SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF
3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN
ANALOGUES

J 2017

SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF 3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN ANALOGUES

FARSA, Oldřich, Jakub KÁŇA, Irena MACKŮ, Jana ŽELAZKOVÁ, Jana PODLIPNÁ et. al.

Základní údaje

Originální název

SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF 3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN ANALOGUES

Autoři

FARSA, Oldřich (203 Česká republika, garant, domácí), Jakub KÁŇA, Irena MACKŮ (203 Česká republika), Jana ŽELAZKOVÁ (203 Česká republika), Jana PODLIPNÁ, Aleš CIRKVA, Jaroslav MAXA a Kamil ŠŤASTNÝ

Vydání

ACTA POLONIAE PHARMACEUTICA, WARSAW, POLSKIE TOWARZYSTWO FARMACEUTYCZNE, 2017, 0001-6837

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

30104 Pharmacology and pharmacy

Stát vydavatele

Polsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Europe PMC

Impakt faktor

Impact factor: 0.531

Kód RIV

RIV/00216224:14160/17:00120955

Organizační jednotka

Farmaceutická fakulta

UT WoS

000410257700014

Klíčová slova anglicky

aminopeptidase N/CDI3; dioxaborolanols; phenoxypropandiols; inhibitory activity; anticancer activity; antiviral activity; lipophilicity; QSAR

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 10. 8. 2021 09:03, doc. PharmDr. Oldřich Farsa, Ph.D.

Anotace

V originále

Aminopeptidase N (APN) represents a class of zinc metallopeptidases with broad substrate specifity. This enzyme is involved in control of angioneogenesis in cancer and microvascular conditions. It also serves as a superficial cellular receptor that enables attachment of some viruses including coronaviruses to the host cell. APN takes part also in metabolism of some important neuropeptides. That is why APN can be a promising therapeutic target and compounds which influence its activity interesting potential drugs. Here, synthesis of compounds which in most contain 3-phenoxypropan-1,2 diol moiety and evaluation of their inhibition activity against APN is described. 4-[1-, 2- and 3-(Nitrophenoxymethyl)]-[1,3,2]dioxaborolan-2-ols are novel compounds which have never been previously reported in the literature. 3-(Aminophenoxy)propyl-1,2-diols revealed greater activity than both 3-(nitrophenoxy)propyl-1,2-diols and 3-(nitrophenoxymethyl)-[1,3,2]dioxaborolan-2-ols. A QSAR study revealed a linear correlation between lipophilicity and inhibition activity.

Citovat

FARSA, Oldřich, Jakub KÁŇA, Irena MACKŮ, Jana ŽELAZKOVÁ, Jana PODLIPNÁ, Aleš CIRKVA, Jaroslav MAXA a Kamil ŠŤASTNÝ. SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF 3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN ANALOGUES. ACTA POLONIAE PHARMACEUTICA. WARSAW: POLSKIE TOWARZYSTWO FARMACEUTYCZNE, 2017, roč. 74, č. 1, s. 127-135. ISSN 0001-6837.

@article{1727183,
   author = {Farsa, Oldřich and Káňa, Jakub and Macků, Irena and Želazková, Jana and Podlipná, Jana and Cirkva, Aleš and Maxa, Jaroslav and Šťastný, Kamil},
   article_location = {WARSAW},
   article_number = {1},
   keywords = {aminopeptidase N/CDI3; dioxaborolanols; phenoxypropandiols; inhibitory activity; anticancer activity; antiviral activity; lipophilicity; QSAR},
   language = {eng},
   issn = {0001-6837},
   journal = {ACTA POLONIAE PHARMACEUTICA},
   title = {SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF 3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN ANALOGUES},
   url = {https://europepmc.org/article/med/29474769},
   volume = {74},
   year = {2017}
}

TY  - JOUR
ID  - 1727183
AU  - Farsa, Oldřich - Káňa, Jakub - Macků, Irena - Želazková, Jana - Podlipná, Jana - Cirkva, Aleš - Maxa, Jaroslav - Šťastný, Kamil
PY  - 2017
TI  - SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF 3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN ANALOGUES
JF  - ACTA POLONIAE PHARMACEUTICA
VL  - 74
IS  - 1
SP  - 127-135
EP  - 127-135
PB  - POLSKIE TOWARZYSTWO FARMACEUTYCZNE
SN  - 00016837
KW  - aminopeptidase N/CDI3
KW  - dioxaborolanols
KW  - phenoxypropandiols
KW  - inhibitory activity
KW  - anticancer activity
KW  - antiviral activity
KW  - lipophilicity
KW  - QSAR
UR  - https://europepmc.org/article/med/29474769
N2  - Aminopeptidase N (APN) represents a class of zinc metallopeptidases with broad substrate specifity. This enzyme is involved in control of angioneogenesis in cancer and microvascular conditions. It also serves as a superficial cellular receptor that enables attachment of some viruses including coronaviruses to the host cell. APN takes part also in metabolism of some important neuropeptides. That is why APN can be a promising therapeutic target and compounds which influence its activity interesting potential drugs. Here, synthesis of compounds which in most contain 3-phenoxypropan-1,2 diol moiety and evaluation of their inhibition activity against APN is described. 4-[1-, 2- and 3-(Nitrophenoxymethyl)]-[1,3,2]dioxaborolan-2-ols are novel compounds which have never been previously reported in the literature. 3-(Aminophenoxy)propyl-1,2-diols revealed greater activity than both 3-(nitrophenoxy)propyl-1,2-diols and 3-(nitrophenoxymethyl)-[1,3,2]dioxaborolan-2-ols. A QSAR study revealed a linear correlation between lipophilicity and inhibition activity.
ER  -

FARSA, Oldřich, Jakub KÁŇA, Irena MACKŮ, Jana ŽELAZKOVÁ, Jana PODLIPNÁ, Aleš CIRKVA, Jaroslav MAXA a Kamil ŠŤASTNÝ. SYNTHESIS AND AMINOPEPTIDASE N INHIBITING ACTIVITY OF 3-(NITROPHENOXYMETHYL)-[1,3,2]DIOXABOROLAN-2-OLS AND THEIR OPEN ANALOGUES. \textit{ACTA POLONIAE PHARMACEUTICA}. WARSAW: POLSKIE TOWARZYSTWO FARMACEUTYCZNE, 2017, roč.~74, č.~1, s.~127-135. ISSN~0001-6837.

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