Abstract
The synthesis and anti-inflammatory effects of certain pyrazolo[4,3-c]quinoline derivatives 2a–2r are described. The anti-inflammatory activities of these derivatives were evaluated by means of inhibiting nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells. Among them, 3-amino-4-(4-hydroxyphenylamino)- 1H-pyrazolo[4,3-c]-quinoline (2i) and 4-(3-amino-1H-pyrazolo[4,3-c]quinolin-4-ylamino)benzoic acid (2m) exhibited significant inhibition of LPS-stimulated NO production with a potency approximately equal to that of the positive control, 1400W. Important structure features were analyzed by quantitative structure–activity relationship (QSAR) analysis to give better insights into the structure determinants for predicting the inhibitory effects on the accumulation of nitric oxide for RAW 264.7 cells in response to LPS. In addition, our results indicated that their anti-inflammatory effects involve the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) protein expression. Further studies on the structural optimization are ongoing.
| Original language | English |
|---|---|
| Article number | 1036 |
| Journal | Molecules |
| Volume | 23 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - Jan 1 2018 |
| Externally published | Yes |
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Keywords
- 3-c]quinolines
- Anti-inflammatory activity
- Nitric oxide
- Pyrazolo[4
ASJC Scopus subject areas
- Analytical Chemistry
- Chemistry (miscellaneous)
- Molecular Medicine
- Pharmaceutical Science
- Drug Discovery
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
Discovery of pyrazolo[4,3-c]quinolines derivatives as potential anti-inflammatory agents through inhibiting of no production. / Tseng, Chih Hua; Tung, Chun Wei; Peng, Shin I.; Chen, Yeh Long; Tzeng, Cherng Chyi; Cheng, Chih Mei.
In: Molecules, Vol. 23, No. 5, 1036, 01.01.2018.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Discovery of pyrazolo[4,3-c]quinolines derivatives as potential anti-inflammatory agents through inhibiting of no production
AU - Tseng, Chih Hua
AU - Tung, Chun Wei
AU - Peng, Shin I.
AU - Chen, Yeh Long
AU - Tzeng, Cherng Chyi
AU - Cheng, Chih Mei
PY - 2018/1/1
Y1 - 2018/1/1
N2 - The synthesis and anti-inflammatory effects of certain pyrazolo[4,3-c]quinoline derivatives 2a–2r are described. The anti-inflammatory activities of these derivatives were evaluated by means of inhibiting nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells. Among them, 3-amino-4-(4-hydroxyphenylamino)- 1H-pyrazolo[4,3-c]-quinoline (2i) and 4-(3-amino-1H-pyrazolo[4,3-c]quinolin-4-ylamino)benzoic acid (2m) exhibited significant inhibition of LPS-stimulated NO production with a potency approximately equal to that of the positive control, 1400W. Important structure features were analyzed by quantitative structure–activity relationship (QSAR) analysis to give better insights into the structure determinants for predicting the inhibitory effects on the accumulation of nitric oxide for RAW 264.7 cells in response to LPS. In addition, our results indicated that their anti-inflammatory effects involve the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) protein expression. Further studies on the structural optimization are ongoing.
AB - The synthesis and anti-inflammatory effects of certain pyrazolo[4,3-c]quinoline derivatives 2a–2r are described. The anti-inflammatory activities of these derivatives were evaluated by means of inhibiting nitric oxide (NO) production in lipopolysaccharide (LPS)-induced RAW 264.7 cells. Among them, 3-amino-4-(4-hydroxyphenylamino)- 1H-pyrazolo[4,3-c]-quinoline (2i) and 4-(3-amino-1H-pyrazolo[4,3-c]quinolin-4-ylamino)benzoic acid (2m) exhibited significant inhibition of LPS-stimulated NO production with a potency approximately equal to that of the positive control, 1400W. Important structure features were analyzed by quantitative structure–activity relationship (QSAR) analysis to give better insights into the structure determinants for predicting the inhibitory effects on the accumulation of nitric oxide for RAW 264.7 cells in response to LPS. In addition, our results indicated that their anti-inflammatory effects involve the inhibition of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX-2) protein expression. Further studies on the structural optimization are ongoing.
KW - 3-c]quinolines
KW - Anti-inflammatory activity
KW - Nitric oxide
KW - Pyrazolo[4
UR - http://www.scopus.com/inward/record.url?scp=85046637280&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85046637280&partnerID=8YFLogxK
U2 - 10.3390/molecules23051036
DO - 10.3390/molecules23051036
M3 - Article
C2 - 29710774
AN - SCOPUS:85046637280
VL - 23
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 5
M1 - 1036
ER -