Synthesis, characterization, and anti-inflammatory properties of novel ethyl 3-benzoyl-7-(trifluoromethyl)indolizine-1-carboxylate derivatives : In silico and in vitro analysis
© 2024 John Wiley & Sons Ltd..
Series of 7-(Trifluoromethyl) substituted indolizine 4a-g was synthesized using the one-pot method. Spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and HRMS were used for the structure confirmation of newly synthesized compounds. These 4a-g compounds were tested for their anti-inflammatory activity. In this study, we identified novel indolizine derivative compounds 4a-g selectively targeting COX-2 enzyme, tumor necrosis factor-α (TNF-α) and, interleukin-6 (IL-6). The in silico docking studies of 4a-g showed that these compounds have a higher affinity for COX-2 enzyme, TNF- α, and IL-6. In silico ADME profile analysis predicts that these compounds have good gastrointestinal tract and blood-brain barrier absorption. In vitro studies showed that compound 4d significantly reduces the level of COX-2 enzymes as compared to indomethacin. Compounds 4e, 4f, and 4a were also found to significantly reduce the level of TNF-α, while compounds 4f, 4g, and 4d, showed a reduction in the level of IL-6 when compared to indomethacin. Compounds 4a, 4d, and 4f also reduces nitric oxide (NO) level, compared to indomethacin. Overall, the current study illustrates significant anti-inflammatory activities of these novel 7-(Trifluoromethyl) substituted indolizine derivatives.
Medienart: |
E-Artikel |
---|
Erscheinungsjahr: |
2024 |
---|---|
Erschienen: |
2024 |
Enthalten in: |
Zur Gesamtaufnahme - volume:103 |
---|---|
Enthalten in: |
Chemical biology & drug design - 103(2024), 3 vom: 26. März, Seite e14514 |
Sprache: |
Englisch |
---|
Beteiligte Personen: |
Singh, Harshada Rambaboo [VerfasserIn] |
---|
Links: |
---|
Anmerkungen: |
Date Completed 28.03.2024 Date Revised 28.03.2024 published: Print Citation Status MEDLINE |
---|
doi: |
10.1111/cbdd.14514 |
---|
funding: |
|
---|---|
Förderinstitution / Projekttitel: |
|
PPN (Katalog-ID): |
NLM37021160X |
---|
LEADER | 01000caa a22002652 4500 | ||
---|---|---|---|
001 | NLM37021160X | ||
003 | DE-627 | ||
005 | 20240329001059.0 | ||
007 | cr uuu---uuuuu | ||
008 | 240328s2024 xx |||||o 00| ||eng c | ||
024 | 7 | |a 10.1111/cbdd.14514 |2 doi | |
028 | 5 | 2 | |a pubmed24n1353.xml |
035 | |a (DE-627)NLM37021160X | ||
035 | |a (NLM)38531606 | ||
040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
041 | |a eng | ||
100 | 1 | |a Singh, Harshada Rambaboo |e verfasserin |4 aut | |
245 | 1 | 0 | |a Synthesis, characterization, and anti-inflammatory properties of novel ethyl 3-benzoyl-7-(trifluoromethyl)indolizine-1-carboxylate derivatives |b In silico and in vitro analysis |
264 | 1 | |c 2024 | |
336 | |a Text |b txt |2 rdacontent | ||
337 | |a ƒaComputermedien |b c |2 rdamedia | ||
338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
500 | |a Date Completed 28.03.2024 | ||
500 | |a Date Revised 28.03.2024 | ||
500 | |a published: Print | ||
500 | |a Citation Status MEDLINE | ||
520 | |a © 2024 John Wiley & Sons Ltd. | ||
520 | |a Series of 7-(Trifluoromethyl) substituted indolizine 4a-g was synthesized using the one-pot method. Spectroscopic techniques such as IR, 1H-NMR, 13C-NMR, and HRMS were used for the structure confirmation of newly synthesized compounds. These 4a-g compounds were tested for their anti-inflammatory activity. In this study, we identified novel indolizine derivative compounds 4a-g selectively targeting COX-2 enzyme, tumor necrosis factor-α (TNF-α) and, interleukin-6 (IL-6). The in silico docking studies of 4a-g showed that these compounds have a higher affinity for COX-2 enzyme, TNF- α, and IL-6. In silico ADME profile analysis predicts that these compounds have good gastrointestinal tract and blood-brain barrier absorption. In vitro studies showed that compound 4d significantly reduces the level of COX-2 enzymes as compared to indomethacin. Compounds 4e, 4f, and 4a were also found to significantly reduce the level of TNF-α, while compounds 4f, 4g, and 4d, showed a reduction in the level of IL-6 when compared to indomethacin. Compounds 4a, 4d, and 4f also reduces nitric oxide (NO) level, compared to indomethacin. Overall, the current study illustrates significant anti-inflammatory activities of these novel 7-(Trifluoromethyl) substituted indolizine derivatives | ||
650 | 4 | |a Journal Article | |
650 | 4 | |a COX‐2 | |
650 | 4 | |a IL‐6 | |
650 | 4 | |a TNF‐α | |
650 | 4 | |a anti‐inflammatory activity | |
650 | 4 | |a characterization | |
650 | 4 | |a indolizine | |
650 | 4 | |a inflammation | |
650 | 7 | |a Anti-Inflammatory Agents, Non-Steroidal |2 NLM | |
650 | 7 | |a Cyclooxygenase 2 |2 NLM | |
650 | 7 | |a EC 1.14.99.1 |2 NLM | |
650 | 7 | |a Tumor Necrosis Factor-alpha |2 NLM | |
650 | 7 | |a Interleukin-6 |2 NLM | |
650 | 7 | |a Anti-Inflammatory Agents |2 NLM | |
650 | 7 | |a Indomethacin |2 NLM | |
650 | 7 | |a XXE1CET956 |2 NLM | |
650 | 7 | |a Indolizines |2 NLM | |
700 | 1 | |a Kushwaha, Prajjwal |e verfasserin |4 aut | |
700 | 1 | |a Tandon, Reetika |e verfasserin |4 aut | |
700 | 1 | |a Srivastava, Nidhi |e verfasserin |4 aut | |
700 | 1 | |a Chandrashekharappa, Sandeep |e verfasserin |4 aut | |
773 | 0 | 8 | |i Enthalten in |t Chemical biology & drug design |d 2006 |g 103(2024), 3 vom: 26. März, Seite e14514 |w (DE-627)NLM160848377 |x 1747-0285 |7 nnns |
773 | 1 | 8 | |g volume:103 |g year:2024 |g number:3 |g day:26 |g month:03 |g pages:e14514 |
856 | 4 | 0 | |u http://dx.doi.org/10.1111/cbdd.14514 |3 Volltext |
912 | |a GBV_USEFLAG_A | ||
912 | |a GBV_NLM | ||
951 | |a AR | ||
952 | |d 103 |j 2024 |e 3 |b 26 |c 03 |h e14514 |