Table 3.
Synthesis matrix of articles collected in a literature review that report the antibacterial potential of synthetic Chalcones and derivatives against S. aureus
| Chalcone | Type | Synthesis technique | S. aureus strain (s) | MIC/Inhibition Zone | Activity | Quote |
|---|---|---|---|---|---|---|
| (E)-1-(2-hydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)prop-2-en-1-one | Synthetic | – | 1199B |
↓ 50% of the MIC of the antibiotic (128 μg/mL to 64 μg/mL); |
Antibacterial; Synergism with the antibiotic Norfloxacin Inactive as a NorA inhibitor |
Rocha et al. (2021) |
| (E)-1-(2-hydroxyphenyl)-3-(2,4-dimethoxy-3-methylphenyl)prop-2-en-1-one | Synthetic | – | K2068 | ↓ 60.3% of the MIC of BrEt (32 μg/mL to 12.6992 μg/mL) | Inactive for direct antibacterial activity. Synergism with BrEt and potential MepA efflux pump inhibitor | Rocha et al. (2021) |
| (Z)-4-((bis(2-hydroxyethyl)amino)methyl)-7-((1-(4-methoxyphenyl)-3-oxo-3-(thiazol-2-yl) prop-1-en-2-yl) oxy)-2H-chromen-2-one (5i) | Synthetic | – | MRSA | 0.004 mM |
Antibacterial 6X better than the reference antibiotic Norfloxacin |
Hu et al. (2021) |
| 4-bromo-3'-aminochalcone (5f) | Synthetic | Claisen–Schmidt |
MSSA MRSA |
1.9 μg mL; 7.8 µg mL |
Concentration-dependent antibacterial and antibiofilm | Garcia et al. (2021) |
| Chalcones derived from 2-hydroxyacetophenone (A1-A6) | Synthetic | Claisen–Schmidt | RN4220; K4414; 1199B; K2068 | 1024 μg/mL | Clinically irrelevant antibacterial activity; Potential IBEs | Xavier et al. (2021) |
|
Chalcone derivative DBDCPP-3 |
Synthetic | Claisen–Schmidt | – | Over than 15 mm | Bactericide | Shinde et al. (2021) |
|
(E)-3-(furan-2-yl)-1-(2-hydroxy-3,4,6-trimethoxyphenyl)prop 2-en-1-one (Hitfurfural); (E)-1-(2-hydroxy-3,4-dimethoxyphenyl)-3-(thiophen-2-yl)prop-2-en-1-one (Hithiophene) |
Synthetic | Claisen–Schmidt |
1199B K2068 |
1024 μg/mL |
Clinically irrelevant antibacterial activity; Potential NorA and MepA IBEs |
da Silva et al. (2021) |
| (2E)-3-(4-Methoxyphenyl)-1-{4-[(3-phenyl-1,2,4-oxadiazol-5- yl)methoxy]phenyl}prop-2-en-1-one (6a) | Synthetic | – | – |
3.12 μM 2 × more efficient than the standard drug Ciprofloxacin |
Antibacterial | Ibrahim et al. (2021) |
|
(E)-3-(3-bromo-4-methoxyphenyl)-1-(thiazol-2-yl)prop-2-en-1-one (Zn 4 complex) |
Synthetic | Claisen–Schmidt | MTCC 916 | 18 mm | Antibacterial | Johnson and Yardily (2021) |
| (E)-3-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)prop-2-en1-one (3) | Synthetic | Claisen–Schmidt | 1199B | 1000 μg/mL | Clinically irrelevant antibacterial activity; NorA inhibitory potential | Leal et al. (2021) |
| Polymer chalcone (P3) | Synthetic | Claisen–Schmidt | – | 20 mm | Antibacterial | Solmaz et al. (2021) |
| Hybrid Chalcona (1) | Synthetic | Claisen–Schmidt | NCIM 2122 | 10.05 μM | Low antibacterial activity compared to standard drug Ciprofloxacin | Konidala et al. (2021) |
| Chalcone with imide-Zo portion [1,2-a]pyridine (3b, 3d, 3g, 3l and 3m) | Synthetic | Claisen–Schmidt | – | 32 μg/mL and 64 μg/mL | Antibacterial | Soltani et al. (2021) |
| E4,4'-Bromo-4-methylchalcone | Synthetic | Claisen–Schmidt | MRSA | 16 μg/mL | Antibacterial | Aksöz et al. (2021) |
|
Quinoline chalcone: 1-(4-(benzyl sulfonyl) phenyl)- 2,3dibromo-3-(chloroquinoline-3-yl) propane-1- one (7) |
Synthetic | Claisen–Schmidt | – |
At a concentration of 10 mg/disk: 15 mm |
Low antibacterial activity compared to standard drug | Saleh et al. (2020) |
|
Fluorinated chalcone: (E)-3-(1″H-indol-3″-yl)-1-[40 -(trifluoromethyl)phenyl]prop-2-en-1-one |
Synthetic | Claisen–Schmidt | NCIM-2079 | 51 µM | Low antibacterial activity compared to standard drug | Lagu et al. (2020) |
| (E)-1-(4-aminophenyl)-3-(furan-2-yl)-prop-2-en-1-one (AFPO) | Synthetic | Claisen–Schmidt | 10 | ≥ 1024 μg/mL | Irrelevant | Ferraz et al. (2020) |
| (E)-1-(4-aminophenyl)-3-(furan-2-yl)-prop-2-en-1-one (AFPO) | Synthetic | Claisen–Schmidt | 10 |
AFPO + Gentamicin: ↓ 3X AFPO + Penicillin = ↓ 3X |
Synergism (potentiation of antibiotic activity) | Ferraz et al. (2020) |
| Naphthyl Chalcones (3a -3p) | Synthetic | – | MTCC 96 | 24–162 μg/mL | Low antibacterial activity compared to standard drug | Pola et al. (2020) |
| Heteroaromatic Chalcones Derivatives (1a-and 3a-c) | Synthetic | Claisen–Schmidt | N5923 | 13 and 19 mm | Antibacterial | Farooq and Ngaini (2020) |
| Chalcone derivative (1d) | Synthetic | Claisen–Schmidt | – | 11 mm | Antibacterial | Farooq and Ngaini (2020) |
|
Chalcones source of the natural product 2-hydroxy-3,4,6-trimethoxyacetophenone (1–4) |
Synthetic | Claisen–Schmidt |
10 (Multi-resistant); ATCC 25923; |
≥ 1024 μg/mL; 645 μg/mL |
Irrelevant; Low antibacterial activity and synergism with Ciprofloxacin and Gentamicin |
Freitas et al. (2020) |
|
4'-piperazinyl Chalcone—pleuromutilin (14i; 14k) |
Synthetic | Alcoholic condensation |
MRSA (ATCC 33591); MRSA (ATCC 43300); ATCC 25923 |
0.5–1 μg/mL | Antibacterial | Xie et al. (2020) |
| Sulfonamides Chalcones and derivatives: (IV—XXXII) | Synthetic | – | ATCC 25923 | (> 22)—10 (0.156) mm | Inactive for antibacterial activity | Bonakdar et al. (2020) |
| Ferrocenyl Chalcones (Decyl) | Synthetic | Acquired |
NCIMB 8244 MRSA (RCH) |
0.031 mg mL 0.063 mg mL |
Antibacterial | Henry et al. (2020) |
|
Bichalcones and Bispirazoline derivatives (2ª–2d) (3b–3d) |
Synthetic | Acquired | – |
16–32 μg/mL 8 – 32 μg/mL |
Inactive for antibacterial activity | Nisa and Yusuf (2020) |
|
Pyrimidine derived from Chalcone: 9-(Benzo[d][1,3]dioxol-5-yl)- 7-(thiophen-2-yl)pyrido[30,20:4,5] thieno[3,2-d]pyrimidin-4(3H)-one (24a) |
Synthetic | Acquired | ATCC 6538 | 7.81 μg/mL | Antibacterial | Sanad et al. (2020) |
| Triazine Chalcone: 3k | Synthetic | Claisen–Schmidt | NCIM 2178 | 85 mm | Antibacterial | Shinde et al. (2019) |
|
Aminochalcone derivatives: 1–3; 7–8; 11–13; 16 |
Synthetic | Claisen–Schmidt | DSM799 |
0.25 [mg/mL]; 0.125 [mg/mL]; 0.25 [mg/mL]; 0.5 [mg/mL] |
Antibacterial | Kozłowska et al. (2019) |
|
Chalcones and derivatives (6r, 12a); [6s; 12c] 7j–7m |
Synthetic | Claisen–Schmidt |
MSSA (ATCC 29213); MRSA (USA 300) |
(1.56 − 6.25 μg/mL); [3.125 − 6.25 μg/mL]; 1.56 -12.5 μg/mL |
Antibacterial | Zhang et al. (2018b) |
|
Chalcones bonded to Biscoumarine copolyester 4a; 4b; 4c |
Synthetic | Polycondensation | – |
312.5 μg/mL; 625 μg/mL; 156.2 μg/mL |
Antibacterial | Kandaswamy (2019) |
|
1-(2-bromophenyl) ethanone derivatives I1-I5 |
Synthetic | – | NCIM 2079 | They ranged from 31.25 to 500 μg/mL | Significant Antibacterial | Prasad et al. (2018) |
|
Chalcones derivatives 11; 18 |
Synthetic | Claisen–Schmidt |
NTCC8325-4 MRSA 97-7 |
50 and 70 µg/mL; 50 and 90 µg/mL |
Low antibacterial activity | Vásquez-Martínez et al. (2019) |
|
Chalcones derivatives 18; 11 |
Synthetic | Claisen–Schmidt | MRSA 97-7 |
20 μg/mL; 50 μg/mL |
Synergism with the antibiotic methicillin | Vásquez-Martínez et al. (2019) |
|
Chalcone-pyridine hybrids 5j; 5i; 5b; 5f |
Synthetic | – | MTCC 121 |
3.12 μg/mL; 6.25 μg/mL |
Antibacterial | Gondru et al. (2018) |
|
Pyrimidine-2(1H)-ol/-thiol derivatives derived from Chalcones 20–24; 35–39 |
Synthetic | – | ATCC 25923 | 2.1–138.8 µg/mL | Antibacterial | Fandakli et al. (2018) |
|
Chalcones converted to pyrazoles 4h, 4j, 4l, 4m e 4n |
Synthetic | Claisen–Schmidt | – | They ranged from 3.75 to 1.25 µg/mL | Antibacterial | Chowdary et al. (2019) |
|
Benzoxazepines derived from pyrazol-Chalcones 3c; 3h, 5c, 5g; 5b; 5h |
Synthetic | – | – |
30 mm; 28 mm; 27 mm; 32 mm |
Antibacterial | Ashok et al. (2018) |
|
Indolyl Chalcone Derivatives 4b; 5b; 6b, 7; 11 |
Synthetic | – | – |
27 mm; 22 mm; 24 mm, 28 mm |
Antibacterial | Sayed et al. (2018) |
|
Heterocyclic Chalcones 4b* 4c, 4g, 4k |
Synthetic | Claisen–Schmidt | MTCC 096 |
12.5 µg/mL* 6.25 µg/mL |
Antibacterial | Kaushik et al. (2018) |
|
Pyrazole Chalcones 6b; 6c; 7b e 8b |
Synthetic | Claisen–Schmidt | MTCC9886 | 13 ± 0.44 mm; 17 ± 1.10 mm; 15 ± 0.53 mm; 11 ± 2.01 mm | Moderate antibacterial | Kumari et al. (2018) |
|
Triazole-based Chalcones and its derivatives 3f, 5a, 6a, 7b e 8a |
Synthetic | – | – |
44.59 mM; 50.15 mM; 66.61 mM; 76.63 mM; 53.86 mM |
Antibacterial | Santosh et al. (2018) |
|
Anthracene-based Chalcone derivatives ANNP, ANFL; ANID and ANPT |
Synthetic | Claisen–Schmidt | – |
6.25 µg mL; 3.12 µg mL |
Moderate antibacterial | Prakash et al. (2018) |
|
Chalcones derived from acetylpyridines 4; 5; 11; 12 |
Synthetic | – | – | – | Antibacterial | Santra et al. (2018) |
|
β-Carboline Chalcones and their bromide salts 12b, 12c, 12e, 12f, 12g; 13a; 13h |
Synthetic | – | MTCC 96 | Ranged from 440 to > 900 µM | Inactive for antibacterial activity | Reddy et al. (2018) |
| Chalcone-thiazole hybrids (27) | Synthetic | Claisen–Schmidt | ATCC 33592—Methicillin and Gentamicin Resistant | 1.4 µM | Antibacterial | Sashidhara et al. (2015) |
|
1,3- diphenyl-2-propen-1-ones (III-C) |
Synthetic | – | JMC 2151 | 32 ± 1.5 mm | Antibacterial | Alam et al. (2015) |
| Chalcones derivatives: 3ª–3j | Synthetic | – | ATCC 29213; (MRSA) |
16–256 μg/mL 32–64 μg/mL |
Low antibacterial activity | Evranos-Aksöz et al. (2015) |
| 4.5-dihydropyrazol | Synthetic | – | ATCC 29213 | 10–17 mm | Antibacterial | Budak et al. (2017) |
| 2-(4-Methyl-2-oxo-2H-chromen-7-yloxy)-N-(4-((E)-3- (3,4,5-trimethoxyphenyl)acryloyl)phenyl)acetamide | Synthetic | Claisen–Schmidt | ATTC 6538 | 35.8 µg/mL | Antibacterial | El-Sherief et al. (2017) |
|
(4- (4- aryl)-1H- pyrrol-3-yl)(pyren-1-yl)meth- Anone + (3-chloro) |
Synthetic | - | - | 4.1 μg/mL | Antibacterial | Divakar and Shanmugam (2017) |
| monocarbonyl curcuminoids | Synthetic | - | ATCC 25923 | 250 mg/mL | Antibacterial | Ud Din et al. (2017) |
|
2-(2-Hydroxyphenyl)-5-methyl-3-(4-(thiophen-2-yl)-6-(4- methyl-phenyl)-pyrimidin-2-yl) thiazolidin-4-one; 3-Chloro-4-(4-hydroxy-3-methoxyphenyl)-1-(4-(thiophen-2- yl)-6-(4-methyl-phenyl)-pyrimidin-2-yl)azetidin-2-one |
Synthetic | Claisen–Schmidt | – | 100 μg mL | Antibacterial | Patel et al. (2017) |
|
(2E,20 E)-3,30 -(3,30 -(butane-1,4-diylbis(oxy))bis(3,1- phenylene))bis(1-(thiophen-2-yl)prop-2-en-1-one) (2E,20 E)-3,30 -(3,30 -(pentane-1,5-diylbis(oxy))bis(3,1- phenylene))bis(1-(thiophen-2-yl)prop-2-en-1-one) |
Synthetic | Claisen–Schmidt | MTCC 96 | 8 μg/mL | Antibacterial | Yusuf et al. (2017) |
| Chalcones derived from Pyrimidines | Synthetic | – | – | 9–14 mm | Antibacterial | Kumar et al. (2017b) |
| Phenylpropenone pyrrolyl Chalcone | Synthetic | – | – | 6–11 mm | Antibacterial | Kumar et al. (2017a) |
| Chalcones with a triazine nucleus (P1–P3, P5, P6, S6) | Synthetic | – | MTCC 96 | 7–13 mm | Antibacterial | Mahmoodi et al. (2017) |
| Derivatives of (3ar,4S,7R,7as)-2-(4-((E)-3-(3- aryl)acryloyl) phenyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole1,3(2H)-dione (7e, 7l, 7m and 7n) | Synthetic | Claisen–Schmidt | ATCC 29213 | 14 mm | Antibacterial | Kocyigit et al. (2017) |
| (2E)-3-(2,6- dichlorophenyl)-1-(4-methoxyphenyl) prop-2-en-1-one | Synthetic | – | – | 50 mg/mL | Antibacterial | Sadgir et al. (2020) |
| Chalcones derived from Pyrazoline | Synthetic | – | – | 12.5–25 µg/ml | Antibacterial | Desai and Sastry (2017) |
| 6,6-dimethyl3-aryl-3′,4′,6,7-tetrahydro-1′H,3H-spiro[benzofuran-2,2′-naphthalene]-1′,4(5H)- dione (5a) | Synthetic | Claisen–Schmidt | ATCC 29213 | 16 mm | Antibacterial | Ergüntürk et al. (2017) |
| 2-Pyrazoline (5f) | Synthetic | Claisen–Schmidt | MTCC 737 | 10 mg/mL | Antibacterial | Lokeshwari et al. (2017) |
|
2-bromo-4-[3-(2-hydroxyphenyl)-4,5-dihydro-1h-pyrazol-5-yl]-6-methoxyphenol 1-[5-(3-bromo-4-hydroxy-5-methoxyphenyl)-3-(2-hydrophenyl]-4,5-dihydro-1H-pyrazol-1-yl)ethanone |
Synthetic | – | FNCC 0047 | 7.25 mm | Antibacterial | Setyawati et al. (2017) |
|
Cis-3-4-dihydrohamacanthin B; Bromodeoxytopsentin |
Synthetic | – | RN4220; MRSA 252; ATCC 29213 | 12.5 µg/mL; 6.25 µg/mL | Antibacterial | Labrière et al. (2017) |
|
(2E,2′E)-3,3′-(octane-1,8-diylbis(oxy))bis(3,1- phenylene))bis(1-phenylprop-2-ene-1-one) 1,12-bis(3-(1,3-diphenyl-4,5-dihydro-1H-pyrazol5-yl)phenoxy)dodecane |
Synthetic | Claisen–Schmidt | MTCC 96 | 8 μg/mL | Antibacterial | Yusuf et al. (2017) |
|
Jaceosidin; 5,7,4′-triacetoxy jaceosidin |
Synthetic | – |
ATCC 43,300, VRS 10, NRS 17 NRS 1 |
32–128 µg/mL | Antibacterial | Kumar et al. (2016) |
| 3′-formyl-2′,4′,6′-trihydroxydihydrochalcone | Synthetic | – |
ATCC 29,213 MRSA 33,591 |
17.4 μM 36.6 μM |
Antibacterial | Zaki et al. (2016) |
| Quinoline scaffold (3b, 3d, 3g, 3h–j) | Synthetic | Claisen–Schmidt | - | 200 µg/mL | Antibacterial | Dave and Rahatgaonkar (2016) |
| Ferrocenyl chalcones with O-alkylated vanillins | Synthetic | Claisen–Schmidt | ATCC 25923 | 0.625–5 µg/mL | Antibacterial | Muškinja et al. (2016) |
| Complex Chalcones (3e, 3l) | Synthetic | – | ATCC 43300 | 21.8% Redução de crescimento | Antibacterial | Patil et al. (2016) |
|
(E)-3-{5-[(2-Benzoylbenzofuran-5-yl)methyl]-2- hydroxyphenyl}-1-(3,4-dichlorophenyl)prop-2-en-1- one; {5-[3-(8-Fluoro-4-phenyl-2,3-dihydro-1H-benzo- [b][1,4]diazepin-2-yl)-4-hydroxybenzyl]benzofuran2-yl}(phenyl)methanone |
Synthetic | Claisen–Schmidt | – |
55 µg/mL 34 µg/mL |
Antibacterial | SHankar et al. (2016) |
|
(4-Bromo-6,7-dimethoxy-1,1-dioxido-3,4-dihydro-2H-benzo[e][1,2]thiazin-3-yl)(3-chlorophenyl)methanone (4-Bromo-6,7-dimethoxy-1,1-dioxido-3,4-dihydro-2H-benzo[e][1,2]thiazin-3-yl)(3-bromophenyl)methanone (4-Bromo-2-ethyl-6,7-dimethoxy-1,1-dioxido-3,4-dihydro-2H-benzo[e][1,2]thiazin-3-yl)(3-bromophenyl)methanone |
Synthetic | – | ATCC 6538 | 200–400 µg/mL | No significant antibacterial activity | Patel et al. (2016) |
|
Carbazole-based Chalcones (3a, 3h, 3i, 4a, 4h, 4i, 5a, 5h, 5i) |
Synthetic | Claisen–Schmidt | ATCC 6538 | 20 µg/mL | Antibacterial | Ashok et al. (2016) |
| Glabridin-chalcone hybrid molecules (6h, 7e, 8f) | Synthetic | Claisen–Schmidt |
MTCC-96 MRSA-ST 2071 |
12,5 µg/mL | Antibacterial | Kapkoti et al. (2016) |
| Chalcones derived from 1,3-diaryl pyrazole (6g, 6l and 7l) | Synthetic | – | 4220 | 1–64 μg/mL | Antibacterial | Killeen et al. (2016) |
| Chalcones Derivatives (4ª, 4f) | Synthetic | Claisen–Schmidt | 4220, 209 and 503 | 2 μg/mL | Antibacterial | Wei et al. (2016) |
|
1-[7-(diethylamino)-2H-chromen-2on]-3-(p-chlorophenyl)-2-propen-1-one one; 1-[7-(diethylamino)-2H-chromen-2on]-3-(p-fluorophenyl)-2-propen-1-one |
Synthetic | Claisen–Schmidt | – | 100 µg/mL | Antibacterial | Himangini and Pathak (2016) |
| 4,5-Dihydro-3-(1-benzyl-1H-indol-3-yl)-5-(naphthalene-2-yl) isoxazole | Synthetic | Claisen–Schmidt | RCMB 010028 | 23.4 mm | Antibacterial | Abo-Salem et al. (2016) |
| 1,3-thiazine compounds with a Schiff base portion (5a-5e) | Synthetic | Claisen–Schmidt | – | 09–15 mm | Antibacterial | Babu et al. (2015) |
| 2,8- bis(2,4-Dichlorophenyl)-4H,6H-pyrano[3,2-g]chromene-4,6-dione | Synthetic | Claisen–Schmidt | ATCC 29737 | 12.5 µg/mL | Antibacterial | Husain et al. (2015) |
| 2-Chloro-N-{4-[3-(substitutedphenyl)-acryloyl]-phenyl}-acetamide | Synthetic | Claisen–Schmidt | – | 9 mm | Antibacterial | Jayaramu and Maralihallia (2015) |
| 3-(4′-N,N-dimethyl amino phenyl)-5-(2″, 2″-dimethyl, 7″-hydroxy chroman) isoxazole/3-(3′,4′-chloro-phenyl)-5-(2″, 2″-dimethyl, 7″-hydroxy chroman) isoxazole/3-(4′-methoxy-phenyl)-5-(2″, 2″-dimethyl, 7″-hydroxy chroman) isoxazole/3-(4′-cyano phenyl)-5-(2″, 2″-dimethyl, 7″-hydroxy chroman) isoxazole | Synthetic | Claisen–Schmidt | MTCC 96 | 5–20 µg/mL | Antibacterial | Raju et al. (2015) |
| trans-3-(1H-indol-3-yl)-1-(40-benzyloxyphenyl)-2-propen-1-one (2), 1-(400-biphenyl)-3-(30 40-dihydroxyphenyl)-2-propen-1-one (11), 1-(400-hydroxy-300-methylphenyl)-3-(40 -hydroxyphenyl)-2-propen-1-one (14), 3-(40 -chlorophenyl)-1-(400-hydroxyphenyl)-2-propen-1-one (17), LTG-oxime | Synthetic | Claisen–Schmidt |
ATCC 96 MRSA |
12.5–50 mg mL | Antibacterial | Gaur et al. (2015) |
| 6H-benzo[c]chromen-6-ones and Diazepines (10a,b) | Synthetic | Claisen–Schmidt | ATCC 9144 | 0.625 μg/mL | Antibacterial | Mazimba (2015) |
| Chalcone |
Synthetic acquired |
– |
USA 300; USA 300 ΔSRTA |
53.15 μM 76 μM |
Antibacterial and anti-biofilm | Zhang et al. (2017) |
| Apchal and Achlopheny | Synthetic | Claisen–Schmidt | ATCC 25923, 10, 1199B, K2068 | 70% synergism of gentamicin when associated with Apchal and loss of synergism when associated with Aclo-phenyl | Antibacterial. Synergism and antagonism were observed | Siqueira et al. (2020) |
| Apchal and Achlophenyl | Synthetic | Claisen–Schmidt | SA-1199B; K2068 | Synergism with Norfloxacin and ciprofloxacin; synergism with ciprofloxacin and ethidium bromide | Efflux pump inhibitor | Siqueira et al. (2020) |
| 1,3- Bis-(2-hydroxy-phenyl)-propenone, 3-(3-hydroxy-phenyl)-1-(2-hydroxy-phenyl)-propenone e 3-(4-hydroxy-phenyl)-1-(2-hydroxy-phenyl)-propenone | Synthetic | – | MRSA ATCC 43,300, MRSA CC5, CC8, CC45, CC80, CC152 | 37.5 ± 13.2 μg/mL; 97.5 ± 27.5 μg/mL; 110.8 ± 21.1 μg/mL | Antibacterial | Božić et al. (2015) |
| Chalcones and derivatives (6s e12a) | Synthetic | Claisen–Schmidt | Newman (MSSA); MN8 (MRSA); NRS70 (MRSA) |
3.12 μg/mL; 6.25 μg/mL: 0.8 μg/mL |
Antibacterial, anti-biofilm | Zhang et al. (2018a, b) |
| (E)-N-(3-Aminopropyl)-2-(5-((3-methylbut-2-en-1-yl)oxy)-2-(3-(4-((3-methylbut-2-e n-1-yl)oxy)phenyl)acryloyl)phenoxy)acetamide | Synthetic | – | ATCC29213, MRSA N315, MRSA NCTC10442 | 1.56–3.13 μg/mL | Antibacterial | Lin et al. (2020) |
| Thiazolyl-pyrazoline derivatives (7 a) | Synthetic | Claisen–Schmidt | MSSA (ATCC 25,923), MRSA (ATCC 43,300), VISA |
62.5 µg/mL; 125 µg/mL; 31.5 µg/mL; |
Antibacterial | Cuartas et al. (2020) |
| Derivatives of benzo[4,5]isothiazolo[2,3-a]pyrazine-6,6-dioxide | Synthetic | – | ATCC 6538 | > 1600 µg/mL | Inactive for antibacterial activity | Bassin et al. (2017) |
| Derivatives of 2′,6′-dihydroxy-4′-methoxy-3′,5′-dimethyl chalcone (10) | Synthetic | – | ATCC 43,300, Clinical isolate, VRS 10, NRS 17, NRS 1 |
> 128 µg/mL 64 µg/mL 32 µg/mL |
Antibacterial | Kumar et al. (2016) |
| Derivatives of (E)-3-(4-bromophenyl)-1-(p-tolyl) prop-2-en-1-one (3a, 3e, 3j) | Synthetic | – | ATCC 29,737 |
25.4 mm 27.2 mm 26.4 mm |
Antibacterial | Bhirud et al. (2020) |
| 7,4′-dihydroxy-8,3′-diprenylflavone and erysubin F | Synthetic | Claisen–Schmidt |
MRSA, ATCC 43,300 |
15.4 μM 20.5 μM |
Antibacterial | Kwesiga et al. (2020) |
| (2Z)-3-(3-nitrophenyl)-1-{4-[(E)-(piperidin-1-yl)diazenyl]phenyl}prop-2-en-1-one | Synthetic | Claisen–Schmidt | ATCC 12,598 | 12.5 g/mL | Antibacterial | Sivasankerreddy et al. (2018) |
| Xanthohumol, naringenin, and chalconaringenin | Synthetic | – | PCM 2054 |
3.57 mm 3.77 mm 1.92 mm |
Antibacterial | Stompor and Zarowska (2016) |
|
2′-Hydroxychalcone; 2 0-Hydroxy-2-methoxychalcone; 2 0-Hydroxy-4-methoxychalcone; 2 0-Hydroxy-40 -methoxychalcone-3-yl)(3-bromophenyl)methanone |
Synthetic | Claisen–Schmidt | D1 |
0.26 ± 0.09, 0 ± 0.03, 0.88 ± 0.10 0 ± 0.04 |
Antibacterial | Gładkowski et al. (2019) |
|
4-Hydroxyphenyl 3-Hydroxyphenyl |
Synthetic | Claisen–Schmidt | – |
5 µg/mL 10 µg/mL |
Antibacterial | Desai et al. (2017) |
| Aryl substituted dihydrotriazine derivatives (17h) | Synthetic | – |
4220 QRSA CCARM 3505 |
0.5 µg/mL | Antibacterial | Zhang et al. (2018a) |
| Derivatives of 1,2,3-triazoles (25) | Synthetic | Claisen–Schmidt | – | MIC decrease in 55% | Antibacterial | Syed-Aly et al. (2015) |
|
Derivatives of (2-(Pyridinyl)methylene)-1-tetralone Chalcones (5h) |
Synthetic | – | MRSA | Decrease of 75% | Antibacterial | Gibson et al. (2017) |
|
(E)-N-(4-(3-(4-Chlorophenyl)acryloyl)phenyl)-3-(piperidin-1-yl)propanamide, (E)-N-(4-(3-(4-Methoxyphenyl)acryloyl)phenyl)-3-(piperidin-1-yl)propanamide, (E)-3-(Piperidin-1-yl)-N-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenyl)propanamide |
Synthetic | – | IFO 3060 |
2.0 mg/mL 2.4–8.6 mg/mL |
Antibacterial and anti-biofilm | El-Messery et al. (2018) |
|
(2E)-3-(4-{[1-(2-chloro-4-fluorophenyl)-1H-1,2,3-triazol-4-yl]methoxy}-3- methoxyphenyl)-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, (2E)-3-(4-{[1-(2,4-difluorophenyl)-1H-1,2,3-triazol-4-yl]methoxy}-3-methoxyphenyl)-1- (2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, (2E)-3-(4-{[1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl]methoxy}-3-methoxyphenyl)-1-(2- hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, (2E)-3-[3,4-bis({[1-(2,4-difluorophenyl)-1H-1,2,3-triazol-4-yl]methoxy})phenyl]-1-(2- hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one, 2-[3,4-bis({[1-(4-chlorophenyl)-1H-1,2,3-triazol-4-yl]methoxy})phenyl]-5,7-dimethoxy4H-chromen-4-one |
Synthetic | – | ATCC 25323 |
6.25 µg/mL 12.5 µg/mL |
Antibacterial | Kant et al. (2016) |
| 4′-hydroxy-4-methyl chalcone | Synthetic | – | ATCC 29213 | 32 μg/mL | Antibacterial | Evranos-Aksöz et al. (2015) |
| Asymmetric heterocyclic chalcone derivatives and heterocyclic compounds (4, 6, 7, 9) | Synthetic | – | ATCC 25923 | 65–95% of zone of inhibition | Antibacterial | El-Hashash et al. (2015) |
| Derivatives of 3-hydroxy-6-(hydroxymethyl)-2-(2-phenyl-4H-chromen-4-yl)-4H-pyran-4-ones (3a, 3e, 3f e 3 l) | Synthetic | – |
MLS-16 MTCC 2940 |
7.8–15.6 µg/mL | Antibacterial | Bingi et al. (2015) |
| Chalcona derivative: (4[(1E)-3-(pentyloxy)buta-1,3- dien-1-yl]benzene-1,2-diol | Synthetic | Claisen–Schmidt |
ATCC 2592 (MRSA) ATCC 33591 |
0.12 μM | Antibacterial and antibiofilm | Emeri et al. (2019) |
| N-(5a-chloro, 8a-triflouromethyl)-benzyl-N, 1a-dihydro-2H-O, N-isoliquiritigeninoxazine (IMRG4) |
Synthetic Derived from the natural Chalcone Isoliquiritigenin (ISL) |
– | SA-29213; SA-1199;SA-1199B*; SA-K1758; MRSA-P4423; MRSA-P4627; MRSA-P4620; MRSA-B10760; MRSA-ST315; VISA-ST207; VISA-ST1745 | 50 (mg/L); 25(mg/L); 50(mg/L); 25 (mg/L); 50(mg/L); 25(mg/L); 25 (mg/L); 50(mg/L); 25(mg/L); 50 (mg/L); 50(mg/L) |
Antibacterial *NorA efflux pump inhibitor |
Gupta et al. (2019) |
|
(2E)-1-(3′, -methoxy-4′,-hydroxyphenyl)-3-(3-nitrophenyl) prop-2-en1-one (AVMNB) |
Synthetic | Claisen–Schmidt |
ATCC 25923; 10 |
≤ 512 mg/mL | Antibacterial | Garcia et al. (2020) |
|
(2E)-1-(3′, -methoxy-4′,-hydroxyphenyl)-3-(3-nitrophenyl) prop-2-en1-one (AVMNB) |
Synthetic | Claisen–Schmidt |
ATCC 25923; 10 |
MIC↑ | Antagonistic with Cephalexin and Gentamicin antibiotics | Garcia et al. (2020) |
|
2E-1-(2ʹ-hidroxi-3ʹ,4ʹ,6ʹ-trimetoxifenil)-3-(fenil)-prop-2-en-1-ona (HYTPHENYL) |
Synthetic Derived from the natural compound: 2-hydroxy-3,4,6-trimethoxyacetophenone |
Claisen–Schmidt | 358 |
1024 µg/L MIC↓ |
Inactive for antibacterial activity Antibiotic modulator: Synergism with the antibiotic Amikacin |
Teixeira et al. (2019) |
|
(E)-3-(2-methylpyrimidin-5-yl)-1-ferroceynlprop-2-en-1-one (MPFP) |
Synthetic | Claisen–Schmidt | – |
Concentration of 25 μg: 19 mm Concentration of 50 μg: 24 mm Concentration of 75 μg: 31 mm |
Antibacterial | Twinkle et al. (2020) |
|
Cationic derivatives of Chalcones: 5a; 5s; 5b; 5c; 5d, 5g, 5l, 5p, 5q; 5r; 5z; 5ab |
Synthetic | Claisen–Schmidt |
M1-M9 MRSA |
Ranged from 0.25 –32 µg/mL | Antibacterial and synergism with Norfloxacin and Colistin | (CHU et al., 2018) |
| Cationic molecule 5g | Synthetic | Claisen–Schmidt | ATCC29213 | 128 µg/mL | Anti-biofilm | (CHU et al., 2018) |
|
Chalcones derivatives: (E)-2-(4-acetamidophenoxy)-N-(3-(3-(4-methoxyphenyl) acryloyl)phenyl)acetamide (5e); (E)-2-(4-acetamidophenoxy)-N-(3-(3-(4-chlorophenyl)acryloyl) phenyl)acetamide (5b) |
Synthetic | – | – |
Concentration of 100 μg/mL: 9; 10 mm Concentration of 200 μg/mL: 15 mm; 13 mm |
Antibacterial | Babu and Selvaraju (2020) |
|
Chalcones-Sulfonamides 5/6, 8a-f and 9a-f (N = 12 derivatives) |
Synthetic | Claisen–Schmidt | Resistant clinical isolates | > 57 mcM | Inactive for antibacterial activity | Castaño et al. (2019) |
| Thiazole-based Chalcone (Derivative): Compound 18 | Synthetic | – | IFO 3060 | 1 μg/mL | Antibacterial | Alrohily et al. (2019) |
|
Ferrocenyl Chalcone Derivatives: Zn (II) (H1; H5) |
Synthetic | – | ATCC 9144 |
1.349 × 10–8 M/mL 1.268 × 10–7 M/mL |
Significant antibacterial | Liu et al. (2019) |
|
Derivative: (E)-1-(4-brom ophenyl)-3-(4-iodophenyl)prop-2-en-1-one |
Synthetic | Synthesized and characterized using XRD, FT-IR1 H and 13 C NMR | ATCC 12600 | 250 μg/mL | Antibacterial | Zainuri et al. (2017) |
|
Ferrocenyl Chalcone Derivatives: 3a2,3a7 e 3b6 |
Synthetic | – | MRSA, ATCC 43300 |
Concentração de 3 g/L: 11–22 mm |
Antibacterial | Liu et al. (2018) |
|
Chalcones derivatives: 4a; 4e; 4h |
Synthetic | Claisen–Schmidt | ATCC-9144 |
08 µg/mL 08 µg/mL 04 µg/mL |
Antibacterial | Gopi et al. (2016) |
| (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one | Synthetic | Claisen–Schmidt | ATCC 12600 | 500 µg/mL | Antibacterial | Thanigaimani et al. (2015) |
| Derivatives if indolyl-4H-chromene-phenylprop-2-en-1-one (5g; 5h) | Synthetic | Claisen–Schmidt | ATCC 700699 | 9.3 µg/mL | Antibacterial | Subbareddy et al. (2018) |
| Chalcone derivative: 1-hydroxynaphth-2-yl pyrazoline (6b) | Synthetic | Claisen–Schmidt | – | 3.9 µg/mL | Antibacterial | El-Desoky et al, (2018) |
| Chalcone derivative: Pyrazoles (5j; 5h) | Synthetic | Claisen–Schmidt | MTCC 3160 | 6.5 µg/mL | Antibacterial | Mishra et al. (2017) |
|
Derivative of Chalcone (4-bromophenyl)-1-(4-chlorophenyl)prop-2-en-1-one (I): 4-[(E){[4-(4-bromophenyl)-6-(4-chlorophenyl)pyrimidin-2-yl]imino}methyl]benzene-1,3-diol (IJ) |
Synthetic | Claisen–Schmidt | NCIM 2079 | 500 µg/mL | Antibacterial | Prasad et al. (2019) |
| [(Chloroquinolin-4-yl)amino]chalcones 8a–f | Synthetic | Claisen–Schmidt |
ATCC 25923 (MSSA) ATCC 43300 (MRSA) |
> 1000 µg/mL | Inactive for antibacterial activity | Ramírez-Prada et al. (2017) |
| Bichalcones 8 (a–h) | Synthetic | Claisen–Schmidt | – | 16–32 µg/mL | Low antibacterial activity | Yusuf and Solanki (2017) |
a) The spaces filled with (–) mean that the information was absent from the article or was not clear