Citation: Wen-Jing Liu, De-Sheng Mei, Wen-Hu Duan. Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction[J]. Chinese Chemical Letters, ;2013, 24(6): 515-517. shu

Synthesis of 1,7-dimethoxy-2-hydroxyxanthone, a natural product with potential activity on erectile dysfunction

1.
a School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China;
2.
b Department of Medicinal Chemistry, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China

Corresponding author: De-Sheng Mei, Wen-Hu Duan,
Received Date: 6 January 2013
Available Online: 7 March 2013

The natural product, 1,7-dimethoxy-2-hydroxyxanthone (1), isolated from Securidaca inappendiculate Hassk, has a potential in the treatment of erectile dysfunction due to its significant relaxation activity on rabbit Corpus cavernosum. However, the isolation of compound 1 is problematic because of its high similarity in structure to its analogs. In this paper, the first synthesis of 1 was reported featuring two key reactions: a copper-catalyzed coupling reaction and an intramolecular cyclization.
- 1,7-Dimethoxy-2-hydroxyxanthone,
- Erectile dysfunction,
- Synthesis,
- Copper-catalyzed coupling reaction
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  [13] Spectral data of 7-dimethoxy-2-hydroxyxanthone (1): Mp 174-176 8C (lit. [3] mp 174-176 8C); ¹H NMR (400 Hz, CDC_l3): δ 7.70 (d, 1H, J = 3.2 Hz), 7.41 (dd, 2H, J₁ = 9.29.2 Hz, J₂ = 9.23.6 Hz), 7.33 (dd, 1H, J₁ = 9.29.0 Hz, J₂ = 9.23.2 Hz), 7.25 (d, 1H, J = 8.8 Hz), 5.98 (s, 1H), 4.07 (s, 3H), 3.93 (s, 3H); ¹³C NMR (125 MHz, CDC_l3): δ 176.2, 155.9, 151.0, 150.3, 145.1, 144.1, 124.9, 122.3, 122.2, 119.0, 115.5, 114.2, 105.5, 62.6, 55.9; HRMS (EI, m/z): Calcd. for C₁₅H₁₂O₅ (M⁺): 272.0686, found: 272.0685.
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1.
沈阳化工大学材料科学与工程学院沈阳 110142