Development of 8-benzyloxy-substituted quinoline ethers and evaluation of their antimicrobial activities
Tóm tắt
A series of 8-benzyloxy-substituted quinoline ethers (2a–n) compounds were synthesized. All synthesized compounds were screened in vitro for their preliminary antimicrobial activities against two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli), two Gram-positive bacteria (Staphylococcus aureus and Staphylococcus epidermidis), and a fungal species (Aspergillus niger). Among all synthesized compounds, compound 2e showed a significant growth inhibitory activity with MIC value 3.125 μg/mL which was comparable to 8-hydroxyquinoline (2.5 μg/mL) and terbinafine (1.25 μg/mL) against A. niger.
Tài liệu tham khảo
Albrecht M, Osetska O, Frohlich R (2006) The hiratani-double-clasien rearrangment as a key step in the preparationn of sequential bis(8-hydroxyquinoline) ligands. Synlett 6:924–926
Banerjee M, Kumar S, Ghosh S, Paira R, Mondal S, Karmokar S, Chattopadhyay D, Bhadra RK, Mondal NB (2014) Amberlite IRA 402(OH)-mediated synthesis and evaluation of fused tricyclic quinolinium salts as potent non-detergent type microbicidal spermicides. Med Chem Res 23:1488–1500
Bringmann G, Thomale K, Bischof S, Schneider C, Schultheis M, Schwarz T, Moll H (2013) A novel leishmania major Amastigote assay in 96-well format for rapid drug screening and its use for discovery and evaluation of a new class of leishmanicidal quinolinium salts. Antimicrob Agents Chemother 57:3003–3011
Chan SH, Chui CH, Chan SW, Kok SHL, Chan D, Tsoi MYT, Leung PHM, Lam AKY, Chan ASC, Lam KH, Tang JCO (2013) Synthesis of 8-hydroxyquinoline derivatives as novel anti-tumor agents. ACS Med Chem Lett 4:170–174
Chen ZF, Wei JH, Liu YC, Liu M, Gu YQ, Huang KB, Wang M, Liang H (2013) High antitumor activity of 5,7-dihalo-8-quinolinolato cerium complexes. Eur J Med Chem 68:454–462
Denton JR (2010) One-Pot Desulfonylative Alkylation of N-Sulfonyl Azacycles Using Alkoxides Generated by Phase-Transfer Catalysis. Synthesis 5:775–782
El-Agrody AM, Abd-Rabboh HSM, Al-Ghamdi AM (2013) Synthesis, antitumor activity, and structure–activity relationship of some 4H-pyrano[3,2-h]quinoline and 7H-pyrimido[4′,5′:6,5]pyrano[3,2-h]quinoline derivatives. Med Chem Res 22:1339–1355
Ewa B, Maciej W, Marcin S, Grzegorz D, Michał Z, Jan P, Józef O (2012) The development of first Staphylococcus aureus SplB protease inhibitors: Phosphonic analogues of glutamine. Bioorg Med Chem Lett 22:5574–5578
He X, Zhong M, Zhang T, Yang J, Wu Z, Xiao Y, Guo H, Qiu G, Hu X (2012) Synthesis and anticonvulsant activity of 1-(8-(benzyloxy)quinolin-2-yl)-6-substituted-4,6-diazaspiro[2,4]heptane-5,7-diones. Eur J Med Chem 48:338–346
Johnson JR, Russo TA, Drawz SM, Clabots C, Olson R, Kuskowski MA, Rosen H (2013) OxyR contributes to the virulence of a Clonal Group A Escherichia coli strain (O17:K + :H18) in animal models of urinary tract infection, subcutaneous infection, and systemic sepsis. Microb Pathog 64:1–5
Kaur K, Jain M, Reddy RP, Jain R (2010) Quinolines and structurally related heterocycles as antimalarials. Eur J Med Chem 45:3245–3264
Kerr KG, Snelling AM (2009) Pseudomonas aeruginosa: a formidable and ever-present adversary. J Hosp Infect 72:338–344
Ko TC, Hour MJ, Lien JC, Teng CM, Lee KH, Kuo SC, Huang LJ (2001) Synthesis of 4-alkoxy-2-phenylquinoline derivatives as potent antiplatelet agents. Bioorg Med Chem Lett 11:279–282
Krishnakumar V, Nawaz Khan FR, Mandal BK, Mitta S, Dhasamandha R, Govindan VN (2012) Quinoline-3-carboxylates as potential antibacterial agents. Res Chem Intermed 38:1819–1826
Kunitoshi T, Taro T, Minako H, Kohdoh S, Ryota T, Kaoru MT, Masae F, Yoshinori T, Kogyoku S, Mitsuhiro I, Hisashi S, Masahiro Y (2012) Synthesis and structure-activity relationships of 8-substituted-2-aryl-5-alkylaminoquinolines: potent, orally active corticotrophin-releasing factor-1-receptor antagonists. Bioorg Med Chem 20:6559–6578
Kuwabara H, Shibayama Y (2012) Pulmonary aspergilloma with prominent oxalate deposition. Indian J Pathol Microbiol 55:589–590
Lam KH, Gambari R, Lee KKH, Chen YX, Kok SHL, Wong RSM, Lau FY, Cheng CH, Wong WY, Bian ZX, Chan ASC, Tang JCO, Chui CH (2014a) Preparation of 8-hydroxyquinoline derivatives as potential antibiotics against Staphylococcus aureus. Bioorg Med Chem Lett 24:367–370
Lam PL, Lu GL, Hon KM, Lee KW, Ho CL, Wang X, Tang JCO, Lam KH, Wong RSM, Kok SHL, Bian ZX, Li H, Lee KKH, Gambari R, Chui CH, Wong WY (2014b) Development of ruthenium(II) complexes as topical antibiotics against methicillin resistant Staphylococcus aureus. Dalton Trans 43:3949–3957
Lam PL, Kok SHL, Bian ZX, Lam KH, Tang JCO, Lee KKH, Gambari R, Chui CH (2014c) D-glucose as amodifying agent in gelatin/collagen matrix and reservoir nanoparticles for Calendula officinalis delivery. Colloids Surf B Biointerfaces 117:277–283
Landini D, Maia A, Rampoldi A (1986) Stability of quaternary onium salts under phase-transfer conditions in the presence of aqueous alkaline solutions. J Org Chem 51:3187–3191
Liu TC, Wang ML (2008) Kinetic study of S-alkylation of 2-mercaptobenzimidazole catalyzed by tetrabutylammonium bromide. Chem Eng Comm 196:530–548
Lowy FD (1998) Staphylococcus aureus infections. New Engl J Med 339:520–532
Melissa OX, Sales MDPU, Camargo JDJP, Pasqualotto AC, Severo LC (2008) Aspergillus niger causing tracheobronchitis and invasive pulmonary aspergillosis in a lung transplant recipient: case report. Rev Soc Bras Med Trop 41:200–201
Oda M, Saraya T, Wakayama M, Shibuya K, Ogawa Y, Inui T, Yokoyama E, Inoue M, Shimoyamada H, Fujiwara M, Ota T, Takizawa H, Goto H (2013) Calcium oxalate crystal deposition in a patient with Aspergilloma due to Aspergillus niger. J Thorac Dis 5:E174–E178
Otto M (2009) Staphylococcus epidermidis—the ‘accidental’ pathogen. Nat Rev Microbiol 7:555–567
Parthiban P, Aridos G, Rathika P, Ramkumar V, Kabilan S (2009) Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles. Bioorg Med Chem Lett 19:2981–2985
Procop GW, Johnston WW (1997) Diagnostic value of conidia associated with pulmonary oxalosis: evidence of an Aspergillus niger infection. Diagn Cytopathol 17:292–294
Roehrl MHA, Croft WJ, Liao Q, Wang JY, Kradin RL (2007) Hemorrhagic pulmonary oxalosis secondary to a noninvasive Aspergillus niger fungus ball. Virchows Arch 451:1067–1073
Rojas Ruiz FA, García-Sánchez RN, Estupiñan SV, Gómez-Barrio A, Torres Amado DF, Pérez-Solórzano BM, Nogal-Ruiz JJ, Martínez-Fernández AR, Kouznetsov VV (2011) Synthesis and antimalarial activity of new heterocyclic hybrids based on chloroquine and thiazolidinone scaffolds. Bioorg Med Chem 19:4562–4573
Sahu KB, Ghosh S, Banerjee M, Maity A, Mondal S, Paira R, Saha P, Naskar S, Hazra A, Banerjee S, Samanta A, Mondal NB (2013) Synthesis and in vitro study of antibacterial, antifungal activities of some novel bisquinolines. Med Chem Res 22:94–104
Shi A, Nguyen TA, Battina SK, Rana S, Takemoto DJ, Chiang PK, Hua DH (2008) Synthesis and anti-breast cancer activities of substituted quinolines. Bioorg Med Chem Lett 18:3364–3368
Singh N, Paterson DL (2005) Aspergillus infections in transplant recipients. Clin Microbiol Rev 18:44–69
Tavares LC, Johann S, Almeida Alves TM, Guerra JC, Souza-Fagundes M, Cisalpino PS, Bortoluzzi AJ, Caramori GF, Piccoli RDM, Braibante HTS, Braibante MEF, Pizzolatti MG (2011) Quinolinyl and quinolinyl N-oxide chalcones: synthesis, antifungal and cytotoxic activities. Eur J Med Chem 46:4448–4456
Vandekerckhove S, Tran HG, Desmet T, D’hooghe M (2013) Evaluation of (4-aminobutyloxy)quinolines as a novel class of antifungal agents. Bioorg Med Chem Lett 23:4641–4643
Verkade E, Kluytmans J (2014) Livestock-associated Staphylococcus aureus CC398: Animal reservoirs and human infections. J Infect Genet Evol 21:523–530
Walsh TJ, Anaissie EJ, Denning DW, Herbrecht R, Kontoyiannis DP, Marr KA, Morrison VA, Segal BH, Steinbach WJ, Stevens DA, Burik JAV, Wingard JR, Patterson TF (2008) Treatment of aspergillosis: clinical practice guidelines of the Infectious Diseases Society of America. Clin Infect Dis 46:327–360
Weiser R, Donoghue D, Weightman A, Mahenthiralingam E (2014) Evaluation of five selective media for the detection of Pseudomonas aeruginosa using a strain panel from clinical, environmental and industrial sources. J Microbiol Methods 99:8–14
Wu Y, Chen Z, Liu Y, Yu L, Zhou L, Yang S, Lai L (2011) Quinoline-4-methyl esters as human nonpancreatic secretory phospholipase A2 inhibitors. Bioorg Med Chem 19:3266–3361
Xu H, Jian KZ, Guan Q, Ye F, Lv M (2007) Antifungal activity of some diaryl ethers. Chem Pharmaceut Bull 55:1755–1757
Yadav GD, Bisht PM (2004) Selectivity engineering in multiphase transfer catalysis in the preparation of aromatic ethers. J Mol Catal A 223:93–100
Yadav GD, Desai NM (2006) Phase transfer catalysed alkylation of 2′-hydroxy acetophenone with 1-bromopentane: Kinetics and mechanism of liquid–liquid reaction. J Mol Catal A 243:278–285
Ziebuhr W, Hennig S, Eckart M, Kränzler H, Batzilla C, Kozitskaya S (2006) Nosocomial infections by Staphylococcus epidermidis: how a commensal bacterium turns into a pathogen. Int J Antimicrob Agents 28:14–20