91-56-5 Usage
Description
Isatin is an organic compound with the chemical formula C8H5NO2, featuring a core structure of an oxindole. It is a versatile molecule with a wide range of applications in various fields, including pharmaceuticals, dyes, chemical analysis, and as a reactant in organic synthesis.
Uses
Used in Pharmaceutical Industry:
Isatin is used as a medicine intermediate for the production of drugs such as quinophan. It also serves as an endogenous monoamine oxidase (MAO) inhibitor, playing a role in stress and anxiety management. Additionally, it inhibits enzymes like alkaline phosphatase (ALP) and nitric oxide (NO)-stimulated soluble guanylate cyclase.
Used in Dye Industry:
Isatin is utilized as a dye intermediate for the production of dye disperse Yellow E-3G and in the manufacture of vat dyes.
Used in Chemical Analysis:
Isatin is used as a reagent for the determination of copper ions, mercaptans, thiophene, and indoxyl-beta-glucoside. It also acts as a chromatographic spray reagent for amino acid detection.
Used in Organic Synthesis:
Isatin is employed as a reactant in the preparation of various compounds, such as phthalazinone derivatives, spirooxindole derivatives, agents against multidrug-resistant cells expressing P-glycoprotein, thiazolidinones spiro-fused to indolin-2-ones as potent and selective inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase B, and triazole-isatine compounds as potential antibacterial and antifungal agents. It also participates in cascade reactions with heterocyclic ketene aminals and Knoevenagel condensation reactions.
Used in Pigment Preparation:
Isatin serves as a reference material in the preparation of indigo and Maya blue, responsible for the yellow color exhibited by the "Maya Yellow" pigment.
Isatin
Isatin, is also known as indenedione, indole quinone. Its chemical name is indol(o)-2,3-dione,it is orange-red monoclinic prism crystal at room temperature. Bitter. The molecular weight is147.13. Melting point 203.5 ℃ (Part sublimation). Dissolved in water, hot ethanol, benzene, acetone, ether-soluble. Soluble in boiling alcohol, soluble in ether and boiling water? and it is reddish brown , soluble in caustic and solution is purple, it changes to yellow after placement. Its alcohol solution?? has a very unpleasant odor. Weakly alkaline, it can salify with a perchlorate.
Above information of is edited by Andy from lookchem (2016-11-19).
production method
Condensation of chloral and aniline? can generate? oximide-acetanilide, and then by cyclization, hydrolysis , isatin is obtained.
Synthesis Reference(s)
The Journal of Organic Chemistry, 55, p. 197, 1990 DOI: 10.1021/jo00288a033
Flammability and Explosibility
Nonflammable
Biological Activity
isatin is a monoamine oxidase inhibitor.monoamine oxidase inhibitors have been used as therapies for the treatment of depression, particularly in treating atypical depression. monoamine oxidase inhibitors are also used in the treatment of parkinson's disease and other disorders.
in vitro
previous study found that isatin treatment at 1-400 μm for 24h could induce a significant dose-dependent increase in mtt metabolism by sh-sy5y cells, which was not due to the increase in cell division. in addition, isatin at the higher concentrations was able to trigger cell death, though mtt metabolism was still increased, indicating that the surviving cells were hypermetabolic. with a longer treatment, isatin was found to cause cell death in a dose-dependent manner, and the predominant mode of cell death was apoptosis at lower concentrations, while at the highest concentration increasing numbers of necrotic cells were also observed [1].
in vivo
animal study showed that the motor activity of japanese encephalitis virus (jev)-induced rats receiving isatin was improved significantly when compared with that of untreated jev-infected rats. in addition, isatin was able to prevent the decrease in striatal da levels in jev-rats and the increased turnover of dopamine (da) (dopac/da) induced by jev was significantly inhibited by isatin. such results indicated that the exogenously administered isatin was able to improve jev-induced parkinsonism via increasing the striatum da concentrations [2].
IC 50
15 μm
Purification Methods
Crystallise isatin from amyl alcohol and sublime it at 180o/1mm. In aqueous NaOH the ring opens to yield sodium o-aminobenzoylformate. [Beilstein 21 II 327, 567, 21 III/IV 4981, 21/10 V 221.]
references
[1] igosheva n,lorz c,o'conner e,glover v,mehmet h. isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. neurochem int.2005 aug;47(3):216-24.[2] hamaue n,minami m,terado m,hirafuji m,endo t,machida m,hiroshige t,ogata a,tashiro k,saito h,parvez sh. 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. neurotoxicology.2004 jan;25(1-2):205-13.
Check Digit Verification of cas no
The CAS Registry Mumber 91-56-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 1 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 91-56:
(4*9)+(3*1)+(2*5)+(1*6)=55
55 % 10 = 5
So 91-56-5 is a valid CAS Registry Number.
InChI:InChI:1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)
91-56-5Relevant articles and documents
Microwave-Assisted Synthesis, Molecular Docking Studies and Biological Evaluation of Benzothiazole Containing Novel Indole Derivatives
Pandian, P.,Rajkamal, B.,Sultana, Shaheen
, p. 2755 - 2761 (2021/10/25)
The synthesis of novel indole derivatives 4a-o using a microwave assisted method via Schiff’s base and Mannich base reaction mechanism was described. Compounds 3a-c were synthesized via reaction of 2-amino benzothiazole with substituted isatin by Schiff base reaction mechanism. Also, indole derivatives 4a-o were synthesized via reaction of compounds 3a-c with substituted benzaldehydes by Mannich base reaction. The biological potentials of the newly synthesized indole derivatives were evaluated for their anthelmintic activity and in vitro anticancer activity by MTT assay. The anticancer activity results suggested that indole derivatives 4c-o have activity against MCF-7 and SKOV3 cells in comparison with doxorubicin as standard drug. Furthermore, the molecular docking studies of these novel derivatives of indole showed good agreement with the biological results when their binding pattern and affinity towards the active site of EGFR was also investigated.
Design, synthesis, and in vitro and in vivo anti-angiogenesis study of a novel vascular endothelial growth factor receptor-2 (VEGFR-2) inhibitor based on 1,2,3-triazole scaffold
Wang, De-pu,Liu, Kai-li,Li, Xin-yang,Lu, Guo-qing,Xue, Wen-han,Qian, Xin-hua,Mohamed O, Kamara,Meng, Fan-hao
, (2020/12/21)
In the past five years, our team had been committed to click chemistry research, exploring the biological activity of 1,2,3-triazole by synthesizing different target inhibitors. In this study, a series of novel indole-2-one derivatives based on 1,2,3-triazole scaffolds were synthesized for the first time, and their inhibitory activity on vascular endothelial growth factor receptor-2 (VEGFR-2) was tested. Most of the compounds had shown promising activity in the VEGFR-2 kinase assay and had low toxicity to human umbilical vein endothelial cells (HUVECs). The compound 13d (IC50 = 26.38 nM) had better kinase activity inhibition ability than sunitinib (IC50 = 83.20 nM) and was less toxic to HUVECs. Moreover, it had an excellent inhibitory effect on HT-29 and MKN-45 cells. On the one hand, by tube formation assay, transwell, and Western blot analysis, compound 13d could inhibit VEGFR-2 protein phosphorylate on HUVECs, thereby inhibiting HUVECs migration and tube formation. In vivo study, the zebrafish model with VEGFR-2 labeling also verified that compound 13d had more anti-angiogenesis ability than sunitinib. On the other hand, molecular docking and molecular dynamics (MD) simulation results showed that compound 13d could stably bind to the active site of VEGFR-2. Based on the above findings, compound 13d could be considered an effective anti-angiogenesis drug and has more development value than sunitinib.
Cs 2CO 3-Mediated Regio- And Stereoselective Sulfonylation of 1,1-Dibromo-1-alkenes with Sodium Sulfinates
Shiri, Morteza,Salehi, Parvin,Mohammadpour, Zeinab,Salehi, Peyman,Notash, Behrouz
, p. 1149 - 1156 (2020/10/21)
A highly selective synthesis of (Z)-1-bromo-1-sulfonyl alkenes via Cs 2CO 3-promoted sulfonylation of 1,1-dibromo-1-alkenes with sodium sulfinates is described. Notably, using excess amounts of Cs 2CO 3and sodium sulfinate in such a reaction regenerated the parent aldehyde. Interestingly, the reaction of 1-(2,2-dibromovinyl)-2-nitrobenzene in the presence of sulfinates and Cs 2CO 3produced isatin. The Sonogashira cross coupling of synthesized (Z)-1-bromo-1-sulfonyl alkenes with phenylacetylene gave selectively the corresponding sulfonylalkynyl alkenes.