Synthesis of tetracycline analogues and test of their affinity on synthetic hydroxyapatite

Chinese Chemical Letters

Volumn 13, Issue 1, 2002, Pages 13-16

  Weng, Ling Ling ^a   Lin, Gang ^a   Zheng, Hu ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

Affinity; Benzopyran 4 one; Hydroxyapatite; Tetracycline

Indexed keywords

5 OXO [1]BENZOPYRANO[2,3 B]PYRIDINE; HYDROXYAPATITE; INORGANIC COMPOUND; TETRACYCLINE DERIVATIVE; UNCLASSIFIED DRUG;

BINDING AFFINITY; BONE; CHEMICAL BINDING; CHEMICAL COMPOSITION; DRUG ACTIVITY; DRUG SYNTHESIS; REVIEW;

EID: 0036003643     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (11)

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2. (b) H. Zheng, L. L. Weng, ZL94111687.5, US. 5698542, 1997.
3. (c) Bando Nobuyuki, Kawal Tsutomu, Hamazaki, Takashi, Jpn. Kokai Tokkyo Koho JP 04, 178, 359, 1992.
4. (d) Bentz, Hanne; Rosen David, Eur. Pat. Appl. EP512, 844, 1992.
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7. (a) T. Keichi, M. Shinji, I. Takihiro, Jpn Kokai Tokkyo Jp 04, 342, 527, 1992;
8. (b) M. Masamichi, O. Masakatsu, Y. Tatsuro, Jpn Kokai Tokkyo Jp 05, 112, 552, 1993.
9. A. Nohara, T. Umetani, Y. Sanno, Tetrahedron, 1974, 30, 3553.
10. Method A: for example 1a, the solution of 4a (0.44 mmol), acetylacetone (0.44 mmol) and 2 drops of piperidine in 1.5 mL of anhydrous ethanol was refluxed with stirring for 8 hr, cooled then filtrated, the solid was recrystallized from DMF/EtOH to give white crystal. Method B: for example 1e. The solution of 4b (0.44 mmol), ethyl acetoacetate (0.44 mmol), and 3 drops of piperidine in 1.5 mL of ethanol was refluxed with stirring for 8 hr. After being cooled, filtration and filter liquor was concentrated in vacuo, the residue was purified by flash column chromatography to give yellowish-green crystal.
11. +.