58426-37-2Relevant articles and documents
Isolation, Structure Elucidation, Semi-Synthesis, and Structural Modification of C19-Diterpenoid Alkaloids fromAconitum apetalumand Their Neuroprotective Activities
Wan, Lin-Xi,Zhang, Ji-Fa,Zhen, Yong-Qi,Zhang, Lan,Li, Xiaohuan,Gao, Feng,Zhou, Xian-Li
supporting information, p. 1067 - 1077 (2021/04/06)
Five new aconitine-type C19-diterpenoid alkaloids, apetalrines A-E (1-5), were isolated fromAconitum apetalum. Their structures were determined by analysis of 1D and 2D NMR, IR, and HRESIMS data. Semisynthesis of apetalrine B (2) from its parent compound aconorine was achieved to confirm the structure proposed. Twenty derivatives of2(11a-11l12a12b12d12e12j12k12m12n) were synthesized via a unified approach relying on simple coupling reactions. The evaluation of neuroprotective effects of compounds (1-511b11c11f-11i12a12b12d12e12k12m12n) with low cytotoxicity revealed compound2to exhibit good neuroprotective effects in H2O2-treated SH-SY5Y cells at a concentration of 50 μM. A series of studies using flow cytometry, staining, and Western blotting on2indicated that its neuroprotective effects may arise from inhibiting cell apoptosis.
An efficient, convenient synthesis of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides as anticipated antineoplastic agents
Abdel-Hafez, Atef Abdel-Monem
, p. 2297 - 2302 (2007/10/03)
A series of novel medium-sized 13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione macrolides (18-27, 30, 32) were synthesized in an ongoing effort to develop new antineoplastic agents. The synthon 2-(2-aminobenzoylamino)-benzoic acid (7), for preparation of the target compounds, was prepared via the reaction of isatoic anhydride 5 and anthranilic acid 6. Nine compounds (18-20, 24-27, 30, 32) were subjected to National Cancer Institute (NCI) in vitro disease-oriented human cells screening panel assay. Among the compounds tested, 6-benzyl-13H-dibenzo[d,h][1,3,7]oxadiazecine-8,14-dione (26, NSC 721327), bearing the benzyl group at position 6, showed cytotoxic activity and subpanel selectivity against leukemia (CCRF-CEM), colon (HCC-2998), CNS (SNB-75) and melanoma (UACC-257) panels at log10 GI50 (M), compound concentration that inhibits 50% of cell growth, ranging from -4.08 to -4.59.
Acylanthranils. 12. Reaction of Acetylanthranil with Alcohols To Give Products of Self-Condensation
Errede, L.A.,Hill, J.R.,McBrady, J.J.
, p. 3829 - 3835 (2007/10/02)
Material-balance studies on the reaction of acetylanthranil (I) in acidified alcohol showed that the end produt is neither the expected N-(2-carboxyphenyl)acetimidate, 3, nor the o-acetamidobenzoate ester, 4, but rather mixtures of N-(2-carboxyphenyl)-2-methylquinazol-4-one (5), o-(o-acetamidobenzamido)benzoic acid (6), CH3CO2R, and R2O, where R is the alkyl group of the alcohol.The stoichiometry in anhydrous media is consistent with the following equation: 2I + (1+2x)ROH -> (1-x)5 + x6 + CH3CO2R + xROR.Time studies of this self-condensation, monitored by proton NMR, showed that the acetimidate 3 is indeed formed as expected, but it establishes equilibrium with 1 within minutes.The acetimidate, however, reacts slowly with solvent and residual 1 to give products 5 and 6, respectively, with concomitant formation of CH3CO2R and ROR as side products.The instantaneous selectivity ratio (1-x)/x increases monotonically with percent conversion to acids 5 and 6.The disappearance of 1 in alcohol solution is pseudo first order.Initially, the rate-controlling step is the slow conversion of 3 to secondary intermediates Y and Z, but ultimately it is the subsequent very slow conversion of Y an Z to end products.
