127956-28-9

Basic information

• Product Name: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE
• Synonyms: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE
• CAS NO: 127956-28-9
• Molecular Formula: C₁₄H₁₅NO₃
• Molecular Weight: 245.277
• Mol File: 127956-28-9.mol

Chemical Properties

• Boiling Point: 380.0±34.0 °C(Predicted)
• Appearance: /
• Density: 1.13±0.1 g/cm3(Predicted)
• CAS DataBase Reference: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE(127956-28-9)
• EPA Substance Registry System: TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE(127956-28-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 127956-28-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE is utilized as a key intermediate in organic synthesis for the preparation of a variety of indole derivatives. Its presence in this process is crucial due to its ability to facilitate the creation of complex organic molecules that are otherwise challenging to synthesize.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE is employed as a building block for the development of pharmaceutical compounds. Its distinctive structural features contribute to the design of new drugs and therapeutic agents, potentially leading to advancements in treatment options for various medical conditions.
Used in Pharmaceutical Industry:
TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE is used as a precursor in the pharmaceutical industry for the synthesis of indole-based drugs. Its role in this industry is pivotal as it aids in the production of compounds that can be further modified to possess specific therapeutic properties.

Upstream product

• 298-12-4 Glyoxilic acid 
• 127956-24-5 tert-butyl 6-methyl-1H-indole-1-carboxylate 
• 34619-03-9 tert-butyldicarbonate 
• 3420-02-8 6-methylindole 
• 127956-25-6 6-(bromomethyl)-1-(tert-butoxycarbonyl)indole 
• 1196-70-9 indole-6-carboxaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 

Downstream Products

• 460096-23-5 6-(2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-indole-1-carboxylic acid tert-butyl ester 
• 39689-57-1 2-(1H-indol-6-yl)acetonitrile 
• 39689-58-2 2-(indol-6-yl)acetic acid 
• 1298129-85-7 3-[6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid ethyl ester 
• 1298129-79-9 6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester 
• 1298129-83-5 3-[6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid 
• 1298129-74-4 6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-1H-indole 
• 354587-72-7 tert-butyl 6-(hydroxymethyl)-1H-indole-1-carboxylate 
• 127956-27-8 6-(difluoromethyl)indole 
• 1196-70-9 indole-6-carboxaldehyde 
• 460096-33-7 6-(2-benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-indole-1-carboxylic acid tert-butyl ester 

Relevant articles and documents

POLYHETEROCYCLIC COMPOUNDS AS METTL3 INHIBITORS

The present invention relates to compounds of formula (I) that function as inhibitors of METTL3 (N6-adenosine-methyltransferase 70 kDa subunit) enzyme activity: X-Y-Z (I) wherein X, Y and Z are each as defined herein. The present invention also relates to processes for the preparation of these compounds, to pharmaceutical compositions comprising them, and to their use in the treatment of proliferative disorders, such as cancer, and autoimmune diseases, as well as other diseases or conditions in which METTL3 activity is implicated.

Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides

The aromatic ring in benzyl halides and sulfonates imparts unique reactivity at the benzylic carbon atom. Photoredox sp3-sp3 cross-coupling proved ineffective for coupling p-methoxybenzyl chloride (PMBCl), leading to a new strategy for the sp3-sp3 cross-coupling of benzyl halides and sulfonates. This strategy involved LiCl-accelerated synthesis of a Grignard reagent followed by a copper-catalyzed cross-coupling. The conditions worked well for PMBCl due to its exceptional reactivity but other benzyl bromides or sulfonates reacted poorly.

Structure-guided design, synthesis, and biological evaluation of (2-(1 H-Indol-3-yl)-1 H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) methanone (ABI-231) analogues targeting the colchicine binding site in Tubulin

ABI-231 is a potent, orally bioavailable tubulin inhibitor that interacts with the colchicine binding site and is currently undergoing clinical trials for prostate cancer. Guided by the crystal structure of ABI-231 in complex with tubulin, we performed structure-activity relationship studies around the 3-indole moiety that led to the discovery of several potent ABI-231 analogues, most notably 10ab and 10bb. The crystal structures of 10ab and 10bb in complex with tubulin confirmed their improved molecular interactions to the colchicine site. In vitro, biological studies showed that new ABI-231 analogues disrupt tubulin polymerization, promote microtubule fragmentation, and inhibit cancer cell migration. In vivo, analogue 10bb not only significantly inhibits primary tumor growth and decreases tumor metastasis in melanoma xenograft models but also shows a significant ability to overcome paclitaxel resistance in a taxane-resistant PC-3/TxR model. In addition, pharmacological screening suggested that 10bb has a low risk of potential off-target function.

Discovery and Optimization of Indolyl-Containing 4-Hydroxy-2-Pyridone Type II DNA Topoisomerase Inhibitors Active against Multidrug Resistant Gram-negative Bacteria

There exists an urgent medical need to identify new chemical entities (NCEs) targeting multidrug resistant (MDR) bacterial infections, particularly those caused by Gram-negative pathogens. 4-Hydroxy-2-pyridones represent a novel class of nonfluoroquinolone inhibitors of bacterial type II topoisomerases active against MDR Gram-negative bacteria. Herein, we report on the discovery and structure-activity relationships of a series of fused indolyl-containing 4-hydroxy-2-pyridones with improved in vitro antibacterial activity against fluoroquinolone resistant strains. Compounds 6o and 6v are representative of this class, targeting both bacterial DNA gyrase and topoisomerase IV (Topo IV). In an abbreviated susceptibility screen, compounds 6o and 6v showed improved MIC90 values against Escherichia coli (0.5-1 μg/mL) and Acinetobacter baumannii (8-16 μg/mL) compared to the precursor compounds. In a murine septicemia model, both compounds showed complete protection in mice infected with a lethal dose of E. coli.

Synthesis of Aldehydes by Organocatalytic Formylation Reactions of Boronic Acids with Glyoxylic Acid

Reported herein is a conceptually novel organocatalytic strategy for the formylation of boronic acids. New reactivity is engineered into the α-amino-acid-forming Petasis reaction occurring between aryl boronic acids, amines, and glyoxylic acids to prepare aldehydes. The operational simplicity of the process and its ability to generate structurally diverse and valued aryl, heteroaryl, and α,β-unsaturated aldehydes containing a wide array of functional groups, demonstrates the practical utility of the new synthetic strategy.

4,5,6,7-TETRAHYDRO-1 H-PYRAZOLO[4,3-C]PYRIDIN-3-AMINE COMPOUNDS AS CBP AND/OR EP300 INHIBITORS

The present invention relates to compounds of formula (I) or formula (II): and to salts thereof, wherein R1-R4 of formula (I) and R1-R3 of formula (II) have any of the values defined herein, and compositions and uses thereof. The compounds are useful as inhibitors of CBP and/or EP300. Also included are pharmaceutical compositions comprising a compound of formula (I) of formula (II) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various CBP and/or EP300-mediated disorders.

AZETIDINE DERIVATIVES USEFUL FOR THE TREATMENT OF METABOLIC AND INFLAMMATORY DISEASES

Compounds are disclosed that have a formula represented by the following: These compounds may be prepared as a pharmaceutical composition, and may be used for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example inflammatory conditions, infectious diseases, autoimmune diseases, diseases involving impairment of immune cell functions, cardiometabolic diseases, and/or proliferative diseases.

INDOLE AND INDAZOLE ANALOGS AS GLYCOGEN SYNTHASE ACTIVATORS

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful

NOVEL CURCUMIN DERIVATIVE

The present invention provides a novel compound that is structurally similar to curcumin and has a suppressive effect on Aβ aggregation, a degradative effect on Aβ aggregates, an inhibitory effect on β-secretase, and a protective effect on neurons. The novel compound is a compound represented by the following general formula (Ia) or a salt thereof: wherein R1 represents a 4-hydroxy-3-methoxyphenyl group or the like, and R2 represents a 1H-indol-6-yl group or the like.

5-Sulphanyl-4h-1,2,4-triazole derivatives and their use as medicine

The invention concerns novel 5-sulphanyl-4H-1,2,4-triazole derivatives of formula (1), wherein: R1, R2 and R3 represent variable groups and the methods for preparing them by liquid-phase parallel synthesis processes. Said product exhibit good affinity for certain sub-types of somatostatin receptors; they are particularly useful for treating pathological conditions or diseases wherein one (or more) somatostatin receptors is (are) involved. The invention also concerns pharmaceutical compositions containing said products and their use for preparing a medicine.