4'-(chloroacetyl)acetanilide is an organic compound that has been studied for its potential medicinal properties. It is a derivative of acetanilide, which is a common analgesic and antipyretic. The chloroacetyl group is attached to the para position of the benzene ring, which is known to influence the compound's chemical and pharmacological properties. The compound can be synthesized by reacting acetanilide with chloroacetyl chloride in the presence of a base, such as triethylamine. Studies on 4'-(chloroacetyl)acetanilide have focused on its potential as an anti-inflammatory agent. It has been shown to inhibit the production of pro-inflammatory cytokines, such as TNF-alpha and IL-1 beta, in various cell models. The compound's mechanism of action is thought to involve the inhibition of the enzyme COX-2, which is involved in the production of prostaglandins, which are inflammatory mediators. Further research is needed to fully understand the therapeutic potential of 4'-(chloroacetyl)acetanilide and to explore its potential applications in the treatment of inflammatory conditions.'
4'-(chloroacetyl)acetanilide : An alpha-chloroketone that is acetanilide in the para- position is substituted by a chloroacetyl group. [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]
| ID Source | ID |
|---|---|
| PubMed CID | 8805 |
| CHEMBL ID | 1408847 |
| CHEBI ID | 76355 |
| SCHEMBL ID | 1273600 |
| Synonym |
|---|
| 4-chloroacetylacetanilide |
| 4'-(chloroacetyl)-acetanilide |
| n-[4-(chloroacetyl)phenyl]acetamide |
| 4-(chloroacetyl)acetanilide |
| NCGC00091384-01 |
| 4'-chloroacetyl (acetanilide) |
| ccris 130 |
| 4'-(chloroacetyl)acetanilide |
| brn 2724140 |
| einecs 205-416-8 |
| acetamide, n-(4-(chloroacetyl)phenyl)- |
| hsdb 4110 |
| n-(4-(chloroacetyl)phenyl)acetamide |
| nsc 768 |
| n-[4-(2-chloroacetyl)phenyl]acetamide |
| nsc768 |
| wln: g1vr dmv1 |
| p-(acetylamino)phenacyl chloride |
| acetanilide, 4'-(chloroacetyl)- |
| nsc-768 |
| acetamide, n-[4-(chloroacetyl)phenyl]- |
| 4'-chloroacetyl(acetanilide) |
| nci-c03770 |
| 1-acetylamino-4-chloroacetylbenzene |
| 1-acetamido-4-chloroacetylbenzene |
| p-acetamidophenacyl chloride |
| 140-49-8 |
| 4'-(2-chloroacetyl)acetanilide, 97% |
| NCGC00091384-02 |
| 4'-(chloracetyl)acetanilide |
| AKOS000200680 |
| 4'-acetamido-2-chloroacetophenone |
| smr001371996 |
| MLS002454375 |
| STK802190 |
| AE-641/30206027 |
| NCGC00091384-03 |
| NCGC00091384-05 |
| NCGC00091384-04 |
| HMS3039D03 |
| dtxsid4020294 , |
| cas-140-49-8 |
| NCGC00256406-01 |
| tox21_302954 |
| dtxcid20294 |
| tox21_201314 |
| NCGC00258866-01 |
| unii-87iak033nk |
| acetamide, n-(4-(2-chloroacetyl)phenyl)- |
| 87iak033nk , |
| 1-14-00-00367 (beilstein handbook reference) |
| 4-(2-chloroacetyl)acetanilide |
| n-(4-(2-chloroacetyl)phenyl)acetamide |
| 4'-(2-chloroacetyl)acetanilide |
| FT-0631813 |
| 4'-chloroacetyl(acetanilide) [hsdb] |
| 4-acetamidophenacyl chloride |
| n-(4-chloroacetylphenyl)acetamide |
| p-acetamidophenacyl cloride |
| BBL027954 |
| 2-chloro-1-(4-acetamidophenyl)ethanone |
| 4-acetaminophenacyl chloride |
| p-chloroacetylacetanilide |
| 4-acetylaminophenacyl chloride |
| p-(2-chloroacetyl)acetanilide |
| CHEBI:76355 , |
| SCHEMBL1273600 |
| p-acetaminophenacylchlorid |
| W-108205 |
| 4-chloroacetyl acetanilide |
| n-[4-(2-chloroacetyl)phenyl]acetamide # |
| 4'-[chloroacetyl]acetanilide |
| CHEMBL1408847 |
| acetamide, n-[4-(2-chloroacetyl)phenyl]- |
| mfcd00040869 |
| Z56914790 |
| BCP20761 |
| Q27145911 |
| CS-0204309 |
| AS-17309 |
| 4-acetamido-2-chloroacetophenone |
| 4/'-(chloroacetyl)-acetanilide |
| n-[4-(2-chloro-acetyl)-phenyl]-acetamide |
| EN300-05225 |
| Class | Description |
|---|---|
| alpha-chloroketone | A chloroketone in which the chlorine and oxo substituents are on adjacent carbon atoms. |
| acetamides | Compounds with the general formula RNHC(=O)CH3. |
| aromatic ketone | A ketone in which the carbonyl group is attached to an aromatic ring. |
| [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) |
|---|---|---|---|---|---|---|---|
| interleukin 8 | Homo sapiens (human) | Potency | 66.8242 | 0.0473 | 49.4806 | 74.9780 | AID651758 |
| acetylcholinesterase | Homo sapiens (human) | Potency | 35.5742 | 0.0025 | 41.7960 | 15,848.9004 | AID1347399 |
| Nrf2 | Homo sapiens (human) | Potency | 14.1254 | 0.0920 | 8.2222 | 23.1093 | AID624171 |
| thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 70.7946 | 0.1000 | 20.8793 | 79.4328 | AID588453 |
| pregnane X receptor | Rattus norvegicus (Norway rat) | Potency | 79.4328 | 0.0251 | 27.9203 | 501.1870 | AID651751 |
| hypoxia-inducible factor 1 alpha subunit | Homo sapiens (human) | Potency | 15.2299 | 3.1890 | 29.8841 | 59.4836 | AID1224846; AID1224894 |
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 11.6870 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 23.0999 | 0.0041 | 10.8903 | 31.5287 | AID504466 |
| TDP1 protein | Homo sapiens (human) | Potency | 1.7589 | 0.0008 | 11.3822 | 44.6684 | AID686978; AID686979 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 25.8721 | 0.0007 | 14.5928 | 83.7951 | AID1259368; AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 43.6303 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID588515; AID743035; AID743036; AID743042; AID743053; AID743054; AID743063 |
| thioredoxin glutathione reductase | Schistosoma mansoni | Potency | 12.5893 | 0.1000 | 22.9075 | 100.0000 | AID485364 |
| Smad3 | Homo sapiens (human) | Potency | 35.4813 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
| aldehyde dehydrogenase 1 family, member A1 | Homo sapiens (human) | Potency | 0.0447 | 0.0112 | 12.4002 | 100.0000 | AID1030 |
| hypoxia-inducible factor 1, alpha subunit (basic helix-loop-helix transcription factor) | Homo sapiens (human) | Potency | 25.1189 | 0.0013 | 7.7625 | 44.6684 | AID2120 |
| estrogen receptor 2 (ER beta) | Homo sapiens (human) | Potency | 24.3365 | 0.0006 | 57.9133 | 22,387.1992 | AID1259377 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 64.0829 | 0.0010 | 22.6508 | 76.6163 | AID1224838; AID1224839; AID1224893 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 47.1309 | 0.0002 | 14.3764 | 60.0339 | AID588533; AID720691; AID720692 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 56.5262 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159553; AID1159555 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 18.1902 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531; AID588544 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 32.7688 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| farnesoid X nuclear receptor | Homo sapiens (human) | Potency | 43.5150 | 0.3758 | 27.4851 | 61.6524 | AID588526; AID743217; AID743220; AID743239 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 38.9771 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982; AID720659 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 49.3538 | 0.0002 | 29.3054 | 16,493.5996 | AID1259244; AID1259248; AID588513; AID588514; AID743069; AID743075; AID743078; AID743079; AID743080; AID743091 |
| bromodomain adjacent to zinc finger domain 2B | Homo sapiens (human) | Potency | 89.1251 | 0.7079 | 36.9043 | 89.1251 | AID504333 |
| P53 | Homo sapiens (human) | Potency | 39.8107 | 0.0731 | 9.6858 | 31.6228 | AID504706 |
| peroxisome proliferator-activated receptor delta | Homo sapiens (human) | Potency | 32.8177 | 0.0010 | 24.5048 | 61.6448 | AID588534; AID588535; AID743215 |
| peroxisome proliferator activated receptor gamma | Homo sapiens (human) | Potency | 32.5850 | 0.0010 | 19.4141 | 70.9645 | AID588536; AID588537; AID743094; AID743140; AID743191 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 29.1527 | 0.0237 | 23.2282 | 63.5986 | AID588541; AID588543; AID743222; AID743223 |
| IDH1 | Homo sapiens (human) | Potency | 29.0929 | 0.0052 | 10.8652 | 35.4813 | AID686970 |
| heat shock 70kDa protein 5 (glucose-regulated protein, 78kDa) | Homo sapiens (human) | Potency | 28.1838 | 0.0165 | 25.3078 | 41.3999 | AID602332 |
| aryl hydrocarbon receptor | Homo sapiens (human) | Potency | 57.2825 | 0.0007 | 23.0674 | 1,258.9301 | AID651777; AID743085; AID743122 |
| cytochrome P450, family 19, subfamily A, polypeptide 1, isoform CRA_a | Homo sapiens (human) | Potency | 6.8590 | 0.0017 | 23.8393 | 78.1014 | AID743083 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 61.4415 | 0.0016 | 28.0151 | 77.1139 | AID1259385 |
| activating transcription factor 6 | Homo sapiens (human) | Potency | 10.9635 | 0.1434 | 27.6121 | 59.8106 | AID1159516 |
| nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_a | Homo sapiens (human) | Potency | 37.3485 | 19.7391 | 45.9784 | 64.9432 | AID1159509 |
| v-jun sarcoma virus 17 oncogene homolog (avian) | Homo sapiens (human) | Potency | 24.5442 | 0.0578 | 21.1097 | 61.2679 | AID1159526 |
| Histone H2A.x | Cricetulus griseus (Chinese hamster) | Potency | 65.2390 | 0.0391 | 47.5451 | 146.8240 | AID1224845; AID1224896 |
| cellular tumor antigen p53 isoform a | Homo sapiens (human) | Potency | 31.6228 | 0.3162 | 12.4435 | 31.6228 | AID902 |
| chromobox protein homolog 1 | Homo sapiens (human) | Potency | 44.6684 | 0.0060 | 26.1688 | 89.1251 | AID540317 |
| thyroid hormone receptor beta isoform a | Homo sapiens (human) | Potency | 38.1519 | 0.0100 | 39.5371 | 1,122.0200 | AID588545; AID588547 |
| potassium voltage-gated channel subfamily H member 2 isoform d | Homo sapiens (human) | Potency | 28.1838 | 0.0178 | 9.6374 | 44.6684 | AID588834 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 9.2984 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| histone deacetylase 9 isoform 3 | Homo sapiens (human) | Potency | 33.6929 | 0.0376 | 17.0823 | 61.1927 | AID1259364; AID1259388 |
| heat shock protein beta-1 | Homo sapiens (human) | Potency | 10.8703 | 0.0420 | 27.3789 | 61.6448 | AID743210; AID743228 |
| nuclear factor NF-kappa-B p105 subunit isoform 1 | Homo sapiens (human) | Potency | 19.9526 | 4.4668 | 24.8329 | 44.6684 | AID651749 |
| serine/threonine-protein kinase PLK1 | Homo sapiens (human) | Potency | 5.3233 | 0.1683 | 16.4040 | 67.0158 | AID720504 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 45.2600 | 0.0006 | 27.2152 | 1,122.0200 | AID720636; AID743202; AID743219 |
| urokinase-type plasminogen activator precursor | Mus musculus (house mouse) | Potency | 12.5893 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
| plasminogen precursor | Mus musculus (house mouse) | Potency | 12.5893 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
| urokinase plasminogen activator surface receptor precursor | Mus musculus (house mouse) | Potency | 12.5893 | 0.1585 | 5.2879 | 12.5893 | AID540303 |
| nuclear receptor ROR-gamma isoform 1 | Mus musculus (house mouse) | Potency | 13.4270 | 0.0079 | 8.2332 | 1,122.0200 | AID2546; AID2551 |
| lethal factor (plasmid) | Bacillus anthracis str. A2012 | Potency | 12.5893 | 0.0200 | 10.7869 | 31.6228 | AID912 |
| DNA dC->dU-editing enzyme APOBEC-3F isoform a | Homo sapiens (human) | Potency | 5.6234 | 0.0259 | 11.2398 | 31.6228 | AID602313 |
| Voltage-dependent calcium channel gamma-2 subunit | Mus musculus (house mouse) | Potency | 34.3762 | 0.0015 | 57.7890 | 15,848.9004 | AID1259244 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 26.3537 | 0.0023 | 19.5956 | 74.0614 | AID651631; AID651743; AID720552 |
| Glutamate receptor 2 | Rattus norvegicus (Norway rat) | Potency | 34.3762 | 0.0015 | 51.7393 | 15,848.9004 | AID1259244 |
| Nuclear receptor ROR-gamma | Homo sapiens (human) | Potency | 9.4392 | 0.0266 | 22.4482 | 66.8242 | AID651802 |
| TAR DNA-binding protein 43 | Homo sapiens (human) | Potency | 10.0000 | 1.7783 | 16.2081 | 35.4813 | AID652104 |
| ATPase family AAA domain-containing protein 5 | Homo sapiens (human) | Potency | 24.3365 | 0.0119 | 17.9420 | 71.5630 | AID651632; AID720516 |
| Ataxin-2 | Homo sapiens (human) | Potency | 24.3365 | 0.0119 | 12.2221 | 68.7989 | AID651632 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| 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. |
| AID504812 | Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| 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. |
| 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. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID504810 | Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign | 2010 | Endocrinology, Jul, Volume: 151, Issue:7 | A small molecule inverse agonist for the human thyroid-stimulating hormone receptor. |
| [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 (20.00) | 29.6817 |
| 2010's | 3 (60.00) | 24.3611 |
| 2020's | 1 (20.00) | 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 (12.56) 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 | 5 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||