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[ CAS No. 766-80-3 ] {[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 [ 766-80-3 ]

CAS No. :766-80-3 MDL No. :MFCD00000597
Formula : C7H6BrCl Boiling Point : -
Linear Structure Formula :- InChI Key :LZIYAIRGDHSVED-UHFFFAOYSA-N
M.W : 205.47 Pubchem ID :69838
Synonyms :

Safety of [ 766-80-3 ]

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 [ 766-80-3 ]

* 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 [ 766-80-3 ]
  • Downstream synthetic route of [ 766-80-3 ]

[ 766-80-3 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 873-63-2 ]
  • [ 766-80-3 ]
Reference: [1] Bulletin of the Chemical Society of Ethiopia, 2012, vol. 26, # 2, p. 305 - 309
[2] Journal of the Chemical Society, 1926, p. 220
[3] Journal of the Chemical Society, 1927, p. 2241
[4] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467
[5] Chemical Communications, 2014, vol. 50, # 28, p. 3692 - 3694
[6] MedChemComm, 2015, vol. 6, # 6, p. 1104 - 1116
[7] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 561 - 569
[8] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 790 - 804
[9] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[10] Chinese Chemical Letters, 2016, vol. 27, # 2, p. 295 - 301
[11] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 413 - 421
  • 2
  • [ 108-41-8 ]
  • [ 766-80-3 ]
YieldReaction ConditionsOperation in experiment
83% With sodium bromate; 2,2'-azobis(isobutyronitrile); sulfuric acid; sodium bromide; dibenzoyl peroxide In dichloromethane; waterReflux m-chlorotoluene (5.1 g, 40 mmol)Sodium bromate (2.1 g, 14 mmol), sodium bromide (2.9 g, 28 mmol)Dichloromethane (25 mL) was added to a reaction flask equipped with a stirred, reflux condenser, thermometer and tail gas absorber,Heated to reflux,(0.025 g AIBN, 0.025 g BPO dissolved in 5 mL of dichloromethane) was added rapidly to the total volume of the initiator solution,Sulfuric acid (2.1 g, 21 mmol concentrated sulfuric acid diluted with 2.5 mL of water) and the remaining initiator solution were slowly added dropwise, followed by gas chromatography,After the reaction was complete, the mixture was cooled to room temperature, saturated sodium bisulfite solution (10 mL) was added, stirred to red to fade,The aqueous phase was extracted twice with dichloromethane (10 mL x 2), the organic phases were combined and washed with saturated sodium chloride solution, dried and concentratedThe crude product was purified by column chromatography (elution solvent as petroleum ether) to give 6.8 g of m-chlorobenzyl bromide in 83percent yield. The product is colorless liquid
70% With Oxone; water; potassium bromide In dichloromethane at 20℃; for 20 h; Irradiation; Sealed tube General procedure: KBr (29.8 mg, 0.25 mmol, 1.0 equiv), 1-ethyl-4-nitrobenzene (1a) (41.6 mg, 0.275 mmol, 1.1 equiv), Oxone (153.9 mg, 0.25 mmol, 1.0 equiv), CH2Cl2 (0.25 mL) and H2O (180.0 mg, 0.18 mL, 40.0 equiv) were added, in accordance with the order, to a 15-mL oven-driedtube. The reaction tube was equipped with a magnetic stir bar and sealed with a Teflon-lined cap at once after the addition of the H2O. Then, the tube was placed on a magnetic stirrer (speed 300 rpm) and irradiated with a 0.5 W LED at a distance of 5 cm for 20 h at rt. After the reaction was finished, the reaction mixture was quenched with Na2SO3. Water (15 mL) was added and the mixture extracted with CH2Cl2 (3 × 5 mL). The organic phase was combined and dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give the crude product that was purified by flash column chromatography (petroleum ether/EtOAc mixtures). Compound 3a was obtained as a light yellow solid; yield: 53.6 mg (93percent).
Reference: [1] Patent: CN107098791, 2017, A, . Location in patent: Paragraph 0043-0045
[2] Synthetic Communications, 2010, vol. 40, # 7, p. 998 - 1003
[3] Synthesis (Germany), 2018, vol. 50, # 24, p. 4933 - 4939
[4] Chinese Chemical Letters, 2011, vol. 22, # 4, p. 382 - 384
[5] Journal of the Chemical Society, 1932, p. 55,66
[6] Journal of the American Chemical Society, 1948, vol. 70, p. 2310,2313
[7] Journal of Organic Chemistry, 1939, vol. 3, p. 347,350
[8] Journal of the Chemical Society, 1927, p. 2241
[9] Journal of the American Chemical Society, 1933, vol. 55, p. 2896,2898
[10] Journal of the Chemical Society, 1936, p. 1448,1450
[11] Journal of the Chemical Society, 1954, p. 2887,2891
[12] Journal of the Indian Chemical Society, 1951, vol. 28, p. 277
[13] Journal of the American Chemical Society, 1961, vol. 83, p. 943 - 949
[14] Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 43 - 67
[15] Journal of Organic Chemistry, 1992, vol. 57, # 10, p. 2967 - 2970
[16] Journal of Organic Chemistry, 1998, vol. 63, # 10, p. 3497 - 3498
[17] Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 4, p. 711 - 719[18] Zhurnal Organicheskoi Khimii, 1987, vol. 23, # 4, p. 788 - 797
[19] Journal of Organic Chemistry, 1992, vol. 57, # 10, p. 2967 - 2970
[20] Helvetica Chimica Acta, 2009, vol. 92, # 3, p. 555 - 566
[21] Journal of Chemical Research, 2012, vol. 36, # 5, p. 258 - 260
  • 3
  • [ 70450-41-8 ]
  • [ 766-80-3 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 2, p. 692 - 697
  • 4
  • [ 620-20-2 ]
  • [ 766-80-3 ]
Reference: [1] Journal of the American Chemical Society, 1980, vol. 102, # 2, p. 692 - 697
  • 5
  • [ 191097-25-3 ]
  • [ 191096-80-7 ]
  • [ 766-80-3 ]
Reference: [1] Patent: US5696117, 1997, A,
  • 6
  • [ 587-04-2 ]
  • [ 766-80-3 ]
Reference: [1] Chemical Communications, 2014, vol. 50, # 28, p. 3692 - 3694
[2] MedChemComm, 2015, vol. 6, # 6, p. 1104 - 1116
[3] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 561 - 569
[4] Medicinal Chemistry Research, 2016, vol. 25, # 4, p. 790 - 804
[5] Chinese Chemical Letters, 2016, vol. 27, # 7, p. 1058 - 1063
[6] Chinese Chemical Letters, 2016, vol. 27, # 2, p. 295 - 301
  • 7
  • [ 108-41-8 ]
  • [ 70288-97-0 ]
  • [ 766-80-3 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 4, p. 382 - 384
  • 8
  • [ 535-80-8 ]
  • [ 766-80-3 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 1, p. 413 - 421
  • 9
  • [ 108-41-8 ]
  • [ 7726-95-6 ]
  • [ 766-80-3 ]
Reference: [1] Journal of the Chemical Society, 1927, p. 2241
  • 10
  • [ 506-68-3 ]
  • [ 876476-09-4 ]
  • [ 766-80-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1933, vol. 507, p. 1,9
  • 11
  • [ 506-68-3 ]
  • [ 854392-02-2 ]
  • [ 52245-37-1 ]
  • [ 766-80-3 ]
Reference: [1] Chemische Berichte, 1937, vol. 70, p. 1241,1249
  • 12
  • [ 766-80-3 ]
  • [ 4152-90-3 ]
Reference: [1] Journal of the Chemical Society, 1961, p. 1414 - 1416
  • 13
  • [ 766-80-3 ]
  • [ 89-20-3 ]
Reference: [1] Journal of Organic Chemistry, 1961, vol. 26, p. 2310 - 2316
  • 14
  • [ 766-80-3 ]
  • [ 766-83-6 ]
Reference: [1] Synthesis, 1979, p. 502 - 504
  • 15
  • [ 143-33-9 ]
  • [ 766-80-3 ]
  • [ 1529-41-5 ]
YieldReaction ConditionsOperation in experiment
87% at 80℃; for 2 h; Example 257; 2-(5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazol-3-yl)-5-(1-(3-chlorophenyl)cyclopropyl)-1,3,4-oxadiazole; Step 1: 2-(3-chlorophenyl)acetonitrile; The experimental procedure was followed by the method of Bruno P. Imbimbo et al [J. Med. Chem. 2005, 48, 5707-7520]. A solution of 3-chlorobenzylbromide (5 g, 24.3 mmol) and sodium cyanide (1.3 g, 26.8 mmol) in ethanol (50 ml) was heated to 80° C. for 2 hours. After resulting solution was cooled to room temperature and concentrated under reduced pressure. The residue was suspended in water and organic layer was extracted with ethyl acetate. The solution was evaporated and crude compound was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to yield 2-(3-chlorophenyl)acetonitrile (3.2 g, 87percent yield) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.36-7.32 (m, 1H), 7.20-7.17 (m, 3H), 7.06-7.04 (m, 1H), 3.68 (s, 2H).
Reference: [1] Patent: US2008/81812, 2008, A1, . Location in patent: Page/Page column 62
  • 16
  • [ 151-50-8 ]
  • [ 766-80-3 ]
  • [ 1529-41-5 ]
Reference: [1] Journal of the Indian Chemical Society, 1951, vol. 28, p. 470
  • 17
  • [ 766-80-3 ]
  • [ 21327-86-6 ]
Reference: [1] Journal of Organic Chemistry, 1961, vol. 26, p. 2310 - 2316
  • 18
  • [ 766-80-3 ]
  • [ 74-89-5 ]
  • [ 39191-07-6 ]
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
  • 19
  • [ 766-80-3 ]
  • [ 1956-15-6 ]
Reference: [1] Journal of Organic Chemistry, 1993, vol. 58, # 4, p. 957 - 958
  • 20
  • [ 766-80-3 ]
  • [ 80126-51-8 ]
Reference: [1] Liebigs Annalen der Chemie, 1989, p. 1215 - 1232
  • 21
  • [ 766-80-3 ]
  • [ 188814-25-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4524 - 4534
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