1-(1-Hydroxyethyl)-7, 8-dihydroindolo [2, 3-a] pyridine [3, 4-g] quinolizin-5 (13H)-one (angustoline) monohydrate from Nauclea subdita (Rubiaceae)

The title compound (trivial name: angustoline monohydrate), C20H17N3O2 H2O, features a fused-ring system formed by one five- and four six-membered rings. The nearly planar benzimidazole portion (r.m.s. deviation = 0.008 A˚) and the nearly planar 2,7-naphthyridin-1-one portion (r.m.s. deviation = 0...

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Bibliographic Details
Main Authors: Liew, Sook Yee, Mukhtar, Mat Ropi, Awang, Khalijah, Mustafa, Mohd Rais, Ng, Seik Weng
Format: Article
Language:en
Published: 2011
Subjects:
Online Access:http://eprints.um.edu.my/2430/1/1-%281-Hydroxyethyl%29-7%2C_8-dihydroindolo_%5B2%2C_3-a%5D_pyridine_%5B3%2C_4-g%5D_quinolizin-5_%2813H%29-one_%28angustoline%29_monohydrate_from_Nauclea_subdita_%28Rubiaceae%29.pdf
http://eprints.um.edu.my/2430/
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Summary:The title compound (trivial name: angustoline monohydrate), C20H17N3O2 H2O, features a fused-ring system formed by one five- and four six-membered rings. The nearly planar benzimidazole portion (r.m.s. deviation = 0.008 A˚) and the nearly planar 2,7-naphthyridin-1-one portion (r.m.s. deviation = 0.022 A˚) of the fused-ring system are slightly twisted, with a dihedral angle of 9.47 (8), owing to the tetrahedral nature of the two methylene linkages in the central six-membered ring. The secondary N atom acts as a hydrogen-bond donor to the water molecule of crystallization. In the crystal, the amino and hydroxy groups, and the water molecule are engaged in hydrogen bonding, generating a three-dimensional network.