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[ CAS No. 18880-00-7 ] {[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 [ 18880-00-7 ]

CAS No. :18880-00-7 MDL No. :MFCD00000180
Formula : C11H15Br Boiling Point : -
Linear Structure Formula :C(CH3)3C6H4CH2Br InChI Key :QZNQSIHCDAGZIA-UHFFFAOYSA-N
M.W : 227.14 Pubchem ID :87836
Synonyms :

Calculated chemistry of [ 18880-00-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.45
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.55
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.87
Log Po/w (XLOGP3) : 5.36
Log Po/w (WLOGP) : 3.73
Log Po/w (MLOGP) : 4.27
Log Po/w (SILICOS-IT) : 4.02
Consensus Log Po/w : 4.05

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.86
Solubility : 0.00311 mg/ml ; 0.0000137 mol/l
Class : Moderately soluble
Log S (Ali) : -5.11
Solubility : 0.00175 mg/ml ; 0.0000077 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.87
Solubility : 0.00305 mg/ml ; 0.0000134 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.65

Safety of [ 18880-00-7 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 18880-00-7 ]

* 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 [ 18880-00-7 ]
  • Downstream synthetic route of [ 18880-00-7 ]

[ 18880-00-7 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 98-51-1 ]
  • [ 18880-00-7 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane; hexane Referential Example 19
Production of N-(4-tert-Butylbenzyl)methylamine (Alternative Method)
p-tert-butyltoluene (14.8 g; 0.10 mol) was dissolved in carbon tetrachloride, and N-bromosuccinimide (17.8 g; 0.10 mol) and benzoyl peroxide (200 mg) were added thereto.
The mixture was refluxed for 2 hours, and then cooled.
Insoluble matter was filtered off, followed by washing with carbon tetrachloride.
The filtrate was concentrated under reduced pressure, and the residue was dissolved in n-hexane, followed by drying over magnesium sulfate.
The solvent was evaporated under reduced pressure, to thereby yield 22.7 g of p-tert-butylbenzyl bromide (yield: 100percent).
89% With sodium chlorite; hydrogen bromide In dichloromethane; water at 20 - 30℃; Reflux; Irradiation comprising the steps of: S11. Add 1 lmol of 40percent hydrobromic acid to 300 ml of water to form a dilute acid solution; S12. 1000 ml of reaction flask was charged with 300 ml of dichloromethane and 1 mol of p-methyl-tert-butylbenzene, stirred at 30 ° C Adding to said dilute acid solution; S13. In the case of incandescent light, in the range of 0.5 to 1 hour, add 1 to 15 equivalents of sodium chlorite relative to HBr; S14. Under light conditions, the reaction was stirred at room temperature for 1-2 hours and then heated to reflux for 3-4 hours. The 4-tert-butylbenzyl bromide product obtained in the examples of the present invention had a yield of 89percent or more and a content of 97.8percent.
79% With bromine In chloroform for 0.0208333 h; Flow reactor; Irradiation; Green chemistry General procedure: A CHCl3 solution of alkylbenzene (0.5 M) was placed in a syringe, and a CHCl3 solution of Br2 (0.6 M) was placed in another syringe wrapped with aluminium foil. The reaction streams were introduced to each of the inlets of the capillary microreactor through a 25 cm FEP tubing segment. The injection rates for toluene and Br2 varied but were equal for both solutions. Sunlight was focussed with a Fresnel lens, and solar tracking was conducted manually every 15 min. The results ofthe reaction were collected into a brown vial containing an aqueous solution of Na2S2O3. After extraction with additional CHCl3, the organic layer was analysed. The crude yield and selectivity were calculated through GC/MS or 1H NMR analysis. The mixtures were purified via column chromatography.
Reference: [1] Patent: US6586633, 2003, B1,
[2] Patent: CN105315127, 2016, A, . Location in patent: Paragraph 0044-0050
[3] Tetrahedron Letters, 2009, vol. 50, # 16, p. 1861 - 1865
[4] Synthesis, 2009, # 11, p. 1807 - 1810
[5] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003
[6] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
[7] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 4, p. 403 - 407
[8] Australian Journal of Chemistry, 2015, vol. 68, # 11, p. 1653 - 1656
[9] Synlett, 2003, # 5, p. 702 - 704
[10] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
[11] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1993, # 1, p. 53 - 57
[12] Chemical Science, 2018, vol. 9, # 40, p. 7843 - 7858
[13] Journal of the Chemical Society, 1936, p. 300
[14] Roczniki Chemii, 1934, vol. 14, p. 1249,1252[15] Chem. Zentralbl., 1935, vol. 106, # I, p. 2807
[16] Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 269,270, 275
[17] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[18] Journal of the Indian Chemical Society, 1990, vol. 67, # 11, p. 909 - 911
[19] Journal of Medicinal Chemistry, 1989, vol. 32, # 5, p. 1098 - 1108
[20] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 21, p. 2735 - 2740
[21] Journal of the American Chemical Society, 1999, vol. 121, # 45, p. 10538 - 10544
[22] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
[23] Helvetica Chimica Acta, 2009, vol. 92, # 3, p. 555 - 566
[24] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
[25] European Journal of Organic Chemistry, 2014, vol. 2014, # 16, p. 3402 - 3410
  • 2
  • [ 877-65-6 ]
  • [ 18880-00-7 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
[2] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1190 - 1193
[3] Organic Letters, 2018, vol. 20, # 10, p. 2980 - 2983
[4] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1991, # 12, p. 2067 - 2080
  • 3
  • [ 50-00-0 ]
  • [ 253185-03-4 ]
  • [ 18880-00-7 ]
YieldReaction ConditionsOperation in experiment
86.3% at 120℃; for 8 h; 50 grams (0.37 mol) of tert-butylbenzene, 12.3 grams (0.40 mol) of paraformaldehyde and 100 mL of acetic acid were mixed in a flask. 109.6 grams of hydrogen bromide (HBr) in 33percent (w/w) acetic acid solution was slowly added into the flask dropwise within 30 minutes and then heated to 120° C. and stirred for 7.5 hours. Samples were obtained and extracted with water and dichloromethane. Organic phase was obtained and subjected to thin-layer chromatography (TLC) for tracing reaction. Until reactants were consumed, 200 mL of water was added into the reaction mixture and then extracted with 200 mL dichloromethane for three times. Organic phases were collected, concentrated and distilled under a condition of a temperature of 165170° C. and a pressure of 4.85.5.x.10-1 torr to obtain distilled fractions. 73.02 grams of compound 1 was obtained with a yield of 86.3percent.
Reference: [1] Patent: US2012/264981, 2012, A1, . Location in patent: Page/Page column 3
[2] Journal of the Chemical Society, 1962, p. 3915 - 3926
  • 4
  • [ 32857-63-9 ]
  • [ 18880-00-7 ]
Reference: [1] Organic Letters, 2017, vol. 19, # 7, p. 1634 - 1637
  • 5
  • [ 618-32-6 ]
  • [ 877-65-6 ]
  • [ 38612-06-5 ]
  • [ 18880-00-7 ]
Reference: [1] Patent: WO2016/202894, 2016, A1, . Location in patent: Page/Page column 50; 150; 182; 183
  • 6
  • [ 253185-03-4 ]
  • [ 18880-00-7 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1953, p. C 51
[2] Patent: EP645458, 1995, A1,
  • 7
  • [ 98-51-1 ]
  • [ 61024-94-0 ]
  • [ 18880-00-7 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 17, p. 6023 - 6026
  • 8
  • [ 98-51-1 ]
  • [ 939-97-9 ]
  • [ 18880-00-7 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8037 - 8044
  • 9
  • [ 98-51-1 ]
  • [ 18880-00-7 ]
  • [ 75966-32-4 ]
Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
[2] Tetrahedron Letters, 2006, vol. 47, # 40, p. 7245 - 7247
[3] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1097 - 1099
[4] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
[5] Angewandte Chemie, 1980, vol. 92, # 6, p. 471 - 472
[6] Helvetica Chimica Acta, 2009, vol. 92, # 3, p. 555 - 566
  • 10
  • [ 1058648-72-8 ]
  • [ 18880-00-7 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 25, p. 3274 - 3276
  • 11
  • [ 1058648-68-2 ]
  • [ 18880-00-7 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 25, p. 3274 - 3276
  • 12
  • [ 98-51-1 ]
  • [ 64-19-7 ]
  • [ 877-65-6 ]
  • [ 939-97-9 ]
  • [ 67364-88-9 ]
  • [ 18880-00-7 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8037 - 8044
[2] Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8037 - 8044
[3] Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8037 - 8044
[4] Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8037 - 8044
  • 13
  • [ 98-51-1 ]
  • [ 1099597-89-3 ]
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Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 45, p. 11559 - 11563
  • 14
  • [ 98-51-1 ]
  • [ 61024-94-0 ]
  • [ 129167-74-4 ]
  • [ 18880-00-7 ]
Reference: [1] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
  • 15
  • [ 98-51-1 ]
  • [ 64-19-7 ]
  • [ 939-97-9 ]
  • [ 67364-88-9 ]
  • [ 18880-00-7 ]
Reference: [1] Chemistry - A European Journal, 2007, vol. 13, # 28, p. 8037 - 8044
  • 16
  • [ 98-51-1 ]
  • [ 939-97-9 ]
  • [ 18880-00-7 ]
  • [ 75966-32-4 ]
Reference: [1] European Journal of Organic Chemistry, 2006, # 2, p. 483 - 488
[2] Synthesis, 2003, # 15, p. 2289 - 2291
  • 17
  • [ 939-97-9 ]
  • [ 18880-00-7 ]
Reference: [1] Synlett, 2016, vol. 27, # 9, p. 1391 - 1396
  • 18
  • [ 98-51-1 ]
  • [ 61024-94-0 ]
  • [ 18880-00-7 ]
  • [ 75966-32-4 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
[2] Tetrahedron Letters, 2006, vol. 47, # 7, p. 1097 - 1099
[3] Tetrahedron, 2009, vol. 65, # 22, p. 4429 - 4439
  • 19
  • [ 108-88-3 ]
  • [ 18880-00-7 ]
Reference: [1] Roczniki Chemii, 1934, vol. 14, p. 1249,1252[2] Chem. Zentralbl., 1935, vol. 106, # I, p. 2807
  • 20
  • [ 877-65-6 ]
  • [ 98-88-4 ]
  • [ 38612-06-5 ]
  • [ 18880-00-7 ]
Reference: [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 33, p. 4541 - 4547
  • 21
  • [ 98-51-1 ]
  • [ 939-97-9 ]
  • [ 18880-00-7 ]
  • [ 98-73-7 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1996, # 10, p. 2501 - 2525
  • 22
  • [ 103323-56-4 ]
  • [ 18880-00-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1998, vol. 71, # 6, p. 1401 - 1407
  • 23
  • [ 615-43-0 ]
  • [ 18880-00-7 ]
  • [ 49671-76-3 ]
Reference: [1] Synlett, 2017, vol. 28, # 4, p. 504 - 508
  • 24
  • [ 18880-00-7 ]
  • [ 123-38-6 ]
  • [ 80-54-6 ]
YieldReaction ConditionsOperation in experiment
83.3% With sodium hydroxide In tetrahydrofuran; water; toluene at 70 - 75℃; for 5 h; 2.3 grams (57.7 mmol) of sodium hydroxide, 0.33 grams (0.88 mmol) of 4-tertbutylbenzyl triethyl ammonium iodide, 7.5 mL of water, 4.2 mL of toluene, 1 mL of THF were added into a flask and heated to 70 to 75° C. Mixture of 10 grams (44.0 mmol) of 4-tertbutylbenzyl bromide and 3.55 grams (61.2 mmol) of propanal was added dropwise and slowly into the flask within 2 hours while the mixed solution in the flask was vigorously stirred, followed by stirring at 70 to 75° C. for another 3 hours when addition was finished. Reaction was traced by gas chromatography. The reaction mixture was extracted with 30 mL of water to obtain an organic layer when reaction was completed. The organic layer was dehydrated with anhydrous sodium sulfate, filtered off salt to isolate mother liquid, and stripped off solvent by vacuum distillation. 7.49 grams of lysmeral was obtained with a yield of 83.3percent.
82.6% With sodium hydroxide In tetrahydrofuran; water; toluene at 70 - 75℃; for 5 h; 2.3 grams (57.7 mmol) of sodium hydroxide, 0.26 grams (0.88 mmol) of PTC 1, 7.5 mL of water, 4.2 mL of toluene, 1 mL of THF were mixed in a flask and then heated to 70-75° C. Mixture of 10 grams (44.0 mmol) of compound 1 and 3.55 grams (61.2 mmol) of propanal was added into the flask dropwise within 2 hours while the reaction mixture was vigorously stirred. While addition was finished, the reaction mixture was stirred at 70-75° C. for 3 hours and traced by GC. When the reaction stopped, 30 mL water was added for extraction to obtain an organic phase. The organic phase was dehydrated with anhydrous sodium sulfate, filtered and concentrated by vacuum distillation. 7.43 grams of lysmeral was obtained with a yield of 82.6percent and verified to have a purity of 97.27percent by GC analysis.Results of analysis by NMR are shown as follows:1H NMR (CDCl3) δ 9.73 (t, 1H, J=6.851), 7.34 (ddd, 1H, J=8.032, J=3.716, J=0.000), 7.13 (ddd, 1H, J=8.032, J=3.732, J=0.000), 7.11 (ddd, 1H, J=8.032, J=3.716, J=0.000), 7.32 (ddd, 1H, J=8.032, J=3.732, J=0.000), 2.6 (dd, 2H, J=6.945, J=6.851), 3.0 (tq, 1H, J=6.945, J=6.911), 1.32 (m, 9H), 1.1 (d, 3H, J=6.911).
Reference: [1] Patent: US2012/264975, 2012, A1, . Location in patent: Page/Page column 4
[2] Patent: US2012/264981, 2012, A1, . Location in patent: Page/Page column 4
  • 25
  • [ 201230-82-2 ]
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Reference: [1] Tetrahedron Letters, 2000, vol. 41, # 40, p. 7601 - 7604
[2] Mendeleev Communications, 2009, vol. 19, # 5, p. 256 - 257
  • 26
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 18, p. 4143 - 4150
[2] Journal of the Chemical Society, 1937, p. 1774,1777
[3] Roczniki Chemii, 1934, vol. 14, p. 1249,1252[4] Chem. Zentralbl., 1935, vol. 106, # I, p. 2807
[5] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7289 - 7298
  • 27
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Reference: [1] Chemical Research in Toxicology, 1996, vol. 9, # 2, p. 445 - 450
  • 28
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  • [ 5406-86-0 ]
Reference: [1] Chemical Research in Toxicology, 1996, vol. 9, # 2, p. 445 - 450
[2] Journal of Medicinal Chemistry, 2011, vol. 54, # 20, p. 7289 - 7298
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