Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype

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5-(4-Methyl­phen­yl)-1,3,4-oxadiazol-2-amine

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The title compound, C(12)H(8)N(4)O(2)·C(8)H(6)O(4), was synthesized from 4-[5-(4-pyrid-yl)-1,3,4-oxadiazol-2-yl]pyridine N-oxide and isophthalic acid. The two mol-ecules are linked through O-H⋯O and O-H⋯N hydrogen bonds. Weak intra-molecular π-π inter-actions between the two hydrogen-bonded chains result in the formation a one-dimensional supra-molecular curved tape (the face-to-face distance b...

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In the title compound, C(23)H(20)F(3)N(5)O, the piperazine ring adopts a chair conformation. The quinoline ring makes dihedral angles of 56.61 (11), 49.94 (12) and 42.58 (14)° with the piperazine ring, the 1,3,4-oxadiazole ring and the benzene ring, respectively. An intra-molecular C-H⋯O hydrogen bond generates an S(7) ring motif. In the crystal, mol-ecules are linked into infinite chains along...

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The title compound, C(18)H(18)ClN(3)O(3)S(2), adopts by folding the form of a distorted disc. Inter-planar angles are 29.51 (7) and 63.43 (7)° from the five-membered ring to the aromatic systems and 34.80 (6)° between these two latter rings. The absolute configuration was confirmed by determination of the Flack parameter. In the crystal, the mol-ecules are linked by four hydrogen bonds, one cla...

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4-[4-(4-Amino-1,2,5-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl]-1,2,5-oxadiazol-3-amine

The complete molecule of the compound, C(6)H(4)N(8)O(3), is generated by a crystallographic twofold rotation axis that runs through the central ring. The flanking ring is twisted by 20.2 (1)° with respect to the central ring. One of the amino H atoms forms an intra-molecular N-H⋯N hydrogen bond; adjacent mol-ecules are linked by N-H⋯N hydrogen bonds forming a chain running along [10-2].

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ژورنال

عنوان ژورنال: Bioorganic & Medicinal Chemistry Letters

سال: 2014

ISSN: 0960-894X

DOI: 10.1016/j.bmcl.2014.07.089