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

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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 [ 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 :

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 Ų

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:
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.

  • Upstream synthesis route of [ 622-95-7 ]
  • Downstream synthetic route of [ 622-95-7 ]

[ 622-95-7 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 622-95-7 ]
  • [ 2948-92-7 ]
  • [ 442-52-4 ]
YieldReaction ConditionsOperation in experiment
65% With tetra-(n-butyl)ammonium iodide In tetrahydrofuran at 20℃; for 16 h; Under a nitrogen atmosphere, compound 10 (0.24mmol, 49mg) was dissolved in freshly distilled THF (0.75mL), then cooled to 0°C. To this solution was added 60percent NaH in oil (0.36mmol, 14.4mg) and the mixture was stirred at 0°C for 5min. 4-Chlorobenzyl bromide (0.26mmol, 54mg) was added followed by the addition of tetrabutylammonium iodide (0.024mmol, 9mg). The mixture was stirred at rt overnight, then diluted with water (2mL) and EtOAc (5mL). The aqueous phase was separated and extracted twice with EtOAc. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. The crude was purified by chromatography on silica gel (eluent: EtOAc) to afford the desired target 11 in 65percent yield (m=51mg) as a colorless solid. Mp 101–102°C. 1H NMR (300MHz, CDCl3) δ 7.83–7.77 (m, 1H), 7.32–7.22 (m, 5H), 7.06 (d, J=8.7Hz, 2H), 5.58 (s, 2H), 3.90 (s, 2H), 2.58 (m, 4H), 1.76 (m, 4H); 13C NMR (75MHz, CDCl3) δ 152.3, 142.5, 135.9, 135.3, 133.6, 129.1 (2C), 128.1 (2C), 122.9, 122.7, 120.0, 109.7, 54.8 (2C), 53.2, 46.8, 23.7 (2C); HRMS (ESI) Calcd for C19H21N3Cl [M+H]+ 326.1424, Found 326.1427; FTIR (neat) cm−1 2958, 2927, 2875, 2810, 1488, 1463, 1403, 1294, 1088, 1034, 1014, 742, 487.
195 mg
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.0833333 h; Inert atmosphere
Stage #2: With tetrabutylammomium bromide In tetrahydrofuran; mineral oil at 20℃; Inert atmosphere
1-(4-Chlorobenzyl)-2-(pyrrolidin-1-ylmethyl)-1H-benzimidazole dihydrochloride (1). Under an atmosphere of nitrogen, compound 36 (250 mg, 1.24 mmol, 1 equiv) was dissolved in freshly distilled warm tetrahydrofuran (THF) (2.5 mL), then cooled to 0 °C.
To this solution was added 60percent NaH in oil (100 mg, 60 mg pure, 2.48 mmol, 2 equiv) and the mixture stirred at 0 °C for 5 min. 4-Chlorobenzyl bromide (255 mg, 1.24 mmol, 1 equiv) was added followed by the addition of tetra-n-butylammonium bromide (23 mg, 0.07 mmol, 6 mol percent).
The mixture was stirred at rt overnight, then diluted with a solution of water (2 drops) in THF (5 mL).
The solution was filtered through Celite, and the Celite was washed with THF (50 mL) and then EtOAc (50 mL).
The filtrate was concentrated and the remaining residue purified by flash column chromatography on silica gel (EtOAc) to give the free base (195 mg) as an oil (Rf = 0.46, EtOAc).
To a solution of the free base in MeOH (2 mL) was added a solution of 37percent aqueous HCl (158 mg, 1.60 mmol, 2.7 equiv) in MeOH (2 mL).
The mixture was concentrated, Et2O (5 mL) was added, and the mixture concentrated again.
High-vacuum drying gave the product (242 mg, 0.61 mmol, 49percent) as a white solid; mp 232-234 °C; Rf = 0 (EtOAc); 1H NMR (400 MHz, CD3OD): δ 2.10-2.26 (m, 4H), 3.55-3.78 (m, 4H), 5.21 (s, 2H), 5.95 (s, 2H), 7.31 (d, J = 8.4 Hz, 2H), 7.40 (d, J = 8.4 Hz, 2H), 7.53-7.68 (m, 3H), 7.92 (d, J = 8.0 Hz, 1H); 13C NMR (100 MHz, CD3OD): δ 24.0, 48.0, 50.0, 56.5, 114.4, 117.3, 128.0, 128.1, 129.9, 130.4, 134.0, 134.3, 135.1, 135.7, 144.5; HRMS (ESI) [M-Cl]+ Calcd for C19H21N3Cl: 326.1424. Found: 326.1433.
Reference: [1] Tetrahedron, 2015, vol. 71, # 4, p. 700 - 708
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6788 - 6795
  • 2
  • [ 622-95-7 ]
  • [ 104-86-9 ]
Reference: [1] Journal of the Chemical Society, 1931, p. 1225,1232
[2] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
[3] Organic Letters, 2014, vol. 16, # 17, p. 4424 - 4427
  • 3
  • [ 106-38-7 ]
  • [ 106-43-4 ]
  • [ 104-83-6 ]
  • [ 622-95-7 ]
  • [ 589-17-3 ]
Reference: [1] Monatshefte fur Chemie, 1999, vol. 130, # 12, p. 1493 - 1497
  • 4
  • [ 622-95-7 ]
  • [ 74-89-5 ]
  • [ 104-11-0 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 1, p. 40 - 44
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 15, p. 2882 - 2891
  • 5
  • [ 622-95-7 ]
  • [ 15184-98-2 ]
  • [ 104-11-0 ]
Reference: [1] Green Chemistry, 2018, vol. 20, # 14, p. 3339 - 3345
  • 6
  • [ 622-95-7 ]
  • [ 74-89-5 ]
  • [ 6970-85-0 ]
  • [ 104-11-0 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 1206
  • 7
  • [ 7677-24-9 ]
  • [ 622-95-7 ]
  • [ 140-53-4 ]
Reference: [1] Synlett, 2009, # 8, p. 1291 - 1294
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 10, p. 2828 - 2832
  • 8
  • [ 151-50-8 ]
  • [ 622-95-7 ]
  • [ 140-53-4 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986, vol. 35, # 6, p. 1239 - 1242[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 6, p. 1365 - 1368
[3] American Chemical Journal, 1880, vol. 2, p. 88
[4] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350
  • 9
  • [ 143-33-9 ]
  • [ 622-95-7 ]
  • [ 140-53-4 ]
Reference: [1] Journal of Physical Organic Chemistry, 2000, vol. 13, # 10, p. 587 - 590
  • 10
  • [ 106-43-4 ]
  • [ 57310-39-1 ]
  • [ 622-95-7 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
  • 11
  • [ 622-95-7 ]
  • [ 2012-74-0 ]
Reference: [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1986, vol. 35, # 6, p. 1239 - 1242[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 6, p. 1365 - 1368
  • 12
  • [ 622-95-7 ]
  • [ 14091-08-8 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 6, p. 2353 - 2355
  • 13
  • [ 84713-70-2 ]
  • [ 622-95-7 ]
  • [ 7424-00-2 ]
Reference: [1] Synthesis, 1984, # 4, p. 313 - 315
  • 14
  • [ 622-95-7 ]
  • [ 25015-63-8 ]
  • [ 517920-59-1 ]
YieldReaction ConditionsOperation in experiment
90% With magnesium; triethylamine In tetrahydrofuran at 65℃; for 15 h; Example 8Preparation of pinacol ester of 4-chlorobenzylboronic acid Magnesium turnings (2.4 mg, 0.1 mmol, 10 mol percent) are introduced into a 2 necks Schlenk-type flask, provided with a magnetic stirring bar and topped by a coolant, then 10 ml of distilled THF are added. Triethylamine (59 mg, 1 mmol) and pinacolborane (0.384 g, 3 mmol) are introduced therein. 4-chlorobenzyl bromide (0.207 g, 1 mmol) dissolved into 10 ml of distilled THF is then added drop by drop in the solution using a dropping funnel. Thereafter, the reactive mixture is stirred for approximately 15 hours at THF reflux (65° C.).At the end of the reaction, the crude reaction product is hydrolyzed by 20 ml of water neutral and extracted by diethyl ether (3.x.40 ml). The joined organic phases are washed by 2.x.ml of neutral water then dried on MgSO4. After solvent evaporation, the pinacol ester is obtained with a yield of 90percent at a total conversion of the starting bromide (yield/conversion of 90percent). The resulting boronic ester is analyzed by GC, NMR 1H and 13C and GC/MS.CharacterizationsNMR 1H: 7.2 (2H, D, 8 Hz); 6.9 (2H, D, 8 Hz); 1.9 (2H, s); 1.3 (12H, s).NMR 13C: 138; 131.3; 130.5; 128.8; 83.8; 33.5; 21.4.Mass spectrometry: 254-252 (M+, 1-4percent); 127 (32percent); 126 (20percent); 125 (100percent); 124 (20percent); 63 (12percent).
Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 34, p. 11825 - 11827
[2] Journal of the American Chemical Society, 2010, vol. 132, # 34, p. 11825 - 11827
[3] Patent: US2011/282090, 2011, A1, . Location in patent: Page/Page column 8
  • 15
  • [ 622-95-7 ]
  • [ 73183-34-3 ]
  • [ 517920-59-1 ]
YieldReaction ConditionsOperation in experiment
31% With copper(l) iodide; lithium methanolate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 14 h; Inert atmosphere 4-Chlorobenzyl bromide (640 mg, 3.12 mmol), boronic acid pinacol ester (1.2 mg, 10 mmol), CuI (97 mg,0.5 mmol), LiOMe (365 mg, 4.68 mmol), PPh3 (106 mg, 0.41 mmol) and DMF (15 mL) were added to a 100 mL reaction flask. After replacing three times with nitrogen, the reaction was carried out at room temperature for 14 h, and TLC was monitored until the starting material was completely reacted. The reaction solution was poured into 100 mL of water, and the CuI was removed by filtration and washed three times with EA. The filtrate was collected and separated, and the aqueous phase was extracted with EA (60 mL*3). The title compound 30b (250 mg, 31percent) was obtained.
Reference: [1] Patent: CN108341777, 2018, A, . Location in patent: Paragraph 0445-0448
  • 16
  • [ 622-95-7 ]
  • [ 375854-57-2 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467
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