 8-dihydro-6H-pyrimido [5, 4-b] [1, 4] oxazine (190 mg, 73%) as an off-white solid. 1H-NMR (DMSO-<, 500 MHz): delta 7.73 (s, 1H), 7.42 (d, 2H), 7.33 (d, 2H), 4.78 (s, 2H), 4.20-4.18 (m, 2H), 3.52-3.49 (m, 2H); LCMS: 295.8 (M+); (column; X- Select CSH C-18 (50 3.0 mm, 3.5 mupiiota); RT 3.81 min. 0.05% Aq TFA: ACN; 0.80 mL/min); UPLC (purity): 91.4%; (column; Acquity UPLC BEH C-18 2.1 X 50 mm, 1.7 mupiiota); RT 2.52 min. ACN: 0.025% TFA (Aq); 0.50 mL/min; TLC: 30% EtOAc:hexanes (R 0.6).
  • 19
  • [ 622-95-7 ]
  • [ 208580-23-8 ]
  • 1-(4-chlorobenzyl)-7-[4-(5-fluoro-2-pyridyloxy)phenylamino]-3-(ethoxycarbonyl)quinolin-4(1H)-one [ No CAS ]
  • 20
  • [ 34113-69-4 ]
  • [ 622-95-7 ]
  • C21H15Cl3O3 [ No CAS ]
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; ;