ACS Infectious Diseases
IC5: Brown solid, 33% yield. MS (HRMS) m/z = 324.1932
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[M+Na]+ (calculated = 324.1934). 1H-NMR (400 MHz,
CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.39 (d, J = 8.4 Hz, 1H),
7.25 (m, 1H), 7.09 – 7.04 (m, 1H), 6.56 (s, 1H), 5.18 (s, 1H),
2.37 – 2.30 (m, 2H), 1.51 – 1.48 (m, 2H), 1.25 – 1.14 (m, 12H),
0.85 (t, J = 7.0 Hz, 3H). 13C-NMR (101 MHz, CDCl3) δ
210.60, 159.92, 156.49, 135.87, 125.03, 121.17, 120.45,
111.69, 102.87, 80.13, 37.92, 31.83, 29.72, 29.33, 29.22,
28.99, 23.77, 22.66, 14.12.
Figure 4. Difference between the bacterial response with and
without an aromatic ring. QS IC50 and EC50 values in V.
cholerae
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IC5I2: Brown solid, 29% yield. MS (HRMS) m/z = 450.0899
[M+Na]+ (calculated = 450.0906). 1H-NMR (400 MHz,
CDCl3) δ 8.45 (s, 1H), 7.37 (s, 1H), 7.33 – 7.24 (m, 1H), 7.22
(s, 1H), 7.06 (d, J = 8.4 Hz, 1H), 5.18 (s, 1H), 2.49 – 2.09 (m,
3H), 1.50 – 1.43 (m, 2H), 1.21 (m, 2H), 1.13– 1.10 (m, 9H),
0.81 (t, J = 7.0 Hz, 3H). 13C-NMR (101 MHz, CDCl3) δ
210.26 (s), 135.75 (s), 130.80 (s), 130.13 (s), 129.30 (s),
122.24 (s), 120.73 (s), 112.04 (s), 79.93 (s), 57.64 (s), 37.90
(s), 31.80 (s), 29.29 (s), 29.17 (s), 28.94 (s), 23.73 (s), 22.62
(s), 14.08 (s).
EXPERIMENTAL
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Chemicals: All reagents and solvents were purchased from
commercial sources and used without further purification
unless noted otherwise. All of the compounds were identified
by 1H-NMR and 13C-NMR spectroscopy and showed purity of
>95%.
10IC3a: Brown solid, 56% yield: 1H-NMR (400 MHz,
CDCl3) δ 8.76 (s, 1H), 8.47 (d, J = 5.1 Hz, 1H), 7.90 (s, 1H),
7.47 – 7.37 (m, 1H), 7.33 – 7.27 (m, 2H), 7.12 – 6.97 (dd, J =
15.4 Hz, J = 8 Hz, 1H), 6.77 (d, J = 15.2 Hz, 1H), 2.30 (d, J =
7.2 Hz, 2H), 1.54 – 1.51 (m, 2H), 1.31 – 1.29 (m, 8H), 0.89 (t,
IC6: Brown solid, 30% yield. MS (HRMS) m/z = 324.1937
[M+Na]+ (calculated = 324.1934). 1H-NMR (400 MHz,
CDCl3) δ 8.27 (s, 1H), 7.60 (s, 1H), 7.39 (d, J = 8.4 Hz, 1H),
7.24 (t, J = 2.7 Hz, 1H), 7.08 – 7.02 (m, 1H), 6.56 (s, 1H), 5.18
(s, 1H), 2.45 – 2.20 (m, 4H), 1.59 – 1.40 (m, 2H), 1.25 – 1.09
(m, 10H), 0.85 (t, J = 7.0 Hz, 3H). 13C-NMR (101 MHz,
CDCl3) δ 210.28, 135.95, 132.01, 125.13, 121.31, 119.41,
111.83, 110.20, 102.69, 80.04, 37.93, 31.83, 23.73, 22.65,
14.10.
J = 5.9 Hz, 3H).
13C-NMR (101 MHz, CDCl3) δ 186.17,
146.32, 136.69, 132.03, 127.18, 126.04, 123.80, 122.64,
122.55, 118.33, 111.72, 32.65, 31.80, 29.73, 29.28, 29.15,
28.45, 22.68, 14.13.
6IC3a: White solid, 88% yield. 1H-NMR (400 MHz,
Acetone) δ 8.37 – 8.33 (m, 1H), 8.22 (d, J = 2.8 Hz, 1H), 7.49
(d, J = 7.0 Hz, 1H), 7.23 – 7.18 (m, 2H), 2.87 (t, J = 7.4 Hz,
3H), 2.06 – 2.04 (m, 2H), 1.76 – 1.70 (m, 2H), 1.38 – 1.34 (m,
5H), 0.89 (t, J = 6.7 Hz, 4H). 13C-NMR (101 MHz, Acetone)
δ 195.25, 137.00, 132.48, 125.98, 122.85, 121.63, 117.36,
111.74, 39.05, 31.56, 24.80, 22.39, 13.42.
IC6I2: Brown solid, 35% yield. MS (HRMS) m/z = 450.0897
[M+Na]+ (calculated = 450.0906). 1H-NMR (400 MHz,
CDCl3) δ 8.53 (s, 1H), 7.46 (d, J = 8.2 Hz, 1H), 7.34 – 7.27
(m, 2H), 7.13 (d, J = 8.2 Hz, 1H), 5.17 (d, J = 3.6 Hz, 1H),
2.45 – 2.19 (m, 2H), 1.52 – 1.44 (m, 2H), 1.25 (t, J = 9.5 Hz,
2H), 1.22 – 1.08 (m, 10H), 0.86 (t, J = 6.9 Hz, 3H). 13C-NMR
(101 MHz, CDCl3) δ 209.98, 135.77, 129.40, 127.93, 127.27,
121.61, 120.32, 110.34, 79.78, 57.38, 37.87, 31.80, 29.30,
29.16, 28.92, 23.66, 22.63, 14.09.
7IC3a: White solid, 76% yield. 1H-NMR (400 MHz,
Acetone) δ 8.35 (d, J = 6.4 Hz, 1H), 8.23 (d, J = 2.3 Hz, 1H),
7.50 – 7.48 (m, 1H), 7.21 – 7.19 (m, 2H), 2.87 (t, J = 7.4 Hz,
2H), 1.78 – 1.67 (m, 2H), 1.46 – 1.25 (m, 7H), 0.89 (d, J = 6.2
Hz, 3H). 13C-NMR (101 MHz, Acetone) δ 195.22, 137.00,
132.47, 125.99, 122.84, 122.00, 121.63, 117.36, 111.74,
39.11, 31.66, 25.07, 22.38, 13.47.
8IC3a: White solid, 70% yield. 1H-NMR (400 MHz,
Acetone) δ 8.35 (dd, J = 7.6, 1.6 Hz, 1H), 8.23 (d, J = 3.1 Hz,
1H), 7.51 – 7.48 (m, 1H), 7.22 – 7.18 (m, 2H), 2.90 – 2.83 (t,
J = 7.4, 2H), 1.73 – 1.71 (m, 2H),1.39 - 1.36 (m, 3H), 1.31 –
1.28 (m, 3H), 0.88 (t, J =6.7 Hz, 3H). 13C-NMR (101 MHz,
Acetone) δ 195.72, 137.51, 132.96, 126.50, 123.37, 122.53,
122.15, 117.90, 112.25, 39.62, 32.19, 25.63, 22.94, 13.99.
9IC3a: White solid, 91% yield. 1H-NMR (400 MHz,
Acetone) δ 8.38 – 8.30 (m, 1H), 8.22 (d, J = 2.8 Hz, 1H), 7.48
(d, J = 7.0 Hz, 1H), 7.23 – 7.15 (m, 2H), 2.86 (t, J = 7.4 Hz,
2H), 1.72 (d, J = 7.2 Hz, 2H), 1.36 (m, 9H), 0.88 (d, J = 6.6
Hz, 3H). 13C-NMR (101 MHz, Acetone) δ 196.12, 137.87,
133.35, 133.18, 126.85, 123.72, 122.87, 122.51, 118.23,
112.62, 39.93, 32.43, 25.68, 23.26, 14.29.
10IC3a: White solid, 81% yield. 1H-NMR (400 MHz, CDCl3)
δ 8.66 (s, 1H), 8.44 – 8.37 (m, 1H), 7.88 (d, J = 2.9 Hz, 1H),
7.48 – 7.37 (m, 1H), 7.29 (m, 2H), 2.92 – 2.81 (m, 2H), 1.77
(dd, J = 14.9, 7.4 Hz, 2H), 1.27 (m, 12H), 0.87 (s, 3H). 13C-
NMR (101 MHz, CDCl3) δ 196.61, 136.27, 130.75, 125.52,
123.65, 122.60, 122.55, 118.32, 111.22, 40.04, 31.89, 29.58,
29.31, 25.19, 22.67, 14.12.
Supporting Information.
For all compounds: synthesis procedures, 1H-NMR, 13C-NMR and
MS. Procedures for the bioassays and additional data.
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