Sancycline

Base Information

• Chemical Name: Sancycline
• CAS No.: 808-26-4
• Molecular Formula: C₂₁H₂₂N₂O₇
• Molecular Weight: 414.415
• Mol file: 808-26-4.mol

Synonyms:2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-(6CI,7CI,8CI);2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-,[4S-(4a,4aa,5aa,12aa)]-;4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;6-Demethyl-6-deoxytetracycline;Bonomycin;GS 2147;Norcycline;Sancycline;

Chemical Property of Sancycline

Chemical Property:

• Vapor Pressure: 3E-17mmHg at 25°C
• Melting Point: 224-228 °C (dec)
• Refractive Index: 1.734
• Boiling Point: 750.9 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 407.9 °C
• PSA: 161.39000
• Density: 1.61 g/cm³
• LogP: 0.82090
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Aqueous Acid (Slightly), Chloroform (Slightly), Methanol (Slightly), Water (Slig

Purity/Quality:

99% ^*data from raw suppliers

Sancycline hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Sancycline is a semisynthetic tetracycline antibiotic that is more active than tetracycline against 339 strains of anaerobic bacteria (average MIC90s = 1 and 32 μg/ml, respectively). Sancycline is active against tetracycline-resistant E. coli, S. aureus, and E. faecalis strains with MICs ranging from 0.06 to 1 μg/ml. In vivo, sancycline is active against S. aureus in mice with ED50 values of 0.46 and 0.6 mg/kg for intravenous and subcutaneous administration, respectively.
• Uses: A semi-synthetic antibiotic related to tetracycline Sancycline is a rare semi-synthetic tetracycline prepared by hydrogenolysis of the chloro and benzylic hydroxy moieties of declomycin, first reported in 1962. As the simplest of the early tetracyclines, sancycline was the first to be totally synthesised by Conover and co-workers. Like other tetracyclines, sancycline acts by reversibly binding to the 30S ribosomal subunit and inhibiting protein translation by blocking entry of aminoacyl-tRNA into the ribosome A site. Sancycline is a tetracycline bacteriostatic antibiotic which also binds to the Tet repressor protein (TetR).

Technology Process of Sancycline

There total 17 articles about Sancycline 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: 90.7%

6-demethyltetracycline (987-02-0) → sancycline (808-26-4,2696-12-0,15964-02-0,39105-46-9)

Guidance literature:

With methanesulfonic acid; 5%-palladium/activated carbon; hydrogen; In methanol; N,N-dimethyl-formamide; at 30 - 35 ℃; for 5h; under 3000.3 - 6000.6 Torr; Solvent; Temperature; Reagent/catalyst;

Reference yield: 88.0%

Demeclocycline (127-33-3) → sancycline (808-26-4,2696-12-0,15964-02-0,39105-46-9)

Guidance literature:

With 10% rhodium on carbon; hydrogen; toluene-4-sulfonic acid; In methanol; at 20 ℃; for 15h; under 11251.1 - 18751.9 Torr; Reagent/catalyst; Pressure; Solvent; Autoclave;

Reference yield: 71.9%

7-diazosancycline hexafluorophosphate → (4S,4aS,5aR,12aS)-4-(dimethylamino)-7-fluoro-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide (61618-26-6) + sancycline (808-26-4,2696-12-0,15964-02-0,39105-46-9)

Guidance literature:

With 1-butyl-3-methylimidazolium Tetrafluoroborate; Reagent/catalyst; Irradiation;

upstream raw materials:

7-amino-6-desmethyl-6-deoxytetracycline

acetic acid

Demeclocycline

demeclocycline hydrochloride

Downstream raw materials:

7-amino-6-desmethyl-6-deoxytetracycline

minocycline Hydrochloride

[4S-(4a,12aα)]-7-nitro-3,10,12,12a-tetrahydroxy-1,11-dioxo-1,4,4a,5,5a,6,11,12a octahydro-naphthacene-2-carboxylic acid amide

Refernces

• 1、 -. "Preparation method of minocycline hydrochloride". . . Retrieved 2017/08/30.
• 2、 -. "A mountain of tigecycline preparation method". Paragraph 0031; 0032; 0033; 0034; 0035; 0036-0050. . Retrieved 2017/06/19.