1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione is a synthetic compound that has garnered significant attention in research, particularly within the field of medicinal chemistry. Its importance stems from its potential as a:
**1. Anticancer Agent:**
* This compound exhibits potent anticancer activity against various tumor cell lines, including leukemia, breast cancer, and lung cancer.
* Its mechanism of action is believed to involve inhibition of protein kinases, which are critical for cell growth and proliferation.
**2. Anti-Inflammatory Agent:**
* It demonstrates anti-inflammatory properties, potentially through inhibition of the production of inflammatory mediators such as cytokines.
* This aspect has opened up avenues for its potential use in treating inflammatory conditions like arthritis and inflammatory bowel disease.
**3. Anti-Bacterial Agent:**
* Studies have shown that 1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione exhibits antibacterial activity against certain bacteria, including strains resistant to conventional antibiotics.
**4. Neuroprotective Agent:**
* Preclinical studies suggest that this compound may possess neuroprotective effects, potentially by reducing oxidative stress and promoting neuronal survival.
**5. Investigational Drug Target:**
* The compound's unique chemical structure and pharmacological properties make it an attractive target for further investigation and potential drug development.
**Research Importance:**
* Understanding the exact mechanisms of action of this compound is crucial for optimizing its efficacy and safety.
* Researchers are actively engaged in preclinical and clinical studies to evaluate its therapeutic potential for various diseases.
* Further investigation may lead to the development of new and improved treatments based on the structural framework of this compound.
**Note:** While 1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione holds promise for medicinal applications, it is important to remember that it is still in the research and development phase. Its safety and efficacy in humans need to be thoroughly evaluated through further clinical trials before it can be considered for therapeutic use.
ID Source | ID |
---|---|
PubMed CID | 1901244 |
CHEMBL ID | 375126 |
CHEBI ID | 92273 |
SCHEMBL ID | 5426477 |
Synonym |
---|
AKOS000448309 |
apoptosis activator 2 |
79183-19-0 |
HMS3268L07 |
BRD-K15164005-001-01-5 |
cid_1901244 |
bdbm22796 |
1-[(3,4-dichlorophenyl)methyl]-2,3-dihydro-1h-indole-2,3-dione |
isatin-based compound, 16 |
NCGC00025353-01 |
tocris-2098 |
HSCI1_000276 |
CBMICRO_042945 |
BIM-0043056.P001 |
1-(3,4-dichlorobenzyl)-1h-indole-2,3-dione |
apoptosis activator ii |
STK215768 |
CHEMBL375126 |
EC-000.2382 |
1-[(3,4-dichlorophenyl)methyl]indole-2,3-dione |
1-(3,4-DICHLOROBENZYL)INDOLINE-2,3-DIONE , |
MLS-0469602.0001 |
AB00102233-01 |
11E-386S |
CS-3545 |
J-503075 |
SCHEMBL5426477 |
1-[(3,4-dichlorophenyl)methyl]-1h-indole-2,3-dione |
c15h9cl2no2 |
HB1293 |
mdk83190 |
AC-32079 |
HY-18633 |
mfcd00141556 |
EX-A147 |
DTXSID30365533 |
CHEBI:92273 |
HMS3651L12 |
SR-01000411093-1 |
SR-01000411093-2 |
sr-01000411093 |
apoptosisactivator2 |
SW219926-1 |
FT-0732905 |
BCP06746 |
Q27164035 |
n-(3,4-dichlorobenzyl)-1h-indole-2,3-dione |
S2927 |
HMS3677G05 |
1-((3,4-dichlorophenyl)methyl)-1h-indole-2,3-dione |
HMS3413G05 |
BRD-K15164005-001-02-3 |
apoptosis-activator-ii |
CCG-267529 |
1h-indole-2,3-dione, 1-((3,4-dichlorophenyl)methyl)- |
1-((3,4-dichlorophenyl)methyl)indole-2,3-dione |
RSY8DE8DGH , |
BP-25394 |
unii-rsy8de8dgh |
Class | Description |
---|---|
indoles | Any compound containing an indole skeleton. |
[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) |
---|---|---|---|---|---|---|---|
Chain A, TYROSYL-DNA PHOSPHODIESTERASE | Homo sapiens (human) | Potency | 0.0708 | 0.0040 | 23.8416 | 100.0000 | AID485290 |
Chain A, HADH2 protein | Homo sapiens (human) | Potency | 12.5893 | 0.0251 | 20.2376 | 39.8107 | AID886 |
Chain B, HADH2 protein | Homo sapiens (human) | Potency | 12.5893 | 0.0251 | 20.2376 | 39.8107 | AID886 |
Chain A, Cruzipain | Trypanosoma cruzi | Potency | 15.8489 | 0.0020 | 14.6779 | 39.8107 | AID1476 |
15-lipoxygenase, partial | Homo sapiens (human) | Potency | 10.0000 | 0.0126 | 10.6917 | 88.5700 | AID887 |
phosphopantetheinyl transferase | Bacillus subtilis | Potency | 50.1187 | 0.1413 | 37.9142 | 100.0000 | AID1490 |
USP1 protein, partial | Homo sapiens (human) | Potency | 50.1187 | 0.0316 | 37.5844 | 354.8130 | AID504865 |
TDP1 protein | Homo sapiens (human) | Potency | 2.2723 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
Microtubule-associated protein tau | Homo sapiens (human) | Potency | 14.1254 | 0.1800 | 13.5574 | 39.8107 | AID1460 |
aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 0.0648 | 0.0112 | 12.4002 | 100.0000 | AID1030; AID493210 |
thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 39.8107 | 0.0013 | 18.0743 | 39.8107 | AID926; AID938 |
heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa) | Homo sapiens (human) | Potency | 50.1187 | 0.0165 | 25.3078 | 41.3999 | AID602332 |
cytochrome P450 2D6 isoform 1 | Homo sapiens (human) | Potency | 3.9811 | 0.0020 | 7.5337 | 39.8107 | AID891 |
cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 11.0792 | 0.3162 | 12.4435 | 31.6228 | AID902; AID924 |
polyunsaturated fatty acid lipoxygenase ALOX12 | Homo sapiens (human) | Potency | 22.3872 | 1.0000 | 12.2326 | 31.6228 | AID1452 |
vitamin D3 receptor isoform VDRA | Homo sapiens (human) | Potency | 3.9811 | 0.3548 | 28.0659 | 89.1251 | AID504847 |
nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 35.4813 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
cytochrome P450 3A4 isoform 1 | Homo sapiens (human) | Potency | 7.9433 | 0.0316 | 10.2792 | 39.8107 | AID884; AID885 |
lethal factor (plasmid) | Bacillus anthracis str. A2012 | Potency | 19.9526 | 0.0200 | 10.7869 | 31.6228 | AID912 |
Gamma-aminobutyric acid receptor subunit pi | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Polyunsaturated fatty acid lipoxygenase ALOX15B | Homo sapiens (human) | Potency | 7.9433 | 0.3162 | 12.7657 | 31.6228 | AID881 |
Integrin beta-3 | Homo sapiens (human) | Potency | 15.8489 | 0.3162 | 11.4157 | 31.6228 | AID924 |
Integrin alpha-IIb | Homo sapiens (human) | Potency | 15.8489 | 0.3162 | 11.4157 | 31.6228 | AID924 |
Gamma-aminobutyric acid receptor subunit beta-1 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit delta | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit gamma-2 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit alpha-5 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit alpha-3 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit gamma-1 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit alpha-2 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit alpha-4 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit gamma-3 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit alpha-6 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Histamine H2 receptor | Cavia porcellus (domestic guinea pig) | Potency | 7.9433 | 0.0063 | 8.2350 | 39.8107 | AID881 |
Gamma-aminobutyric acid receptor subunit alpha-1 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit beta-3 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit beta-2 | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Inositol monophosphatase 1 | Rattus norvegicus (Norway rat) | Potency | 22.3872 | 1.0000 | 10.4756 | 28.1838 | AID1457 |
GABA theta subunit | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
Gamma-aminobutyric acid receptor subunit epsilon | Rattus norvegicus (Norway rat) | Potency | 7.9433 | 1.0000 | 12.2248 | 31.6228 | AID885 |
[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) |
---|---|---|---|---|---|---|---|
Apoptotic peptidase activating factor 1 | Homo sapiens (human) | IC50 (µMol) | 34.0000 | 0.0375 | 18.6232 | 53.2000 | AID602460 |
caspase-9 isoform alpha precursor | Homo sapiens (human) | IC50 (µMol) | 22.7000 | 0.0256 | 16.5070 | 52.8000 | AID602461 |
caspase-3 isoform a preproprotein | Homo sapiens (human) | IC50 (µMol) | 22.7000 | 0.0256 | 20.3235 | 74.3000 | AID602461 |
Coagulation factor XII | Homo sapiens (human) | Ki | 12.1926 | 0.0025 | 1.8669 | 7.2500 | AID1798240 |
Cholinesterase | Homo sapiens (human) | Ki | 12.2605 | 0.0000 | 1.5173 | 9.7300 | AID1798240; AID281481 |
Liver carboxylesterase 1 | Oryctolagus cuniculus (rabbit) | Ki | 12.1926 | 0.0136 | 1.7025 | 7.2500 | AID1798240 |
Acetylcholinesterase | Homo sapiens (human) | Ki | 18.1938 | 0.0000 | 1.2786 | 9.7300 | AID1798240; AID281480 |
Liver carboxylesterase 1 | Homo sapiens (human) | Ki | 10.1657 | 0.0025 | 2.0136 | 8.4800 | AID1798240; AID281478 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1508630 | Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay | 2021 | Cell reports, 04-27, Volume: 35, Issue:4 | A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. |
AID1347154 | Primary screen GU AMC qHTS for Zika virus inhibitors | 2020 | Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49 | Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors. |
AID281479 | Inhibition of rabbit liver carboxylesterase expressed in sf21 cells | 2007 | Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8 | Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. |
AID281477 | Inhibition of human intestinal carboxylesterase expressed in sf21 cells | 2007 | Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8 | Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. |
AID281481 | Inhibition of human BChE | 2007 | Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8 | Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. |
AID1824507 | Antiproliferative activity against human K562 cells assessed as growth inhibition measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID281480 | Inhibition of human AChE | 2007 | Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8 | Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. |
AID1824518 | Induction of apoptosis in human MCF7 cells assessed as decrease in Bcl2 expression upto 5 uM measured after 48 hrs by immunoblotting analysis | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824516 | Induction of apoptosis in human MCF7 cells assessed as NFkappaB activity upto 5 uM measured after 48 hrs by immunoblotting analysis | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824515 | Antiproliferative activity against human HCT-116p53KO subline assessed as growth inhibition measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824508 | Antiproliferative activity against human MCF7 cells assessed as growth inhibition under hypoxia conditions measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824514 | Antiproliferative activity against human HCT-116 assessed as growth inhibition measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824517 | Induction of apoptosis in human MCF7 cells assessed as PARP cleavage upto 5 uM measured after 48 hrs by immunoblotting analysis | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824502 | Antiproliferative activity against human K562/4 cells assessed as growth inhibition measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824520 | Induction of apoptosis in human MCF7 cells assessed as decrease in ERalpha protein expression upto 5 uM measured after 48 hrs by immunoblotting analysis | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824506 | Antiproliferative activity against human MCF7 cells assessed as growth inhibition measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824512 | Antiproliferative activity against human MDA-MB-231 cells assessed as growth inhibition under hypoxia conditions measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1824519 | Induction of apoptosis in human MCF7 cells assessed as decrease in BAD protein expression upto 5 uM measured after 48 hrs by immunoblotting analysis | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID281478 | Inhibition of human liver CE1 expressed in sf21 cells | 2007 | Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8 | Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. |
AID1824511 | Antiproliferative activity against human MDA-MB-231 cells assessed as growth inhibition under normoxia conditions measured after 72 hrs by MTT assay | 2022 | European journal of medicinal chemistry, Jan-15, Volume: 228 | Synthesis, biological evaluation, and in silico studies of potential activators of apoptosis and carbonic anhydrase inhibitors on isatin-5-sulfonamide scaffold. |
AID1798240 | Enzyme Inhibition Assay from Article 10.1021/jm061471k: \\Selective inhibition of carboxylesterases by isatins, indole-2,3-diones.\\ | 2007 | Journal of medicinal chemistry, Apr-19, Volume: 50, Issue:8 | Selective inhibition of carboxylesterases by isatins, indole-2,3-diones. |
AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | 2014 | Journal of biomolecular screening, Jul, Volume: 19, Issue:6 | A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum. |
AID1794808 | Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL). | |||
[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 | 1 (16.67) | 24.3611 |
2020's | 4 (66.67) | 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 (13.03) 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] |