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Pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dithione.

ABSTRACT: The seven-membered fused-ring in the title compound, C(12)H(12)N(2)S(2), adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methine C atom the prow). This methine C atom and the tertiary N atom also belong to a five-membered ring, which has an envelope conformation. In the crystal structure, mol-ecules are linked about a center of inversion by pairs of N-H⋯S hydrogen bonds.

SUBMITTER: Ourahou S

PROVIDER: S-EPMC3006926 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The compound, C(15)H(16)N(2)O(2), features a pyrroline ring fused with a seven-membered diazepine ring; the latter system adopts a boat conformation (with the methine C atom as the prow and the two C atoms of the aromatic ring as the stern). A CH(2)-CH(2) segment of the pyrroline ring is disordered over two positions in a 1:1 ratio.

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Project description:In the two mol-ecules of the asymmetric unit of the title compound, C(12)H(11)N(3)O(4), the seven-membered diazepine ring adopts a boat conformation (with the two phenyl-ene C atoms representing the stern and the methine C atom the prow). The five-membered pyrrole ring, which has an envelope conformation, makes dihedral angles of 60.47?(10) and 54.69?(9)° with the benzene ring of the benzodiazepine unit in the two mol-ecules. In the crystal, inter-molecular N-H?O hydrogen bonds and ?-? stacking inter-actions [centroid-centroid distance = 3.8023?(7)-3.8946?(7)?Å] lead to the formation of a three-dimensional framework.

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Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of (S)-10-propargyl-pyrrolo-[2,1-c][1,4]benzodiazepine-5,11-dione.

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Project description:The title compound, C(12)H(11)BrN(2)O(2), was prepared by an intra-cyclization reaction of (S)-1-(5-bromo-2-nitro-benz-yl)-5-oxopyrrolidine-2-carb-oxy-lic acid methyl ester in the presence of EtOH/Fe. The five-membered pyrrolidinone ring adopts an approximate envelope conformation, while the seven-membered diazepanone ring displays a twisted boat conformation. Inter-molecular classical N-H?O hydrogen bonds and weak C-H?O inter-actions help to stabilize the crystal structure.

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DNA Sequence Preference and Adduct Orientation of Pyrrolo[2,1-c][1,4]benzodiazepine Antitumor Agents.

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