Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H5NO2 |
| Molecular Weight | 147.1308 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=C1NC2=C(C=CC=C2)C1=O
InChI
InChIKey=JXDYKVIHCLTXOP-UHFFFAOYSA-N
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
| Molecular Formula | C8H5NO2 |
| Molecular Weight | 147.1308 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Isatin (1H-indole-2,3-dione) is a naturally occurring
heterocycle that was first synthesised by Erdmann and
Laurent in 1840. Isatin possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro. Isatin is an endogenous monoamine oxidase (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Lanthanum(III) and praseodymium(III) complexes with isatin thiosemicarbazones. | 2005-09 |
|
| Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. | 2005-08 |
|
| Isatin-Schiff base copper(II) complexes and their influence on cellular viability. | 2005-07 |
|
| Synthesis and evaluation of isatin derivatives as effective SARS coronavirus 3CL protease inhibitors. | 2005-06-15 |
|
| Total synthesis of nigellicine and nigeglanine hydrobromide. | 2005-06-09 |
|
| Enzymatic properties of a member (AKR1C19) of the aldo-keto reductase family. | 2005-06 |
|
| TiCl4 catalyzed tandem construction of C-C and C-O bonds: a simple and one-pot atom-economical stereoselective synthesis of spiro-oxindoles. | 2005-05-28 |
|
| Photoreactions of 1-acetylisatin with alkynes: regioselectivity in oxetene formation and easy access to 3-alkylideneoxindoles and dispiro[oxindole[3,2']furan[3',3' ']oxindole]s. | 2005-05-13 |
|
| Natriuretic peptide interaction with [3H]isatin binding sites in rat brain. | 2005-05-03 |
|
| Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives. | 2005-05-02 |
|
| Newer aminopyrimidinimino isatin analogues as non-nucleoside HIV-1 reverse transcriptase inhibitors for HIV and other opportunistic infections of AIDS: design, synthesis and biological evaluation. | 2005-05 |
|
| Demonstration of isoleucine 199 as a structural determinant for the selective inhibition of human monoamine oxidase B by specific reversible inhibitors. | 2005-04-22 |
|
| Combinatorial optimization of isatin-beta-thiosemicarbazones as anti-poxvirus agents. | 2005-04-21 |
|
| Metal-mediated entry to functionalized 3-substituted 3-hydroxyindolin-2-ones via regiocontrolled carbonylallylation, bromoallylation, 1,3-butadien-2-ylation, propargylation, or allenylation reactions of isatins in aqueous media. | 2005-04-15 |
|
| Parallel liquid-phase synthesis of N-substituted 6-aminosulfonyl-2-oxo-1,2-dihydroquinoline-4-carboxamide and 6-aminosulfonylquinoline-4-carboxamide derivatives. | 2005-03-15 |
|
| Biological activities of isatin and its derivatives. | 2005-03 |
|
| A novel one-pot synthesis of some new interesting pyrrole derivatives. | 2005-02-18 |
|
| In vivo effects of isatin on rat platelet eicosanoids. | 2005-02 |
|
| Antimicrobial and mutagenic properties of organotin(IV) complexes with isatin and N-alkylisatin bisthiocarbonohydrazones. | 2005-02 |
|
| [The effect of long-term administration of isatin and himantan to mice on sensitivity of brain monoamine oxidase B to inhibition by deprenyl in vivo and in vitro]. | 2005-01-05 |
|
| Protein engineering of toluene ortho-monooxygenase of Burkholderia cepacia G4 for regiospecific hydroxylation of indole to form various indigoid compounds. | 2005-01 |
|
| New anticonvulsant agents. | 2005 |
|
| Identification of indigoid dyes in natural organic pigments used in historical art objects by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry. | 2004-12 |
|
| Design, synthesis and biological evaluation of novel non-nucleoside HIV-1 reverse transcriptase inhibitors with broad-spectrum chemotherapeutic properties. | 2004-11-15 |
|
| An isatin-beta-thiosemicarbazone-resistant vaccinia virus containing a mutation in the second largest subunit of the viral RNA polymerase is defective in transcription elongation. | 2004-10-22 |
|
| Isatin-derived antibacterial and antifungal compounds and their transition metal complexes. | 2004-10 |
|
| Atrial natriuretic peptide modulates the hyperpolarization-activated current (If) in human atrial myocytes. | 2004-08-15 |
|
| Local injection of receptor tyrosine kinase inhibitor MAE 87 reduces retinal neovascularization in mice. | 2004-07-15 |
|
| 2,2'-Pyridylisatogen tosylate antagonizes P2Y1 receptor signaling without affecting nucleotide binding. | 2004-07-15 |
|
| Comparison of gene expression patterns between 2,3,7,8-tetrachlorodibenzo-p-dioxin and a natural arylhydrocarbon receptor ligand, indirubin. | 2004-07 |
|
| Generation of new protein kinase inhibitors utilizing cytochrome p450 mutant enzymes for indigoid synthesis. | 2004-06-03 |
|
| Low-molecular-weight, biologically active compounds from marine Pseudoalteromonas species. | 2004-06 |
|
| Propargylic sulfones possessing a 2-nitroimidazole function: novel hypoxic-cell radiosensitizers with intracellular non-protein thiol depletion ability. | 2004-05-17 |
|
| A microtitre format assay for proline in human serum or plasma. | 2004-05 |
|
| Bremazocine increases C-type natriuretic peptide levels in aqueous humor and enhances outflow facility. | 2004-05 |
|
| Superoxide converts indigo carmine to isatin sulfonic acid: implications for the hypothesis that neutrophils produce ozone. | 2004-04-30 |
|
| Inhibition of brain mitochondrial monoamine oxidases by the endogenous compound 5-hydroxyoxindole. | 2004-03-01 |
|
| Anticonvulsant activity of Schiff bases of isatin derivatives. | 2004-03 |
|
| Electrogenerated chemiluminescence reaction of lucigenin with isatin at a platinum electrode. | 2004-02-26 |
|
| Effect of acute stress and gender on isatin in rat tissues and serum. | 2004-02 |
|
| Synthesis, characterization and biological activity of Ni, Cu and Zn complexes of isatin hydrazones. | 2004-02 |
|
| Inhibition of RANTES expression by indirubin in influenza virus-infected human bronchial epithelial cells. | 2004-01-01 |
|
| Comparative study of the effects of isatin, an endogenous MAO-inhibitor, and selegiline on bradykinesia and dopamine levels in a rat model of Parkinson's disease induced by the Japanese encephalitis virus. | 2004-01 |
|
| Tribulin and endogenous MAO-inhibitory regulation in vivo. | 2004-01 |
|
| Synthesis and evaluation of isatins and thiosemicarbazone derivatives against cruzain, falcipain-2 and rhodesain. | 2003-10-20 |
|
| Synthesis, antitubercular activity and pharmacokinetic studies of some Schiff bases derived from 1-alkylisatin and isonicotinic acid hydrazide (INH). | 2003-10 |
|
| Facile one pot microwave induced solvent-free synthesis and antifungal, antitubercular screening of spiro [1,5]-benzothiazepin-2,3'[3'H]indol-2[1'H]-ones. | 2003-10 |
|
| Discovery of inhibitors that elucidate the role of UCH-L1 activity in the H1299 lung cancer cell line. | 2003-09 |
|
| Are isatin and isatoic anhydride antiaromatic and aromatic respectively? A combined experimental and theoretical investigation. | 2003-07-21 |
|
| Computer visualisation of the active site of monoamine oxidase-A by means of selective inhibitors. | 2003 |
Sample Use Guides
Rats: Isatin (100 mg/kg, i.p.) inhibited APO-induced rotations of Parkinsonian rats to 39.1+/-3.7% of the control (n=12), while it had no apparent effects on electrical stimuli-induced DA release either in normal rats or in model rats. In addition, the content of 5-hydroxytryptamine but not DA was increased in both normal rats and model rats after isatin (100 mg/kg, i.p.) was administered.
Route of Administration:
Intraperitoneal
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:03:23 GMT 2025
by
admin
on
Mon Mar 31 21:03:23 GMT 2025
|
| Record UNII |
82X95S7M06
|
| Record Status |
Validated (UNII)
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| Record Version |
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ISATIN
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7054
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DB02095
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91-56-5
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82X95S7M06
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m6418
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