1035979-44-2

Usage

Uses

Used in Pharmaceutical Industry:
(4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride is used as an antimicrobial agent for the treatment of bacterial infections. Its unique structure allows it to target and inhibit the growth of various pathogenic bacteria, making it a valuable addition to the arsenal of antibiotics.
Used in Oncology:
In the field of oncology, (4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride is used as an antineoplastic agent for the treatment of various types of cancer. Its complex structure enables it to interact with cellular targets and disrupt essential biological processes, leading to the inhibition of tumor growth and proliferation.
Used in Drug Delivery Systems:
(4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride can be incorporated into drug delivery systems to improve the efficacy and bioavailability of other therapeutic agents. Its versatile chemical structure allows for the development of targeted drug delivery systems, enhancing the therapeutic potential of various treatments.
Used in Chemical Research:
(4S,4aS,5aR,12aS)-4-(DiMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-7-[(MethoxyMethylaMino)Methyl]-1,11-dioxo-2-naphthacenecarboxaMide hydrochloride also serves as a valuable research tool in the field of organic chemistry. Its unique structure and functional groups make it an interesting subject for studies on chemical synthesis, molecular interactions, and the development of new chemical compounds with potential applications in various industries.

Synthetic route

C2HF3O2*C24H29N3O8 (1035978-85-8) → (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide mono hydrochloride (1035979-44-2)

Conditions	Yield
With hydrogenchloride In methanol

(4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide (1035654-66-0) → (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide mono hydrochloride (1035979-44-2)

Conditions	Yield
With hydrogenchloride In ethanol; water at 5℃; pH=1.3 - 1.6;
With hydrogenchloride In ethanol pH=1.3 - 1.6;

7-formylsancycline (1035655-10-7) → (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide mono hydrochloride (1035979-44-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium cyanoborohydride / N,N-dimethyl acetamide / 0.25 h / 20 °C / Inert atmosphere 2: hydrogenchloride / ethanol; water / 5 °C / pH 1.3 - 1.6 View Scheme

Upstream product

• 1035978-85-8 C₂HF₃O₂*C₂₄H₂₉N₃O₈ 
• 1035654-66-0 (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide 
• 1035655-10-7 7-formylsancycline 

Relevant academic research and scientific papers

METHODS OF USING (4S,4AS,5AR,12AS)-4-DIMETHYLAMINO-3,10,12,12A-TETRAHYDROXY-7-[(METHOXY(METHYL)AMINO)-METHYL]-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-NAPHTHACENE-2-CARBOXYLIC ACID AMIDE

A method of treating a bacterial infection, e.g., a bacterial infection with methicillin resistant Staphylococcus aureus, Helicobacter pylori, Chlamydia trachomatis, or Chlamydia pneumonia, comprising administering to a subject (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide or a pharmaceutically acceptable salt thereof is disclosed. More specifically, a method of treating a bacterial infection comprising administering to a subject crystalline mono hydrochloride salt, crystalline mono mesylate salt or crystalline mono sulfate salt of (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide is disclosed.

CRYSTALLINE SALTS OF (4S,4AS,5AR,12AS)-4-DIMETHYLAMINO-3,10,12,12A-TETRAHYDROXY-7-[(METHOXY(METHYL)AMINO)-METHYL]-1,11-DIOXO-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-NAPHTHACENE-2-CARBOXYLIC ACID AMIDE AND METHODS OF USING THE SAME

A crystalline mono hydrochloride salt of (4S,4aS,5aR,12aS)-4-dimethylamino- 3,10, 12, 12a-tetrahydroxy-7-[(methoxy(methyl)amino)-methyl]- 1, 11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene-2-carboxylic acid amide is disclosed having improved stability. In addition, a crystalline mono mesylate salt and crystalline mono sulfate salt of (4S,4aS,5aR,12aS)-4-dimethylamino-3,10,12,12a-tetrahydroxy-7- [(methoxy(methyl)amino)-methyl]-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydro-naphthacene- 2-carboxylic acid amide are also disclosed having improved stability. A pharmaceutical composition containing the crystalline salts and methods of treating inflammatory skin disorders and bacterial infections comprising administering the crystalline salts are also disclosed.

SUBSTITUTED TETRACYCLINE COMPOUNDS FOR TREATMENT OF INFLAMMATORY SKIN DISORDERS

Methods and compositions for the treatment of skin disorders (e.g., acne, rosacea) are described.