Table 2 Structure of CBD analogs and summary of effect of modification to different positions on antimicrobial activity against MRSA and N. gonnorrhoeae (MIC, μg mL−1, n = 4).
# | Compound name | Core Scaffold | R1 | R2 | R3 | R4 | R5 | S. aureus MRSA ATCC 43300 | N. gonorrhoeae ATCC 19424 |
|---|---|---|---|---|---|---|---|---|---|
Control: Vancomycin | 1 | nd | |||||||
Control: Colistin | nd | 32 | |||||||
Control: Daptomycin | 1–2 | >64 | |||||||
Control: Clindamycin | >64 | 1 | |||||||
Control: Mupirocin | 0.125–0.5 | ≤0.03–0.06 | |||||||
1 | Cannabidiol | A | nPr | H | OH | OH | Me | 1–2 | 0.125–2 |
2 | 7-hydroxycannabidiol | A | nPr | H | OH | OH | CH2OH | 16 | 0.25–2 |
3 | MTC-005 | A | nPr | H | OH | OH | CH2OMe | 16 | 4–16 |
4 | 7-nor-7-carboxycannabidiol | A | nPr | H | OH | OH | CO2H | 64–>64 | 0.5–2 |
5 | MTC-002 | A | nPr | H | OH | OH | CONHMe | 16 | 2–4 |
6 | Cannabidivarin | A | Me | H | OH | OH | Me | 2–4 | ≤0.03–0.5 |
7 | 7-nor-7-hydroxymethyl-cannabidivarin | A | Me | H | OH | OH | CH2OH | 64 | >64 |
8 | 7-nor-7-carboxy-cannabidivarin | A | Me | H | OH | OH | CO2H | >64 | 2–16 |
9 | MTC-007 | A | nPent | H | OH | OH | Me | 0.5–2 | 0.5–4 |
10 | MTC-017 | A | (CH2)2Ph | H | OH | OH | Me | 2 | 0.5–4 |
11 | MTC-011 | A | nPr | H | H | OH | Me | 64–>64 | 1–8 |
12 | MTC-012 | A | nPr | H | OMe | OH | Me | >64 | 8–32 |
13 | MTC-013 | A | nPr | H | OMe | OMe | Me | >64 | >64 |
14 | Cannabidiolic acid (CBDA) | A | nPr | CO2H | OH | OH | Me | 16–32 | 1–2 |
15 | MTC-018 | B | nPent | – | – | – | – | 1–2 | 1–2 |
16 | MTC-008 | B | (CH2)2Ph | – | – | – | – | 2–4 | 1–4 |
17 | MTC-014 | C | – | – | – | – | – | 0.25–0.5 | 0.25–0.5 |
18 | MTC-009 | D | – | – | – | – | – | 1–2 | 0.5–2 |
19 | Tetrahydrocannabivarin (THCV) | E | Me | H | – | – | – | 64 | 16 |
20 | Tetrahydrocannabivarinic acid (THCVA) | E | Me | CO2H | – | – | – | 32–64 | 4–16 |
21 | (−)-Δ9-THC | E | nPr | H | – | – | – | 4–8 | 4–8 |
22 | Δ9-tetrahydrocannabinolic acid A (THCA-A) | E | nPr | CO2H | – | – | – | 8 | 0.5–8 |
23 | (−)-Δ8-THC | F | – | – | – | – | – | 4–8 | 2–4 |
24 | Cannabinolic acid A (CBNA) | G | – | – | – | – | – | 4–16 | 0.25–4 |
25 | Cannabigerol (CBG) | H | – | H | – | – | – | 4–8 | 1–2 |
26 | Cannabigerolic acid (CBGA) | H | – | CO2H | – | – | – | 2–4 | 1–2 |
