90815-02-4

Basic information

• Product Name: 1-(3,4-DICHLORO-BENZYL)-1H-INDOLE-3-CARBALDEHYDE
• Synonyms: ASISCHEM T01200;ART-CHEM-BB B014322;AKOS B014322;1-(3,4-DICHLORO-BENZYL)-1H-INDOLE-3-CARBALDEHYDE;1-[(3,4-DICHLOROPHENYL)METHYL]-1H-INDOLE-3-CARBOXALDEHYDE;1H-INDOLE-3-CARBOXALDEHYDE, 1-[(3,4-DICHLOROPHENYL)METHYL]-;ALINDA 99186;ZERENEX ZX009992
• CAS NO: 90815-02-4
• Molecular Formula: C₁₆H₁₁Cl₂NO
• Molecular Weight: 304.17
• Mol File: 90815-02-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3,4-DICHLORO-BENZYL)-1H-INDOLE-3-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-DICHLORO-BENZYL)-1H-INDOLE-3-CARBALDEHYDE(90815-02-4)
• EPA Substance Registry System: 1-(3,4-DICHLORO-BENZYL)-1H-INDOLE-3-CARBALDEHYDE(90815-02-4)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 90815-02-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(3,4-Dichloro-benzyl)-1H-indole-3-carbaldehyde is used as an intermediate in organic synthesis for the creation of various chemical products. Its reactivity and structural features allow it to be a key component in the synthesis of complex molecules.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1-(3,4-Dichloro-benzyl)-1H-indole-3-carbaldehyde is used as a starting material for the development of new drugs. Its potential applications in drug discovery make it a valuable compound for researchers working on novel therapeutic agents.
Used in Drug Development:
1-(3,4-Dichloro-benzyl)-1H-indole-3-carbaldehyde is employed as a building block in the design and synthesis of new drug candidates. Its unique properties and reactivity contribute to the development of innovative pharmaceuticals with potential therapeutic benefits.
Overall, 1-(3,4-Dichloro-benzyl)-1H-indole-3-carbaldehyde is a versatile chemical compound with a wide range of applications in organic synthesis, pharmaceutical research, and drug development. Its unique properties and potential uses make it an important compound for various scientific and industrial purposes.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 120-72-9 indole 
• 102-47-6 3,4-Dichlorophenylmethyl chloride 

Downstream Products

• 1399879-55-0 (E)-4,4'-(6-(2-((1-(3,4-dichlorobenzyl)-1H-indol-3-yl)methylene)hydrazinyl)-1,3,5-triazine-2,4-diyl)dimorpholine 
• 1399879-65-2 (E)-4,4'-(6-(2-((1-(3,4-dichlorobenzyl)-1H-indol-3-yl)methylene)hydrazinyl)pyrimidine-2,4-diyl)dimorpholine 
• 1394047-60-9 (E)-4-(2-(2-((1-(3,4-dichlorobenzyl)-1H-indol-3-yl)methylene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-thieno[3,2-d]pyrimidin-4-yl)morpholine 
• 92407-93-7 [1-(3,4-dichlorobenzyl)-1H-indol-3-yI]methanol 
• 93548-97-1 1-(3,4-Dichloro-benzyl)-1H-indole-3-carboxylic acid 

Relevant articles and documents

Synthesis, characterization, and biological evaluation of indole aldehydes containing N-benzyl moiety

The present study describes the synthesis, characterization and biological evaluation of N-benzyl indole aldehydes. The biological activities of the newly synthesized compounds were examined by investigating their antioxidant and anti-inflammatory activities. The potential of these compounds as an antioxidant was determined by 2,2-diphenylpicrylhydrazyl, Nitric oxide, Superoxide, peroxide radical scavenging methods. We found that aldehydes 4a, 4b, 4c, and 4e and shows promising in vitro DPPH scavenging antioxidant activity while aldehyde 4b and 4e show good in vitro anti-inflammatory activity.

Discovery and synthesis of novel indole derivatives-containing 3-methylenedihydrofuran-2(3H)-one as irreversible LSD1 inhibitors

Lysine-specific demethylase 1 (LSD1), demethylase against mono- and di - methylated histone3 lysine 4, has emerged as a promising target in oncology. More specifically, it has been demonstrated as a key promoter in acute myeloid leukemia (AML), and several LSD1 inhibitors have already entered into clinical trials for the treatment of AML. In this paper, a series of new indole derivatives were designed and synthesized based on a lead compound obtained by a high-throughput screening with our in-house compound library. Among the synthetic compounds, 9e was characterized as a potent LSD1 inhibitor with an IC50 of 1.230 μM and can inhibit the proliferation of THP-1 cells effectively. And most importantly, this is the first irreversible LSD1 inhibitor that is not derived from monoamine oxidase inhibitors. Hence, the discovery of 9e may serve as a proof of concept work for AML treatment.

Design, synthesis and anticancer activity of 4-morpholinothieno[3,2-d]- pyrimidine derivatives bearing arylmethylene hydrazine moiety

Three series of 4-morpholinothieno[3,2-d]pyrimidine derivatives containing arylmethylene hydrazine moiety (11a-f, 13a-k and 15a-h) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. The synthesized compounds were evaluated for their cytotoxicity against three cancer cell lines (H460, HT-29, MDA-MB-231). Most of them exhibited moderate to significant cytotoxicity and high-selectivity against one or more cell lines, especially compounds 11c, 13b, 15f and 15g possessing dramatically increased cytotoxicity as compared with the positive controls, which were further evaluated for six other cancer cell lines and one normal cell line. The most promising compound 11c, bearing 3,4-methylenedioxy phenyl group, showed remarkable cytotoxicity against H460, HT-29 and MDA-MB-231 cell lines with IC50 values of 0.003 μM, 0.42 μM and 0.74 μM, which was 1.6- to 290-fold more potent than GDC-0941.

Design, synthesis and 3D-QSAR analysis of novel 2-hydrazinyl-4- morpholinothieno[3,2-d]pyrimidine derivatives as potential antitumor agents

A series of 2-hydrazinyl-4-morpholinothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their cytotoxic activities against five cancer cell lines. Most of them exhibited moderate to significant cytotoxic activities and high-selectivity against one or more cell lines, and nearly all of them had higher potency than positive controls against MDA-MB-231 cell line. The most promising compound 15f showed strong cytotoxic activities against H460, HT-29 and MDA-MB-231 cell lines, which were 1.7- to 66.5-folds more active than 2-(1H-Indazol-4-yl)-6-((4-(methylsulfonyl)-1-piperazinyl)methyl)-4-(4- morpholinyl)thieno[3,2-d]pyrimidine(GDC-0941). To investigate the SARs of thieno[3,2-d]pyrimidine derivatives in more details, CoMFA (q2 = 0.436, r2 = 0.937) and CoMSIA (q2 = 0.706, r2 = 0.947) models on H460 cell line were established. The generated 3D-QSAR models can be used for further rational design of novel thienopyrimidines as highly potent and selective cytotoxic agents.

Synthesis and biological evaluation of novel 6-hydrazinyl-2,4-bismorpholino pyrimidine and 1,3,5-triazine derivatives as potential antitumor agents

A series of 6-hydrazinyl-2,4-bismorpholino pyrimidine and 1,3,5-triazine derivatives (5a-5l and 8a-8o) were synthesized and their chemical structures as well as the relative stereochemistry were confirmed. All the synthesized compounds were evaluated for antiproliferative activity against three cancer cell lines (H460, HT-29, and MDA-MB-231). Several potent compounds were further evaluated against two other cell lines (U87MG, H1975). Most of the prepared compounds, particularly compounds 5c and 5j with IC50 values (0.07 and 0.05 μM, respectively) in the nM range, exhibited moderate to excellent antiproliferative activity and high selectivity against the H460 cancer cell line as compared with compound 1. The most promising compound 5j, possessing a cyano group at the 3-position of the benzene ring, showed strong antiproliferative activity against H460, HT-29, and MDA-MB-231 cell lines with IC50 values of 0.05, 6.31, and 6.50 μM, which were 4.6- to 190.4-fold more active than compound 1 (9.52, 29.24, and 36.21 μM), respectively. Copyright

Syntheses and in vitro antimycotic activities of 1-benzyl-3-(1-imidazolylmethyl)indoles

Syntheses of seventeen 1-benzyl-3-(1-imidazolylmethyl)indoles with substituents at the benzyl moiety and at the indole C-2 position are described. The compounds were tested for their antifungal activities in vitro determination of the minimum inhibitory concentration (MIC). Three compounds exhibited appreciable activities against Cr. neoformans.