1601-18-9

Usage

Chemical Properties

Pale Green Solid

Uses

Selective COX-2 inhibitor

InChI:InChI=1/C20H18ClNO4/c1-12-16(11-19(23)26-3)17-10-15(25-2)8-9-18(17)22(12)20(24)13-4-6-14(21)7-5-13/h4-10H,11H2,1-3H3

Upstream product

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 77-76-9 2,2-dimethoxy-propane 
• 122-01-0 4-chloro-benzoyl chloride 
• 7588-36-5 methyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate 
• 67-56-1 methanol 
• 186581-53-3 diazomethane 
• 85622-93-1 temozolomide 
• 74-88-4 methyl iodide 
• 6260-97-5 (4-chlorophenyl)(5-methoxy-2-methyl-1H-indol-1-yl)methanone 
• 128368-43-4 2-isopropenyl-4-methoxyaniline 
• 19501-58-7 4-methoxyphenylhydrazine hydrochloride 
• 2833-24-1 methyl (E)-4-oxo-2-pentenoate 
• 1076-74-0 5-methoxy-2-methyl-1H-indole 

Downstream Products

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 1442444-07-6 methyl [1-(4-chlorobenzoyl)-2-formyl-5-methoxy-1Hindol-3-yl]acetate 
• 1442444-06-5 methyl [2-tert-butyldimethylsiloxymethyl-1-(4-chlorobenzoyl)-5-methoxy-1H-indol-3-yl]acetate 
• 1442444-04-3 methyl [1-(4-chlorobenzoyl)-2-chloromethyl-5-methoxy-1H-indol-3-yl]acetate 
• 867154-15-2 [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hydrazide 
• 1262801-27-3 3-[2-{5-((1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)methyl)-1,3,4-oxadiazol-2-ylthio}acetyl]-2H-chromen-2-one 
• 536-40-3 4-chlorobenzoic acid hydrazide 

Relevant academic research and scientific papers

Organoiridium catalyzed hydrogen isotope exchange: Ligand effects on catalyst activity and regioselectivity

Several iridium complexes [Ircod)L2]X (L = phosphine ligand) were used as precatalysts for the exchange labeling of a range of model compounds with deuterium gas. Complexes with monodentate L (e.g. PMePh2, PPh3 and substituted derivatives thereof) catalyzed exchange selectively of hydrogens four bonds away from a coordinative heteroatom in the substrate, while those with bidentate L (bis(diphenylphosphino)ethane (dppe) and bis(diphenylphosphino)butane) catalyzed exchange of hydrogens both four and five bonds away from a coordinative heteroatom. At heavier loadings, some monodentate complexes also catalyzed five-bond labeling of some substrates. [Ir(cod)(dppe)]BF4 catalyzed the tritium labeling of methyl 6-methoxynaphth-2-ylacetate at C1 and C3.

Indole derivatives as cyclooxygenase inhibitors: Synthesis, biological evaluation and docking studies

A new series of 2-(5-methoxy-2-methyl-1H-indol-3-yl)-N-[(E)-(substituted phenyl) methylidene] acetohydrazide derivatives (S1–S18) were synthesized and evaluated for their anti-inflammatory activity, analgesic activity, ulcerogenic activity, lipid peroxidation, ulcer index and cyclooxygenase expression activities. All the synthesized compounds were in good agreement with spectral and elemental analysis. Three synthesized compounds (S3, S7 and S14) have shown significant anti-inflammatory activity as compared to the reference drug indomethacin. Compound S3 was further tested for ulcerogenic index and cyclooxygenase (COX) expression activity. It was selectively inhibiting COX-2 expression and providing the gastric sparing activity. Docking studies have revealed the potential of these compounds to bind with COX-2 enzyme. Compound S3 formed a hydrogen bond between OH of Tyr 355 and NH2 of Arg 120 with carbonyl group and this hydrogen bond was similar to that formed by indomethacin. This study provides insight for compound S3, as a new lead compound as anti-inflammatory agent and selective COX-2 inhibitor.

Photolysis of indomethacin in methanol

A novel photo-oxidation product containing a six-membered 1,2-dioxane ring was isolated from the photolysis of indomethacin in methanol and a possible mechanism is proposed.

1H NMR and molecular modeling study on the inclusion complex β-cyclodextrin-indomethacin

The solution structure of the inclusion complex between β-cyclodextrin (2) and the nonsteroidal anti-inflammatory agent indomethacin sodium salt (1) [1-(p-chlorobenzoyl)-5-methoxy-2-methylin-doleacetic acid sodium salt] is investigated in D2O solution via 1H NMR spectroscopy. The guest molecule 1 exists in solution as a mixture of E and Z isomers in fast exchange on the NMR time scale, as shown by NOE experiments. Low-temperature 1H NMR spectra on indomethacin methyl ester (3) (soluble in CH2Cl2-d2) showed that the Z isomer is the most thermodynamically stable. Geometrical features of the host-guest inclusion complex between 2 and 1 are inferred from intermolecular dipolar contacts obtained by 1D NOE difference spectra and 2D ROESY experiments. A more detailed picture of the solution structure of the complex is obtained by combining NMR structural information and molecular dynamics and energy calculations on the inclusion complexes. Computations took into account the existence of two diastereomeric forms of the guest (E and Z), the two possible sites of interaction of the guest molecule with the cavity (i.e. the p-chlorobenzoyl ring and the indole ring system), and the different topologies for the entry of the guest into the host's cavity. The main finding that can be obtained from both experimental and theoretical data is that the complexation selectively stabilizes the E isomer with respect to Z. The inclusion complex is characterized by the interaction of the p-chlorobenzoyl moiety of 1E with the lipophilic cavity of the host 2, the entry being through the larger rim of the truncated cone of 2.

Preparation method of carboxylic ester compound

The invention relates to a preparation method of a carboxylic ester compound, which comprises the following steps: reacting carboxylic acid with methanol in air under the catalysis of nitrite to obtain an ester compound, the preparation method disclosed by the invention has the advantages of rich raw material sources, cheap and easily available catalyst, mild reaction conditions, simplicity and convenience in operation and the like, a series of fatty carboxylic acids can be modified with high yield, and particularly, the traditional esterification method is generally not suitable for esterification of drug molecules. By utilizing the method, a series of known drug molecules can be modified, so that a shortcut is provided for discovering new drug molecules.

Green Esterification of Carboxylic Acids Promoted by tert-Butyl Nitrite

In this work, the green esterification of carboxylic acids promoted by tert-butyl nitrite has been well developed. This transformation is compatible with a broad range of substrates and exhibits excellent functional group tolerance. Various drugs and substituted amino acids are applicable to this reaction under near neutral conditions, with good to excellent yields.

A Metal-Free Direct Arene C?H Amination

The synthesis of aryl amines via the formation of a C?N bond is an essential tool for the preparation of functional materials, active pharmaceutical ingredients and bioactive products. Usually, this chemical connection is only possible by transition metal-catalyzed reactions, photochemistry or electrochemistry. Here, we report a metal-free arene C?H amination using hydroxylamine derivatives under benign conditions. A charge transfer interaction between the aminating reagents TsONHR and the arene substrates enables the chemoselective amination of the arene, even in the presence of various functional groups. Oxygen was crucial for an effective conversion and its accelerating role for the electron transfer step was proven experimentally. In addition, this was rationalized by a theoretical study which indicated the involvement of a dioxygen-bridged complex with a “Sandwich-like” arrangement of the aromatic starting materials and the aminating agents at the dioxygen molecule. (Figure presented.).

Anti-Markovnikov hydroarylation of alkenes via polysulfide anion photocatalysis

A protocol for anti-Markovnikov hydroarylation of alkenes with aryl halides has been developed using polysulfide anions as photocatalysts in the presence of the Hantzsch ester and water under irradiation with visible light.

REAGENTS AND PROCESS FOR DIRECT C-H FUNCTIONALIZATION

Thianthrene derivative of the Formula (I): wherein R1 to R8 may be the same or different and are selected from hydrogen, Cl, F, a partially or fully fluorinated C1 to C6 alkyl group, and wherein n is 0 or 1, with the proviso that at least one of R1 to R8 is not hydrogen and process for C-H functionalization of aromatic compounds using this compound.

Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement

An unprecedented approach for efficient synthesis of functionalized allylic gem-difluorides via catalytic fluorinative Meyer–Schuster-like rearrangement is disclosed. This transformation proceeded with readily accessible propargylic fluorides, and low-cost B–F reagents and electrophilic reagents by sulfide catalysis. A series of iodinated, brominated, and trifluoromethylthiolated allylic gem-difluorides that were difficult to access by other methods were facilely produced with a wide range of functional groups. Importantly, the obtained iodinated products could be incorporated into different drugs and natural products, and could be expediently converted into many other valuable gem-difluoroalkyl molecules as well. Mechanistic studies revealed that this reaction went through a regioselective fluorination of alkynes followed by a formal 1,3-fluorine migration under the assistance of the B–F reagents to give the desired products.