226883-77-8

Basic information

• Product Name: 1-benzyl-5-chloro-1H-indole-3-carbaldehyde
• Synonyms: 1-benzyl-5-chloro-1H-indole-3-carbaldehyde
• CAS NO: 226883-77-8
• Molecular Formula: C₁₆H₁₂ClNO
• Molecular Weight: 269.72558
• Mol File: 226883-77-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-benzyl-5-chloro-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-benzyl-5-chloro-1H-indole-3-carbaldehyde(226883-77-8)
• EPA Substance Registry System: 1-benzyl-5-chloro-1H-indole-3-carbaldehyde(226883-77-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 226883-77-8(Hazardous Substances Data)

Usage

Appearance

Yellow to brown solid the compound has a solid state and exhibits a yellow to brown color.

Strong odor

The compound is known to have a pungent and powerful smell.

Common use

Organic synthesis and as a reagent in chemical reactions it is frequently used as a starting material or intermediate in the synthesis of other compounds, as well as a reagent to facilitate various chemical reactions.

Potential applications

Pharmaceutical and agrochemical industries the compound may be used in the development of new drugs or agrochemicals due to its unique properties and reactivity.

Unique properties

The presence of the indole ring, chlorine atom, and formyl group (-CHO) in its structure contribute to its distinctive chemical properties.

Functional group reactivity

The compound is known for its reactivity due to the presence of the indole ring, chlorine atom, and formyl group, which can undergo various chemical reactions.

Biological activities

Antimicrobial and antioxidant properties 1-benzyl-5-chloro-1H-indole-3-carbaldehyde has been studied for its potential to exhibit antimicrobial (fighting against microorganisms) and antioxidant (protecting cells from damage by neutralizing free radicals) activities.

Versatile applications

The compound is of interest in various fields of chemistry and biology, including organic synthesis, pharmaceuticals, agrochemicals, and biological research.

Upstream product

• 827-01-0 5-chloro-1H-indole-3-carboxaldehyde 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 172596-64-4 1-benzyl-5-chloroindole-3-carboxylic acid 
• 1207733-67-2 C₂₀H₁₇ClN₄O 
• 1207615-67-5 (Z)-5-((1-benzyl-5-chloro-1H-indol-3-yl)methylene)imidazolidine-2,4-dione 
• 1207615-77-7 C₂₀H₁₄ClN₃O₃ 
• 1360583-82-9 dimethyl 2-(1-benzyl-5-chloro-1H-indol-3-yl)cyclopropane-1,1-dicarboxylate 
• 1360583-76-1 dimethyl 2-[(1-benzyl-5-chloro-1H-indol-3-yl)methylene]malonate 

Relevant articles and documents

Catalytic Enantioselective Diels-Alder Reactions of Benzoquinones and Vinylindoles with Chiral Magnesium Phosphate Complexes

Tetrahydrocarbazole and its derivatives have received much attention due to the prevalence of this scaffold in natural products and their use in organic synthesis. We have developed a Diels-Alder reaction of benzoquinones and 3-vinylindoles catalyzed by c

Microwave assisted synthesis and in vitro cytotoxicities of substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones against human tumor cell lines

The synthesis of several novel substituted (Z)-2-amino-5-(1-benzyl-1H-indol-3-yl)methylene-1-methyl-1H-imidazol-4(5H)-ones structurally related to aplysinopsin have been carried out under microwave irradiation and conventional heating methods. The analogs 3a, 3b, 3d-3g, 3k and 3l were evaluated for their in vitro cytotoxic activity against an NCI 60 human tumor cell line panel. Compound 3f exhibited good growth inhibitory properties against all but four of the human cancer cell lines examined, and afforded LC50 values a cytotoxic agent. Thus, the aplysinopsin analog 3f was regarded as a useful lead compound for further structural optimization.

Novel substituted (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-diones and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-triones as potent radio-sensitizing agents

A series of (Z)-5-((N-benzyl-1H-indol-3-yl)methylene)imidazolidine-2,4-dione (9a-9m) and 5-((N-benzyl-1H-indol-3-yl)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione (10a-10i) derivatives that incorporate a variety of aromatic substituents in both the indole and N-benzyl moieties have been synthesized. These analogs were evaluated for their radiosensitization activity against the HT-29 cell line. Three analogs, 10a, 10b, and 10c were identified as the most potent radiosensitizing agents.

Aplysinopsin analogs: Synthesis and anti-proliferative activity of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-diones

A series of substituted (Z)-5-(N-benzylindol-3-ylmethylene)imidazolidine-2,4-dione (3) analogs structurally related to aplysinopsin, and that incorporate a variety of substituents in both the indole and N-benzyl moieties have been synthesized under microwave irradiation and conventional heating methods These analogs were evaluated for their anti-proliferative activity against MCF-7 and MDA-231 breast cancer cell lines, and A549 and H460 lung cancer cell lines. Two analogs, 3f and 3j had IC50 values of 4.4 and 5.2 μM, respectively, compared to 5-fluorouracil (IC50 = 15.2 μM) against MCF-7 cells.

Indole amide derivatives: Synthesis, structure-activity relationships and molecular modelling studies of a new series of histamine H1-receptor antagonists

A number of indole amide derivatives bearing a basic side chain, in which the indole ring replaces the isoster benzimidazole nucleus typical of some well-known antihistamines, were prepared and tested for their H1- antihistaminic activity. The 1-benzyl-3-indolecarboxamides 32-42 showed antihistaminic (H1) activity (pA2 6-8); the 3-indolylglyoxylylamides 7-16 and the 2-indolecarboxamides 48-56 showed little or no activity. Insertion of the basic side chain of the active 3-indolecarboxamide derivatives into a piperazine ring (compounds 57-59) led to a dramatic loss of activity. All the active compounds proved to be competitive antagonists, since the values of the regression slope were not statistically different from 1. The most active compounds, 32, 33, 38-41, were also tested both in vitro for their anticholinergic activity and in vivo for their ability to antagonize histamine-induced cutaneous vascular permeability in rats. The biological results and the structure-activity relationships of the novel compounds are discussed in the light of molecular modelling studies, taking the molecule of astemizole as a model, and referring to proposed H1-receptor pharmacophore models.