ChemInform Abstract: INTRAMOLECULAR CYCLIZATION OF 2‐AMINOBENZOPHENONES, A NEW 9‐ACRIDONE SYNTHESIS

Adams, Joyce H.; Gupta, Padma; KHAN, M. S.; Lewis, John R.; Watt, Robert A.

doi:10.1002/chin.197704214

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“…This reaction is believed to go through a Friedel-Crafts-like mechanism for the initial electrophilic aromatic substitution and subsequently form the acridone system through hydrolytic cyclization occurring between the primary amine and the hydroxyl adjacent to the substitution. 11 The reaction gave only minimal yield after refluxing for 48 h and was not repeatable. The workup was difficult due to several factors, including removal of the n-butyl alcohol, removal of inorganic salts, and insolubility of both the desired product and the byproducts.…”

Section: Chemistrymentioning

confidence: 97%

Anti-Herpes Simplex Virus Activity of Substituted 1-Hydroxyacridones

Lowden

Bastow

2003

J. Med. Chem.

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5-Chloro-1,3-dihydroxyacridone, 1, is a potent and selective inhibitor of Herpes Simplex Virus Type-1 (HSV-1).(1) Substituted 1,3-dihydroxyacridones represent a new class of nonnucleoside HSV-1 inhibitors, and biochemical studies indicate a novel mechanism of action for 1, although the target is not yet defined.(2) With the goal of lead optimization, analogues of 1 were synthesized in an effort to describe the structure-activity relationships between 1 and its hypothetical binding site. Modifications of key functional groups led to the identity of several features of 1 that were important for activity. In the process, a more expedient and reliable synthesis of 1 and its analogues was developed. Analogues were evaluated against HSV-1 and HSV-2 using a viral plaque-elimination assay for viral inhibition of HSV-1 and HSV-2, and effects on replication of the host cell were also measured in order to assess a therapeutic index (TI) of selectivity. Several new analogues with significant antiviral activity were identified, including 5-methoxy-1,3-dihydroxyacridone (11), which inhibits replication of several HSV-2 strains with a mean ED(50) of 0.7 muM and a TI range of 25-60-fold.

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Section: Chemistrymentioning

confidence: 97%