1228547-52-1

Basic information

• Product Name: 1H-indole-3-carbaldehyde
• CAS NO: 1228547-52-1
• Molecular Formula: C9H7NO
• Molecular Weight: 145
• Mol File: 1228547-52-1.mol
• Article Data: 252

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-indole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-indole-3-carbaldehyde(1228547-52-1)
• EPA Substance Registry System: 1H-indole-3-carbaldehyde(1228547-52-1)

Safety Data

• Hazardous Substances Data: 1228547-52-1(Hazardous Substances Data)

Usage

Type of compound

Aromatic aldehyde

Derivation

Derived from the indole molecule

Synthesis

Commonly used in the synthesis of various pharmaceuticals and agrochemicals.

Organic light-emitting diodes (OLEDs)

Investigated for its potential use in OLEDs.

Fluorescent probe

Used as a fluorescent probe for detecting amino acids.

Antimicrobial properties

Studied for its potential antimicrobial properties.

Anticancer properties

Studied for its potential anticancer properties.

Applications

Wide range of applications in the chemical and pharmaceutical industries.

Upstream product

• 36104-60-6 3-(1,3-dithiolan-2-yl)-1H-indole 
• 41824-68-4 (Z)-1-(1H-indol-3-yl)-N-methylmethanimine oxide 
• 1461-25-2 tetra-n-butyltin(IV) 
• 141692-10-6 (3-formylindol-4-yl)thallium (III) bistrifluoroacetate 
• 22948-94-3 1-acetyl-3-indolylcarbaldehyde 
• 855433-69-1 (4R)-2-amino-4-carboxy-4hydroxy-5-(1H-indol-3-yl)pentanoic acid 
• 65283-32-1 N-(1H-indol-3-ylmethylene)-N-methylmethanaminium chloride 
• 5457-31-8 (3-indolylmethyl)trimethylammonium iodide 
• 57476-50-3 1-tert-butoxycarbonyl-3-formylindole 
• 392-12-1 Indole-3-pyruvic acid 
• 7664-41-7 ammonia 
• 110-45-2 isopentyl formate 
• 120-72-9 indole 
• 67-66-3 chloroform 

Downstream Products

• 117490-34-3 5-(3-indolylmethylene)hydantoin 
• 10258-18-1 (5Z)-5-((1H-indol-3-yl)methylene)-2-thioxoimidazolidin-4-one 
• 119549-98-3 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-cyclohexyl-phenyl)propan-1-one 
• 119550-00-4 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-chlorophenyl)propan-1-one 
• 119549-90-5 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-bromophenyl)propan-1-one 
• 119549-97-2 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-trimethyl-silylmethylenoxyphenyl)propan-1-one 
• 119549-93-8 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(3-bromophenyl)propan-1-one 
• 119549-92-7 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-phenyl-propan-1-one 
• 119549-95-0 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(4-methoxyphenyl)propan-1-one 
• 119549-96-1 1-(4-Hydroxy-phenyl)-3-(1H-indol-3-yl)-3-[1,2,4]triazol-1-yl-propan-1-one 
• 119549-94-9 3-(3-indolyl)-3-(1,2,4-triazol-1-yl)-1-(3-methoxyphenyl)propan-1-one 
• 5453-51-0 (E)-3'-deimino-2',4'-bis(demethyl)-3'-oxoaplysinopsin 
• 254745-47-6 (R)-N-[(3-indolyl)methylene]-1-(1-napthyl)ethylamine 
• 206183-63-3 2-nitroindole-3-carbaldehyde 

Relevant articles and documents

A mild and selective method for the N-Boc deprotection by sodium carbonate

A cleavage of N-tert-butyloxycarbonyl protection by Na2CO3 is reported. The N-free products are obtained in excellent yields. The compatibility of the method with the presence of acidic or basic groups is demonstrated. The reactions were performed on indole, azaindole, indazole, pyrazole, indolinone, quinolinone, and oxazolone.

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Synthesis of Camalexin and Related Analogues

Camalexin is synthesized on a gram scale by coupling of thiazole and indole in an amidoalkylation–oxidation sequence. Several high-yielding implementations of this two-step approach are demonstrated with variation of either the intermediate acyliminium reagent or the oxidation conditions. Benzo-analogues and aza-analogues of the natural product are also obtained by this method. As a side result, a new formylation of indole is demonstrated.

Chemical structures of novel maillard reaction products under hyperglycemic conditions

Two novel and two known compounds, 4-quinolylaldoxime and indole-3-aldehyde, were isolated from a reaction mixture consisting of D-glucose and L-tryptophan at physiological temperature and pH. The chemical structures of the two novel compounds were elucidated by spectroscopic analysis such as X-ray crystallography. One of the novel compound and the indole-3-aldehyde showed mutagenicity toward Salmonella typhimurium YG1024 with S9 mix. Furthermore, 4-quinolylaldoxime was detected from streptozotocin-induced diabetic rat plasma by LC-MS/MS analysis; however, the isolated compounds were not detected in rat diet extracts. To our knowledge, this is the first report in which 4-quinolylaldoxime was detected in rat plasma. These results suggest that amino-carbonyl reaction products may be formed in diabetic condition and induce genetic damage.

Synthesis, antiproliferative and apoptosis induction potential activities of novel bis(indolyl)hydrazide-hydrazone derivatives

In recent years, indole-indazolyl hydrazide-hydrazone derivatives with strong cell growth inhibition and apoptosis induction characteristics are being strongly screened for their cancer chemo-preventive potential. In the present study, N-methyl and N,N-dimethyl bis(indolyl)hydrazide-hydrazone analog derivatives were designed, synthesized and allowed to evaluate for their anti-proliferative and apoptosis induction potential against cervical (HeLa), breast (MCF-7 and MDA-MB-231) and lung (A549) cancer cell lines relative to normal HEK293 cells. The MTT assay in conjunction with mitochondrial potential assays and the trypan blue dye exclusion were employed to ascertain the effects of the derivatives on the cancer cells. Further, mechanistic studies were conducted on compound 14a to understand the biochemical mechanisms and functional interactions with various signaling pathways triggered in HeLa and MCF-7 cells. Compound 14a induced apoptosis via caspase independent pathway through the participation of mitogen-activated protein kinases (MAPK) such as extracellular signal related kinase (ERK) and p38 as well as p53 pathways. It originates the activation of pro-apoptotic proteins such as Bak and Mcl-1s and also strongly induced the generation of reactive oxygen species. In downstream signaling pathway, activated p53 protein interacted with MAPK pathways, including SAPK/c-Jun N-terminal protein kinase (JNK), p38 and ERK kinases resulting in apoptotic cell death. The involvement of MAPK cascades such as p38, ERK and p38 on compound 14a induced apoptotic cell death was evidenced by the fact that the inclusion of specific inhibitors of p38, ERK1/2 and JNK MAPK (SB2035809, PD98059 and SP600125) prevented the compound 14a towards induced apoptosis. The results clearly showed that MAP kinase cascades were crucial for apoptotic response in compound 14a induced cellular killing and were dependent on p53 activity. Based on the results, compound 14a was identified as a promising candidate for cancer therapeutics and these findings furnish a basis for further in vivo experiments on anti-proliferative activity.

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A Modular Formal Total Synthesis of (±)-Cycloclavine

Cycloclavine is a clavine-type Ergot alkaloid noteworthy for its unique pentacyclic skeleton featuring a 3-azabicyclo[3.1.0]hexane substructure. A short convergent route to the racemic alkaloid is described which comprises only eight linear steps and requires only four chromatographic purifications. The two key building blocks can be prepared in high yield from commercially available starting materials. Two consecutive coupling reactions, namely a selective alkylation of a dienolate and a Heck reaction, are the key steps of the reaction sequence. (Chemical Equation Presented).

Formyl-and acetylindols: Vibrational spectroscopy of an expectably pharmacologically active compound family

In the peresent paper, indole and its seven derivatives were compared, namely 3-formylindole, 1-methyl-3-formylindole, 1-ethyl-3-formylindole, 3-acetylindole, 1-methyl-3-acetylindole, 1-ethyl-3-acetylindole and 1,3-diacetylindole. The substitution of indole in position 3 with aldehydes and with alkyl groups cause only minor changes in the molecular geometry, however, substantially larger alterations are found in the charge distribution and in the vibrational force constants. The appearance of the aldhyde groups increased the degree of association as it was observable on the shape of infrared NH stretching band and its shifts. The alkyl substitution shifts the aldehyde carbonyl stretch band frequencies to somewhat higher values. The effect of the second acetyl group in position 1 is not comparable with those of the 1-alkyl groups. The latter effect is observable in the molecular geometry, however, it is more pronounced in the changes of the net charge distribution, the vibrational force constants and the infrared spectra.

Direct N-Alkyl Azidonation of N,N-Dialkylarylamines with the Iodosylbenzene/Trimethylsilylazide Reagent Combination

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Photooxidative decarboxylation of indole-3-acetic acid by pyrimido[5,4-g]pteridine N-oxide as a biomimetic reaction

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Structural study of Nitrovinylindoles: (I) 2-methyl-3-(2'-methyl-2'-nitrovinyl)indole and (II) 3-(2'-nitrovinyl)indole

Compound (I) is 2-methyl-3-(2'-methyl-2'-nitrovinyl)indole, C12H12N2O2, Mr =216,24, monoclinic, P21/n, a = 16.710(1), b = 7.627(1), c = 17.646(1) Angstroem, β = 104.8(1) deg, V = 2174.7(1) Angstroem3, Z = 8, Dx = 1.321 g cm-3, Mo Kα, λ = 0.71073 Angstroem, μ = 0.858 ca-1, F(000) = 912, room temperature, R = 0.061 for 1956 observed reflections.Compound (II) is 3-(2'-nitrovinyl)indole, C10H8N2O2, Mr = 188.18, monoclinic, P21/n, a = 10.178(1), b = 10.608(1), c = 8.411(1) Angstroem, β = 105.5(2) deg, V = 875.0(1) Angstroem3, Z = 4, Dx = 1.4284 g cm-3, Cu Kα, λ = 1.5418 Angstroem, μ = 8.068 cm-1, F(000) = 392, room temperature, R = 0.040 for 1330 observed reflections.Compounds (I) and (II) have a similar geometry, the only significant difference lying in the rotation of the nitrovinyl chain.This feature could be responsible for the difference in biological activity.In both compounds, the molecules are associated, forming chargetransfer complexes.

Solid-state photodecarboxylation induced by exciting the CT bands of the complexes of arylacetic acids and 1,2,4,5-tetracyanobenzene

Crystalline charge transfer complexes (3a, 3b, and 3c) of 1- and 2-naphthylacetic and 3-indoleacetic acid (1a, 1b, and 1c) with 1,2,4,5-tetracyanobenzene (2) were prepared by crystallization from the acetonitrile solutions. Irradiation of 3a and 3b gave methylnaphthalenes by decarboxylation and naphthyl(2,4,5-tricyanophenyl)methanes by subsequent dehydrocyanating condensation in the solid state. On the other hand, the photoreactivity of the crystal 3c was low; similar photoreaction occurred only at high temperature. These solid-state reactions are induced by exciting the CT bands of 3a and 3b. The product selectivities were different from those of the solution photoreaction. The relationships between the photoreactivities and the crystal structures of 3a and 3c are discussed.

Synthesis of an azide-tethered 4H-furo[3,4-b]indole

We describe the synthesis of a novel azide-tethered 4H-furo[3,4-b]indole as a putative intermediate for a projected route to the 2-acylindole class of indole alkaloids. O N3 Me N N N H N H H O

Anti-leukemic properties of aplysinopsin derivative ee-84 alone and combined to bh3 mimetic a-1210477

Aplysinopsins are a class of marine indole alkaloids that exhibit a wide range of biological activities. Although both the indole and N-benzyl moieties of aplysinopsins are known to possess antiproliferative activity against cancer cells, their mechanism of action remains unclear. Through in vitro and in vivo proliferation and viability screening of newly synthesized aplysinopsin analogs on myelogenous leukemia cell lines and zebrafish toxicity tests, as well as analysis of differential toxicity in noncancerous RPMI 1788 cells and PBMCs, we identified EE-84 as a promising novel drug candidate against chronic myeloid leukemia. This indole derivative demonstrated drug-likeness in agreement with Lipinski’s rule of five. Furthermore, EE-84 induced a senescent-like phenotype in K562 cells in line with its cytostatic effect. EE-84-treated K562 cells underwent morphological changes in line with mitochondrial dysfunction concomitant with autophagy and ER stress induction. Finally, we demonstrated the synergistic cytotoxic effect of EE-84 with a BH3 mimetic, the Mcl-1 inhibitor A-1210477, against imatinib-sensitive and resistant K562 cells, highlighting the inhibition of antiapoptotic Bcl-2 proteins as a promising novel senolytic approach against chronic myeloid leukemia.

PHOTOCHEMICAL OXIDATIVE Cα-Cβ CLEAVAGE OF TRYPTOPHAN SIDE-CHAIN BY PYRIMIDOPTERIDINE N-OXIDE

Tryptophan derivatives 1 undergo with ease the oxidative Cα-Cβ bond cleavage by pyrimidopteridine N-oxide 2 under irradiation with UV-visible light in the presence of acid-catalyst to give 3-indolecarboxaldehydes 3 and the corresponding glycine derivatives 4.

Aerobic oxidation of indole-3-acetic acid catalysed by anionic and cationic peanut peroxidase

The catalytic properties of anionic and cationic peanut peroxidases with regards to the oxidation of indole-3-acetic acid (IAA) by molecular oxygen at low pH have been studied. Transient kinetic studies demonstrate that only cationic peroxidases (peanut and horseradish) but not anionic peroxidases (such as anionic tobacco and anionic peanut peroxidases) form a stable compound III in the course of IAA oxidation. The failure to observe inhibition in the presence of superoxide dismutase is consistent with the formation of compound III from a ternary complex comprising ferric enzyme, IAA and dioxygen at the initiation step. Product analysis by HPLC showed an enhanced rate of IAA oxidation in the presence of superoxide dismutase. Co- addition of superoxide dismutase and catalase demonstrates that this stimulation is not due to the formation of hydrogen peroxide. The correlation between initial rates of IAA degradation and product accumulation indicates that skatole hydroperoxide is a primary reaction product and indole-3- methanol is the product of its subsequent enzymatic reduction. The relative catalytic activities for IAA oxidation by tobacco:horseradish isoenzyme c:anionic peanut:cationic peanut peroxidase are 28:20:2:1.

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ALKALOIDS OF Nitraria komarovii. IV. TOTAL SYNTHESIS OF KOMAROVINE AND KOMAROVIDINE

Two alkaloids of a new type - komarovine and komarovidine - have been isolated from the epigeal part of the Nitraria komarovii.Their structures - 3-(quinolin-8'-yl)-β-carboline and 3-(quinolin-8'-yl)-5,6-dihydro-β-carboline, respectively - have been established by synthesis.

Free-Radical Intermediates and Stable Products in the Oxidation of Indole-3-acetic Acid

The free-radical intermediates and the stable products formed on one-electron oxidation of indole-3-acetic acid (IAA) in aqueous solution were investigated.The dibromine radical anion generated radiolytically reacted with IAA to yield the IAA radical cation.In acid solution, the latter decays by a first-order process (k = 1.8E4 s-1) to yield carbon dioxide and the skatole radical.At pH 7 it deprotonates (pKa = 5.09 +/- 0.02), giving the indolyl radical, which decays only by a bimolecular process (rate constant of first-order reactions -1) which yields indole-3-carbinol as one of the products.Under steady-state irradiation at pH 7 the free radicals had a sufficient lifetime to allow the small fraction of radical cation present in equilibrium to undergo decarboxylation, consistent with the observed formation of carbon dioxide.Glutathione reacted with the indol radical, regenerating IAA, and with the skatole radical to yield skatole.In the presence of oxygen the skatole radical is rapidly converted to a peroxyl radical, which appears to decay only by bimolecular reactions with indole-3-aldehyde as one of the products.No evidence was found for the reaction of the peroxyl radical with glutathione or for elimination of superoxide.

Triphenylphosphine/1,2-Diiodoethane-Promoted Formylation of Indoles with N, N -Dimethylformamide

Despite intensive studies on the synthesis of 3-formylindoles, it is still highly desirable to develop efficient methods for the formylation of indoles, due to the shortcomings of the reported methods, such as inconvenient operations and/or harsh reaction conditions. Here, we describe a Ph3P/ICH2CH2I-promoted formylation of indoles with DMF under mild conditions. A Vilsmeier-type intermediate is readily formed from DMF promoted by the Ph3P/ICH2CH2I system. A onestep formylation process can be applied to various electron-rich indoles, but a hydrolysis needs to be carried out as a second step in the case of electron-deficient indoles. Convenient operations make this protocol attractive.

Streptochlorin analogues as potential antifungal agents: Design, synthesis, antifungal activity and molecular docking study

Streptochlorin is a small molecule of indole alkaloid isolated from marine Streptomyces sp., it is a promising lead compound due to its potent bioactivity in preventing many phytopathogens in our previous study, but further structural modifications are re

Cu(II) complexes of 2-indole thiocarbohydrazones: synthesis, characterization and DNA cleavage studies

Abstract: Two Schiff base ligands FT1 and FT2 and their Cu(II) complexes were synthesized and characterized by 1H NMR, ESI-MS, IR, UV-Visible, Fluorescence spectroscopy, EPR and single-crystal X-ray diffraction studies. FT1 crystallizes in the triclinic system while FT2 in the orthorhombic. The DNA cleavage activity of Cu(II) complexes was studied using plasmid pBR322 DNA by gel electrophoresis. All compounds cleave DNA on photoirradiation by oxidative mechanism. Graphic abstract: Two Schiff base ligands FT1 and FT2 and their Cu(II) complexes were synthesized and characterized by 1H NMR, ESI-MS, IR, UV-Visible, Fluorescence spectroscopy, EPR and single-crystal X-ray diffraction studies. Both the Cu(II) complexes of indole thiocarbohydrazones are shown to cleave plasmid pBR322 DNA by oxidative mechanism.[Figure not available: see fulltext.].