93548-80-2

Usage

Uses

Used in Pharmaceutical Development:
1-(2,6-Dichlorobenzyl)-1H-indole-3-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structural features and reactivity contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemicals:
In the agrochemical industry, 1-(2,6-Dichlorobenzyl)-1H-indole-3-carbaldehyde is used as a building block for the creation of novel agrochemicals. Its chemical properties allow for the development of compounds with enhanced pesticidal, herbicidal, or fungicidal activities.
Used in Organic Synthesis:
1-(2,6-Dichlorobenzyl)-1H-indole-3-carbaldehyde serves as a valuable intermediate in organic synthesis, where it can be used to construct a wide range of complex organic molecules. Its versatility in forming various chemical bonds makes it a useful tool in the synthesis of specialty chemicals and advanced materials.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 1-(2,6-Dichlorobenzyl)-1H-indole-3-carbaldehyde is utilized for the design and synthesis of new bioactive molecules. Its structural diversity and functional group compatibility enable the development of potential drug candidates with improved pharmacological properties and therapeutic potential.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 2014-83-7 1,3-Dichloro-2-chloromethyl-benzene 

Downstream Products

• 151409-98-2 2-[1-(2,6-Dichloro-benzyl)-1H-indol-3-yl]-ethylamine 
• 1415660-25-1 C₂₉H₂₈Cl₂N₆O₂S 
• 1394048-03-3 (E)-4-(2-(2-((1-(2,6-dichlorobenzyl)-1H-indol-3-yl)methylene)hydrazinyl)-6-((4-(methylsulfonyl)piperazin-1-yl)methyl)-thieno[3,2-d]pyrimidin-4-yl)morpholine 

Relevant academic research and scientific papers

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

N6-Substituted Adenosine Receptor Agonists. Synthesis and Pharmacological Activity as Potent Antinociceptive Agents

Novel N6-(indol-3-yl)alkyl derivatives of adenosine were synthesized.The adenosine receptor affinity and the antinociceptive activity of these compounds were assessed in binding studies and the phenylbenzoquinone-induced writhing test.Most of these analogues exhibited a potent analgesic activity without side effects.Among them, compound 3c (UP 202-32) bound to A1 (Ki = 110 nM) and A2 (Ki = 350 nM) adenosine receptors in a specific manner since it did not interact with many other receptors, especially opioid binding sites.The antinociceptive activity in the phenylbenzoquinone assay (ED50 = 3.3 mg/kg po) was antagonized by 8-cyclopentyltheophylline, suggesting that an adenosinergic mechanism underlies the analgesic activity observed with this compound.The data obtained with these new N6-substituted adenosine receptor agonists emphasize the interest of such compounds in the treatment of pain.

Potential antitumor agents. XIII. Indole derivatives related to Lonidamine

The synthesis and the antitumor activities of 1-benzylindole-3-carboxylic acids are reported. Compound 16b, which bears at position 1 the same substituent as Lonidamine (1), proved to be the most active derivative.