152213-40-6

Basic information

• Product Name: 5-AMINO-2-INDOLECARBOXYLIC ACID
• Synonyms: 5-AMINO-2-INDOLE CARBOXYLIC ACID;5-amino-1H-indole-2-carboxylic acid
• CAS NO: 152213-40-6
• Molecular Formula: C₉H₈N₂O₂
• Molecular Weight: 176.17
• Mol File: 152213-40-6.mol

Chemical Properties

• Boiling Point: 518.715 °C at 760 mmHg
• Flash Point: 267.51 °C
• Appearance: /
• Density: 1.51 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.796
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.01±0.30(Predicted)
• CAS DataBase Reference: 5-AMINO-2-INDOLECARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINO-2-INDOLECARBOXYLIC ACID(152213-40-6)
• EPA Substance Registry System: 5-AMINO-2-INDOLECARBOXYLIC ACID(152213-40-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 152213-40-6(Hazardous Substances Data)

Usage

Uses

Used in Biomedical Applications:
5-Amino-2-indolecarboxylic acid is used as a therapeutic agent for its anti-inflammatory properties, helping to reduce inflammation in various conditions. Its antioxidant capabilities also contribute to its potential use in protecting cells from oxidative stress, which is implicated in many diseases.
Used in Anticancer Applications:
In the field of oncology, 5-Amino-2-indolecarboxylic acid is used as an anticancer agent, where it may play a role in inhibiting the growth of cancer cells and potentially reducing the risk of certain types of cancer. 5-Amino-2-indolecarboxylic acid's effects on cancer cell metabolism and its ability to induce apoptosis in cancer cells are areas of active research.
Used in Plant Growth and Development:
5-Amino-2-indolecarboxylic acid is used as a growth regulator in agriculture, where it may influence various aspects of plant growth and development. Its role in plant metabolism and signaling pathways could lead to improved crop yields and resistance to environmental stressors.
Used in Synthesis of Biologically Active Molecules:
As a chemical precursor, 5-Amino-2-indolecarboxylic acid is used in the synthesis of various biologically active molecules, such as pharmaceuticals and other bioactive compounds. Its presence in the metabolic pathways of plants and microorganisms makes it a valuable starting material for the production of these molecules.

InChI:InChI=1/C9H8N2O2/c10-6-1-2-7-5(3-6)4-8(11-7)9(12)13/h1-4,11H,10H2,(H,12,13)

Upstream product

• 71086-99-2 ethyl 5-amino-1H-indole-2-carboxylate 
• 16732-57-3 5-nitro-indole-2-carboxylic acid ethyl ester 
• 481659-88-5 1-ethyl-5-nitro-1H-indole-2-carboxylic acid ethyl ester 
• 409315-76-0 5-isocyanato-indole-2-carboxylic acid ethyl ester 
• 138731-14-3 1H-indole-2,5-dicarboxylic acid 2-ethyl ester 
• 16730-20-4 5-nitro-1H-indole-2-carboxylic acid 

Downstream Products

• 136817-55-5 delavirdine 
• 138730-81-1 5-[(tert-Butyloxycarbonyl)amino]indole-2-carboxylic Acid 
• 152213-39-3 5-[(3-phenyldithio)propionylamino]-indole-2-carboxylic acid 

Relevant articles and documents

Sequence-specific alkylation of double-strand human telomere repeat sequence by pyrrole-imidazole polyamides with indole linkers

We designed and synthesized pyrrole (Py)-imidazole (Im) hairpin polyamide 1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benz[e]indole (seco-CBI) conjugates 1 and 2, which target both strands of -the double-stranded region of the human telomere repeat sequences, 5′-d(TTAGGG)n-3′/5′- d(CCCTAA)n-3′. High-resolution denaturing polyacrylamide gel electrophoresis demonstrated that conjugates 1 and 2 alkylated DNA at the 3′ A of 5′-ACCCTA-3′ and 5′-AGGGTTA-3′, respectively. Cytotoxicities of conjugates 1 and 2 were evaluated using 39 human cancer cell lines; averages of log IC50 values for conjugates 1 and 2 were -6.96 (110 nM) and -7.24 (57.5 nM), respectively. Conjugates 1 and 2 have potential as antitumor drugs capable of targeting telomere repeat sequence.

Synthesis method of indole-2-carboxylic acid and derivative thereof

The invention relates to a synthesis method of indole-2-carboxylic acid and a derivative thereof, belonging to the field of organic synthesis. In the synthesis method, the indole-2-carboxylic acid isprepared through two steps of reaction with phenylhydrazine hydrochloride and ethyl pyruvate as raw materials and sulfuric acid as a catalyst. The synthesis method has a short process and uses fewer raw materials, the total yield of indole-2-carboxylic acid reaches 70% or above. The method can synthesize both indole-2-carboxylic acid and the derivative thereof, thereby being suitable for industrial production.

SECO-CYCLOPROPAPYRROLOINDOLE COMPOUNDS, ANTIBODY-DRUG CONJUGATES THEREOF, AND METHODS OF MAKING AND USE

seco-Cyclopropapyrroloindole compounds of formula (I) where Hal, R1, R2, and R3 are as defined in the application, are potent anti-cancer agents that can be used in antibody-drug conjugates.

NOVEL INDOLE DERIVATIVE FOR ALKYLATING SPECIFIC BASE SEQUENCE OF DNA AND ALKYLATING AGENT AND DRUG EACH COMPRISING THE SAME

There is provided a novel pyrrole-imidazole polyamide compound for alkylating the specific base sequence of DNA, the polyamide compound being capable of being synthesized through fewer reaction steps than known hybrid molecules and having a combination of a high reactivity in DNA alkylation and the ability to recognize a sequence. Furthermore, there is provided an alkylating agent and a molecule serving as a drug, the alkylating agent and the molecule containing the polyamide compound. An indole derivative is represented by general formula (1): wherein R 1 represents a functional group for alkylating DNA; R 2 represents a hydrogen atom, an alkyl group, or an acyl group; and X represents a divalent group having one constitutional unit or having two or more constitutional units which may be the same or different, the constitutional unit being represented by the following formula: (wherein m is an integer of 0 to 10), wherein among the constitutional units, a terminal constitutional unit adjacent to R 2 may be a constitutional unit represented by the following formula: (wherein k is an integer of 0 to 10).

Phosphate mimics and methods of treatment using phosphatase inhibitors

The invention relates to trifluoromethyl sulfonyl and trifluoromethyl sulfonamido compounds and the physiologically acceptable salts and the prodrugs thereof. These compounds are expected to modulate the activity of protein tyrosine enzymes which are related to cellular signal transduction, in particular, protein tyrosine phosphatase, and therefore are expected to be useful in the prevention and treatment of disorders associated with abnormal protein tyrosine enzyme related cellular signal transduction such as cancer, diabetes, immuno-modulation, neurologic degenerative diseases, osteoporosis and infectious diseases. The invention also relates to the use of compounds containing fluoromethyl sulfonyl groups as phosphate mimics. These mimics may be used to inhibit, regulate or modulate the activity of a phosphate binding protein in a cell.