349459-07-0Relevant academic research and scientific papers
With tumor-responsive release drug compound or its pharmaceutically acceptable salts and its preparation, application
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, (2017/03/28)
The invention discloses a compound with a tumor responsive drug release function, or a pharmaceutical salt of the compound, as well as preparation and application of the compound, and belongs to the technical field of drug targeting release. The structural formula of the compound is as shown in the Specifications. The designed and synthesized novel tumor cell-sensitive compound disclosed by the invention can stably exist in the normal physiological environment, can release amsacrine drug when entering into tumor cells and performing a cascade reaction under a high-concentration glutathione environment in the tumor cells, and can be used for prepare a novel targeting antitumor drug. In addition, the preparation method of the compound disclosed by the invention is simple and convenient to operate, moderate in conditions, and high in reaction yield.
Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
Staderini, Matteo,Cabezas, Nieves,Bolognesi, Maria Laura,Menéndez, J. Carlos
, p. 1024 - 1030 (2013/02/23)
Focused microwave irradiation of equimolecular mixtures of 9-chloroacridines, 4-chloroquinolines and 4-chloroquinazolines with amines in the presence of 2 equiv of phenol allows the general, fast and high-yielding synthesis of aminated heterocycles, with a very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic problem of achieving a practical and efficient method for the amination of π-deficient nitrogen heterocycles for medicinal chemistry applications.
Reactivity of Quinone Imine and Quinone Diimine Metabolites of the Antitumor Drug Amsacrine and Related Compounds to Nucleophiles
Lee, Ho H.,Palmer, Brian D.,Denny, William A.
, p. 6042 - 6047 (2007/10/02)
The quinone diimine AQDI (7) and the quinone imine AQI (10) (products of oxidative metabolism of the clinical antileukemia drug amsacrine (1)) and related compounds were prepared, and their reactions with a variety of nucleophiles were studied.Reaction of
Potential Antitumor Agents. 52. Carbamate Analogues of Amsacrine with in Vivo Activity against Multidrug-Resistant P388 Leukemia
Rewcastle, Gordon W.,Baguley, Bruce C.,Atwell, Graham J.,Denny, William A.
, p. 1576 - 1581 (2007/10/02)
Study of a series of aniline-substituted 9-anilinoacridines related to the antileukemic drug amsacrine showed that a 1'-carbamate group provided increased activity against the multidrug-resistant P388/ADR leukemia subline in vivo.Since activity against su
Multi-step process for the production of methanesulfon-m-anisidide, 4'-(9-acridinylamino)-
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, (2008/06/13)
A multi-step method of producing the compound methanesulfon-m-anisidide, 4''-(9-acridinylamino)-, acetate (VII), which may be in free base form and designated NSC 249992, also known as AMSA. This compound is produced by an elegant process from a starting material, 4-butyrylamino-3-methoxy-nitrobenzene, which is later transformed to methanesulfon-m-anisidide, 4''-amino- (IV) and is coupled or joined to 9-chloro-acridine, producing the chloride salt which is later converted to the acetate.
