Synthesis of 2,3,4a,11b-tetrahydro-oxazino[2,3-c]benzopyran-9-carbonitriles as ATP-sensitive potassium channel openers

作者: Chen-Yu Cheng , Hsin-I Chiu , Ming-Jyh Chang , Yen-Chung Lin , Ming-Cheng Tsai

DOI: 10.1016/S0960-894X(98)00046-8

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摘要: Abstract A series of optically active tetrahydro-oxazino[2,3- c ]benzopyran derivatives have been synthesized and evaluated for potassium channel opening activity. (4aR,11bR)-1-Benzoyl-5,5-dimethyl-2,3,4a,11b-tetrahydro-oxazino[2,3- ]benzopyran-9-carbonitrile ((−)- 11e ) was identified as a bladder-selective opener (IC 50, bladder = 8.15 μM, IC portal vein 34.5 μM).

参考文章(12)
Bernard Pirotte, Jeanine Fontaine, Philippe Lebrun, Recent advances in the chemistry of potassium channel openers Current Medicinal Chemistry. ,vol. 2, pp. 573- 582 ,(1995)
James R. Empfield, Keith Russell, Chapter 9. Potassium Channel Openers Annual Reports in Medicinal Chemistry. ,vol. 30, pp. 81- 90 ,(1995) , 10.1016/S0065-7743(08)60922-7
Catherine S.V. Houge-Frydrych, Ivan L. Pinto, An unusual hydroxyl inversion mediated by dast Tetrahedron Letters. ,vol. 30, pp. 3349- 3350 ,(1989) , 10.1016/S0040-4039(00)99241-4
JR Empfield, D Mayhugh, CJ Ohnmacht, CA Frank, T Grant, J Li, None, 4-Sulfonamidoanilide tertiary carbinols: A novel series of potassium channel openers Bioorganic & Medicinal Chemistry Letters. ,vol. 7, pp. 775- 778 ,(1997) , 10.1016/S0960-894X(97)00111-X
Ulrich Quast, Edwin B. Villhauer, The individual enantiomers of cis-cromakalim possess K+ channel opening activity European Journal of Pharmacology. ,vol. 245, pp. 165- 171 ,(1993) , 10.1016/0922-4106(93)90124-R
Panagiotis Zografos, Jack H. Li, Sen T. Kau, Comparison of the in vitro effects of K+ channel modulators on detrusor and portal vein strips from guinea pigs. Pharmacology. ,vol. 45, pp. 216- 230 ,(1992) , 10.1159/000139000
Nam Ho Lee, Alexander R. Muci, Eric N. Jacobsen, Enantiomerically Pure Epoxychromans via Asymmetric Catalysis Tetrahedron Letters. ,vol. 32, pp. 5055- 5058 ,(1991) , 10.1016/S0040-4039(00)93426-9
K. S. Atwal, Myocardial protection with the ATP-sensitive potassium channel openers Current Medicinal Chemistry. ,vol. 3, pp. 227- 238 ,(1996)