Correction: Juhás et al. Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole. Pharmaceuticals 2022, 15, 580
by
, , , , , , , , , and
Martin Juhás
1,*
,
Andrea Bachtíková
1,
Daria Elżbieta Nawrot
1,
Paulína Hatoková
1,
Vinod Sukanth Kumar Pallabothula
1,
Adéla Diepoltová
1,
Ondřej Janďourek
1,
Pavel Bárta
1,
Klára Konečná
1,
Pavla Paterová
2,
Vít Šesták
3 and
Jan Zitko
1,*
1
Faculty of Pharmacy in Hradec Králové, Charles University, Akademika Heyrovského 1203, 500 05 Hradec Králové, Czech Republic
2
Department of Clinical Microbiology, University Hospital Hradec Králové, Sokolská 581, 500 05 Hradec Králové, Czech Republic
3
Department of Clinical Biochemistry and Diagnostics, Faculty of Medicine in Hradec Králové, University Hospital, Sokolská 581, 500 05 Hradec Králové, Czech Republic
*
Authors to whom correspondence should be addressed.
Pharmaceuticals 2023, 16(3), 384; https://doi.org/10.3390/ph16030384
Submission received: 13 February 2023
/
Accepted: 21 February 2023
/
Published: 2 March 2023
(This article belongs to the Section Medicinal Chemistry)
In the original publication [1], there was a mistake in assigning individual compounds to their structural subtype in Figure 2 and Table 1. In correction, subtype I comprises compounds 1–10, and subtype II comprises compounds 11–20. Also, for compounds 11–13 in Table 1, we unified the naming of the Ar substituent, using the pyridinyl convention instead of pyridyl (to achieve consistency with the rest of the paper). The corrected Figure 2 and Table 1 appear below. We made the same changes to Table S2 in the Supplementary Material. The authors apologize for any inconvenience caused and state that the scientific conclusions are unaffected. This correction was approved by the academic editor. The original publication has also been updated.
Reference
- Juhás, M.; Bachtíková, A.; Nawrot, D.E.; Hatoková, P.; Pallabothula, V.S.K.; Diepoltová, A.; Janďourek, O.; Bárta, P.; Konečná, K.; Paterová, P.; et al. Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole. Pharmaceuticals 2022, 15, 580. [Google Scholar] [CrossRef] [PubMed]
Figure 2.
Synthetic procedure used to prepare title compounds. Conditions: a: (for X = S) 1.1 eq. urea, in EtOH, reflux 2 h; b: (for X = O) 10 eq. urea, in MeCN, reflux 16 h or in DMF, 120 °C 2 h; c: 1 eq. acyl chloride, 3 eq. DIPEA or pyridine, in DCM, overnight; d: 10 eq. thionyl chloride, catalytic DMF.
Figure 2.
Synthetic procedure used to prepare title compounds. Conditions: a: (for X = S) 1.1 eq. urea, in EtOH, reflux 2 h; b: (for X = O) 10 eq. urea, in MeCN, reflux 16 h or in DMF, 120 °C 2 h; c: 1 eq. acyl chloride, 3 eq. DIPEA or pyridine, in DCM, overnight; d: 10 eq. thionyl chloride, catalytic DMF.
Table 1.
Structures, log k’w, HepG2 cytotoxicity, and MIC against Mtb H37Ra of the title compounds.
| Structure | Code | Ar | X | log k’w | HepG2 IC50 (µM) | Mtb H37Ra MIC (µg/mL) |
|---|---|---|---|---|---|---|
 | 1a | pyridin-2-yl | S | 1.857 | >1000 * | 31.25 |
| 1b | pyridin-2-yl | O | 0.854 | >1000 * | 62.5 | |
| 2a | pyridin-3-yl | S | 1.251 | >1000 * | 250 | |
| 2b | pyridin-3-yl | O | 0.436 | >1000 * | 31.25 | |
| 3a | pyridin-4-yl | S | 1.306 | >1000 * | 250 | |
| 3b | pyridin-4-yl | O | 0.396 | >1000 * | 15.625 | |
| 4b | 5-Me-pyridin-3-yl | O | 0.888 | >1000 * | 7.81 | |
| 5b | 2-Me-pyridin-4-yl | O | 0.714 | >1000 * | 3.91 | |
| 6a | 2-Cl-pyridin-4-yl | S | 2.013 | >250 ** | ≥500 | |
| 6b | 2-Cl-pyridin-4-yl | O | 1.136 | 664.1 | 3.125 | |
| 7a | 2-Cl-6-Me-pyridin-4-yl | S | 2.319 | >250 ** | ≥500 | |
| 7b | 2-Cl-6-Me-pyridin-4-yl | O | 1.430 | 959.4 | <3.91 | |
| 8a | pyrazin-2-yl | S | 1.222 | n.d. | 62.5 | |
| 8b | pyrazin-2-yl | O | 0.154 | n.d. | 31.25 | |
| 9a | 5-Cl-pyrazin-2-yl | S | 1.941 | n.d. | 31.25 | |
| 9b | 5-Cl-pyrazin-2-yl | O | 0.958 | n.d. | 31.25 | |
| 10a | quinoxalin-2-yl | S | 2.530 | >50 ** | ≥250 | |
| 10b | quinoxalin-2-yl | O | 1.493 | >1000 * | 15.625 | |
 | 11a | pyridin-2-yl | S | 3.102 | >100 ** | 3.91 |
| 11b | pyridin-2-yl | O | 2.038 | 883.4 | 3.91 | |
| 12a | pyridin-3-yl | S | 2.131 | >25 ** | ≥500 | |
| 12b | pyridin-3-yl | O | 1.118 | 610.3 | 125 | |
| 13a | pyridin-4-yl | S | 2.190 | >100 ** | 7.81 | |
| 13b | pyridin-4-yl | O | 1.163 | 879.3 | 31.25 | |
| 14b | 5-Me-pyridin-3-yl | O | 1.478 | >100 ** | ≥250 | |
| 15a | 2-Cl-pyridin-4-yl | S | 3.036 | 102.6 | 3.91 | |
| 15b | 2-Cl-pyridin-4-yl | O | 1.992 | 136.1 | 7.81 | |
| 16a | 2-Cl-6-Me-pyridin-4-yl | S | 3.314 | n.d. | 7.81 | |
| 16b | 2-Cl-6-Me-pyridin-4-yl | O | 2.251 | n.d. | 15.625 | |
| 17a | pyrazin-2-yl | S | 2.365 | n.d. | >50 [11] | |
| 17b | pyrazin-2-yl | O | 1.306 | >1000 * | 15.625 | |
| 18a | 5-Cl-pyrazin-2-yl | S | 3.173 | n.d. | >100 [11] | |
| 18b | 5-Cl-pyrazin-2-yl | O | 2.073 | >100 ** | 15.625 | |
| 19a | quinoxalin-2-yl | S | 3.583 | n.d. | ≥500 | |
| 19b | quinoxalin-2-yl | O | 2.465 | n.d. | ≥500 | |
| 20b | phenyl | O | 2.090 | 330.3 | 62.5 | |
| CIP | - | - | - | - | 0.25 | |
| INH | - | - | - | - | 0.25 | |
| RIF | - | - | - | - | 0.003–0.0015 |
* IC50 above the highest tested concentration; ** exact IC50 value could not be determined due to insolubility in the testing medium at higher concentrations; CIP—ciprofloxacin; INH—isoniazid; RIF—rifampicin; n.d.—not determined.
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Juhás, M.; Bachtíková, A.; Nawrot, D.E.; Hatoková, P.; Pallabothula, V.S.K.; Diepoltová, A.; Janďourek, O.; Bárta, P.; Konečná, K.; Paterová, P.; et al. Correction: Juhás et al. Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole. Pharmaceuticals 2022, 15, 580. Pharmaceuticals 2023, 16, 384. https://doi.org/10.3390/ph16030384
AMA Style
Juhás M, Bachtíková A, Nawrot DE, Hatoková P, Pallabothula VSK, Diepoltová A, Janďourek O, Bárta P, Konečná K, Paterová P, et al. Correction: Juhás et al. Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole. Pharmaceuticals 2022, 15, 580. Pharmaceuticals. 2023; 16(3):384. https://doi.org/10.3390/ph16030384
Chicago/Turabian StyleJuhás, Martin, Andrea Bachtíková, Daria Elżbieta Nawrot, Paulína Hatoková, Vinod Sukanth Kumar Pallabothula, Adéla Diepoltová, Ondřej Janďourek, Pavel Bárta, Klára Konečná, Pavla Paterová, and et al. 2023. "Correction: Juhás et al. Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole. Pharmaceuticals 2022, 15, 580" Pharmaceuticals 16, no. 3: 384. https://doi.org/10.3390/ph16030384
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