Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains
Abstract
:1. Introduction
- A, a diazo function was added in the ortho position, to explore the chemical space near the phenolic group and keep the OH function unsubstituted (1–7, Table 1);
- B, the phenolic group of the EU was alkylated (8–14) or incorporated into a carbamate (16–18) or ester (19 and 20, Table 1) moiety;
- C, the allylic portion of the EU was replaced by a differently substituted tail, including an epoxide ring (21, Table 1), or alcohol chains (22) containing a chalcogen (23–30).
2. Results and Discussion
2.1. Chemistry
2.2. In Vitro Antibacterial Activity Studies against H. pylori
3. Materials and Methods
3.1. Chemistry
Procedure and Characterization Data for Derivatives 1–30
- General Procedure for the Synthesis of Compounds 1–7
- (E)-4-allyl-2-methoxy-6-(p-tolyldiazenyl)phenol (1)
- (E)-4-allyl-2-methoxy-6-[(4-methoxyphenyl)diazenyl]phenol (2)
- (E)-4-[(5-allyl-2-hydroxy-3-methoxyphenyl)diazenyl]benzonitrile (3)
- (E)-4-allyl-2-((4-bromophenyl)diazenyl)-6-methoxyphenol (4)
- (E)-4-allyl-2-[(3-chlorophenyl)diazenyl]-6-methoxyphenol (5)
- (E)-4-allyl-2-[(3,4-dichlorophenyl)diazenyl]-6-methoxyphenol (6)
- (E)-4-allyl-2-[(2-chlorophenyl)diazenyl]-6-methoxyphenol (7)
- General procedure for the synthesis of 8 and 9
- 4-Allyl-1,2-dimethoxybenzene (8)
- 4-Allyl-2-methoxy-1-(prop-2-yn-1-yloxy)benzene (9)
- Synthesis of 2-[(4-allyl-2-methoxyphenoxy)methyl]oxirane (10)
- Synthesis of 2-(4-allyl-2-methoxyphenoxy)ethanol (11)
- General procedure for the synthesis of alcohols 12–14
- 2-(4-Allyl-2-methoxyphenoxy)-1-phenylethanol (12)
- 1-(4-Allyl-2-methoxyphenoxy)-3-phenylpropan-2-ol (13)
- 1-(4-Allyl-2-methoxyphenoxy)-3-phenoxypropan-2-ol (14)
- Synthesis of 1,5-bis(4-allyl-2-methoxyphenoxy)pentane (15)
- General procedure for the synthesis of carbamates 16–18
- 4-Allyl-2-methoxyphenyl phenylcarbamate (16)
- 4-Allyl-2-methoxyphenyl benzylcarbamate (17)
- 4-Allyl-2-methoxyphenyl (4-chlorophenyl)carbamate (18)
- Synthesis of 4-allyl-2-methoxyphenyl acetate (19)
- Synthesis of 4-allyl-2-methoxyphenyl adamantane-1-carboxylate (20)
- General Procedure for the synthesis of β-phenylcalcogeno alcohols 23–25
- Synthesis of 4-[2-hydroxy-3-(phenylthio)propyl]-2-methoxyphenol (23)
- Synthesis of 4-[2-hydroxy-3-(phenylselanyl)propyl]-2-methoxyphenol (24)
- Synthesis of 4-[2-hydroxy-3-(phenyltellanyl)propyl]-2-methoxyphenol (25)
- Synthesis of 4-[2-hydroxy-3-(pentylthio)propyl]-2-methoxyphenol (26)
- Synthesis of 4-[3-(butylselanyl)-2-hydroxypropyl]-2-methoxyphenol (27)
- Synthesis of 4,4′-[selenobis(2-hydroxypropane-3,1-diyl)]bis(2-methoxyphenol) (28)
3.2. Anti-H. pylori Activity Testing
3.3. In Silico Studies
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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MIC/MBC (µg/mL) on H. pylori Strains * | MIC50/MIC90 µg/mL | MBC90 µg/mL | ||||||
---|---|---|---|---|---|---|---|---|
Series | CPD | R | NCTC 11637 ** | F1 *** | 23 *** | F40/499 *** | ||
A | 1 | 64/128 | 64/128 | 64/128 | 128/128 | 64/128 | 128 | |
2 | 32/64 | 32/64 | 32/32 | 32/64 | 32/32 | 64 | ||
3 | >128/>128 | >128/>128 | >128/>128 | >128/>128 | >128/>128 | >128 | ||
4 | 128/128 | 128/128 | 128/128 | 128/128 | 128/128 | 128 | ||
5 | 8/8 | 8/8 | 16/16 | 8/8 | 8/16 | 16 | ||
6 | 128/>128 | 128/128 | 128/>128 | 128/128 | 128/>128 | >128 | ||
7 | 8/8 | 8/8 | 16/16 | 8/8 | 8/16 | 16 | ||
B | 8 | 64/64 | 64/128 | 128/128 | 128/128 | 64/128 | 128 | |
9 | 32/64 | 32/32 | 32/32 | 64/64 | 32/64 | 64 | ||
10 | 32/32 | 32/32 | 32/64 | 32/64 | 32/32 | 64 | ||
11 | 64/64 | 32/32 | 64/64 | 32/32 | 32/64 | 64 | ||
12 | 8/8 | 8/8 | 8/8 | 8/8 | 8/8 | 8 | ||
13 | 16/32 | 8/8 | 16/16 | 8/8 | 8/16 | 32 | ||
14 | 16/32 | 8/8 | 16/16 | 8/8 | 8/16 | 32 | ||
15 | 128/128 | 32/64 | 128/128 | 32/64 | 32/128 | 128 | ||
16 | 16/16 | 16/32 | 32/32 | 16/16 | 16/32 | 32 | ||
17 | 8/16 | 8/8 | 8/8 | 8/8 | 8/8 | 16 | ||
18 | 16/32 | 16/16 | 16/16 | 8/8 | 16/16 | 32 | ||
19 | 64/64 | 64/64 | 128/128 | 64/128 | 64/128 | 128 | ||
20 | 32/64 | 32/64 | 64/64 | 32/32 | 32/64 | 64 | ||
C | 21 | 64/128 | 64/64 | 128/>128 | 32/32 | 64/128 | >128 | |
22 | 128/128 | 64/64 | 128/128 | 64/64 | 64/128 | 128 | ||
23 | 8/8 | 8/8 | 8/8 | 8/8 | 8/8 | 8 | ||
24 | 8/16 | 8/8 | 4/8 | 2/2 | 4/8 | 16 | ||
25 | 16/16 | 4/8 | 4/8 | 4/4 | 4/16 | 16 | ||
26 | 16/16 | 8/8 | 8/16 | 8/8 | 8/16 | 16 | ||
27 | 16/32 | 16/16 | 16/16 | 16/16 | 16/16 | 32 | ||
28 | 64/64 | 32/32 | 32/64 | 16/16 | 32/64 | 64 | ||
29 | 4/4 | 4/4 | 2/4 | 2/2 | 2/4 | 4 | ||
30 | 16/16 | 4/8 | 4/8 | 4/4 | 4/16 | 16 | ||
EU Parent compound | 32/64 | 64/128 | 64/64 | 64/128 | 64/128 | 128 | ||
Metronidazole (MTZ) | 256/256 | 2/2 | 1/1 | 32/32 | 2/256 | 256 | ||
Clarithromycin (CLR) | 0.064/0.064 | 4/8 | 0.064/0.064 | 8/8 | 0.064/8 | 8 | ||
Amoxicillin (AMX) | 0.016/0.016 | 0.064/0.064 | 0.016/0.016 | 0.016/0.032 | 0.016/0.064 | 0.064 | ||
Antibiotic susceptibility | MTZ+ CLR− AMX− | MTZ− CLR+ AMX− | MTZ− CLR− AMX− | MTZ+ CLR+ AMX− |
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Carradori, S.; Ammazzalorso, A.; Niccolai, S.; Tanini, D.; D’Agostino, I.; Melfi, F.; Capperucci, A.; Grande, R.; Sisto, F. Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains. Pharmaceuticals 2023, 16, 1317. https://doi.org/10.3390/ph16091317
Carradori S, Ammazzalorso A, Niccolai S, Tanini D, D’Agostino I, Melfi F, Capperucci A, Grande R, Sisto F. Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains. Pharmaceuticals. 2023; 16(9):1317. https://doi.org/10.3390/ph16091317
Chicago/Turabian StyleCarradori, Simone, Alessandra Ammazzalorso, Sofia Niccolai, Damiano Tanini, Ilaria D’Agostino, Francesco Melfi, Antonella Capperucci, Rossella Grande, and Francesca Sisto. 2023. "Nature-Inspired Compounds: Synthesis and Antibacterial Susceptibility Testing of Eugenol Derivatives against H. pylori Strains" Pharmaceuticals 16, no. 9: 1317. https://doi.org/10.3390/ph16091317