52191-26-1

Basic information

• Product Name: 3-(CHLOROACETAMIDOETHYL)INDOLE
• Synonyms: 3-(CHLOROACETAMIDOETHYL)INDOLE;2-CHLORO-N-(2-INDOL-3-YLETHYL)ETHANAMIDE;2-CHLORO-N-[2-(1H-INDOL-3-YL)ETHYL]ACETAMIDE;2-Chloro-N-[2-(1H-indol-3-yl)ethyl]ethanamide, 3-{2-[(Chloroacetyl)amino]ethyl}-1H-indole;2-chloro-N-[2-(1H-indol-3-yl)ethyl]ethanamide;Tryptamine, N-chloroacetyl-;2-Chloro-N-[2-(1H-indol-3-yl)ethyl]acetamide98%
• CAS NO: 52191-26-1
• Molecular Formula: C₁₂H₁₃ClN₂O
• Molecular Weight: 236.7
• Mol File: 52191-26-1.mol

Chemical Properties

• Melting Point: 93 °C
• Boiling Point: 511.8 °C at 760 mmHg
• Flash Point: 263.3 °C
• Appearance: /
• Density: 1.279 g/cm³
• Vapor Pressure: 1.37E-10mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 14.25±0.46(Predicted)
• CAS DataBase Reference: 3-(CHLOROACETAMIDOETHYL)INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CHLOROACETAMIDOETHYL)INDOLE(52191-26-1)
• EPA Substance Registry System: 3-(CHLOROACETAMIDOETHYL)INDOLE(52191-26-1)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 52191-26-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-(Chloroacetamidoethyl)indole is used as a building block in the synthesis of complex molecular structures, contributing to the creation of novel compounds with diverse applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(Chloroacetamidoethyl)indole is utilized as a precursor in the production of various drugs and biologically active compounds, facilitating the development of new therapeutic agents.
Used in Antifungal Applications:
3-(Chloroacetamidoethyl)indole is used as an antifungal agent, exhibiting potential to combat fungal infections by disrupting essential cellular processes in fungi.
Used in Antibacterial Applications:
3-(Chloroacetamidoethyl)indole is also used as an antibacterial agent, showing promise in inhibiting bacterial growth and potentially contributing to the development of new antibiotics to address antibiotic resistance.
Used in Drug Discovery:
3-(Chloroacetamidoethyl)indole is employed in drug discovery research, where its unique structure and properties are explored for the development of new pharmaceuticals with improved efficacy and safety profiles.

InChI:InChI=1/C12H13ClN2O/c13-7-12(16)14-6-5-9-8-15-11-4-2-1-3-10(9)11/h1-4,8,15H,5-7H2,(H,14,16)

Upstream product

• 61-54-1 tryptamine 
• 79-04-9 chloroacetyl chloride 
• 27243-15-8 N-succinimidyl 2-chloroacetate 
• 79-11-8 chloroacetic acid 

Downstream Products

• 503544-97-6 N-[2-(3-indolyl)ethyl]-2-(4-methylphenylsulfonyl)acetamide 
• 135710-19-9 2-(3,4-Dichloro-phenyl)-1-(1-pyrrolidin-1-ylmethyl-1,3,4,9-tetrahydro-β-carbolin-2-yl)-ethanone 
• 473893-99-1 1-{2-(1H-benzo[b]azol-3-yl)ethyl}-3-(4-methylphenylsulfonyl)-2,6-azinanedione 
• 1016-47-3 N-Acetyltryptamine 
• 14482-90-7 6,7,9,10-tetrahydroazepino<4,5-b>indol-8(5H)-one 
• 57964-75-7 1,3,4,5,6,7-hexahydro-6-oxoazocino<4,5,6-cd>indole 

Relevant articles and documents

AN ACTIVITY-GUIDE MAP OF ELECTROPHILE-CYSTEINE INTERACTIONS IN PRIMARY HUMAN IMMUNE CELLS

Disclosed herein are methods, pharmaceutical compositions, and vaccines for modulating an immune response. Also disclosed herein are methods, pharmaceutical compositions, and vaccines for inducing an immune response.

Organocatalytic Cascade Reactions for the Diversification of Thiopyrano-Piperidone Fused Rings Utilizing Trienamine Activation

An aminocatalytic privileged diversity-oriented synthesis (ApDOS) strategy utilizing trienamine catalysis for the construction of diverse and complex thiopyrans-piperidone fused rings through a thia-Diels–Alder/nucleophilic ring-closing sequence by using dithioamides as activated heterodienophiles is reported. Following this strategy, a super cascade reaction to assemble nine fused rings can be achieved by employing a bis-dithioamide. Additionally, by linking an indole moiety on the dithioamide, a Pictet–Spengler type reaction can be promoted once the cascade sequence has been achieved, leading to more complex penta- hexa- and heptacyclic fused ring derivatives in a one-pot process. This investigation opens new perspectives for the synthesis of a new class of complex and diverse thiopyrans that contribute to populate new relevant regions in the chemical space.

Insecticidal activity of indole derivatives against Plutella xylostella and selectivity to four non-target organisms

The diamondback moth Plutella xylostella (Linnaeus, 1758) (Lepidoptera: Plutellidae) is a destructive pest of brassica crops of economic importance that have resistance to a range of insecticides. Indole derivates can exert diverse biological activities, and different effects may be obtained from small differences in their molecular structures. Indole is the parent substance of a large number of synthetic and natural compounds, such as plant and animal hormones. In the present study, we evaluate the insecticidal activity of 20 new synthesized indole derivatives against P. xylostella, and the selectivity of these derivatives against non-target hymenopteran beneficial arthropods: the pollinator Apis mellifera (Linnaeus, 1758) (Hymenoptera: Apidae), and the predators Polybia scutellaris (White, 1841), Polybia sericea (Olivier, 1791) and Polybia rejecta (Fabricius, 1798) (Hymenoptera: Vespidae). Bioassays were performed in the laboratory to determine the lethal and sublethal effects of the compounds on P. xylostella and to examine their selectivity to non-target organisms by topical application and foliar contact. The treatments consisted of two synthesized derivatives (most and least toxic), the positive control (deltamethrin) and the negative control (solvent). The synthesized compound 4e [1-(1H-indol-3-yl)hexan-1-one] showed high toxicity (via topical application and ingestion) and decreased the leaf consumption by P. xylostella, displaying a higher efficiency than the pyrethroid deltamethrin, widely used to control this pest. In addition, the synthesized indole derivatives were selective to the pollinator A. mellifera and the predators P. scutellaris, P. sericea and P. rejecta, none of which were affected by deltamethrin. Our results highlight the promising potential of the synthesized indole derivatives for the generation of new chemical compounds for P. xylostella management.

COMPOSITIONS AND METHODS OF MODULATING IMMUNE RESPONSE

Disclosed herein are methods, pharmaceutical compositions, and vaccines for modulating an immune response. Also disclosed, herein are methods, pharmaceutical compositions, and vaccines for inducing an immune response.

8-aminoquinoline-melatonin complex and pharmaceutical composition thereof

The invention relates to synthesized 8-aminoquinoline-melatonin complex, in particular to an 8-aminoquinoline-melatonin complex and a pharmaceutical composition thereof. The 8-aminoquinoline-melatonin complex is of a structure as shown in the structural formula (I); on one hand, the compounds can selectively chelate copper ions; on the other hand, the compounds play a role in well protecting nerves and nerve cells to improve AD (Alzheimer's disease) symptoms. The invention further relates to a pharmaceutical composition or nerve cell protective agent comprising the complex or pharmaceutically acceptable salt thereof. The invention further relates to pharmaceutical application of the complex.

Synthesis, biological evaluation, and structure-activity relationships of potent noncovalent and nonpeptidic cruzain inhibitors as anti-Trypanosoma cruzi agents

The development of cruzain inhibitors has been driven by the urgent need to develop novel and more effective drugs for the treatment of Chagas' disease. Herein, we report the lead optimization of a class of noncovalent cruzain inhibitors, starting from an inhibitor previously cocrystallized with the enzyme (Ki = 0.8 μM). With the goal of achieving a better understanding of the structure-activity relationships, we have synthesized and evaluated a series of over 40 analogues, leading to the development of a very promising competitive inhibitor (8r, IC50 = 200 nM, Ki = 82 nM). Investigation of the in vitro trypanocidal activity and preliminary cytotoxicity revealed the potential of the most potent cruzain inhibitors in guiding further medicinal chemistry efforts to develop drug candidates for Chagas' disease.

Synthesis, activity, and QSAR studies of tryptamine derivatives on third-instar larvae of aedes aegypti linn

Special attention has been given to the mosquito Aedes aegypti Linn. (Diptera: Culicidae) owing to numerous dengue epidemic outbreaks worldwide. Failure to control vector spreading is accounted for unorganized urban growth and resistance to larvicides and insecticides. Therefore, researchers are currently searching for new and more efficient larvicides and insecticides to aid dengue control measures. Triptamine is known to affect insect behavior, development, and physiology. Expression of this compound in plants has reduced the growth rate of herbivore insects. In view of these facts, it was of our interest to synthesize triptamine amide derivatives as potential larvicides against Ae. aegypti, establishing a Structure-Activity Relationship. Eleven amide derivatives of triptamine were synthesized, characterized, and evaluated for their larvicidal activity against third-instar Ae. aegypti larvae. N-(2-(1H-indol-3-yl)ethyl)-2,2,2-trichloroacetamide exhibited the highest overall larvicidal potency, while N-(2-(1H-Indol-3-yl)ethyl) acetamide displayed the lowest larvicidal potency. A regression equation correlating the larvicidal activity with Log P was obtained. We have found a clear relationship between the larvicidal activity of non-chlorinated compounds and Log P. Analysis of the relationship between Log P and larvicidal activity against Ae. aegypti may be useful in the evaluation of potential larvicidal compounds.

Bioreduction of β-carboline imines to amines employing Saccharomyces bayanus

β-Carboline imine reductions mediated by Saccharomyces bayanus have been described achieving moderate to good enantiomeric excesses of the amine products. The enantiomeric excesses of the bioreduction showed a dependence on the imine substituents. Compoun

Synthesis of bioactive 2-aza-analogues of ipecac and alangium alkaloids

License to kill: Substitution of the methine carbon C2 in the ipecac or alangium alkaloids by nitrogen yields functional mimetics with low micromolar to high naonomolar IC50 values against Trypanosoma brucei, the parasite that causes African tr

Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones

A novel and effective synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones via Smiles rearrangement is presented. Treatment of N-substituted 2-chloro(or hydroxy)acetamide, 2-tetrahydropyranyl-4-chloro-5-hydroxy(or chloro)pyridazin-3-one and cesium carbonate in refluxing acetonitrile was afforded the corresponding pyridazino[4,5-b][1,4]oxazin-3,8-diones in excellent yield.