16287-49-3Relevant articles and documents
Benzodiazepine compounds and preparation method thereof
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Paragraph 0101-0106, (2020/03/05)
The invention belongs to the technical field of biological medicines, and particularly relates to benzodiazepine compounds and a preparation method thereof. A series of the benzodiazepine compounds provided by the invention are novel in structure, have certain drug potential, and have positive significance when applied to development of novel drugs. According to the invention, an N-heterocyclic bridged benzimidazolium salt is used as a raw material, inherent water in an organic solvent is utilized, and a ring opening-ring expanding reaction is conducted under the action of a catalyst so as toprepare the benzodiazepine compounds with an N-heterocyclic bridged seven-membered ring structure. The method provided by the invention has the advantages of mild conditions, no need for treatment ofthe solvent, simple steps, good regioselectivity and high atom economy.
Synthesis of Benzodiazepines Through Ring Opening/Ring Closure of Benzimidazole Salts
Tao, Sheng,Bu, Qingqing,Shi, Qianqian,Wei, Donghui,Dai, Bin,Liu, Ning
supporting information, p. 3252 - 3258 (2020/03/04)
Pyrido-benzodiazepine derivatives are undoubtedly one of the most important structural motifs in the marketed drugs and the drug candidates. Commonly synthetic methods for construction of the benzodiazepine ring derivatives are based on the condensation reactions of two highly functionalized synthons. The development of synthesis for these compounds, however, is hampered by the regioselectivity and atom economy. In this work, a one-step synthesis of pyrido-benzodiazepine backbones and its analogues is achieved through continuous ring-opening hydrolysis of benzimidazole salts and intramolecular C?H bond activation. The reaction mechanism is explored by control experiments and density functional theory (DFT) calculations.
Novel Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase. 1. Tricyclic Pyridobenzo- and Dipyridodiazepinones
Hargrave, Karl D.,Proudfoot, John R.,Grozinger, Karl G.,Cullen, Ernest,Kapadia, Suresh R.,et al.
, p. 2231 - 2241 (2007/10/02)
Novel pyridobenzodiazepinones (I), pyridobenzodiazepinones (II), and dipyridodiazepinones (III) were found to inhibit human immunodeficiency virus type 1 (HIV-1) reverse transcriptase in vitro at concentrations as low as 35 nM.In all three series, small substituents (e.g., methyl, ethyl, acetyl) are preferred at the lactam nitrogen, whereas slightly larger alkyl moieties (e.g., ethyl, cyclopropyl) are favored at the other (N-11) diazepinone nitrogen.In general, lipophilic substituents are preferred on the A ring, whereassubstitution on the C ring generally reduces potency relative to the corresponding compounds with no substituents on the aromatic rings.Maximum potency is achieved with methyl substitution at the position ortho to the lactam nitrogen atom; however, in this case an unsubstituted lactam nitrogen is preferred.Additional substituents on the A ring can be readily tolerated.The dipyridodiazepinone derivative 11-cyclopropyl-5,11-dihydro-4-methyl-6H-dipyridodiazepin-6-one (96, nevirapine) is a potent (IC50 = 84 nM) and selective non-nucleoside inhibitor of HIV-1 reverse transcriptase, and has been chosen for clinical evaluation.
