Motretinide

Motretinide

Names
IUPAC name N-ethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenamide
Identifiers
CAS Number	54757-59-4
ChemSpider	4880635
EC Number	260-094-6
Jmol interactive 3D	Image
KEGG	D05082
PubChem	6314185
UNII	W786807KL1
InChI InChI=1S/C23H31NO2/c1-8-24-23(25)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(26-7)20(6)19(21)5/h9-15H,8H2,1-7H3,(H,24,25)/b11-9+,13-12+,16-10+,17-14+ Key: IYIYMCASGKQOCZ-DJRRULDNSA-N InChI=1/C23H31NO2/c1-8-24-23(25)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(26-7)20(6)19(21)5/h9-15H,8H2,1-7H3,(H,24,25)/b11-9+,13-12+,16-10+,17-14+ Key: IYIYMCASGKQOCZ-DJRRULDNBU
SMILES CCNC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C
Properties
Chemical formula	C23H31NO2
Molar mass	353.49774
Pharmacology
ATC code	D10AD05
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
verify (what is  ?)
Infobox references

Motretinide is an anti-acne preparation and aromatic analog of retinoic acid.^[1]

Synthesis

The keratolytic analogue motretinide is effective in treating acne and the excess epithelilial growth characeteristic of psoriasis, demonstrating that an aromatic terminal ring is compatible with activity. The synthesis^[2] passes through the related orally active antipsoriatic/antitumor agent etretinate (3). These synthetic compounds have a wider safety margin than the natural materials.

Motretinide synthesis: W. Bollag et al.,DE 2414619 ; eidem, U.S. Patent 4,215,215 (1974, 1980 both to Hoffmann-La Roche).

Etretinate is synthesized^[3] from 2,3,5-trimethylanisole by sequential Blanc chloromethylation (HCl and formaldehyde) followed by conversion to the ylide with triphenylphosphine and BuLi (2). Wittig olefination then leads to Etretinate (3). Etretinate may then be saponified, activated by PCl3 to the acid chloride, and then reacted with ethylamine to give motretinide (4).

References

1. Zouboulis, C. C. (2001). "Retinoids--which dermatological indications will benefit in the near future?". Skin pharmacology and applied skin physiology 14 (5): 303–315. PMID 11586072.
2. W. Bollag, R. Rueegg, and G. Ryser, CH 616134  (1980); Chem. Abstr., 93, 71312J (1980).
3. EW. Bollag, R. Rueegg, and G. Ryser, CH 616135 (1980); Chem. Abstr., 93_, 71314m (1980).