1196-70-9

Usage

Uses

Used in Pharmaceutical Industry:
Indole-6-carboxaldehyde is used as a reactant in the preparation of analogs of botulinum neurotoxin serotype A protease inhibitors. This application is crucial for developing potential therapeutic agents against botulinum neurotoxin, which is responsible for causing botulism, a severe and sometimes fatal illness.
Used in Organic Synthesis:
Indole-6-carboxaldehyde is used as a reactant in the synthesis of stilbene-based antitumor agents. Stilbenes are a class of organic compounds known for their potential anti-cancer properties, and Indole-6-carboxaldehyde plays a significant role in their synthesis, contributing to the development of new cancer treatments.
Used in Chemical Research:
Indole-6-carboxaldehyde is used as a reactant in the acid-catalyzed preparation of aromatic gem-dihalides from aldehydes and acid halides. This process is essential for the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals, showcasing the compound's utility in chemical research and development.

InChI:InChI=1/C9H7NO/c11-6-7-1-2-8-3-4-10-9(8)5-7/h1-6,10H

Upstream product

• 52415-29-9 6-bromo-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 1075-26-9 6-(hydroxymethyl)indole 
• 31680-07-6 4-methyl-3-nitrobenzaldehyde 
• 32989-68-7 trans-4-(β-dimethylaminovinyl)-3-nitrobenzaldehyde 
• 127956-27-8 6-(difluoromethyl)indole 
• 3420-02-8 6-methylindole 
• 15861-36-6 1H-Indole-6-carbonitrile 
• 1670-82-2 Indole-6-carboxylic acid 
• 50820-65-0 indole-6-carboxylic acid methyl ester 
• 127956-29-0 tert-butyl 6-(difluoromethyl)-1H-indole-1-carboxylate 
• 127956-25-6 6-(bromomethyl)-1-(tert-butoxycarbonyl)indole 
• 127956-28-9 1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde 
• 127956-24-5 tert-butyl 6-methyl-1H-indole-1-carboxylate 

Downstream Products

• 308110-28-3 1-(phenylsulfonyl)-1H-indole-6-carbaldehyde 
• 127956-28-9 1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde 
• 21005-45-8 1-methyl-1H-indole-6-carboxaldehyde 
• 1072121-60-8 (Z)-6-[2-(3,5-dimethoxyphenyl)-ethenyl]-1H-indole 
• 1177251-92-1 6-[(1-benzyl-1H-tetrazol-5-yl)(4-cyclobutyl-1,4-diazepan-1-yl)methyl]-1H-indole 
• 1198207-34-9 (1E,6E)-1-(2-bromo-5-hydroxyphenyl)-7-(1H-indol-6-yl)hepta-1,6-diene-3,5-dione 

Relevant academic research and scientific papers

SYNTHESIS AND REACTIVITY OF 6-(FLUOROMETHYL)INDOLE AND 6-(DIFLUOROMETHYL)INDOLE

The N-1 BOC protected precursors of 6-(fluoromethyl)indole and 6-(difluoromethyl)indole were prepared and deprotected via flash vacuum thermolysis.The stability of these newly prepared, unprotected indole derivatives has been characterized and compared to that of a previously known compound, 6(trifluoromethyl)indole.

Synthesis and Evaluation of Indole-Based Autoinducers on Quorum Sensing in Vibrio cholerae

Vibrio cholerae (V. cholerae) uses the autoinducer CAI-1 (cholera autoinducer 1) and several linked quorum sensing systems in order to efficiently sense its ever-changing environment and optimally coordinate population-wide gene expression. Indole has been reported as an important signal that is sensed by V. cholerae, and here, we report the synthesis and evaluation of a focused library of synthetic indole-CAI-1 derivatives as tools to probe quorum sensing (QS) in this human pathogen. Our results show interesting and diverging effects for several conjugates, as compared to CAI-1, on virulence factor production and biofilm formation.

N-(2-ARYLETHYL) BENZYLAMINES AS ANTAGONISTS OF THE 5-HT6 RECEPTOR

The present invention relates to the use compounds of formula I which are antagonists of the 5-HT 6 receptor, for treating a cognitive disorder selected from the group consisting of age-related cognitive decline, mild cognitive impairment and dementia

5-Oxo-ETE receptor antagonists

5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.

HETEROCYCLIC COMPOUNDS, METHODS OF MAKING THEM AND THEIR USE IN THERAPY

In part, the present invention is directed to antibacterial compounds of formula (I) wherein A is a bicyclic heteroaryl ring or a tricyclic ring and R2 is an heterocyclic residue; L is a bond, or L is alkyl, alkenyl or cycloalkyl.

Compounds as delta opioid agonists

Compounds of the formula (I)—shown below—are described. The compounds are useful in the manufacture of a pharmaceutical composition for preventing or treating inflammatory diseases such as arthritis, psoriasis, asthma, or inflammatory bowel disease, disorders of respiratory function, gastrointestinal disorders such as functional bowel disease, functional GI disorders such as irritable bowel syndrome, functional diarrhoea, functional distension, functional pain, non-ulcerogenic dyspepsia or others associated with disorders of motility or secretion, urogenital tract disorders such as incontinence, as analgesics for treating pain including non-somatic pain, or as immunosuppressants to prevent rejection in organ transplant and skin graft.

Certain indole derivatives useful as leukotriene antagonists

A compound of the formula STR1 in which R1 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C1-4 alkyl, aldehydo, --CH2 Z, --CH=CH--Z or --CH2 CH2 Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or --CONR7 R8 where R7 and R8 are each hydrogen or C1-4 alkyl; R3 and R4 are each hydrogen, C1-4 alkyl, optionally substituted phenyl, or C1-4 alkyl substituted by --CONR7 R8 or an optionally protected acid group; R5 is STR2 where W is --CH=CH--, --CH=N--, --N=CH--, --O-- or --S--, R9 is hydrogen, halo, C1-4 alkyl, C1-4 alkoxy or trihalomethyl, and R10 is hydrogen, C1-4 alkyl, C2-6 alkenyl, C3-6 cycloalkyl or C1-4 alkyl-C3-6 cycloalkyl; R6 is hydrogen or C1-4 alkyl; X is --O--(CH2)n CR11 R12, --CR11 R12 --, --CR11 R12.(CH2)n.CR13 R14 -- or --CR11 =CR12 -- where R11, R12, R13 and R14 are each hydrogen or C1-4 alkyl, and n is 0, 1 or 2; and Y is --O--CR15 R16 --, --CR15 =CR16 -- or --CR15 R16.CR17 R18 -- where R15, R16, R17 and R18 are each hydrogen or C 1-4 alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.

N-Benzyl-Indoles, processes for their preparation and pharmaceutical compositions containing them

A compound of the formula in which R1 is hydrogen, halo, C??? alkyl, C??? alkoxy, nitrile, optionally protected carboxy, optionally protected tetrazolyl, trihalomethyl, hydroxy-C??? alkyl, aldehydo,-CH?Z,-CH=CH-Z or-CH?CH?Z where Z is optionally protected carboxy or optionally protected tetrazolyl; R2 is halo, nitrile, an optionally protected acid group or-CONR?R? where R? and R? are each hydrogen or C??? alkyl, R3 and R? are each hydrogen, C??? alkyl, optionally substituted phenyl, or C??? alkyl substituted by-CONR?R? or an optionally protected acid group; R? is where W is-CH=CH-,-CH=N-,-N=CH-,-O-or-S-, R? is hydrogen, halo, C??? alkyl, C? ?? alkoxy or trihalomethyl, and R1? is hydrogen, C? ?? alkyl, C??? alkenyl, C??? cycloalkyl or C??? alkyl-C??? cycloalkyl; R? is hydrogen or C??? alkyl; X is-O-(CH?)nCR11CR12-,-CR11R12-,-CR11R12.(CH?) n.CR13R1?-or-CR11=CR12-where R11, R12, R13 and R1? are each hydrogen or C??? alkyl, and n is 0, 1 or 2; and Y is-O-CR1?R1?-,-CR1?=CR1?-or-CR1? R1?.CR1?R1?-where R1?, R1?, R1? and R1? are each hydrogen or C??? alkyl; or a salt thereof. The compounds in unprotected form are active as leukotriene antagonists.

Aliphatic carboxamides

This invention provides a series of novel heterocyclic aliphatic carboxamides of formula I in which the group >Z--Y--XC=CH--NN--CH=CC=N--NN--N=C and the other radicals have the meanings defined in the following specification. The compounds of formula I are leukotriene antagonists. The invention also provides pharmaceutically acceptable salts of the formula I compounds; pharmaceutical compositions containing the formula I compound, or their salts, for use in the treatment of, for example, allergic or inflammatory diseases, or endotoxic or traumatic shock conditions; and processes for the manufacture of the formula I compounds, as well as intermediates for use in such manufacture.