24279-74-1

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the development of new drugs. Its unique structural features and reactivity make it a valuable component in the creation of complex molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2-CHLORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE serves as an intermediate in the production of crop protection products, leveraging its chemical properties to enhance the effectiveness of these products in safeguarding crops from pests and diseases.
Used in Organic Chemistry Research:
2-CHLORO-1-METHYL-1H-INDOLE-3-CARBALDEHYDE is utilized as a building block in organic chemistry for the exploration and synthesis of novel complex molecules. Its distinctive structure allows researchers to investigate new pathways and reactions, potentially leading to advancements in the field of chemical science.

InChI:InChI=1/C10H8ClNO/c1-12-9-5-3-2-4-7(9)8(6-13)10(12)11/h2-6H,1H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 5059-30-3 2-chloroindole-3-carboxaldehyde 
• 74-88-4 methyl iodide 
• 74-83-9 methyl bromide 

Downstream Products

• 136093-89-5 (4-Methoxy-phenyl)-(3-{[(E)-4-methoxy-phenylimino]-methyl}-1-methyl-1H-indol-2-yl)-amine 
• 136093-91-9 C₂₄H₁₉N₃O₄ 
• 136093-90-8 (1-Methyl-3-{[(E)-4-nitro-phenylimino]-methyl}-1H-indol-2-yl)-(4-nitro-phenyl)-amine 
• 136093-92-0 C₂₂H₂₁N₅ 
• 54778-21-1 2-chloro-1-methyl-1H-indole-3-carboxylic acid 
• 67342-12-5 2-chloro-1-methyl-1H-indole-3-carbonyl chloride 
• 29103-83-1 7-methyl-7H-benzocarbazole 
• 1093860-97-9 7-methyl-5-phenyl-7H-benzo[c]carbazole 
• 1093861-02-9 1-methyl-2-(2-phenyl-2-propenyl)indole-3-carbaldehyde 
• 136093-87-3 {1-Methyl-3-[(E)-phenyliminomethyl]-1H-indol-2-yl}-phenyl-amine 

Relevant academic research and scientific papers

BENZOFURAN-BASED N-ACYLHYDRAZONE DERIVATIVES AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

A benzofuran-based N-acylhydrazone derivative according to the present invention has an excellent anticancer effect while having low toxicity and excellent solubility, and, thus, a pharmaceutical composition comprising the derivative can be usefully used to prevent or treat a cell proliferative disorder including various cancers. To this end, the present invention provides a compound represented by chemical formula 1, a stereoisomer thereof, or a pharmaceutically acceptable salt thereof.

Synthesis and Antimicrobial Activities of Novel Quinazolinone Acylhydrazone Derivatives Containing the Indole Moiety

A series of novel quinazolinone acylhydrazone derivatives containing the indole moiety were designed, synthesized, and evaluated for their inhibition activities against some important phytopathogens in vitro. Antibacterial experiments indicated that some compounds exhibited remarkable inhibition activities against tested bacteria. Especially, the EC50 values of 7a (EC50?=?55.13?μg/mL against Xoo, EC50?=?56.92?μg/mL against Rs) demonstrated the best antibacterial activities against Xoo and Rs than the other compounds, and the control agents Bismerthiazol (EC50?=?89.80?μg/mL against Xoo) and Thiodiazole copper (EC50?=?189.52?μg/mL against Rs), moreover, compound 7o (EC50?=?50.80?μg/mL) displayed the excellent activity against Xac than the control Bismerthiazol (EC50?=?56.92?μg/mL).

Copper-catalyzed Synthesis of N-alkylated 2-(4-substituted-1H-1,2,3-triazol-1-yl)-1H-indole-3-carbaldehyde by Step-wise and One-pot Three-component Huisgen's 1,3-dipolar Cycloaddition Reaction

An efficient method for the synthesis of N-alkylated 2-(4-substituted-1H-1,2,3-triazol-1-yl)-1H-indole-3-carbaldehyde has been developed starting from oxindole and indole using Huisgen's 1,3-dipolar cycloaddition reaction of organic azides to alkynes. The effect of catalysts and solvent on these reactions has been investigated. Among all these conditions, while using CuSO4·5H2O, DMF was found to be the best system for this reaction. It could also be prepared in a one-pot three-component manner by treating equimolar quantities of halides, azides, and alkynes. The Huisgen's 1,3-dipolar cycloaddition reaction was performed using CuSO4·5H2O in DMF with easy work-up procedure.

Reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehydes with barbituric acids and 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Formation of compound with extremely short intramolecular hydrogen bond in eight-membered pseudocycle

New indolin-2-one derivatives, containing in its molecules eight-membered pseudo-cycle with unusually short intramolecular hydrogen bond in OHO-bridge have been synthesized by reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehyde with barbituric acids or 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Under the action of amines they undergo fragmentation to 5-aminomethylenebarbituric acids or 4-aminomethylenepyrazolones and 1-alkyl-1,3-dihydroindol-2-ones.

Tandem copper (Cu) catalysed N-arylation-vinylogous nitroaldol condensation of 3,5-disubstituted 4-nitropyrazoles

A tandem process involving copper catalysed N-arylation and vinylogous nitroaldol condensation is described. The reaction of 3,5-dialkyl substituted 4-nitropyrazoles and ortho-halo substituted (hetero)aryl aldehydes or ketones furnished 3-nitropyrazolo[1,5-a]quinoline and heteroaryl-fused 3-nitropyrazolo[1,5-a]pyridine derivatives in moderate to high yields.

Substituent-guided switch between C-H activation and decarboxylative cross-coupling during palladium/copper-catalyzed cascade reactions of 2-aminobenzoates with 2-haloarylaldehydes

Cascade switch: Phenanthridines, pyrazole[4,3-c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu-catalyzed reaction between potassium 2-aminobenzoates and 2-haloarylaldehydes (see scheme). Although the reactions of 2-aminobenzoates proceeded via a cascade imination/C-H functionalization, the reactions of 6-nitro-2-aminobenzoates ensued via a tandem imination/decarboxylative cross-coupling. Copyright

An efficient one-pot, three-component reaction: Synthesis of complex-annelated α-carbolines via an intramolecular [3+2]-dipolar cycloaddition reaction

Novel annelated α-carbolines have been synthesized from oxindole using three components in a one-pot procedure involving an intramolecular [3+2]-dipolar cycloaddition reaction of azides to nitriles. Georg Thieme Verlag Stuttgart ? New York.

Substituted indoles as inhibitors of poly (ADP-ribose) polymerase (PARP)

The present invention relates to a series of substituted indole derivatives of the formula I: wherein R, R1, R2, R3, R4, X and Y are as defined herein. This invention also relates to methods of making these compounds. The compounds of this invention are inhibitors of poly(adenosine 5′-diphosphate ribose) polymerase (PARP) and are therefore useful as pharmaceutical agents, especially in the treatment and/or prevention of a variety of diseases, including diseases associated with the central nervous system and cardiovascular disorders.

Aryllead(IV) reagents in synthesis: formation of the C11 quaternary center of N-methylwelwitindolinone C isothiocyanate.

The reaction of lead(IV) 4-indolyl triacetate with substituted methyl 2-oxo-1-cyclohexanecarboxylates has been investigated as a route to the natural product N-methylwelsitindolinone C isothiocyanate. Reaction of lead(IV) reagent 18 with beta-ketoester 20 affords the desired coupled material in excellent yield and diastereoselectivity. Reaction: see text.

Propenone derivatives

The present invention relates to propenone derivatives represented by the following formula (I): STR1 wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR5 (wherein Y represents S or O; and R5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R2 and R3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R2 and R3 are combined to form substituted or unsubstituted methylene or ethylene; R4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.