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[ CAS No. 823-78-9 ] {[proInfo.proName]}

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Chemical Structure| 823-78-9
Chemical Structure| 823-78-9
Structure of 823-78-9 * Storage: {[proInfo.prStorage]}
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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 [ 823-78-9 ]

CAS No. :823-78-9 MDL No. :MFCD00000176
Formula : C7H6Br2 Boiling Point : -
Linear Structure Formula :- InChI Key :ZPCJPJQUVRIILS-UHFFFAOYSA-N
M.W : 249.93 Pubchem ID :69979
Synonyms :

Calculated chemistry of [ 823-78-9 ]      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 : 46.98
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) : -9.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : -2.07
Log Po/w (WLOGP) : 3.19
Log Po/w (MLOGP) : 3.83
Log Po/w (SILICOS-IT) : 3.53
Consensus Log Po/w : 2.18

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.51
Solubility : 76.7 mg/ml ; 0.307 mol/l
Class : Very soluble
Log S (Ali) : 2.6
Solubility : 98800.0 mg/ml ; 395.0 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -4.51
Solubility : 0.00771 mg/ml ; 0.0000308 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.78

Safety of [ 823-78-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 823-78-9 ]

* 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 [ 823-78-9 ]
  • Downstream synthetic route of [ 823-78-9 ]

[ 823-78-9 ] Synthesis Path-Upstream   1~29

  • 1
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  • [ 932-77-4 ]
Reference: [1] Synthesis, 2008, # 24, p. 3937 - 3940
  • 2
  • [ 7791-25-5 ]
  • [ 591-17-3 ]
  • [ 94-36-0 ]
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  • [ 620-20-2 ]
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Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2940
  • 3
  • [ 591-17-3 ]
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YieldReaction ConditionsOperation in experiment
75% With N-Bromosuccinimide; tetrachlorosilane In acetonitrile at 20℃; for 8 h; General procedure: To a mixture of NXS and substrate (1 or 6) in CH3CN at room temperature was added SiCl4 and the mixture left to stir until TLC showed the disappearance of the starting material. The reaction was then poured onto H2O and the mixture extracted with CH2Cl2. The extracts were combined, dried over MgSO4 and evaporated. The residue was purified by recrystallization (pet. ether-Et2O, 3:1) to give pure 2b-2g, 3b, or by silica gel column chromatography (hexane-EtOAc 10:1 or 30:1) to give pure 2a,h,i, 3a-5 or 7-9, respectively
62.5% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 3 h; Heating / reflux A mixture of 3-bromotoluene (42.8 g, 0.25 mol), N-bromosuccinimide (48.9 g, 0.275 mol) and benzoyl peroxide (0.75 g) in tetrachloromethane (500 mL) was stirred and heated to reflux for 3 h. The mixture was left to stand overnight at laboratory temperature, the solid was filtered off, washed with tetrachloromethane and the filtrates were evaporated. The residue was distilled in vacuo to yield 52.7 g (62.5percent) of 1-bromo-3-bromomethylbenzene, b.p. 135-140° C./1.6 kPa.
62.5% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 20℃; Heating / reflux Example 1; {4-[2-(2-Bromo-10,11-dihydro-dibenzo [a,d]cyclohepten-5-ylidene)-ethylsu Ifanyl]-2-methyl- phenoxy} -acetic acid; A mixture of 3-bromotoluene (42.8 g, 0,25 mol), N-bromosuccinimide (48.9 g, 0.275 mol) and benzoyl peroxide (0.75 g) in tetrachloromethane (500 mL) was stirred and heated to reflux for 3 h. The mixture was left to stand overnight at laboratory temperature, the solid was filtered off, washed with tetrachloromethane and the filtrates were evaporated. The residue was distilled in vacuo to yield 52.7 g (62.5 percent) of 1-bromo-3-bromomethylbenzene, b. p. 135- 140 ° C/1.6 kPa.
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
[2] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003
[3] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4026 - 4029
[4] Patent: US2009/12171, 2009, A1, . Location in patent: Page/Page column 11
[5] Patent: WO2005/105736, 2005, A1, . Location in patent: Page/Page column 28
[6] Organic Letters, 2012, vol. 14, # 9, p. 2414 - 2417
[7] Journal of the American Chemical Society, 1951, vol. 73, p. 2940
[8] Journal of the Chemical Society, 1926, p. 220
[9] Journal of the American Chemical Society, 1948, vol. 70, p. 2310,2313
[10] Journal of the American Chemical Society, 1961, vol. 83, p. 943 - 949
[11] Tetrahedron Letters, 1996, vol. 37, # 42, p. 7611 - 7614
[12] Acta Crystallographica Section C: Crystal Structure Communications, 2003, vol. 59, # 4, p. o216-o218
[13] Journal of Organic Chemistry, 2007, vol. 72, # 4, p. 1073 - 1087
[14] Patent: US6586633, 2003, B1,
[15] Helvetica Chimica Acta, 2009, vol. 92, # 3, p. 555 - 566
[16] Journal of Medicinal Chemistry, 2013, vol. 56, # 6, p. 2556 - 2567
[17] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
[18] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 4
  • [ 15852-73-0 ]
  • [ 823-78-9 ]
Reference: [1] Organic Process Research and Development, 2002, vol. 6, # 2, p. 190 - 191
[2] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
[3] Organic Letters, 2008, vol. 10, # 11, p. 2143 - 2145
[4] Journal of the American Chemical Society, 2015, vol. 137, # 30, p. 9567 - 9570
  • 5
  • [ 1878-67-7 ]
  • [ 823-78-9 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 7, p. 1634 - 1637
  • 6
  • [ 15852-73-0 ]
  • [ 823-78-9 ]
  • [ 932-77-4 ]
Reference: [1] Synthesis, 2008, # 24, p. 3937 - 3940
  • 7
  • [ 591-17-3 ]
  • [ 585-76-2 ]
  • [ 823-78-9 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 8, p. 669 - 672
  • 8
  • [ 123-72-8 ]
  • [ 158526-66-0 ]
  • [ 38788-38-4 ]
  • [ 823-78-9 ]
Reference: [1] Journal of Organometallic Chemistry, 1994, vol. 473, # 1-2, p. 71 - 84
  • 9
  • [ 7791-25-5 ]
  • [ 591-17-3 ]
  • [ 94-36-0 ]
  • [ 823-78-9 ]
  • [ 620-20-2 ]
  • [ 932-77-4 ]
Reference: [1] Journal of the American Chemical Society, 1951, vol. 73, p. 2940
  • 10
  • [ 71323-99-4 ]
  • [ 823-78-9 ]
  • [ 4885-18-1 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 446
  • 11
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 78-67-1 ]
  • [ 591-17-3 ]
  • [ 823-78-9 ]
Reference: [1] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1953, vol. &lt;B&gt; 56, p. 75,78
  • 12
  • [ 56-23-5 ]
  • [ 78-67-1 ]
  • [ 591-17-3 ]
  • [ 7726-95-6 ]
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Reference: [1] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1953, vol. &lt;B&gt; 56, p. 75,78
  • 13
  • [ 506-68-3 ]
  • [ 876476-08-3 ]
  • [ 823-78-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 14
  • [ 506-68-3 ]
  • [ 823-78-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 15
  • [ 506-68-3 ]
  • [ 857825-62-8 ]
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Reference: [1] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 16
  • [ 823-78-9 ]
  • [ 15852-73-0 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 4177
[2] Synthetic Communications, 2011, vol. 41, # 18, p. 2712 - 2718
  • 17
  • [ 823-78-9 ]
  • [ 35287-42-4 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 26, p. 9308 - 9319
  • 18
  • [ 823-78-9 ]
  • [ 35287-42-4 ]
  • [ 142906-81-8 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 335 - 341
  • 19
  • [ 823-78-9 ]
  • [ 10269-01-9 ]
Reference: [1] Journal of the Chemical Society, 1932, p. 696,703
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
  • 20
  • [ 823-78-9 ]
  • [ 4885-18-1 ]
YieldReaction ConditionsOperation in experiment
80% With dimethyl amine In benzene (i)
Dimethylamine (51.4 g, 1.14 mol) was reacted with 3-bromobenzyl bromide (95 g, 0.38 mol) in benzene at 5° and the mixtue was acidified with hydrochloric acid and the mixture was extracted with aqueous 3N hydrochloric acid.
The aqueous extracts were made alkaline with aqueous potassium hydroxide and the oil which separated out was distilled to give 3-bromo-N,N-dimethylbenzylamine (65 g, 80percent) b.p. 118°/20 mmHg.
Reference: [1] Patent: US4496567, 1985, A,
  • 21
  • [ 823-78-9 ]
  • [ 124-40-3 ]
  • [ 4885-18-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1325 - 1330
[2] Journal of the Chemical Society, 1930, p. 2107,2112
[3] Archiv der Pharmazie, 1962, vol. 295 /67, p. 690 - 697
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 15, p. 3993 - 3997
[5] Journal of the American Chemical Society, 2015, vol. 137, # 18, p. 5887 - 5890
  • 22
  • [ 100-97-0 ]
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  • [ 4885-18-1 ]
Reference: [1] Journal of the Chemical Society, 1930, p. 2107,2112
  • 23
  • [ 71323-99-4 ]
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  • [ 4885-18-1 ]
Reference: [1] Journal of the Chemical Society, 1929, p. 446
  • 24
  • [ 823-78-9 ]
  • [ 32194-76-6 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2819,2824
[2] Journal of the Chemical Society, 1954, p. 2819,2824
  • 25
  • [ 823-78-9 ]
  • [ 30163-20-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 21, p. 6607 - 6619
[2] Journal of medicinal chemistry, 1967, vol. 10, # 1, p. 64 - 66
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  • [ 28286-79-5 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 4177
  • 27
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  • [ 67344-77-8 ]
YieldReaction ConditionsOperation in experiment
63.2% With hydrogenchloride; triethylamine In methanol; methylamine Referential Example 3
Production of N-(3-Bromobenzyl)methylamine
Triethylamine (19.2 g; 100.5 mmol) was dissolved in 40percent solution of methylamine in methanol (150 ml).
While the resultant solution was stirred in an ice bath, a solution of 3-bromobenzylbromide (25.1 g; 100.5 mmol) in methanol (40 ml) was added dropwise.
After completion of the addition, the mixture was removed from the ice bath, and stirred for 15 hours at room temperature.
Methanol and excess methylamine were evaporated under reduced pressure, and the residue was taken up in a mixture of ether and 2N hydrochloric acid (100 ml-100 ml).
The aqueous layer was alkalinized with aqueous sodium hydroxide solution, and the mixture was extracted with chloroform (100 ml).
The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over anhydrous sodium sulfate.
The solvent was evaporated under reduced pressure, to thereby yield 12.7 g of the target compound as a yellow-orange oily substance (yield: 63.2percent).
1H-NMR (CDCl3, ppm); 2.44 (3H, s), 3.72 (2H, s), 7.16~7.26 (2H, m), 7.38 (1H, m), 7.49 (1H, s).
Reference: [1] Patent: US6586633, 2003, B1,
  • 28
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  • [ 74-89-5 ]
  • [ 67344-77-8 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 1, p. 40 - 44
[2] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 29
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  • [ 171663-13-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 14, p. 3720 - 3731
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