10553-14-7

Basic information

• Product Name: 7-NITROINDOLE-3-CARBOXALDEHYDE
• Synonyms: 7-NITRO-1H-INDOLE-3-CARBALDEHYDE;7-NITROINDOLE-3-ALDEHYDE;7-NITROINDOLE-3-CARBOXALDEHYDE;7-NITROINDOLE-3-CARBOXYALDEHYDE;7-Nitroindole-3-carboxaldehyde 98%;Zinc02572407;7-Nitro-1H-indole-3-carboxaldehyde 95+%;3-Carboxy-7-nitro-1H-indole
• CAS NO: 10553-14-7
• Molecular Formula: C₉H₆N₂O₃
• Molecular Weight: 190.16
• Product Categories: Indole
• Mol File: 10553-14-7.mol

Chemical Properties

• Boiling Point: 441.47 °C at 760 mmHg
• Flash Point: 220.794 °C
• Appearance: /Solid
• Density: 1.517 g/cm³
• Vapor Pressure: 5.43E-08mmHg at 25°C
• Refractive Index: 1.764
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 12.47±0.30(Predicted)
• CAS DataBase Reference: 7-NITROINDOLE-3-CARBOXALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-NITROINDOLE-3-CARBOXALDEHYDE(10553-14-7)
• EPA Substance Registry System: 7-NITROINDOLE-3-CARBOXALDEHYDE(10553-14-7)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 10553-14-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-NITROINDOLE-3-CARBOXALDEHYDE is used as a starting material for the synthesis of various organic compounds and pharmaceuticals. Its unique chemical properties and potential therapeutic effects make it a valuable component in the development of new drugs.
Used in Medicinal Chemistry:
7-NITROINDOLE-3-CARBOXALDEHYDE is used as a research compound for its antimicrobial and anti-inflammatory properties. Its ability to target specific biological pathways and modulate immune responses makes it a promising candidate for the treatment of various diseases and conditions.
Used in Bioimaging Studies:
7-NITROINDOLE-3-CARBOXALDEHYDE is used as a fluorescent probe in bioimaging studies. Its optical properties allow for the visualization of cellular structures and processes, providing valuable insights into biological mechanisms and potential therapeutic targets.

InChI:InChI=1/C9H6N2O3/c12-5-6-4-10-9-7(6)2-1-3-8(9)11(13)14/h1-5,10H

Upstream product

• 6960-42-5 7-nitro-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 100-97-0 hexamethylenetetramine 
• 50-00-0 formaldehyd 

Downstream Products

• 1214362-44-3 7-aminoindole-3-carbaldehyde 
• 1423754-19-1 (S)-2-((R)-2-nitro-1-(7-nitro-1-tosyl-1H-indol-3-yl)ethyl)pentanal 
• 1423754-13-5 C₁₇H₁₃N₃O₆S 
• 247186-91-0 4-(3-cyano-1H-indol-7-ylsulfamoyl)-benzoic acid 
• 247186-93-2 N-(3-cyano-7-indolyl)-4-nitrobenzenesulfonamide 
• 247186-94-3 4-amino-N-(3-cyano-1H-indol-7-yl)-benzenesulfonamide 
• 165669-10-3 3-cyano-7-nitroindole 
• 165669-11-4 7-amino-1H-indole-3-carbonitrile 

Relevant articles and documents

Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)

The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)

Synthesis and evaluation of fuligocandin b derivatives with activity for overcoming TRAIL resistance

The tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) signaling pathway induces apoptosis in cancer cells but not in normal cells. Therefore, this pathway has attracted attention regarding possible clinical treatment of cancer. However, many

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Elaboration of thorough simplified vinca alkaloids as antimitotic agents based on pharmacophore similarity

Thorough simplification of vinca alkaloids based on pharmacophore similarity has been conducted. A concise process for the syntheses of target compounds was successfully developed with yields from poor to excellent (19-98%). Cell growth inhibitory activities of these synthesized compounds were evaluated in five cancer cell lines including MCF-7, MDA-MB-231, HepG2, HepG2/ADM and K562. Almost all compounds exhibited moderate antitumor activity with optimal IC50 value of 0.89 ± 0.07 μM in MCF-7 cells. Investigation of structure-activity relationship (SAR) indicates that electron-withdraw substituents on the ring contribute to the enhancement of the antitumor activities. The simplified vinca alkaloids are confirmed as antimitotic agents, which inhibit the polymerization of tubulin just like vinblastine.

Organocatalytic asymmetric Michael addition of aliphatic aldehydes to indolylnitroalkenes: Access to contiguous stereogenic tryptamine precursors

Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1- ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.

Synthesis of 4-, 5-, 6-, and 7-azidotryptamines

Synthesis of azidotryptamines from commercially available nitroindoles via the corresponding amino tryptamines in good overall yields (15-38%) is presented.

Design, structure-activity relationships, X-ray crystal structure, and energetic contributions of a critical P1 pharmacophore: 3-Chloroindole-7-yl- based factor Xa inhibitors

An indole-based P1 moiety was incorporated into a previously established factor Xa inhibitor series. The indole group was designed to hydrogen-bond with the carbonyl of Gly218, while its 3-methyl or 3-chloro substituent was intended to interact with Tyr228. These interactions were subsequently observed in the X-ray crystal structure of compound 18. SAR studies led to the identification of compound 20 as the most potent FXa inhibitor in this series (IC50 = 2.4 nM, EC2xPT = 1.2 μM). An in-depth energetic analysis suggests that the increased binding energy of 3-chloroindole-versus 3-methylindole- containing compounds in this series is due primarily to (a) the more hydrophobic nature of chloro- versus methyl-containing compounds and (b) an increased interaction of 3-chloroindole versus 3-methylindole with Gly218 backbone. The stronger hydrophobicity of chloro- versus methyl-substituted aromatics may partly explain the general preference for chloro- versus methyl-substituted P1 groups in FXa, which extends beyond the current series.

Lactam inhibitors of factor Xa and method

Lactam inhibitors are provided which have the structure including pharmaceutically acceptable salts thereof and all stereoisomers thereof, and prodrug esters thereof, wherein n is 1 to 5; and and R1, R2, R3, R4, R5 , R6, R7, R8, R9, R10, R10a, 1011 and R12 are as defined herein. These compounds are inhibitors of Factor Xa and thus are useful as anticoagulants. A method for treating cardiovascular diseases associated with thromboses is also provided.