ChemInform Abstract: Synthesis and in vitro Antifungal Activities of New 2‐Aryl‐6,7‐methylenedioxy‐3,4‐dihydroisoquinolin‐2‐ium Bromides.

Yang, Xin; Yao, Yao; Qin, Yuyan; Hou, Zhe; Yang, Rui; Miao, Fei; Zhou, Le

doi:10.1002/chin.201401174

Cited by 1 publication

(8 citation statements)

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“…For nitro-substituted compounds, the presence of 2′-NO 2 (5-31) caused reduction of the activities against all three fungi, and the presence of 3′-NO 2 (5-30) could lead to an increase of the activities against A. alternate and V. mali, similar to that observed for 2-aryl-3,4-dihydroisoquinolin-2-ium bromides 8 and 2-aryl-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium bromides. 9 However, 4′-NO 2 in three series of the compounds has different effects on the activity. For 5-29, the introduction of 4′-NO 2 led to a decrease of the activities against all three fungi, whereas for 2-(4-nitrophenyl)-3,4-dihydroisoquinolin-2-ium bromides and 2-(4-nitrophenyl)-6,7-methylenedioxy-3,4-dihydroisoquinolin-2-ium bromides, the presence of 4′-NO 2 could increase the activities against both A. alternate and V. mali.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…1 4.60 (2H, t, J = 7.9 Hz, H-3), 3.55 (2H, t, J = 7.9 Hz, H-4); 13 4.65 (2H, t, J = 7.9 Hz,H-3), 3.54 (2H, t, J = 7.9 Hz, H-4); 13 2-(4-Bromophenyl)-6-chloro-3,4-dihydroisoquinolin-2-ium bromide (5)(6)(7)(8). Yield: 76%; yellow powder; mp 211.9−212.4 °C; IR, υ max (KBr) cm −1 : 1621 (s, CN); UV λ max (lg ε) (MeOH) 331 (4.00) nm; 1 H NMR (500 MHz, CD 3 OD) δ: 9.58 (1H, s, H-1), 8.05 (1H, d, J = 8.2 Hz, H-8), 7.88 (2H, d, J = 8.8 Hz, H-2′,6′), 7.80 (2H, d, J = 8.8 Hz, H-3′,5′), 7.71 (1H, s, H-5), 7.69 (1H, d, J = 8.2 Hz, H-7), 4.65 (2H, t, J = 8.0 Hz, H-3), 3.54 (2H, t, J = 8.0 Hz, H-4); 13 6-Chloro-2-(3-iodophenyl)-3,4-dihydroisoquinolin-2-ium bromide (5)(6)(7)(8)(9)(10)(11)(12). Yield: 67%; yellow powder; mp 177.1−177.5 °C; IR, υ max (KBr) cm −1 : 1620 (s, CN); UV λ max (lg ε) (MeOH) 319 (4.07) nm; 1 H NMR (500 MHz, CD 3 OD) δ: 9.57 (1H, s, H-1), 8.28 (1H, s, H-2′), 8.05 (2H, t, J = 7.8 Hz), 7.88 (1H, d, J = 8.3 Hz, H-8), 7.71 (1H, s, H-5), 7.69 (1H, d, J = 8.3 Hz, H-7), 7.47 (1H, t, J = 8.1 Hz), 4.63 (2H, t, J = 7.9 Hz, H-3), 3.53 (2H, t, J = 7.9 Hz, H-4); 13 4.58 (2H, t, J = 7.9 Hz, H-3), 3.54 (2H, t, J = 7.9 Hz, H-4); 13 7.90 (1H, dd, J = 8.5,2.0 Hz, H-5′), 7.86 (1H, d, J = 8.5 Hz, H-6′), 7.75 (1H, s, H-5), 7.72 (1H, dd, J = 8.2,1.9 Hz, H-7), 4.52 (2H, t, J = 7.9 Hz, H-3), 3.61 (2H, t, J = 7.9 Hz, H-4); 13 6-Chloro-2-(2-(trifluoromethyl)phenyl)-3,4-dihydroisoquinolin-2ium bromide (5-25).…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…The antifungal activities in vitro of all the synthetic compounds against three plant pathogenic fungi ( A. alternate, C. lunata and V. mali ) were assayed by the mycelium linear growth rate method as previously reported. ,,, The test fungi maintained on potato dextrose agar (PDA) medium slants were subcultured for 48 h in Petri dishes prior to testing and used for inoculation of fungal strains on PDA plates.…”

Section: Methodsmentioning

confidence: 99%

“…In our previous research, sanguinarine and chelerythrine (Figure ), two common quaternary benzo[c]phenanthridine alkaloids, were proven to be promising lead compounds for the development of new isoquinoline antimicrobial agents . Meanwhile, the iminium moiety (CN + ) in their structures was found to be essential for their antimicrobial and acaricidal activities. − After this, based on the SAR of sanguinarine and chelerythrine, we designed a series of their structural analogues, 2-aryl-3,4-dihydroisoquinolin-2-iums (Figure ) and evaluated their bioactivities against phytopathogenic fungi. , Most of them showed higher activities than their model compounds (sanguinarine and chelerythrine) and a commercial fungicide thiabendazole. In addition, these compounds also showed high safety to plant growth .…”

Section: Introductionmentioning

confidence: 99%

“…C NMR (125 MHz, CD 3 OD) δ: 171.1 (C-1), 146.3 (C-1′), 141.0, 139.5, 136.7, 136.5, 132.7, 129.0, 128.1, 125.6, 123.5, 118.6 (2 × C), 52.1 (C-3), 25.1 (C-4); HR-MS [M -Br] + : Calcd for C 15 H 11 Br 2 ClN + , 397.8941, found 397.8923; Negative ESI-MS m/z: 78.7 [ 79 Br − ], 80.7 [ 81 Br − ].6-Chloro-2-(2,6-difluorophenyl)-3,4-dihydroisoquinolin-2-ium bromide(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19). Yield: 58%; yellow powder; mp 195.6−196.0 °C; IR, υ max (KBr) cm −1 : 1629 (s, CN); UV λ max (lg ε) (MeOH) 319 (3.89) nm; 1 H NMR (500 MHz, CD 3 OD) δ: 9.62 (1H, s, H-1), 8.07 (1H, d, J = 8.2 Hz, H-8), 7.79−7.72 (3H, m), 7.44 (2H, t, J = 8.5 Hz), 4.57(2H, t, J = 7.9 Hz, H-3), 3.56(2H, t, J = 7.9 Hz, H-4);13 C NMR (125 MHz, CD 3 OD) δ: 156.0 (d, J = 255.2 Hz, C-2′,6′), 146.7 (C-1′), 140.0, 136.9, 133.3, 129.1, 129.0, 123.7, 119.8, 113.0 (dd, J = 19.3,3.5 Hz, C-3′,5′), 52.1 (C-3), 25.1 (C-4); HR-MS [M -Br] + : Calcd for C 15 H 11 ClF 2 N + , 278.0543, found 278.0539; Negative ESI-MS m/z: 78.7 [ 79 Br − ], 80.7 [ 81 Br − ].…”

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confidence: 99%

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New Class of 2-Aryl-6-chloro-3,4-dihydroisoquinolinium Salts as Potential Antifungal Agents for Plant Protection: Synthesis, Bioactivity and Structure–Activity Relationships

Yang

Gao

Zhao

et al. 2015

J. Agric. Food Chem.

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Thirty-four new 2-aryl-6-chloro-3,4-dihydroisoquinolin-2-ium bromides were synthesized, and their structures were elucidated by spectroscopic analysis. Antifungal activities against Alternaria alternate, Curvularia lunata and Valsa mali were evaluated by the mycelium linear growth rate method. SAR was discussed also. All compounds showed some activity against each of the fungi at 25 μg/mL. Compared to azoxystrobin, a commercial fungicide, 31 out of 34 test compounds showed higher inhibition rates against C. lunata and 10 were more effective against A. alternate and V. mali. Compounds 5-4, 5-2 and 5-34 showed the highest activity against A. alternate (EC50 = 10.3 μg/mL), C. lunata (EC50 = 4.6 μg/mL) and V. mali (EC50 = 3.9 μg/mL), respectively, superior to azoxystrobin (EC50 = 12.8, 71.9, 37.2 μg/mL). Compound 5-4 displayed good activities against each of the fungi with EC50 of 10.3, 4.7, and 18.0 μg/mL while 5-34 displayed excellent activities against V. mali (EC50 = 3.9 μg/mL) and C. lunata (EC50 = 5.8 μg/mL). The SAR showed that the type and position of substituents on the C-ring had significant effects on the activity. Generally, the presence of 2'-F, 4'-F or 2'-CH3 could significantly improve the activities, whereas OH, OMe, NO2 or CF3 groups decreased the activities. Thus, it was concluded that the present research provided a new series of 2-aryl-6-chloro-3,4-dihydroisoquinolin-2-iums with excellent antifungal potency, and the results were of importance for the structure optimization design, synthesis and development of more potent isoquinoline antifungal agents.

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Section: ■ Results and Discussionmentioning

confidence: 99%