Synthesis and characterization of 13-cis-retinoic acid derivatives

Hunan Daxue Xuebao/Journal of Hunan University Natural Sciences

Volumn 31, Issue 4, 2004, Pages 6-10

  Xiang, Jian Nan ^a   Chen, Chao Yue ^a   Liu, Zhi Chang ^a   Zeng, Yong ^b   Dang, Kui Feng ^a   Deng, Xiao Qiang ^a   Yin, Xia ^a  

^a HUNAN UNIVERSITY   (China)

^b Hanshou Zhengyang Co Ltd   (China)

Author keywords

13 cis retinoic acid; Characterization; Retinamide; Retinoate; Retinoid

Indexed keywords

BIOCHEMISTRY; CATALYSTS; CHARACTERIZATION; ISOMERIZATION; SYNTHESIS (CHEMICAL);

DICYCLOHEXYICARBODIIMIDE; REACTION CONDITIONS; RETINAMIDE; RETINOATE; RETINOID;

DERIVATIVES;

EID: 7944222838     PISSN: 10002472     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. JISUN PAIR, SILKE VOGEL, ROSEANN PIANTEDOSI, et al. 9-cis-retinoids: Biosynthesis of 9-cis-Retinoic Acid [J]. Biochemistry, 2000, 39(27): 8073-8084.
2. JOEL R, WALKER, GALAL ALSHFIE. Hussein Abou-Issa, et al. An Improved Synthesis of the C-linked Glucuronide of N-(4-Hydroxyphenyl)retinamide [J]. Bioorganic and Medicinal Chemistry Letters, 2002, 12: 2447-2450.
3. GUY SOLLADIE, ANDRE GIRARDIN. Synthesis of New Aromatic Analogues by Low-Valent Titanium Induced Reductive Elimination [J]. J Org Chem, 1989, 54(11): 2620-2628.
4. SHEALY. Synthesis and Properties of Some 13-cis- and All-Trans-Retinamides [J]. J Pharm Sci, 1984, 73(6): 745-751.
5. AKIMORI WADA, CHISAID TODE. Retinoids and Related Compounds: A Convenient Synthesis of Retinoic Acid Analogs Having an Anthraquinone Ring [J]. Synthesis, 1995: 1107-1110.
6. THOMAS E GUNDERSEN, RUNE BLOMHOFF. Qualitative and quantitative liquid chromatographic determination of natural retinoids in biological samples [J]. Journal of Chromatography A, 2001, 935, 13-43.
7. WILLIAM P PURCELL, MEMPHIS TENN. 9-cis Retinoic acid esters and amides and uses thereof [P]. US Pat: 5,837,728, 1998-11-17.
8. HARLIE A PARISH, WILLIAM P PURCELL. Topical prodrugs for treatment of acne and skin diseases [P]. US Pat: 4,677,120, 1987-06-30.
9. CYNTHIA A MARYANOFF, SOLEBURY TOWNSHIP, BUCKS COUNTY. Process for Preparing Retinoyl Chorides [P]. US Pat: 4,743,400, 1998-05-10.
10. ARUN B BARUA, JAMES A OLSON. Preparation of retinamides by use of retinoyl fluoride [J]. J Lipid Res, 1985, 26(2): 258-262.
11. ARUN B BARUA, JAMES A OLSON. Chemical synthesis of all-trans retinoyl β-glucuronide [J]. J Lipid Res, 1985, 26(10): 1277-1282.
12. PASCALE JOLIMAITRE, CHRISTIANE ANDRE-BARRES, MYRIAM MALET-MARTINO, et al. A New Method for the Synthesis of 5-Fluorouracil Prodrugs [J]. Synlett, 1999: 1829-1831.
13. SOO-JONG UM, YOUN-JA KWON, HYE-SOOK HAN. et al. Synthesis and Biological Activity of Novel Retinamide and Retinoate Derivatives [J]. Chem Pharm Bull, 2004, 52(5): 501-506.
14. ROBERT J GANDER, JOHN A GURNEY. Benzyl all-trans-Retinoate Used for the Treatment of Acne [P]. US Pat: 4,304,787, 1981-12-08.
15. CHARLES SANG MAM, JEAN-YVES WINUM. A simple, general and efficient method for O and N-Retinoylation application to the synthesis of 2-Retinoyl-Lecithin [J]. Synthetic Communications, 1998, 28(16): 2945-2958.
16. VICTOR M SAMOKYSZYN, WALTER E GALL, GREGORY ZAWADA, et al. 4-Hydroxyretinoic Acid, a Novel Substrate for Human Liver Microsomal UDP-glucuronosyl-transferase (s) and Recombinant UGT2B7 [J]. J Bio Chem, 2000, 275(10): 6908-6914.