Structures of 1-(3,3-dimethylamino)propyl naphtho[2,1-b]thiophene-4- carboxylate and N-(3,3-dimethylamino)propyl-8-methoxynaphtho[2,1- b]thiophene-4-carboxamide, intercalators into double-helical DNA.
(1) C18H19NO2S, Mr = 313.42, monoclinic, P2(1)/c, a = 11.503 (3), b = 15.932 (2), c = 9.133 (2) A, beta = 102.17 (2) degrees, V = 1636.1 A3, lambda(Cu K alpha) = 1.54178 A, mu = 1.762 mm-1, F(000) = 664, T = 293 (1) K, R = 0.047 for 2044 significant reflections. (2) C19H21NO3S, Mr = 343.45, triclinic, Pl, a = 9.873 (2), b = 13.163 (3), c = 14.065 (3) A, alpha = 101.33, beta = 94.30 (3), gamma = 91.35 (3) degrees, V = 1785.8 A3, Z = 4, Dx = 1.28 Mg m-3, lambda(Cu K alpha) = 1.54178 A, mu = 1.699 mm-1, F(000) = 728, T = 293 (1) K, R = 0.052 for 1787 significant reflections. The torsion angle between the naphthothiophene ring and the carbonyl O atom of the side chain is 5.5 (4) degrees in structure (1) and 25 (2) and -32 (2) degrees in the two independent molecules of (2). This difference is due to out-of-plane distortions in (2) that arise from steric hindrance between H atoms on the amide and the ring system, at position 2.
McKenna
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Cancer Research Campaign Biomolecular Structure Unit, Institute of Cancer Research, Sutton, Surrey, England.
Neidle
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Wilson
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D007364:Intercalating Agents / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*; D014961:X-Ray Diffraction
D007364:Intercalating Agents; D009281:Naphthalenes; D013876:Thiophenes; C074021:N-(3,3-dimethylamino)propyl-8-methoxynaphtho(2,1-b)thiophene-4-carboxamide; C074020:1-(3,3-dimethylamino)propyl naphtho(2,1-b)thiophene-4-carboxylate