7264-10-0

Basic information

• Product Name: DOXYCYCLINE
• Synonyms: (4S,4aR,5S,5aR,6R,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide
• CAS NO: 7264-10-0
• Molecular Formula: C22H24N2O8
• Molecular Weight: 0
• Mol File: 7264-10-0.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: DOXYCYCLINE(CAS DataBase Reference)
• NIST Chemistry Reference: DOXYCYCLINE(7264-10-0)
• EPA Substance Registry System: DOXYCYCLINE(7264-10-0)

Safety Data

• Hazardous Substances Data: 7264-10-0(Hazardous Substances Data)

Upstream product

• 3963-95-9 methacycline hydrochloride 
• 10592-13-9 doxycycline hydrochloride 
• 564-25-0 doxycycline 

Relevant articles and documents

Preparation method of doxycycline hydrochloride intermediate hydride

The invention discloses a preparation method of a doxycycline hydrochloride intermediate hydride. The preparation method comprises adding dried oxytetracycline chloride into a dehydration pot containing HF, carrying out reaction dehydration, carrying out standing, evaporating and concentrating to remove HF, collecting the concentrated solution through methanol, neutralizing the methanol solution containing the concentrated solution through calcium hydroxide or calcium oxide powder, carrying out a hydrogenation reaction process on the neutralized methanol solution in the presence of a Pd/C catalyst and an inhibitor, filtering the reaction product, and carrying out a salt formation reaction process on the filtrate and a sulfonyl salicylate methanol solution to obtain the doxycycline hydrochloride intermediate hydride. The preparation method is free of p-toluenesulfonic acid, has simple processes, can be operated easily and greatly reduces a production cost.

SYNTHESIS OF TETRACYCLINES AND ANALOGUES THEREOF

The tetracycline class of antibiotics has played a major role in the treatment of infectious diseases for the past 50 years. However, the increased use of the tetracyclines in human and veterinary medicine has led to resistance among many organisms previously susceptible to tetracycline antibiotics. The modular synthesis of tetracyclines and tetracycline analogs described provides an efficient and enantioselective route to a variety of tetracycline analogs and polycyclines previously inaccessible via earlier tetracycline syntheses and semi-synthetic methods. These analogs may be used as anti-microbial agents or anti-proliferative agents in the treatment of diseases of humans or other animals.

Ligand effects in the hydrogenation of methacycline to doxycycline and epi-doxycycline catalysed by rhodium complexes molecular structure of the key catalyst [closo-3,3-(η2,3-c7h7ch2)-3,1,2-rhc2b9h11]

The catalytic reduction of the exocyclic methylene group of methacycline (A) leads to the formation of two diastereoisomers, doxycycline (B, the α-epimer) and 6-epi-doxycycline (C, the β-epimer), with a selectivity which markedly depends on the nature of hydrocarbon and carborane ligands of closo-(π-cyclodienyl)rhodacarborane catalysts. Neutral norbornadienyl complexes with unsubstituted carborane ligands [closo-3,3-(η2,3-C7H7CH2)-3,1,2-RhC2B9H11] (1) and [closo-2,2-(η2,3-C7H7CH2)-2,1,7-RhC2B9H11] (7) are more active and afford higher selectivity in the formation of doxycycline than those having mono-or di-substituents at the carborane cage, [closo-3,3-(cyclodienyl)-1-R-2-R′-3,1,2-RhC2B9H9] (R = H, R′ = Me, PhCH2; R = R′ = Me; cyclodienyl = η2,3-C7H7CH2 or η-C10H13) as well as those from the closely related series of η5-cyclopentadienyl complexes [(η2,3-C7H7CH2)Rh(η5-C5Rn)]+PF-6 (Rn = H5, Me5, or H2-1,2,4-Ph3). Mechanistic aspects of the hydrogenation reaction of methacycline are sketched. The results of the X-ray diffraction study of the best catalyst 1 are reported.