Consensus-Based Pharmacophore Mapping for New Set of
N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides

J 2020

Consensus-Based Pharmacophore Mapping for New Set of N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides

BAK, A., J. KOS, H. MICHNOVA, Tomáš GONĚC, S. POSPISILOVA et. al.

Basic information

Original name

Consensus-Based Pharmacophore Mapping for New Set of N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides

Authors

BAK, A. (guarantor), J. KOS, H. MICHNOVA, Tomáš GONĚC (203 Czech Republic, belonging to the institution), S. POSPISILOVA, V. KOZIK, A. CIZEK, A. SMOLINSKI and J. JAMPILEK

Edition

International Journal of Molecular Sciences, Basel, Multidisciplinary Digital Publishing Institute, 2020, 1422-0067

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

30104 Pharmacology and pharmacy

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

URL

Impact factor

Impact factor: 5.923

RIV identification code

RIV/00216224:14160/20:00116869

Organization unit

Faculty of Pharmacy

DOI

http://dx.doi.org/10.3390/ijms21186583

UT WoS

000580310500001

Keywords in English

hydroxynaphthalenecarboxamides; lipophilicity; antistaphylococcal activity; antitubercular activity; MIC; MTT assay; CoMSA; IVE-PLS; similarity-activity landscape index

Abstract

V originále

A series of twenty-two novelN-(disubstituted-phenyl)-3-hydroxynaphthalene- 2-carboxamide derivatives was synthesized and characterized as potential antimicrobial agents.N-[3,5-bis(trifluoromethyl)phenyl]- andN-[2-chloro-5-(trifluoromethyl)phenyl]-3-hydroxy- naphthalene-2-carboxamide showed submicromolar (MICs 0.16-0.68 mu M) activity against methicillin-resistantStaphylococcus aureusisolates.N-[3,5-bis(trifluoromethyl)phenyl]- andN-[4-bromo-3-(trifluoromethyl)phenyl]-3-hydroxynaphthalene-2-carboxamide revealed activity againstM. tuberculosis(both MICs 10 mu M) comparable with that of rifampicin. Synergistic activity was observed for the combinations of ciprofloxacin withN-[4-bromo-3-(trifluoromethyl)phenyl]- andN-(4-bromo-3-fluorophenyl)-3-hydroxynaphthalene-2-carboxamides against MRSA SA 630 isolate. The similarity-related property space assessment for the congeneric series of structurally related carboxamide derivatives was performed using the principal component analysis. Interestingly, different distribution of mono-halogenated carboxamide derivatives with the -CF(3)substituent is accompanied by the increased activity profile. A symmetric matrix of Tanimoto coefficients indicated the structural dissimilarities of dichloro- and dimetoxy-substituted isomers from the remaining ones. Moreover, the quantitative sampling of similarity-related activity landscape provided a subtle picture of favorable and disallowed structural modifications that are valid for determining activity cliffs. Finally, the advanced method of neural network quantitative SAR was engaged to illustrate the key 3D steric/electronic/lipophilic features of the ligand-site composition by the systematic probing of the functional group.

Citovat

BAK, A., J. KOS, H. MICHNOVA, Tomáš GONĚC, S. POSPISILOVA, V. KOZIK, A. CIZEK, A. SMOLINSKI and J. JAMPILEK. Consensus-Based Pharmacophore Mapping for New Set of N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides. International Journal of Molecular Sciences. Basel: Multidisciplinary Digital Publishing Institute, 2020, vol. 21, No 18, p. 1-23. ISSN 1422-0067. Available from: https://dx.doi.org/10.3390/ijms21186583.

@article{1690116,
   author = {Bak, A. and Kos, J. and Michnova, H. and Goněc, Tomáš and Pospisilova, S. and Kozik, V. and Cizek, A. and Smolinski, A. and Jampilek, J.},
   article_location = {Basel},
   article_number = {18},
   doi = {http://dx.doi.org/10.3390/ijms21186583},
   keywords = {hydroxynaphthalenecarboxamides; lipophilicity; antistaphylococcal activity; antitubercular activity; MIC; MTT assay; CoMSA; IVE-PLS; similarity-activity landscape index},
   language = {eng},
   issn = {1422-0067},
   journal = {International Journal of Molecular Sciences},
   title = {Consensus-Based Pharmacophore Mapping for New Set of N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides},
   url = {https://pubmed.ncbi.nlm.nih.gov/32916824/},
   volume = {21},
   year = {2020}
}

TY  - JOUR
ID  - 1690116
AU  - Bak, A. - Kos, J. - Michnova, H. - Goněc, Tomáš - Pospisilova, S. - Kozik, V. - Cizek, A. - Smolinski, A. - Jampilek, J.
PY  - 2020
TI  - Consensus-Based Pharmacophore Mapping for New Set of N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides
JF  - International Journal of Molecular Sciences
VL  - 21
IS  - 18
SP  - 1-23
EP  - 1-23
PB  - Multidisciplinary Digital Publishing Institute
SN  - 14220067
KW  - hydroxynaphthalenecarboxamides
KW  - lipophilicity
KW  - antistaphylococcal activity
KW  - antitubercular activity
KW  - MIC
KW  - MTT assay
KW  - CoMSA
KW  - IVE-PLS
KW  - similarity-activity landscape index
UR  - https://pubmed.ncbi.nlm.nih.gov/32916824/
L2  - https://pubmed.ncbi.nlm.nih.gov/32916824/
N2  - A series of twenty-two novelN-(disubstituted-phenyl)-3-hydroxynaphthalene- 2-carboxamide derivatives was synthesized and characterized as potential antimicrobial agents.N-[3,5-bis(trifluoromethyl)phenyl]- andN-[2-chloro-5-(trifluoromethyl)phenyl]-3-hydroxy- naphthalene-2-carboxamide showed submicromolar (MICs 0.16-0.68 mu M) activity against methicillin-resistantStaphylococcus aureusisolates.N-[3,5-bis(trifluoromethyl)phenyl]- andN-[4-bromo-3-(trifluoromethyl)phenyl]-3-hydroxynaphthalene-2-carboxamide revealed activity againstM. tuberculosis(both MICs 10 mu M) comparable with that of rifampicin. Synergistic activity was observed for the combinations of ciprofloxacin withN-[4-bromo-3-(trifluoromethyl)phenyl]- andN-(4-bromo-3-fluorophenyl)-3-hydroxynaphthalene-2-carboxamides against MRSA SA 630 isolate. The similarity-related property space assessment for the congeneric series of structurally related carboxamide derivatives was performed using the principal component analysis. Interestingly, different distribution of mono-halogenated carboxamide derivatives with the -CF(3)substituent is accompanied by the increased activity profile. A symmetric matrix of Tanimoto coefficients indicated the structural dissimilarities of dichloro- and dimetoxy-substituted isomers from the remaining ones. Moreover, the quantitative sampling of similarity-related activity landscape provided a subtle picture of favorable and disallowed structural modifications that are valid for determining activity cliffs. Finally, the advanced method of neural network quantitative SAR was engaged to illustrate the key 3D steric/electronic/lipophilic features of the ligand-site composition by the systematic probing of the functional group.
ER  -

BAK, A., J. KOS, H. MICHNOVA, Tomáš GONĚC, S. POSPISILOVA, V. KOZIK, A. CIZEK, A. SMOLINSKI and J. JAMPILEK. Consensus-Based Pharmacophore Mapping for New Set of N-(disubstituted-phenyl)-3-hydroxyl-naphthalene-2-carboxamides. \textit{International Journal of Molecular Sciences}. Basel: Multidisciplinary Digital Publishing Institute, 2020, vol.~21, No~18, p.~1-23. ISSN~1422-0067. Available from: https://dx.doi.org/10.3390/ijms21186583.

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