6-Nitro-2,3-dihydro-1H-pyrrolo­[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

In the two mol­ecules of the asymmetric unit of the title compound, C12H11N3O4, the seven-membered diazepine ring adopts a boat conformation (with the two phenyl­ene 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 mol­ecules. In the crystal, inter­molecular N—H⋯O hydrogen bonds and π–π stacking inter­actions [centroid–centroid distance = 3.8023 (7)–3.8946 (7) Å] lead to the formation of a three-dimensional framework

9α-Acet­oxy-1β,10α-ep­oxy­parthenolide

The title compound, C17H22O6, was semi-synthesized from 9-hy­droxy­arthenolide, which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule contains fused five- and ten-membered rings: the five-membered lactone ring has a twisted conformation, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the rings is 24.76 (9)°

Synthèse de dérivés de la quinazoline

Les composés hétérocycliques à six chaînons sont plus attractifs. Ils constituent la base de nombreux produits pharmaceutiques agrochimiques et vétérinaires. En particulier les dérivés de quinazolines (hetérocycles fusionnés au benzène), constituent une classe importante de produits chimiques en raison de leurs nombreuses applications dans divers domaines.Nous décrivons, dans cet article, quelles principales méthodes de synthèse de dérivés de la quinazoline, ainsi que la méthodologie développée par notre laboratoire

Synthèse de nouveaux dérivés du 9-hydroxy-parthénolide contenant un noyau -1,2,3-triazole substitué

National audienc

Crystal structure of N-(1-acetyl-3-chloro-1H-indazol-6-yl)-4-methoxybenzenesulfonamide

In the title compound, C16H14ClN3O4S, the six-membered ring of the indazole group is connected to a sulfonamide group. The indazole system is essentially planar, with the greatest deviation from the mean plane being 0.007 (2) Å. The dihedral angle between the two six-membered rings is 74.99 (9)°. The crystal structure exhibits inversion dimers in which molecules are linked by pairs of N—H...O and C—H...O hydrogen bonds

A dereplication strategy for the identification of new phenolic compounds from Anvillea radiata (Coss. & Durieu)

AbstractPhenolic compounds were selectively extracted from aerial parts of Anvillea radiata using Accelerated Solvent Extraction (ASE) in two steps. Given the two molecular families (flavonoids and germacranolides) described as present in the plant material, a first extraction step using chloroform as the extraction solvent was carried out to remove the germacranolides, the most abundant compounds. The minor phenolic compounds were then selectively extracted and enriched from the plant residue by methanol. Characterization of twenty five phenolic compounds in the methanolic extract was performed using HPLC-DAD-ESI-MS/MS and HPLC-HRMS analyses. Seven compounds corresponded to chlorogenic acid and dicaffeoylquinic acid derivatives and eighteen flavonoids (from which five aglycones and thirteen glycosides) were identified and some of them for the first time.The presence of these phenolic compounds, identified in the whole aerial parts, was then followed in each organ (flower, leave and stem). The chromatographic profiles of the stem and leave were very close, while the flower one was more different. However most of the compounds identified in aerial parts were recovered in each organ, mainly difference on peak intensity could be observed. The most abundant compound in flowers was found to be a di-caffeoylquinic acid derivative while isorhamnetin and spinacitin diglucoside derivatives were the most abundant ones in stems and leaves

Synthesis and biological evaluation of 9α- and 9β-hydroxyamino-parthenolides as novel anticancer agents

A series of 9α-hydroxyamino-parthenolides 3-10, 9β-hydroxyamino-parthenolides 11-13 and 9α-hydroxy-1β,10α-epoxyamino-parthenolides 15-19 were efficiently synthesized starting from 9α-hydroxyparthenolide 1 and 9β-hydroxyparthenolide 2, which were isolated from Anvillea radiata. Compounds 1-13 and 15-19 were evaluated for their in vitro anticancer activity by the MTT colorimetric assay against one murine and six human cancer cell lines. This work provides new details about the structural requisites for anticancer activity

Access and modulation of substituted pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones

International audienceThe first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki–Miyaura or Buchwald–Hartwig coupling reactions in C-6 position was investigated from 6-chloropyrrolo[3,4-c]pyrazole-4,6-(2H,5H)–diones. This method provides novel access to various 1,6 di-substituted pyrrolo[3,4-c] pyrazole-4,6-(2H,5H)–diones