Teclozan

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Teclozan
Teclozan.png
Systematic (IUPAC) name
2,2-Dichloro-N-[[4-[[(2,2-dichloroacetyl)-(2-ethoxyethyl)amino]methyl]phenyl]methyl]-N-(2-ethoxyethyl)acetamide
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
?
Identifiers
CAS number 5560-78-1
ATC code P01AC04
PubChem CID 21723
ChemSpider 20418
UNII K9RIF0COUB YesY
KEGG D06051 YesY
Chemical data
Formula C20H28Cl4N2O4 
Mol. mass 502.26 g/mol
 YesY (what is this?)  (verify)

Teclozan is an antiprotozoal agent.

It is a dichloroacetamide,[1] (c.f. chloramphenicol and Cetophenicol).

Synthesis[edit]

The synthesis begins with alkylation of the alkoxide derived from ethanolamine with ethyl iodide to give the aminoether.

Reaction of 1,4-bis(bromomethyl)benzene with 2-nitropropane in the presence of base leads to dialdehyde.

The reaction probably proceeds by O-alkylation on the nitropropyl anion followed by bond reorganization and subsequent hydrolysis of the resulting enol ether.

Teclozan synthesis:[2]

Reductive alkylation of the dialdehyde with aminoether gives diamine. Acylation by means of dichloroacetyl chloride affords teclozan.

Symetine[edit]

The presence of the dichloroacetamide grouping is apparently not an absolute requirement for antiamoebic activity.

Symetine synthesis: K. Gerzon and E. R. Shepard, U.S. Patent 2,759,977 (1956); Chem. Abstr., 51: 3664a (1956).

Reductive amination of dialdehyde with n-hexylamine followed by Eschweiler–Clarke methylation by heating with formaldehyde in formic acid then leads to the antiamoebic drug symetine.

References[edit]

  1. ^ Slighter RG, Yarinsky A, Drobeck HP, Bailey DM (August 1980). "Activity of quinfamide against natural infections of Entamoeba criceti in hamsters: a new potent agent for intestinal amoebiasis". Parasitology 81 (1): 157–68. doi:10.1017/S0031182000055128. PMID 6252530. 
  2. ^ Surrey, Alexander R. (1961). "New Amorbacides--VI. The Preparation of some N,N'-Disubstituted-N,N'-bis(haloacyl)-1,4-xylylenediamines". Journal of Medicinal and Pharmaceutical Chemistry 3 (3): 409–417. doi:10.1021/jm50016a001.  edit