17630-76-1

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloroisatin is used as a reagent for the synthesis of Schiff bases, which are essential in the development of various pharmaceutical compounds. The formation of these bases through the reaction with 2-methyl-4-nitroaniline or 4-amino-4,5-dihydro-1H-1,2,3-triazole-5-one contributes to the creation of new drug candidates with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-Chloroisatin serves as a valuable intermediate for the production of various organic compounds. Its ability to form Schiff bases with different amino compounds allows for the development of a wide range of chemical products, including those with potential applications in materials science, agrochemicals, and other industries.

InChI:InChI=1/C8H4ClNO2/c9-4-1-2-6-5(3-4)7(11)8(12)10-6/h1-3H,(H,10,11,12)

Upstream product

• 128-09-6 N-chloro-succinimide 
• 91-56-5 indole-2,3-dione 
• 861381-87-5 5-chloro-2-methoxy-indol-3-one 
• 64-17-5 ethanol 
• 65798-06-3 N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide 
• 705288-14-8 5-chloro-2-nitro-mandelonitrile 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 85124-16-9 5-Chloroisatin 3-oxime 
• 201230-82-2 carbon monoxide 
• 7647-01-0 hydrogenchloride 
• 7722-84-1 dihydrogen peroxide 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 64-19-7 acetic acid 

Downstream Products

• 577-74-2 6-chloro-2-(3-fluoro-4-methoxy-phenyl)-3-methyl-quinoline-4-carboxylic acid 
• 391-21-9 6-chloro-2-(2-fluoro-5-methyl-phenyl)-quinoline-4-carboxylic acid 
• 386-08-3 6-chloro-2-(2-fluoro-5-methyl-phenyl)-3-phenyl-quinoline-4-carboxylic acid 
• 126088-20-8 6-chloro-2-(4-chlorophenyl)quinoline-4-carboxylic acid 
• 62482-28-4 6-chloroquinoline-2,4-dicarboxylic acid 
• 856177-13-4 6-chloro-3-hydroxy-quinoline-4-carboxylic acid 
• 6633-62-1 6-chloro-2-phenylquinoline-4-carboxylic acid 
• 103914-61-0 6-chloro-2-(p-tolyl)quinoline-4-carboxylic acid 
• 122262-53-7 6-chloro-2-(4-chloro-phenyl)-3-hydroxy-quinoline-4-carboxylic acid 
• 60434-13-1 5-chloro-1-methylindoline-2, 3-dione 
• 854867-53-1 6-chloro-2-(4-hydroxy-phenyl)-3-methyl-quinoline-4-carboxylic acid 

Relevant academic research and scientific papers

Sio2 mediated reaction of isatin with N-halosaccharins: A regiospecific preparation of 5-haloisatins

N-halosaccharins (5 mmol) react smoothly at room temperature with isatin (5 mmol) in the presence of SiO2 (5 g) to produce specifically the 5-halo derivative. Using this procedure, 5-chloroisatin was obtained in 48% purified yield (72 h), 5-bromoisatin in 58% (12 h) and 5-iodoisatin in 80% (8 h).

A Facile Synthesis of Novel Isatinspirooxazine Derivatives and Potential in vitro Anti-Proliferative Activity

Novel isatinspirooxazine derivatives were designed and synthesized as potential anti-proliferative agents. The new compounds were obtained from aldol condensation reactions between isatin and 3-(hydroxyimino)butan-2-one in the presence of an organic base in order to generate an aldol adduct, followed by cyclization in trifluoroacetic acid, providing the desired isatinspirooxazines in 30 to 80percent yield. All the synthesized compounds, including the starting material and the synthetic intermediates, were tested for in vitro anti-proliferative activity against cell lines MCF-7 and MDA-MB231 (breast cancer) and A549 (lung cancer), highlighting the compound 4-methyl,5'-methyl-spiro[(5-aza-4-eno-3-one-cyclohexane)-1,3'-(1H-indol-one)] with an IC50 (half maximal inhibitory concentration) = 0.34 μM, more potent than the reference drug, doxorubicin (IC50 = 1.88 μM), in breast cancer line MDA-MB231.

Study on synthesis of some substituted N-propargyl isatins by propargylation reaction of corresponding isatins using potassium carbonate as base under ultrasound- and microwave-assisted conditions

Substituted N-propargyl isatins were synthesized by SN2 reaction of corresponding substituted isatins with propargyl bromide in the presence of anhydrous K2CO3 as base. We reported about study on systematically synthesis of these compounds using heating procedures under different reaction conditions, including microwave-assisted heating conditions at power of 100?W (Procedure A), conventional heating conditions in water bath at 50?°C in acetonitrile (Procedure B), and conventional heating conditions in water bath at 50?°C in DMF (procedure C). The best procedure A was deduced based on the investigations on the reaction conditions. Almost all substituted N-propargyl isatins were new, except compounds with R of H, 5-Me, 5-Cl and 5-Br substituents. The structures of the obtained compounds were confirmed by the modern spectroscopic methods.

Synthesis and evaluation of tryptanthrins as antitumor agents

Here, an efficient and convenient method has been developed for the rapid preparation of N-substituted tryptanthrin analogues through the reaction of tryptanthrins and secondary amines under mild reaction conditions. All compounds were tested for their anti-tumor activity in cancer cell lines by MTT assay. The results showed that some of them exhibited anti-tumor activity against human tumor cell lines A549, HCT116, MDA-MB-231 with IC50 mean values at a low micromolar level. In particular, compound 3b induced G2/S cell cycle arrest and apoptosis in A549 cells dose-dependently.

R4NHal/NOHSO4: A Usable System for Halogenation of Isoxazoles, Pyrazoles, and beyond

A new convenient and versatile halogenating system (R4NHal/NOHSO4), giving straightforward and general access to halogenated 3,5-diaryl- and alkylarylisoxazoles, pyrazoles and electron-rich benzenes from the corresponding scaffolds, is suggested. The method provides excellent regioselectivity, scalability to the gram scale, and a broad scope for both aromatics and halogens. A three-step, one-pot reaction protocol was developed, and a series of 3,5-diaryl-4-haloisoxazoles has been efficiently synthesized from 1,2-diarylcyclopropanes under suggested nitrosating-halogenating conditions.

Further Studies on Triazinoindoles as Potential Novel Multitarget-Directed Anti-Alzheimer's Agents

The inadequate clinical efficacy of the present anti-Alzheimer's disease (AD) drugs and their low impact on the progression of Alzheimer's disease in patients have revised the research focus from single targets to multitarget-directed ligands. A novel series of substituted triazinoindole derivatives were obtained by introducing various substituents on the indole ring for the development of multitarget-directed ligands as anti-AD agents. The experimental data indicated that some of these compounds exhibited significant anti-AD properties. Among them, 8-(piperidin-1-yl)-N-(6-(pyrrolidin-1-yl)hexyl)-5H-[1,2,4]triazino[5,6-b]indol-3-amine (60), the most potent cholinesterase inhibitor (AChE, IC50 value of 0.32 μM; BuChE, IC50 value of 0.21 μM), was also found to possess significant self-mediated Aβ1-42 aggregation inhibitory activity (54% at 25 μM concentration). Additionally, compound 60 showed strong antioxidant activity. In the PAMPA assay, compound 60 exhibited blood-brain barrier penetrating ability. An acute toxicity study in rats demonstrated no sign of toxicity at doses up to 2000 mg/kg. Furthermore, compound 60 significantly restored the cognitive deficits in the scopolamine-induced mice model and Aβ1-42-induced rat model. In the in silico ADMET prediction studies, the compound satisfied all the parameters of CNS acting drugs. These results highlighted the potential of compound 60 to be a promising multitarget-directed ligand for the development of potential anti-AD drugs.

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides

Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.

1-benzylisatin derivative as well as synthesis method and application thereof

The invention relates to a 1-benzylisatin derivative as well as a synthesis method and application thereof, belongs to the technical field of medicines, and relates to a general formula (I) in which R1, R2 and R3 are different substituents. The invention discloses structures of the compounds, a synthesis method of the compounds, inhibitory activity of acetylcholin esterase and inhibitory activityof histone deacetylase 6; and the compounds can be further developed into drugs for treating Alzheimer's disease.

A rhodium(ii) catalysed domino synthesis of azepino fused diindoles from isatin tethered: N -sulfonyl-1,2,3-triazoles and indoles

An efficient and convenient protocol for the synthesis of a novel class of azepino fused diindoles from isatin tethered N-sulfonyl-1,2,3-triazoles and indoles has been disclosed. The reaction proceeds via denitrogenative aza-vinyl rhodium carbene formation to give a carbonyl ylide, which with indole results in 1,3-dipolar cycloaddition followed by sequential semipinacol rearrangement/ring expansion/oxidation to produce azepino fused diindoles. The reaction shows a broad substrate scope giving up to 81% yield. Furthermore, reversible catalytic hydrogenation and photophysical studies were carried out to demonstrate the application of these molecules.

Synthesis and Ameliorative Effect of Isatin–Mesalamine Conjugates on Acetic Acid-induced Colitis in Rats

A series of new isatin–mesalamine conjugates (9a–g) were synthesized via conjugation of isatin (3a) and its derivatives (3b–3d, 4, 5, and 6) with mesalamine (7) by using chloroacetyl chloride as a bifunctional linker. Compounds 3a–3d were prepared by employing Sandmeyer reaction. Compounds 4, 5, and 6 were obtained from isatin (3a) via previously reported methods. The synthesized compounds were characterized by IR, mass, 1H NMR, and 13C NMR spectral techniques. Synthesized compounds (3a–d, 4, 5, 6, and 9a–g) were evaluated for in vitro antioxidant activity by DPPH assay method using ascorbic acid as standard. Hybrids 9b (IC50?=?368.6?±?3.5?μM) and 9f (IC50?=?335.1?±?2.9?μM) showed better antioxidant activity than its parent compounds such as 3a (IC50?=?556.8?±?2.9?μM), 5 (IC50?=?511.9?±?3.6?μM), and 7 (IC50?=?768.9?±?2.7?μM). Acetic acid-induced ulcerative colitis in rat model was chosen to examine the antioxidant potential of the synthesized hybrids (9b and 9f) in the amelioration of ulcerative colitis. Colonic myeloperoxidase and malondialdehyde enzymes were used as biomarkers of anti-ulcerative colitis activity. In the present study, hybrids 9b and 9f reduced the levels of colonic myeloperoxidase and malondialdehyde enzymes significantly (p??0.05) when compared with control (colitic), at a dose (0.03?mM/12.5?mg/kg b.w. p.o.) (50%) less than that of its parent moieties mesalamine (0.16?mM/25?mg/kg) and isatin (0.16?mM/25?mg/kg). Thus, the molecular hybridization was proved to be significant in enhancing the activity of hybrids 9b and 9f by reducing the dose.