38088-96-9

Basic information

• Product Name: 2-Methoxyphenanthridine-6(5H)-one
• Synonyms: 2-Methoxy-6(5H)-phenanthridinone;2-Methoxyphenanthridine-6(5H)-one
• CAS NO: 38088-96-9
• Molecular Formula: C14H11NO2
• Molecular Weight: 225.24
• Mol File: 38088-96-9.mol
• Article Data: 12

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Methoxyphenanthridine-6(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxyphenanthridine-6(5H)-one(38088-96-9)
• EPA Substance Registry System: 2-Methoxyphenanthridine-6(5H)-one(38088-96-9)

Safety Data

• Hazardous Substances Data: 38088-96-9(Hazardous Substances Data)

Usage

Description

2-Methoxyphenanthridine-6(5H)-one is a derivative of phenanthridine, a nitrogen-based polycyclic aromatic hydrocarbon (PAH). It is characterized by the presence of a methoxy group attached to the 2-position and a ketone group at the 6-position of the phenanthridine core. 2-Methoxyphenanthridine-6(5H)-one exhibits unique chemical properties and potential biological activities, making it a promising candidate for various applications.

Uses

Used in Pharmaceutical Industry:
2-Methoxyphenanthridine-6(5H)-one is used as a key intermediate in the synthesis of potential HIV-1 integrase inhibitors. These inhibitors are designed to target and inhibit the activity of the integrase enzyme, which is essential for the replication of the HIV virus. By blocking the integrase enzyme, these compounds can potentially suppress the viral replication process and help in the treatment of HIV/AIDS.
In the development of HIV-1 integrase inhibitors, 2-Methoxyphenanthridine-6(5H)-one serves as a crucial building block for the creation of novel and effective antiviral agents. Its unique chemical structure allows for the design of molecules with improved binding affinity, selectivity, and pharmacokinetic properties, which are essential for the success of any drug candidate.
Furthermore, the use of 2-Methoxyphenanthridine-6(5H)-one in the preparation of HIV-1 integrase inhibitors highlights its potential as a versatile and valuable compound in the field of medicinal chemistry. Its ability to be modified and incorporated into various chemical scaffolds makes it an attractive candidate for the development of new drugs targeting a wide range of diseases and conditions.

Upstream product

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Relevant articles and documents

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

Rhodium(I)-Catalyzed Aryl C-H Carboxylation of 2-Arylanilines with CO2

An unprecedented Rh(I)-catalyzed, amino-group-assisted C-H carboxylation of 2-arylanilines with CO2 under redox-neutral conditions has been developed. This reaction was promoted by a phosphine ligand with t-BuOK as the base and did not require the use of additional strong organometallic reagent. It enabled an efficient direct conversion of a broad range of 2-(hetero)arylanilines including electron-deficient heteroarenes to various phenanthridinones. Possible intermediates of the reaction were also evaluated in the preliminary mechanistic studies.

Palladium-Catalyzed C-H Activation and Cyclization of Anilides with 2-Iodoacetates and 2-Iodobenzoates: An Efficient Method toward Oxindoles and Phenanthridones

A concise approach to the synthesis of oxindoles and phenanthridones from anilides is described. In the presence of catalytic amount of Pd(OAc)2, 2-iodoacetates and 2-iodobenzoates can be used to functionalize ortho C-H bond of anilides, which subsequently undergo intramolecular cyclization to give the products. A possible reaction mechanism that involves a PdII/PdIV catalytic cycle is proposed with the support of detailed mechanistic studies.