26960-68-9

Basic information

• Product Name: 1-benzyl-5-chloroisatin
• Synonyms: 1-benzyl-5-chloroisatin
• CAS NO: 26960-68-9
• Molecular Weight: 271.703
• Mol File: 26960-68-9.mol
• Article Data: 63

Chemical Properties

• CAS DataBase Reference: 1-benzyl-5-chloroisatin(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-chloroisatin(26960-68-9)
• EPA Substance Registry System: 1-benzyl-5-chloroisatin(26960-68-9)

Safety Data

• Hazardous Substances Data: 26960-68-9(Hazardous Substances Data)

Upstream product

• 17630-76-1 5-chloroindole 2,3-dione 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 106-47-8 4-chloro-aniline 
• 936840-09-4 benzyl(4-chloro-2-ethynylphenyl)amine 
• 620-05-3 iodomethylbenzene 
• 65798-06-3 N-(4-chlorophenyl)-2-(hydroxyimino)ethanamide 

Downstream Products

• 1379685-41-2 1-benzyl-6-chloroquinazolin-4(1H)-one 
• 38154-87-9 2-(benzylamino)-5-chlorobenzoic acid 
• 1455123-91-7 C₂₂H₁₆ClN₃OS 
• 1394951-51-9 1-benzyl-5-chloro-3-phenylindolin-2-one 
• 619319-83-4 1-benzyl-5-chloroindolin-2-one 

Relevant articles and documents

Synthesis, structural properties and potent bioactivities supported by molecular docking and DFT studies of new hydrazones derived from 5-chloroisatin and 2-thiophenecarboxaldehyde

New hydrazones were synthesized by employing a convergent synthetic methodology involving condensation of N-alkyl 5-chloroisatins with hydrazone derived from 2-thiophenecarboxaldehyde. The synthesized compounds were fully characterized using UV/Vis., Infrared, 1H and 13C NMR spectroscopies as well as single crystal X-rays diffraction analysis. Bader's theory of ‘atoms in molecules’ confirmed the existence of all nonbonding interactions. Connectivity between isomers of synthesized compounds was characterized by the distribution of critical points, isatin surfaces, and bond paths. The presence of electrostatic potential on oxygen and hydrogen atoms was evaluated by means of MEP calculations, which showed that the oxygen atom acts as nucleophilic center for electrophilic hydrogen atom. Compound 6 exhibited potent anti-oxidant potential (DPPH, ABTS, NBT) with IC50 values of 46 ± 0.72 μM/mL. These compounds were also screened for in vitro cholinesterases inhibition, where compound 6 presented effective inhibition against AChE and BChE in comparison to the standard drugs; allanzanthane and galanthamine in a dose reliant mode. The IC50 values of both compounds (6 and 7) against AChE were determined to be 20.21 ± 0.06 & 16.22 ± 0.18 μM and against BChE, as 28.01 ± 0.01 & 20.11 ± 0.12 μM, respectively. Molecular docking studies supported these results and helped to establish structure activity relationship. The results reported in this manuscript are anticipated to be beneficial for understanding the solid-state architecture of the X-ray structures of new hydrazone conjugates of 5-chloroisatin & 2-thiophenecarboxaldehyde. On the other hand their intriguing biological potentials can create quest among scientific community to further analyze such molecules for drug discovery purposes.

Rhodium-catalyzed asymmetric addition of aryl- and alkenylboronic acids to isatins

(Chemical Equation Presented) Mopping up the rhodium: A rhodium-catalyzed asymmetric addition of aryl-boronic acids to isatins has been developed to produce biologically relevant 3-aryl-3-hydroxy-2-oxindoles in high yield (see scheme). High enantioselectivity was observed with (R)-MeO-mop as a ligand, and the reaction could be extended to the addition of alkenyl groups.

Novel 2-indolinone thiazole hybrids as sunitinib analogues: Design, synthesis, and potent VEGFR-2 inhibition with potential anti-renal cancer activity

Novel 2-indolinone thiazole hybrids were designed and synthesized as VEGFR-2 inhibitors based on sunitinib, an FDA-approved anticancer drug. The proposed structures of the prepared 2-indolinone thiazole hybrids were confirmed based on their spectral data and CHN analyses. The target compounds were screened in vitro for their anti-VEGFR-2 activity. All tested compounds exhibited a potent submicromolar inhibition of VEGFR-2 kinase with IC50 values ranging from 0.067 to 0.422 μM, relative to sunitinib reference drug (IC50 = 0.075 ± 0.002 μM). Compounds 5, 15a, 15b, 17, 19c displayed excellent VEGFR-2 inhibitory activity, comparable or nearly equipotent to sunitinib. Compound 13b stood out as the most potent against VEGFR-2 showing IC50 value of 0.067 ± 0.002 μM, lower than that of sunitinib. In addition, the most potent derivatives were assessed for their anticancer activity against two renal cancer cell lines. Compound 13b (IC50 = 3.9 ± 0.13 μM) was more potent than sunitinib (IC50 = 4.93 ± 0.16 μM) against CAKI-1 cell line. Moreover, thiazole 15b displayed excellent anticancer activity against CAKI-1 cell line (IC50 = 3.31 ± 0.11 μM), superior to that of sunitinib (IC50 = 4.93 ± 0.16 μM). Thiazole 15b was also equipotent to sunitinib (IC50 = 1.23 ± 0.04 μM) against A498 cell line. Besides, compound 15b revealed a safety profile much better than that of sunitinib against normal human renal cells. Furthermore, a docking study revealed a proper fitting of the most active compounds into the ATP binding site of VEGFR-2, rationalizing their potent anti-VEGFR-2 activity.

Discovery of Isatin-Based Carbohydrazones as Potential Dual Inhibitors of Fatty Acid Amide Hydrolase and Monoacylglycerol Lipase

Using ligand-based design strategy, a set of isatin-3-carbohydrazones was designed, synthesized and evaluated for dual fatty acid amide hydrolase (FAAH) and monoacylglycerol lipase (MAGL) inhibition properties. Compound 5-chloro-N′-(5-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 b) emerged as a potent MAGL inhibitor with nanomolar activity (IC50=3.33 nM), while compound 5-chloro-N′-(1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 j) was the most potent selective FAAH inhibitor (IC50=37 nM). Compound 5-chloro-N′-(6-chloro-2-oxoindolin-3-ylidene)-2-hydroxybenzohydrazide (13 c) showed dual FAAH-MAGL inhibitory activity with an IC50 of 31 and 29 nM respectively. Enzyme kinetics studies revealed that the isatin-based carbohydrazones are reversible inhibitors for both FAAH and MAGL. Further, blood-brain permeability assay confirmed that the lead compounds (13 b, 13 c, 13 g, 13 m and 13 q) are suitable as CNS candidates. Molecular dynamics simulation studies revealed the putative binding modes and key interactions of lead inhibitors within the enzyme active sites. The lead dual FAAH-MAGL inhibitor 13 c showed significant antioxidant activity and neuroprotection in the cell-based cytotoxicity assay. In summary, the study yielded three potent FAAH/MAGL inhibitor compounds (13 b, 13 c and 13 j) with acceptable pharmacokinetic profile and thus can be considered as promising candidates for treating neurological and mood disorders.

Investigations on Anticancer Potentials by DNA Binding and Cytotoxicity Studies for Newly Synthesized and Characterized Imidazolidine and Thiazolidine-Based Isatin Derivatives

Imidazolidine and thiazolidine-based isatin derivatives (IST-01–04) were synthesized, characterized, and tested for their interactions with ds-DNA. Theoretical and experimental findings showed good compatibility and indicated compound–DNA binding by mixed

Applications of Ytterbium(II) Reagent as Grignard Reagent and Single-Electron Transfer Reagent in the Synthesis of 3-Substituted 2-Oxindoles

The use of ytterbium(II) reagent as both nucleophilic reagent and single-electron transfer reagent in the reaction of isatin derivatives with ytterbium(II) reagent is reported. From a synthetic point of view, a general, efficient, and experimentally simple one-pot method for the preparation of 3-substituted 2-oxindoles was developed.

Direct catalytic synthesis of β-(C3)-substituted pyrroles: A complementary addition to the Paal-Knorr reaction

The synthesis of β-(C3)-functionalized pyrroles is a challenging task and requires a multistep protocol. An operationally simple direct catalytic synthesis of β-substituted pyrroles has been developed. This one-pot multicomponent method combined aqueous succinaldehyde as 1,4-dicarbonyl, primary amines, and isatins to access hydroxyl-oxindole β-tethered pyrroles. Direct synthesis of the β-substituted free NH-pyrrole is the central intensity of this work. DFT-calculations and preliminary mechanism investigation support the possible reaction pathway. This journal is

Palladium catalyzed divergent cycloadditions of vinylidenecyclopropane-diesters with methyleneindolinones enabled by zwitterionic π-propargyl palladium species

A palladium-catalyzed divergent synthesis of spirooxindoles fused with a five- or a six-membered ring by a cycloaddition reaction of vinylidenecyclopropane-diesters with methyleneindolinones was disclosed. This protocol features anin situgenerated unprecedented zwitterionic π-propargyl palladium species in cycloaddition reactions and a switchable process between (3+2) and (4+2) cycloadditions by changing the phosphine ligand.

Catalytic Asymmetric Halogenation/Semipinacol Rearrangement of 3-Hydroxyl-3-vinyl Oxindoles: A Stereodivergent Kinetic Resolution Process

A highly enantioselective halogenation/semipinacol rearrangement of isatin-derived allylic alcohols has been developed with a chiral N,N′-dioxide/ScIII complex as catalyst. This strategy involved a pivotal stereodivergent kinetic resolution process and provided a facile and efficient entry to optically active halo-substituted quinolone derivatives and quinoline alkaloids with a quaternary stereocenter simultaneously under mild reaction conditions. Based on the control experiments together with kinetic studies and DFT calculations, a possible catalytic cycle was proposed to illustrate the reaction process and enantiocontrol.

Carbene-Catalyzed Enantioselective Aromatic N-Nucleophilic Addition of Heteroarenes to Ketones

The aromatic nitrogen atoms of heteroarylaldehydes are activated by carbene catalysts to react with ketone electrophiles. Multi-functionalized cyclic N,O-acetal products are afforded in good to excellent yields and optical purities. Our reaction involves the formation of an unprecedented aza-fulvene-type acylazolium intermediate. A broad range of N-heteroaromatic aldehydes and electron-deficient ketone substrates works effectively in this transformation. Several of the chiral N,O-acetal products afforded through this protocol exhibit excellent antibacterial activities against Ralstonia solanacearum (Rs) and are valuable in the development of novel agrichemicals for plant protection.