24438-49-1

Upstream product

• 16130-32-8 (4-chlorophenyl)(3-(2-hydroxyethyl)-5-methoxy-2-methyl-1H-indol-1-yl)methanone 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 1448723-52-1 C₂₅H₂₁ClN₄O₇S 
• 1429887-51-3 3-allyl-5-methoxy-2-methyl-1-[(4-methylphenyl)sulfonyl]-1H-indole 
• 1429887-67-1 zhucan-7-13 
• 24438-50-4 3-allyl-5-methoxy-2-methyl-1-(4-chlorobenzoyl)indole 
• 24438-51-5 zhucan-7-15 
• 1314595-90-8 N-(2-iodo-4-methoxylphenyl)-4-methylbenzenesulfonamide 
• 69643-52-3 hex-5-en-2-ynyl bromide 
• 191348-14-8 2-iodo-4-methoxylaniline 
• 122-01-0 4-chloro-benzoyl chloride 
• 873657-15-9 3-(tert-butyldimethylsiloxy)ethyl-1-(4-chlorobenzoyl)-5-methoxy-2-methylindole 
• 873657-14-8 N-(4-chlorobenzoyl)-2-iodo-4-methoxyaniline 

Downstream Products

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 1376615-37-0 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetaldehyde oxime 
• 1376615-38-1 2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)acetaldehyde O-methyl oxime 

Relevant academic research and scientific papers

SYNTHESIS OF DEUTERATED ALDEHYDES

Described are methods for preparing a deuterated aldehyde using N-heterocyclic carbene catalysts in a solvent comprising D2O. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions without functionality manipulation.

Silver-Promoted Direct Phosphorylation of Bulky C(sp2)-H Bond to Build Fully Substituted β-Phosphonodehydroamino Acids

A general and practical cross-dehydrogenative coupling protocol between readily available trisubstituted α,β-dehydro α-amino carboxylic esters and H-phosphites is described. This C(sp2)-H phosphorylation reaction proceeds with absolute Z-selectivity promoted by silver salt in a radical relay manner. The bulky tetrasubstituted β-phosphonodehydroamino acids were obtained in grams and added new modules to the toolkit for peptide modifications.

Modified McFadyen-Stevens reaction for a versatile synthesis of aliphatic/aromatic aldehydes: Design, optimization, and mechanistic investigations

The traditional McFadyen-Stevens reaction requires harsh alkaline reaction conditions, thus precluding application to the synthesis of aliphatic aldehydes. Our modified McFadyen-Stevens reaction enables the transformation from the N,N-acylsulfonyl hydrazine to the corresponding aldehyde upon treatment with an imidazole-TMS imidazole combination without relying on oxidative or reductive reagents. The reduced basicity and in situ protection of the resulting aldehyde widens the substrate scope to include aliphatic aldehydes, even ones bearing an α-hydrogen atom. Close examination of the side reactions for particular substrates in combination with theoretical considerations via DFT calculations led to a mechanistic understanding of the McFadyen-Stevens reaction involving an acyl diazene and a hydroxy carbene as reasonable intermediates.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

Coupling and cyclization of O-iodoanilines and propargylic bromides via allenes: An efficient entry to indomethacin

A sequential allene synthesis and cyclization has been realized in a one-pot manner. A Pd(0)-catalyzed one-pot reaction of N-Ts or -Ms 2-iodoanilines and propargylic bromides afforded indoles with pharmaceutical importance highly efficiently with diversity via sequential carbon-carbon bond coupling forming allenes and azapalladation. With this newly established methodology, an efficient approach to indomethacin, an anti-inflammatory drug (NSAID), has been accomplished.

DRUG DERIVATIVES

The present invention relates to derivatives of known active pharmaceutical compounds. These derivatives are differentiated from the parent active compound by virtue of being redox derivatives of the active compound. This means that one or more of the functional groups in the active compound has been converted to another group in one or more reactions which may be considered to represent a change of oxidation state. We refer to these compounds generally as redox derivatives. The derivatives of the invention may be related to the original parent active pharmaceutical compound by only a single step transformation, or may be related via several synthetic steps including one or more changes of oxidation state. In certain cases, the functional group obtained after two or more transformations may be in the same oxidation state as the parent active compound (and we include these compounds in our definition of redox derivatives). In other cases, the oxidation state of the derivative of the invention may be regarded as being different from that of the parent compound. In many cases, the compounds of the invention have inherent therapeutic activity on their own account. In some cases, this activity relative to the same target or targets of the parent compound is as good as or better than the activity which the parent compound has against the target or targets.

A new entry to the synthesis of 2,3-disubstituted indoles

(Chemical Equation Presented) The Stille coupling of N-acyl-2-iodoanilines with the 1-(tributylstannyl)-1-substituted allenes affected the successive one-step formation of the 2-methyl-3-substituted indoles. Alternatively, the other type of 2-alkyl-3-substituted indoles could be synthesized in a one-pot operation, which consists of the Stille coupling reaction with the 1-(tributylstannyl)-1,3-disubstituted allenes, followed by TBAF treatment. This procedure could be applied to the synthesis of indomethacin.

Pharmaceutically useful derivatives of thiazolidine-4-carboxylic acid

Compounds of formula in which R, R1 and Y have the meanings shown in the description, their preparation by condensing an aldehyde or a ketone with cysteine or a derivative thereof and their use in the pharmaceutical field. The compounds of formula I possess antipyretic, anti--inflammatory, mucolytic and analgesic activity together with a low capacity to cause gastric injuries. The compounds of formula I, furthermore, are particularly useful in the treatment of ischemia and reperfusion syndromes.