1-oxo-1,2,3,4-tetrahydroisoquinoline, also known as **1-tetrahydroisoquinolinone** or **THIQ**, is a heterocyclic compound with a nitrogen atom and a carbonyl group. Here's a breakdown of its structure and significance:
**Structure:**
* **Core Structure:** It is built on a **tetrahydroisoquinoline** framework, which is a bicyclic system with a benzene ring fused to a six-membered ring containing a nitrogen atom.
* **Carbonyl Group:** The 1-oxo prefix indicates a carbonyl group (C=O) attached to the first carbon atom of the tetrahydroisoquinoline ring.
**Importance in Research:**
1. **Pharmacological Activity:**
* **Antidepressant Potential:** THIQ has shown promising activity as a potential antidepressant. Its mechanism of action is related to its ability to modulate neurotransmitter systems, including serotonin and dopamine pathways.
* **Anticancer Activity:** Studies have indicated that THIQ and its derivatives possess anticancer properties. They can potentially inhibit tumor cell growth and induce apoptosis (programmed cell death).
* **Anti-Inflammatory Effects:** THIQ may have anti-inflammatory effects, potentially due to its interactions with signaling pathways involved in inflammation.
2. **Chemical Scaffold for Drug Discovery:**
* **Versatile Template:** The tetrahydroisoquinoline core is a versatile scaffold in medicinal chemistry. By modifying substituents on the ring, researchers can create a wide range of compounds with diverse pharmacological properties.
* **Improved Drug Properties:** THIQ derivatives can be optimized for better drug-like properties, such as solubility, bioavailability, and metabolic stability, enhancing their potential as therapeutic agents.
3. **Biological Studies:**
* **Neurological Research:** THIQ is used as a tool to study the role of neurotransmitters in the brain and to explore potential therapeutic targets for neurological disorders.
* **Cellular Signaling Studies:** Its ability to interact with cellular signaling pathways makes it valuable for investigating the mechanisms of various biological processes.
**Challenges and Future Directions:**
* **Toxicity and Selectivity:** Like many potential drugs, THIQ and its derivatives require careful evaluation for potential toxicity and off-target effects to ensure safe and effective therapeutic use.
* **Clinical Development:** Further research is needed to translate the promising preclinical findings of THIQ and its analogs into successful clinical trials for specific medical conditions.
**Overall, 1-oxo-1,2,3,4-tetrahydroisoquinoline (THIQ) is a fascinating molecule with significant potential in drug discovery and research related to various biological and pharmacological fields.**
1-oxo-1,2,3,4-tetrahydroisoquinoline: structure given in first source
ID Source | ID |
---|---|
PubMed CID | 150896 |
CHEMBL ID | 1688212 |
SCHEMBL ID | 67710 |
SCHEMBL ID | 11267501 |
MeSH ID | M0157627 |
Synonym |
---|
AC-5218 |
1,2,3,4-tetrahydroisoquinolin-1-one |
EN300-43275 |
3,4-dihydro-1(2h)-isoquinolinone |
F2189-0996 |
OPREA1_511002 , |
3,4-dihydro-2h-isoquinolin-1-one |
1196-38-9 |
AKOS002232785 |
AKOS003625709 |
STK926192 |
CHEMBL1688212 , |
joz , |
bdbm50339016 |
1-keto-1,2,3,4-tetrahydroisoquinoline |
1-oxo-1,2,3,4-tetrahydroisoquinoline |
1(2h)-isoquinolinone, 3,4-dihydro- |
3,4-dihydroisoquinolin-1(2h)-one |
FT-0600427 |
AM20020275 |
AB07451 |
SCHEMBL67710 |
3NUU |
YWPMKTWUFVOFPL-UHFFFAOYSA-N |
3,4-dihydroisoquinoline-1(2h)-one |
SCHEMBL11267501 |
DTXSID40152517 |
3,4-dihydroisocarbostyril |
J-511194 |
mfcd00853963 |
CS-W008863 |
Z56801375 |
3,4-dihydro-1-isoquinolinone |
dihydroisoquinolone |
Q27461749 |
SY021304 |
hydroxy-3,4-dihydroisoquinoline |
7R-1504 |
BCP27476 |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
3-phosphoinositide-dependent protein kinase 1 | Homo sapiens (human) | IC50 (µMol) | 169.0000 | 0.0025 | 1.4513 | 9.0000 | AID580957 |
Poly [ADP-ribose] polymerase 1 | Homo sapiens (human) | IC50 (µMol) | 100.0000 | 0.0002 | 0.8123 | 9.8100 | AID1252347 |
Protein mono-ADP-ribosyltransferase PARP10 | Homo sapiens (human) | IC50 (µMol) | 85.9839 | 0.5623 | 4.1053 | 9.7724 | AID1252345; AID1252346; AID1515545 |
Protein mono-ADP-ribosyltransferase PARP11 | Homo sapiens (human) | IC50 (µMol) | 7.9716 | 2.1000 | 5.0453 | 8.0000 | AID1515546 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1252345 | Inhibition of PARP-10 L926G mutant (unknown origin) mediated ADP-ribosylation of SRPK2 by fluorescence analysis using 3 uM SRPK2 as a substrate | 2015 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21 | Selective inhibition of PARP10 using a chemical genetics strategy. |
AID1252346 | Inhibition of PARP-10 (unknown origin) mediated ADP-ribosylation of SRPK2 by fluorescence analysis using 3 uM SRPK2 as a substrate | 2015 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21 | Selective inhibition of PARP10 using a chemical genetics strategy. |
AID1376993 | Antibacterial activity against Staphylococcus aureus ATCC 29213 at 50 ug/ml after 24 hrs by MTT assay | 2017 | Journal of natural products, 06-23, Volume: 80, Issue:6 | Mollecarbamates, Molleureas, and Molledihydroisoquinolone, o-Carboxyphenethylamide Metabolites of the Ascidian Didemnum molle Collected in Madagascar. |
AID1376992 | Antibacterial activity against Escherichia coli ATCC 25922 at 50 ug/ml after 24 hrs by MTT assay | 2017 | Journal of natural products, 06-23, Volume: 80, Issue:6 | Mollecarbamates, Molleureas, and Molledihydroisoquinolone, o-Carboxyphenethylamide Metabolites of the Ascidian Didemnum molle Collected in Madagascar. |
AID1376991 | Antibacterial activity against Pseudomonas aeruginosa ATCC 47085 at 50 ug/ml after 24 hrs by MTT assay | 2017 | Journal of natural products, 06-23, Volume: 80, Issue:6 | Mollecarbamates, Molleureas, and Molledihydroisoquinolone, o-Carboxyphenethylamide Metabolites of the Ascidian Didemnum molle Collected in Madagascar. |
AID1918421 | Inhibition of human NNMT measured after 20 mins by luminescence based methyltransferase assay | |||
AID1515546 | Inhibition of full length human His-SUMO-tagged PARP11 expressed in Escherichia coli BL21 assessed as reduction in MARylation of His6-tagged SRPK2 substrate after 60 mins in presence of NAD+ by chemifluorescence assay | 2019 | ACS medicinal chemistry letters, Jan-10, Volume: 10, Issue:1 | Rational Design of Cell-Active Inhibitors of PARP10. |
AID580957 | Inhibition of His-tagged-truncated human PDK1 preincubated with substrate biotinylated-AKT3 for 30 mins measured after 3 hrs by Scintillation proximity assay | 2010 | ACS medicinal chemistry letters, Nov-11, Volume: 1, Issue:8 | Aminoindazole PDK1 Inhibitors: A Case Study in Fragment-Based Drug Discovery. |
AID1515545 | Inhibition of human PARP10 catalytic domain assessed as reduction in MARylation of His6-tagged SRPK2 substrate after 60 mins in presence of NAD+ by chemifluorescence assay | 2019 | ACS medicinal chemistry letters, Jan-10, Volume: 10, Issue:1 | Rational Design of Cell-Active Inhibitors of PARP10. |
AID1252347 | Inhibition of PARP1 (unknown origin) by fluorescence analysis | 2015 | Bioorganic & medicinal chemistry letters, Nov-01, Volume: 25, Issue:21 | Selective inhibition of PARP10 using a chemical genetics strategy. |
AID1515547 | Selectivity ratio of IC50 for full length human His-SUMO-tagged PARP11 expressed in Escherichia coli BL21 to IC50 for human PARP10 catalytic domain | 2019 | ACS medicinal chemistry letters, Jan-10, Volume: 10, Issue:1 | Rational Design of Cell-Active Inhibitors of PARP10. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 1 (12.50) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 0 (0.00) | 29.6817 |
2010's | 6 (75.00) | 24.3611 |
2020's | 1 (12.50) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (12.92) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 8 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |