2-(3-oxo-1,2-benzothiazol-2-yl)-N-phenylacetamide, also known as **thiazolidine-2,4-dione**, is a heterocyclic compound with a benzothiazole ring system.
**Structure and Properties:**
* **Benzothiazole ring:** This core structure contains a sulfur atom and a nitrogen atom within a six-membered ring.
* **3-oxo group:** A carbonyl group attached to the third position of the benzothiazole ring.
* **Acetamide group:** A carboxamide group attached to the second position of the benzothiazole ring, further connected to a phenyl group.
**Importance in Research:**
Thiazolidine-2,4-dione and its derivatives have shown promising biological activity and are actively researched for various applications:
* **Anti-inflammatory activity:** These compounds have been demonstrated to inhibit the production of inflammatory mediators like prostaglandins and leukotrienes, making them potential candidates for treating inflammatory conditions.
* **Antioxidant activity:** Thiazolidine-2,4-dione derivatives possess free radical scavenging properties, contributing to their potential role in protecting cells from oxidative damage.
* **Anti-cancer activity:** Some studies suggest that these compounds exhibit cytotoxic effects against various cancer cell lines, potentially through apoptosis induction and cell cycle arrest.
* **Antibacterial activity:** The heterocyclic nature of thiazolidine-2,4-dione derivatives has been linked to their potential antibacterial properties.
* **Anti-diabetic activity:** Some research indicates that these compounds might help regulate blood glucose levels and improve insulin sensitivity, making them promising for diabetes treatment.
**Current Research:**
Current research focuses on synthesizing new derivatives of thiazolidine-2,4-dione with improved pharmacological properties. Researchers are exploring different substituents on the phenyl group and the benzothiazole ring to enhance the desired biological activity and reduce potential side effects.
**Overall, 2-(3-oxo-1,2-benzothiazol-2-yl)-N-phenylacetamide and its derivatives are promising candidates for developing new drugs in various therapeutic areas, including inflammation, oxidative stress, cancer, and diabetes. Ongoing research aims to further elucidate their mechanisms of action and optimize their pharmacological profiles for clinical application.**
ID Source | ID |
---|---|
PubMed CID | 44602374 |
CHEMBL ID | 1709906 |
CHEBI ID | 93426 |
Synonym |
---|
ksc-4-244 |
KUC104122N , |
kuc104122 |
smr001831621 |
MLS003116067 , |
CHEMBL1709906 |
2-(3-oxidanylidene-1,2-benzothiazol-2-yl)-n-phenyl-ethanamide |
2-(3-oxo-1,2-benzothiazol-2-yl)-n-phenylacetamide |
2-(3-keto-1,2-benzothiazol-2-yl)-n-phenyl-acetamide |
bdbm61925 |
cid_44602374 |
CHEBI:93426 |
Q27165128 |
Class | Description |
---|---|
benzothiazoles | |
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] |
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Nrf2 | Homo sapiens (human) | Potency | 12.5893 | 0.0920 | 8.2222 | 23.1093 | AID624171 |
glp-1 receptor, partial | Homo sapiens (human) | Potency | 10.0000 | 0.0184 | 6.8060 | 14.1254 | AID624417 |
GLS protein | Homo sapiens (human) | Potency | 7.0795 | 0.3548 | 7.9355 | 39.8107 | AID624170 |
TDP1 protein | Homo sapiens (human) | Potency | 2.1853 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
Smad3 | Homo sapiens (human) | Potency | 17.7828 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
hypothetical protein, conserved | Trypanosoma brucei | Potency | 3.9811 | 0.2239 | 11.2451 | 35.4813 | AID624173 |
67.9K protein | Vaccinia virus | Potency | 10.0000 | 0.0001 | 8.4406 | 100.0000 | AID720579 |
IDH1 | Homo sapiens (human) | Potency | 29.0929 | 0.0052 | 10.8652 | 35.4813 | AID686970 |
serine/threonine-protein kinase PLK1 | Homo sapiens (human) | Potency | 1.1917 | 0.1683 | 16.4040 | 67.0158 | AID720504 |
Vpr | Human immunodeficiency virus 1 | Potency | 56.2341 | 1.5849 | 19.6264 | 63.0957 | AID651644 |
Glycoprotein hormones alpha chain | Homo sapiens (human) | Potency | 10.0000 | 4.4668 | 8.3448 | 10.0000 | AID624291 |
Guanine nucleotide-binding protein G | Homo sapiens (human) | Potency | 44.6684 | 1.9953 | 25.5327 | 50.1187 | AID624287 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase | Plasmodium berghei | IC50 (µMol) | 10.6233 | 0.8890 | 21.0286 | 71.5000 | AID504765; AID540252; AID540269 |
hexokinase | Trypanosoma brucei brucei TREU927 | IC50 (µMol) | 6.6900 | 0.2008 | 4.6024 | 22.3780 | AID2230 |
glucose-6-phosphate 1-dehydrogenase isoform b | Homo sapiens (human) | IC50 (µMol) | 12.7000 | 8.8700 | 12.8518 | 17.8000 | AID504792 |
rac GTPase-activating protein 1 isoform a | Homo sapiens (human) | IC50 (µMol) | 73.1100 | 7.3900 | 57.8904 | 301.2400 | AID624330 |
Neutrophil elastase | Homo sapiens (human) | IC50 (µMol) | 6.6900 | 0.0063 | 2.0734 | 22.3780 | AID2230 |
Replicase polyprotein 1ab | Severe acute respiratory syndrome coronavirus 2 | IC50 (µMol) | 0.1652 | 0.0002 | 2.4585 | 9.9600 | AID1888964 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
AID588497 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
AID588501 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Current protocols in cytometry, Oct, Volume: Chapter 13 | Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2006 | Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5 | Microsphere-based protease assays and screening application for lethal factor and factor Xa. |
AID588499 | High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set | 2010 | Assay and drug development technologies, Feb, Volume: 8, Issue:1 | High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors. |
AID619593 | Antifungal activity against Candida albicans RC-201 after 24 hrs by broth microdilution method | 2011 | Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19 | Antifungal activity of a series of 1,2-benzisothiazol-3(2H)-one derivatives. |
AID619592 | Antifungal activity against Candida albicans CAF-2 after 24 hrs by broth microdilution method | 2011 | Bioorganic & medicinal chemistry, Oct-01, Volume: 19, Issue:19 | Antifungal activity of a series of 1,2-benzisothiazol-3(2H)-one derivatives. |
AID1888963 | Inhibition of SARS-CoV-2 main protease using Mca-AVLQSGFRK(Dnp)K as substrate at 40 uM preincubated with enzyme for 10 mins followed by substrate addition and measured every 30 secs for 10 mins by fluorescence based analysis | 2022 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 58 | Discovery of highly potent SARS-CoV-2 M |
AID1888964 | Inhibition of SARS-CoV-2 main protease using Mca-AVLQSGFRK(Dnp)K as substrate preincubated with enzyme for 10 mins followed by substrate addition and measured every 30 secs for 10 mins by fluorescence based analysis | 2022 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 58 | Discovery of highly potent SARS-CoV-2 M |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 1 (16.67) | 29.6817 |
2010's | 3 (50.00) | 24.3611 |
2020's | 2 (33.33) | 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 (12.72) 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 | 6 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |