[4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide

Base Information

• Chemical Name: [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide
• CAS No.: 149934-16-7
• Molecular Formula: C23H26N4O9
• Molecular Weight: 502.47
• Mol file: 149934-16-7.mol

Synonyms:(4S,4aS,5aR,12aS)-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide;[4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide;9-Nitro Minocycline

Chemical Property of [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide

Chemical Property:

• PSA: 210.45000
• LogP: 1.31830

Purity/Quality:

90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 9-Nitrominocycline is a 9-substituted Minocycline (M344800) derivative used as antibacterial agent. 9-Nitrominocycline is used as a reagent in the preparation of tigecycline from minocycline hydrochloride.
• Indications: Minoxidil, an antihypertensive agent, produces arteriolar vasodilation by an unknown mechanism. In limited clinical studies, minoxidil increases penile rigidity and has been used in the long-term treatment of organic impotence.
• Biological Functions: Minoxidil (Loniten) is an orally effective vasodilator. It is more potent and longer acting than hydralazine and does not accumulate significantly in patients with renal insufficiency. It depends on in vivo metabolism by hepatic enzymes to produce an active metabolite, minoxidil sulfate. Minoxidil sulfate activates potassium channels, resulting in hyperpolarization of vascular smooth muscle and relaxation of the blood vessel.
• Clinical Use: The major indications for the use of minoxidil are (1) severe hypertension that may be life threatening and (2) hypertension that is resistant to milder forms of therapy. Compromises in renal function do not prolong either the plasma or the therapeutic half-life of minoxidil, and therefore, it seems to be particularly important for hypertensive patients with chronic renal failure.

Technology Process of [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide

There total 4 articles about [4S-(4α,4aα,5aα,12aα)]-4,7-Bis(diMethylaMino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxo-2-naphthacenecarboxaMide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

minocycline Hydrochloride (13614-98-7) → (4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide (149934-16-7)

Guidance literature:

minocycline Hydrochloride; With sulfuric acid; at 5 ℃; for 3h; under 50 - 760.051 Torr;

With nitric acid; In water; at 6 ℃; for 1.66667h; Product distribution / selectivity;

Reference yield:

minocycline disulfate → (4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide (149934-16-7)

Guidance literature:

With sulfuric acid; nitric acid; In water; Product distribution / selectivity;

Reference yield:

MINOCYCLINE (10118-90-8) → (4S,4aS,5aR,12S)-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-9-nitro-1,11-dioxanaphthacene-2-carboxamide (149934-16-7)

Guidance literature:

With sulfuric acid; nitric acid; at 0 ℃; for 1h;

DOI:10.1016/j.bmcl.2005.09.078

upstream raw materials:

MINOCYCLINE

minocycline Hydrochloride

Downstream raw materials:

[4S-(4aα,12aα)]-9-amino-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide

Refernces

• 1、 Nishioka, Takuya,Yamamoto, Yuji,Hashino, Kimikazu,Matsumoto, Kazuko. "Minocycline-based europium(III) chelate complexes: Synthesis, luminescent properties, and labeling to streptavidin". . p. 2357 - 2374. Retrieved 2009.
• 2、 -. "TIGECYCLINE AND METHODS OF PREPARING INTERMEDIATES". Page/Page column 18. . Retrieved 2009/04/24.