151409-85-7

Basic information

• Product Name: 1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbaldehyde
• Synonyms: 1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbaldehyde
• CAS NO: 151409-85-7
• Molecular Weight: 258.32
• Mol File: 151409-85-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbaldehyde(151409-85-7)
• EPA Substance Registry System: 1-(2-morpholin-4-yl-ethyl)-1H-indole-3-carbaldehyde(151409-85-7)

Safety Data

• Hazardous Substances Data: 151409-85-7(Hazardous Substances Data)

Usage

Chemical class

Aldehyde

Structure

Consists of an indole ring substituted with a 2-morpholin-4-yl-ethyl group at the 1-position, and an aldehyde group at the 3-position.

Applications

a. Organic synthesis
b. Medicinal chemistry
c. Building block for the development of pharmaceutical drugs and biologically active molecules

Unique structure

Valuable intermediate in the synthesis of complex organic compounds

Potential applications

a. Drug discovery and development
b. Biological activities, including antitumor and antimicrobial properties

Importance

Its unique structure and functional groups make it a valuable compound in the field of chemistry and pharmaceuticals.

Upstream product

• 487-89-8 Indole-3-carboxaldehyde 
• 3647-69-6 4-(2-chloroethyl)morpholine hydrochride 

Downstream Products

• 1206536-26-6 [1-(2-morpholin-4-yl-ethyl)-1H-indol-3-ylmethyl]-p-tolyl-amine 
• 1206536-25-5 (4-chloro-phenyl)-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-ylmethyl]-amine 
• 1206536-23-3 (4-methoxy-phenyl)-[1-(2-morpholin-4-yl-ethyl)-1H-indol-3-ylmethyl]-amine 

Relevant articles and documents

A near-infrared and lysosomal targeting thiophene-BODIPY photosensitizer: Synthesis and its imaging guided photodynamic therapy of cancer cells

In this study, a novel NIR and lysosomal targeting thiophene-BODIPY photosensitizer SBOP-Lyso was synthesized to explore its potential applications in photodynamic therapy of A549 cells. In the strategy of designing SBOP-Lyso, S atom in thiophene as well as heavy atom I were introduced to promote ISC efficiency to ensure high singlet oxygen yield. A common lysosome targeted group (M1: 1-(2-morpholinoethyl)-1H-indole-3-carbaldehyde) was linked to SBOP to extend its wavelength to the NIR region. Its absorption peak was at 660 nm (εmax = 5.2 × 104 cm?1 M?1) and its corresponding emission peak was located at 705 nm. Singlet oxygen could be quickly generated by SBOP-Lyso in the presence of 660 nm LED irradiation and the singlet oxygen yield was up to 44.1%. In addition, it also had good biocompatibility and could enter cells or zebrafish in a short time. SBOP-Lyso had negligible dark cytotoxicity (cell survival rate > 80%) and excellent phototoxicity (IC50 = 0.2 μM). DCFH-DA (ROS indicator) proved that SBOP-Lyso could generate singlet oxygen with 660 nm LED irradiation. Singlet oxygen produced by SBOP-Lyso could kill cancer cells in PDT process and it had the ability to effectively inhibit A549 cells migration. Besides that, lysosomal colocalization assay showed that it had good lysosomal localization ability (Pearson colocation coefficient, R = 0.93). Considering the above results, SBOP-Lyso as a unique lysosome-targeted photosensitizer with excellent properties would exhibit positive results in PDT process of cancer cells.

Novel indole-BODIPY photosensitizers based on iodine promoted intersystem crossing enhancement for lysosome-targeted imaging and photodynamic therapy

In this work, we report the new lysosome-targeting indole-BODIPY derivatives BDP-Lys, IBDP-Lys, and I2BDP-Lys. BDP-Lys dye was designed for fluorescence imaging through introduction of an indole-containing morpholine moiety to a BODIPY core. Monoiodine and diiodine were incorporated into BDP-Lys dye to develop the photosensitizers IBDP-Lys and I2BDP-Lys. The maximum absorption (λabs) for IBDP-Lys and I2BDP-Lys displayed a redshift at approximately 11 nm and 27 nm, respectively, compared with the BDP-Lys dye (λabs= 504 nm). Similarly, the maximum emission also exhibited a redshift. The fluorescence quantum yield (ΦF) of IBDP-Lys (ΦF= 0.37%) and I2BDP-Lys (ΦF= 0.71%) was much lower than that of BDP-Lys dye (ΦF= 7.48%). The singlet oxygen quantum yields were measured as 43.10% for IBDP-Lys and 71.00% for I2BDP-Lys, which were higher than the iodine-free dye BDP-Lys. The theoretical calculation reasonably explains that iodine atoms promoted the intersystem crossing (ISC) process, and di-iodine further enhanced the ISC in indole-BODIPY dyes. Moreover, monoiodine photosensitizer IBDP-Lys was able to balance the generation of singlet oxygen and biocompatibility in cancer treatment. IBDP-Lys exhibited low dark toxicity (cell viability >90%), satisfactory biocompatibility, and precise lysosome targeting, with a Pearson coefficient of 0.93. The IBDP-Lys photosensitizer also was able to kill tumour cells. Considering the above results, the novel structure of indole-BODIPY photosensitizers could serve as a potential platform for lysosome-targeted imaging and photodynamic therapy.

Synthesis and pharmacological evaluation of analogs of indole-based cannabimimetic agents

Aminoalkylindoles (AAIs), although structurally dissimilar from the classical cannabinoids, are known to be capable of binding to cannabinoid receptors and of evoking cannabinomimetic responses. With the aim of investigating the structure-activity relationships (SAR) for the binding of non-classical agonists to CB1 and CB2 cannabinoid receptors, we designed and synthesized a series of indole derivatives. The compounds were tested for their analgesic action by formalin test and compared to WIN 55212-2, an AAI acting to the cannabinoid receptors. In receptor binding assay, compound 5 showed affinity for the CB1 receptor comparable to WIN 55212-2.